ChemWiki - User contributions [en]

It:Piperine

2006-10-30T11:10:47Z

Chl105: /* References */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

==Background==

The familiar spicy flavor of peppers that is black spicy, making you sneeze comes from the molecule piperine. Piperine, with the chemical formula C17H19NO3, primarily comes from the Asian vine Piper Nigrum. Pepper have played a large role in the history of the world. Explorers once searched the globe for this tangy spicy that was perfect for the seasoning of their food. But pepper and piperine has far more uses then just for flavoring. Piperine has a wide-range of uses, from pesticides to medical treatments.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==History of Piperine==
Before the invention of processed foods and refrigerators, food could only be preserved by drying. If this did not occur then the food would simply go bad. In order to mask the taste seasonings and spices were added for flavor. Pepper, with piperine's tangy and spicy taste, was one such spice. The Romans traveled the silk road to obtain it from the Middle East and Asia, while from the 1600's to the 1800's the Dutch and English fought over trade routes and land. Although piperine has been used in peppers for thousands of years, however, it was not truly discovered into 1820. Danish physicist, Chemist and professor at the University of Copenhagen, Hans Christian Orsted was the first to identify the compound piperine. The chemical makeup of piperine was later isolated during laboratory synthesis in 1882 and 1894.
== Where is Piperine Found?==
Piperine is found in the fruit of the pepper vine, piper nigrum. . The pepper vine is found in the Malabar Coast of India, southern Asia, South America and Africa. The plant is known for its broad shiny green leaves, and small flowers. The Piperine can be obtained from the oleoresin in the peppercorns. The piperine gives these peppercorns their hot, biting, and very pungent taste. Piperine can also be found in other vegetables and spices such as the famous hot jalapeno peppers. However, for chemical and medical use piperine is produced in the laboratory.

==Characteristics of Piperine==
Piperine is a member of the Lipids family. Lipids are a group defined as consisting of fats or fat like substances. However, Piperine is also characterized as a member of the alkaloids. Alkaloids are similar in the fact that they are all nitrogenous.

Purity in Nature: 98% in piper nigrum. Can only be attained in 100% purity through processing in the laboratory.

==Structure==
Percent Composition by mass:
C= 71% O= 17% H=6% N=5%
Type of Bonding: Piperine has predominantly covalent bonds. However, with its large amount of hydrogen atoms it has been hydrogen bonds as well.

==Chemical Properties of Piperine==
The color of piperine can vary between its version in nature and its version created through synthesis. Piperine is naturally a more yellowish powder, while after synthesis it has a stronger green tint to it.
Piperine is soluble in alcohol, chloroform, ether, benzene and water. Piperine is not very reactive unless in a solution.
Piperine is tasteless unless it is dissolved in a solution. The oil in the peppercorns reacts with piperine to give it its flavor. When piperine looses its characteristic flavor it becomes known as Chavicine. Chavicine has the same molecular formula but a different structure.
When boiled with alcoholic caustic potash piperic acid is produced.
Piperine has the same molecular formula as chavicine, morphine, and volatile oil. Piperine also has the less common names piperoylpiperidine, piperylpiperidine, and piperoylpiperidin

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.
==Other actions of piperine==
Aside from its effects on bioavailability, piperine has a number of other actions in the body. (It is suspected, but not proven, that some of these actions result from piperine’s effects on the bioavailability of other substances.) These actions include:
• Increasing the brain’s production of beta-endorphins

• Pain relief

• Increasing the brain’s production of serotonin

• Anticonvulsant, anti-epileptic action

• Increasing the adrenal glands’ production of epinephrine (adrenaline)

• Altering contractions in the upper and lower digestive tract

• Reducing the stomach’s production of acid (for about 1 hour)

• Decreasing ulceration of the stomach

• Increasing the pancreas’s production of digestive enzymes (amylase, lipase, trypsin and chymotrypsin)

• Stimulating production of melanin

• Reducing inflammation due to irritation or allergy

• Relieving asthma symptoms

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

"Black Pepper and Piperine." Encyclopedia Britanica.com. Revised March 1999. <http://www.britannica.com/bcom/eb/article/0/0,5716,15702+1+15499,00.html>

Lima Morreira, Davyson de. "Piperaceae Home Page" <http://www.sbq.org.br/PN-NET/Piperaceae/index.htm>
"Piperine." ChemFinder. <http://www.americanformulary.com/products/liver.htm>

Cochran, Tim. "Piperine" Cochran Foundation of Medical Research. Revised January 30, 1998. <http://www.cochranfoundation.com/reports/piperin.htm.

"Piperine." Natural Herb Remedies. <http://www.indianherbs.com/piperine.htm>

Hilburn, Wayne M. The New Encyclopedia of Cooking Esoterica. Hilburn's Homepage. Version 1. Revised 2000. <http://www.dmgi.com/encyclop.html>

http://www.cochranfoundation.com/reports/piperin.htm

http://www.delano.com/Articles/piperine-multiplies.html

http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm

http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml

http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_043501.htm

http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html?DOC=HomeMolecule%5Carchive%5Cmotw_piperine_arch.html

It:Piperine

2006-10-30T11:08:47Z

Chl105: /* References */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

==Background==

The familiar spicy flavor of peppers that is black spicy, making you sneeze comes from the molecule piperine. Piperine, with the chemical formula C17H19NO3, primarily comes from the Asian vine Piper Nigrum. Pepper have played a large role in the history of the world. Explorers once searched the globe for this tangy spicy that was perfect for the seasoning of their food. But pepper and piperine has far more uses then just for flavoring. Piperine has a wide-range of uses, from pesticides to medical treatments.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==History of Piperine==
Before the invention of processed foods and refrigerators, food could only be preserved by drying. If this did not occur then the food would simply go bad. In order to mask the taste seasonings and spices were added for flavor. Pepper, with piperine's tangy and spicy taste, was one such spice. The Romans traveled the silk road to obtain it from the Middle East and Asia, while from the 1600's to the 1800's the Dutch and English fought over trade routes and land. Although piperine has been used in peppers for thousands of years, however, it was not truly discovered into 1820. Danish physicist, Chemist and professor at the University of Copenhagen, Hans Christian Orsted was the first to identify the compound piperine. The chemical makeup of piperine was later isolated during laboratory synthesis in 1882 and 1894.
== Where is Piperine Found?==
Piperine is found in the fruit of the pepper vine, piper nigrum. . The pepper vine is found in the Malabar Coast of India, southern Asia, South America and Africa. The plant is known for its broad shiny green leaves, and small flowers. The Piperine can be obtained from the oleoresin in the peppercorns. The piperine gives these peppercorns their hot, biting, and very pungent taste. Piperine can also be found in other vegetables and spices such as the famous hot jalapeno peppers. However, for chemical and medical use piperine is produced in the laboratory.

==Characteristics of Piperine==
Piperine is a member of the Lipids family. Lipids are a group defined as consisting of fats or fat like substances. However, Piperine is also characterized as a member of the alkaloids. Alkaloids are similar in the fact that they are all nitrogenous.

Purity in Nature: 98% in piper nigrum. Can only be attained in 100% purity through processing in the laboratory.

==Structure==
Percent Composition by mass:
C= 71% O= 17% H=6% N=5%
Type of Bonding: Piperine has predominantly covalent bonds. However, with its large amount of hydrogen atoms it has been hydrogen bonds as well.

==Chemical Properties of Piperine==
The color of piperine can vary between its version in nature and its version created through synthesis. Piperine is naturally a more yellowish powder, while after synthesis it has a stronger green tint to it.
Piperine is soluble in alcohol, chloroform, ether, benzene and water. Piperine is not very reactive unless in a solution.
Piperine is tasteless unless it is dissolved in a solution. The oil in the peppercorns reacts with piperine to give it its flavor. When piperine looses its characteristic flavor it becomes known as Chavicine. Chavicine has the same molecular formula but a different structure.
When boiled with alcoholic caustic potash piperic acid is produced.
Piperine has the same molecular formula as chavicine, morphine, and volatile oil. Piperine also has the less common names piperoylpiperidine, piperylpiperidine, and piperoylpiperidin

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.
==Other actions of piperine==
Aside from its effects on bioavailability, piperine has a number of other actions in the body. (It is suspected, but not proven, that some of these actions result from piperine’s effects on the bioavailability of other substances.) These actions include:
• Increasing the brain’s production of beta-endorphins

• Pain relief

• Increasing the brain’s production of serotonin

• Anticonvulsant, anti-epileptic action

• Increasing the adrenal glands’ production of epinephrine (adrenaline)

• Altering contractions in the upper and lower digestive tract

• Reducing the stomach’s production of acid (for about 1 hour)

• Decreasing ulceration of the stomach

• Increasing the pancreas’s production of digestive enzymes (amylase, lipase, trypsin and chymotrypsin)

• Stimulating production of melanin

• Reducing inflammation due to irritation or allergy

• Relieving asthma symptoms

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

"Black Pepper and Piperine." Encyclopedia Britanica.com. Revised March 1999. <http://www.britannica.com/bcom/eb/article/0/0,5716,15702+1+15499,00.html>

Lima Morreira, Davyson de. "Piperaceae Home Page" <http://www.sbq.org.br/PN-NET/Piperaceae/index.htm>
"Piperine." ChemFinder. <http://www.americanformulary.com/products/liver.htm>

Cochran, Tim. "Piperine" Cochran Foundation of Medical Research. Revised January 30, 1998. <http://www.cochranfoundation.com/reports/piperin.htm.

"Piperine." Natural Herb Remedies. <http://www.indianherbs.com/piperine.htm>
Hilburn, Wayne M. The New Encyclopedia of Cooking Esoterica. Hilburn's Homepage. Version 1. Revised 2000. <http://www.dmgi.com/encyclop.html>

http://www.cochranfoundation.com/reports/piperin.htm

http://www.delano.com/Articles/piperine-multiplies.html

http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm

http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml

http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_043501.htm

http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html?DOC=HomeMolecule%5Carchive%5Cmotw_piperine_arch.html

It:Piperine

2006-10-30T11:08:22Z

Chl105: /* References */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

==Background==

The familiar spicy flavor of peppers that is black spicy, making you sneeze comes from the molecule piperine. Piperine, with the chemical formula C17H19NO3, primarily comes from the Asian vine Piper Nigrum. Pepper have played a large role in the history of the world. Explorers once searched the globe for this tangy spicy that was perfect for the seasoning of their food. But pepper and piperine has far more uses then just for flavoring. Piperine has a wide-range of uses, from pesticides to medical treatments.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==History of Piperine==
Before the invention of processed foods and refrigerators, food could only be preserved by drying. If this did not occur then the food would simply go bad. In order to mask the taste seasonings and spices were added for flavor. Pepper, with piperine's tangy and spicy taste, was one such spice. The Romans traveled the silk road to obtain it from the Middle East and Asia, while from the 1600's to the 1800's the Dutch and English fought over trade routes and land. Although piperine has been used in peppers for thousands of years, however, it was not truly discovered into 1820. Danish physicist, Chemist and professor at the University of Copenhagen, Hans Christian Orsted was the first to identify the compound piperine. The chemical makeup of piperine was later isolated during laboratory synthesis in 1882 and 1894.
== Where is Piperine Found?==
Piperine is found in the fruit of the pepper vine, piper nigrum. . The pepper vine is found in the Malabar Coast of India, southern Asia, South America and Africa. The plant is known for its broad shiny green leaves, and small flowers. The Piperine can be obtained from the oleoresin in the peppercorns. The piperine gives these peppercorns their hot, biting, and very pungent taste. Piperine can also be found in other vegetables and spices such as the famous hot jalapeno peppers. However, for chemical and medical use piperine is produced in the laboratory.

==Characteristics of Piperine==
Piperine is a member of the Lipids family. Lipids are a group defined as consisting of fats or fat like substances. However, Piperine is also characterized as a member of the alkaloids. Alkaloids are similar in the fact that they are all nitrogenous.

Purity in Nature: 98% in piper nigrum. Can only be attained in 100% purity through processing in the laboratory.

==Structure==
Percent Composition by mass:
C= 71% O= 17% H=6% N=5%
Type of Bonding: Piperine has predominantly covalent bonds. However, with its large amount of hydrogen atoms it has been hydrogen bonds as well.

==Chemical Properties of Piperine==
The color of piperine can vary between its version in nature and its version created through synthesis. Piperine is naturally a more yellowish powder, while after synthesis it has a stronger green tint to it.
Piperine is soluble in alcohol, chloroform, ether, benzene and water. Piperine is not very reactive unless in a solution.
Piperine is tasteless unless it is dissolved in a solution. The oil in the peppercorns reacts with piperine to give it its flavor. When piperine looses its characteristic flavor it becomes known as Chavicine. Chavicine has the same molecular formula but a different structure.
When boiled with alcoholic caustic potash piperic acid is produced.
Piperine has the same molecular formula as chavicine, morphine, and volatile oil. Piperine also has the less common names piperoylpiperidine, piperylpiperidine, and piperoylpiperidin

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.
==Other actions of piperine==
Aside from its effects on bioavailability, piperine has a number of other actions in the body. (It is suspected, but not proven, that some of these actions result from piperine’s effects on the bioavailability of other substances.) These actions include:
• Increasing the brain’s production of beta-endorphins

• Pain relief

• Increasing the brain’s production of serotonin

• Anticonvulsant, anti-epileptic action

• Increasing the adrenal glands’ production of epinephrine (adrenaline)

• Altering contractions in the upper and lower digestive tract

• Reducing the stomach’s production of acid (for about 1 hour)

• Decreasing ulceration of the stomach

• Increasing the pancreas’s production of digestive enzymes (amylase, lipase, trypsin and chymotrypsin)

• Stimulating production of melanin

• Reducing inflammation due to irritation or allergy

• Relieving asthma symptoms

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

"Black Pepper and Piperine." Encyclopedia Britanica.com. Revised March 1999. <http://www.britannica.com/bcom/eb/article/0/0,5716,15702+1+15499,00.html>
Lima Morreira, Davyson de. "Piperaceae Home Page" <http://www.sbq.org.br/PN-NET/Piperaceae/index.htm>
"Piperine." ChemFinder. <http://www.americanformulary.com/products/liver.htm>
Cochran, Tim. "Piperine" Cochran Foundation of Medical Research. Revised January 30, 1998. <http://www.cochranfoundation.com/reports/piperin.htm.
"Piperine." Natural Herb Remedies. <http://www.indianherbs.com/piperine.htm>
Hilburn, Wayne M. The New Encyclopedia of Cooking Esoterica. Hilburn's Homepage. Version 1. Revised 2000. <http://www.dmgi.com/encyclop.html>
http://www.cochranfoundation.com/reports/piperin.htm
http://www.delano.com/Articles/piperine-multiplies.html
http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm
http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_043501.htm
http://www.chemistry.org/portal/a/c/s/1/acsdisplay.html?DOC=HomeMolecule%5Carchive%5Cmotw_piperine_arch.html

It:Piperine

2006-10-30T11:07:59Z

Chl105: /* Other actions of piperine */

It:Piperine

2006-10-30T11:07:21Z

Chl105: /* Uses of Piperine */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

==Background==

The familiar spicy flavor of peppers that is black spicy, making you sneeze comes from the molecule piperine. Piperine, with the chemical formula C17H19NO3, primarily comes from the Asian vine Piper Nigrum. Pepper have played a large role in the history of the world. Explorers once searched the globe for this tangy spicy that was perfect for the seasoning of their food. But pepper and piperine has far more uses then just for flavoring. Piperine has a wide-range of uses, from pesticides to medical treatments.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==History of Piperine==
Before the invention of processed foods and refrigerators, food could only be preserved by drying. If this did not occur then the food would simply go bad. In order to mask the taste seasonings and spices were added for flavor. Pepper, with piperine's tangy and spicy taste, was one such spice. The Romans traveled the silk road to obtain it from the Middle East and Asia, while from the 1600's to the 1800's the Dutch and English fought over trade routes and land. Although piperine has been used in peppers for thousands of years, however, it was not truly discovered into 1820. Danish physicist, Chemist and professor at the University of Copenhagen, Hans Christian Orsted was the first to identify the compound piperine. The chemical makeup of piperine was later isolated during laboratory synthesis in 1882 and 1894.
== Where is Piperine Found?==
Piperine is found in the fruit of the pepper vine, piper nigrum. . The pepper vine is found in the Malabar Coast of India, southern Asia, South America and Africa. The plant is known for its broad shiny green leaves, and small flowers. The Piperine can be obtained from the oleoresin in the peppercorns. The piperine gives these peppercorns their hot, biting, and very pungent taste. Piperine can also be found in other vegetables and spices such as the famous hot jalapeno peppers. However, for chemical and medical use piperine is produced in the laboratory.

==Characteristics of Piperine==
Piperine is a member of the Lipids family. Lipids are a group defined as consisting of fats or fat like substances. However, Piperine is also characterized as a member of the alkaloids. Alkaloids are similar in the fact that they are all nitrogenous.

Purity in Nature: 98% in piper nigrum. Can only be attained in 100% purity through processing in the laboratory.

==Structure==
Percent Composition by mass:
C= 71% O= 17% H=6% N=5%
Type of Bonding: Piperine has predominantly covalent bonds. However, with its large amount of hydrogen atoms it has been hydrogen bonds as well.

==Chemical Properties of Piperine==
The color of piperine can vary between its version in nature and its version created through synthesis. Piperine is naturally a more yellowish powder, while after synthesis it has a stronger green tint to it.
Piperine is soluble in alcohol, chloroform, ether, benzene and water. Piperine is not very reactive unless in a solution.
Piperine is tasteless unless it is dissolved in a solution. The oil in the peppercorns reacts with piperine to give it its flavor. When piperine looses its characteristic flavor it becomes known as Chavicine. Chavicine has the same molecular formula but a different structure.
When boiled with alcoholic caustic potash piperic acid is produced.
Piperine has the same molecular formula as chavicine, morphine, and volatile oil. Piperine also has the less common names piperoylpiperidine, piperylpiperidine, and piperoylpiperidin

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.
==Other actions of piperine==
Aside from its effects on bioavailability, piperine has a number of other actions in the body. (It is suspected, but not proven, that some of these actions result from piperine’s effects on the bioavailability of other substances.) These actions include:
• Increasing the brain’s production of beta-endorphins
• Pain relief
• Increasing the brain’s production of serotonin
• Anticonvulsant, anti-epileptic action
• Increasing the adrenal glands’ production of epinephrine (adrenaline)
• Altering contractions in the upper and lower digestive tract
• Reducing the stomach’s production of acid (for about 1 hour)
• Decreasing ulceration of the stomach
• Increasing the pancreas’s production of digestive enzymes (amylase, lipase, trypsin and chymotrypsin)
• Stimulating production of melanin
• Reducing inflammation due to irritation or allergy
• Relieving asthma symptoms

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-30T11:06:40Z

Chl105: /* History of Piperine */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

==Background==

The familiar spicy flavor of peppers that is black spicy, making you sneeze comes from the molecule piperine. Piperine, with the chemical formula C17H19NO3, primarily comes from the Asian vine Piper Nigrum. Pepper have played a large role in the history of the world. Explorers once searched the globe for this tangy spicy that was perfect for the seasoning of their food. But pepper and piperine has far more uses then just for flavoring. Piperine has a wide-range of uses, from pesticides to medical treatments.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==History of Piperine==
Before the invention of processed foods and refrigerators, food could only be preserved by drying. If this did not occur then the food would simply go bad. In order to mask the taste seasonings and spices were added for flavor. Pepper, with piperine's tangy and spicy taste, was one such spice. The Romans traveled the silk road to obtain it from the Middle East and Asia, while from the 1600's to the 1800's the Dutch and English fought over trade routes and land. Although piperine has been used in peppers for thousands of years, however, it was not truly discovered into 1820. Danish physicist, Chemist and professor at the University of Copenhagen, Hans Christian Orsted was the first to identify the compound piperine. The chemical makeup of piperine was later isolated during laboratory synthesis in 1882 and 1894.
== Where is Piperine Found?==
Piperine is found in the fruit of the pepper vine, piper nigrum. . The pepper vine is found in the Malabar Coast of India, southern Asia, South America and Africa. The plant is known for its broad shiny green leaves, and small flowers. The Piperine can be obtained from the oleoresin in the peppercorns. The piperine gives these peppercorns their hot, biting, and very pungent taste. Piperine can also be found in other vegetables and spices such as the famous hot jalapeno peppers. However, for chemical and medical use piperine is produced in the laboratory.

==Characteristics of Piperine==
Piperine is a member of the Lipids family. Lipids are a group defined as consisting of fats or fat like substances. However, Piperine is also characterized as a member of the alkaloids. Alkaloids are similar in the fact that they are all nitrogenous.

Purity in Nature: 98% in piper nigrum. Can only be attained in 100% purity through processing in the laboratory.

==Structure==
Percent Composition by mass:
C= 71% O= 17% H=6% N=5%
Type of Bonding: Piperine has predominantly covalent bonds. However, with its large amount of hydrogen atoms it has been hydrogen bonds as well.

==Chemical Properties of Piperine==
The color of piperine can vary between its version in nature and its version created through synthesis. Piperine is naturally a more yellowish powder, while after synthesis it has a stronger green tint to it.
Piperine is soluble in alcohol, chloroform, ether, benzene and water. Piperine is not very reactive unless in a solution.
Piperine is tasteless unless it is dissolved in a solution. The oil in the peppercorns reacts with piperine to give it its flavor. When piperine looses its characteristic flavor it becomes known as Chavicine. Chavicine has the same molecular formula but a different structure.
When boiled with alcoholic caustic potash piperic acid is produced.
Piperine has the same molecular formula as chavicine, morphine, and volatile oil. Piperine also has the less common names piperoylpiperidine, piperylpiperidine, and piperoylpiperidin

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-30T11:06:19Z

Chl105: /* Structure */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

==Background==

The familiar spicy flavor of peppers that is black spicy, making you sneeze comes from the molecule piperine. Piperine, with the chemical formula C17H19NO3, primarily comes from the Asian vine Piper Nigrum. Pepper have played a large role in the history of the world. Explorers once searched the globe for this tangy spicy that was perfect for the seasoning of their food. But pepper and piperine has far more uses then just for flavoring. Piperine has a wide-range of uses, from pesticides to medical treatments.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==History of Piperine==
Before the invention of processed foods and refrigerators, food could only be preserved by drying. If this did not occur then the food would simply go bad. In order to mask the taste seasonings and spices were added for flavor. Pepper, with piperine's tangy and spicy taste, was one such spice. The Romans traveled the silk road to obtain it from the Middle East and Asia, while from the 1600's to the 1800's the Dutch and English fought over trade routes and land. Although piperine has been used in peppers for thousands of years, however, it was not truly discovered into 1820. Danish physicist, Chemist and professor at the University of Copenhagen, Hans Christian Orsted was the first to identify the compound piperine. The chemical makeup of piperine was later isolated during laboratory synthesis in 1882 and 1894.

==Characteristics of Piperine==
Piperine is a member of the Lipids family. Lipids are a group defined as consisting of fats or fat like substances. However, Piperine is also characterized as a member of the alkaloids. Alkaloids are similar in the fact that they are all nitrogenous.

Purity in Nature: 98% in piper nigrum. Can only be attained in 100% purity through processing in the laboratory.

==Structure==
Percent Composition by mass:
C= 71% O= 17% H=6% N=5%
Type of Bonding: Piperine has predominantly covalent bonds. However, with its large amount of hydrogen atoms it has been hydrogen bonds as well.

==Chemical Properties of Piperine==
The color of piperine can vary between its version in nature and its version created through synthesis. Piperine is naturally a more yellowish powder, while after synthesis it has a stronger green tint to it.
Piperine is soluble in alcohol, chloroform, ether, benzene and water. Piperine is not very reactive unless in a solution.
Piperine is tasteless unless it is dissolved in a solution. The oil in the peppercorns reacts with piperine to give it its flavor. When piperine looses its characteristic flavor it becomes known as Chavicine. Chavicine has the same molecular formula but a different structure.
When boiled with alcoholic caustic potash piperic acid is produced.
Piperine has the same molecular formula as chavicine, morphine, and volatile oil. Piperine also has the less common names piperoylpiperidine, piperylpiperidine, and piperoylpiperidin

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-30T11:05:57Z

Chl105: /* Characteristics of Piperine */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

==Background==

The familiar spicy flavor of peppers that is black spicy, making you sneeze comes from the molecule piperine. Piperine, with the chemical formula C17H19NO3, primarily comes from the Asian vine Piper Nigrum. Pepper have played a large role in the history of the world. Explorers once searched the globe for this tangy spicy that was perfect for the seasoning of their food. But pepper and piperine has far more uses then just for flavoring. Piperine has a wide-range of uses, from pesticides to medical treatments.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==History of Piperine==
Before the invention of processed foods and refrigerators, food could only be preserved by drying. If this did not occur then the food would simply go bad. In order to mask the taste seasonings and spices were added for flavor. Pepper, with piperine's tangy and spicy taste, was one such spice. The Romans traveled the silk road to obtain it from the Middle East and Asia, while from the 1600's to the 1800's the Dutch and English fought over trade routes and land. Although piperine has been used in peppers for thousands of years, however, it was not truly discovered into 1820. Danish physicist, Chemist and professor at the University of Copenhagen, Hans Christian Orsted was the first to identify the compound piperine. The chemical makeup of piperine was later isolated during laboratory synthesis in 1882 and 1894.

==Characteristics of Piperine==
Piperine is a member of the Lipids family. Lipids are a group defined as consisting of fats or fat like substances. However, Piperine is also characterized as a member of the alkaloids. Alkaloids are similar in the fact that they are all nitrogenous.

Purity in Nature: 98% in piper nigrum. Can only be attained in 100% purity through processing in the laboratory.

==Structure==
Percent Composition by mass:
C= 71% O= 17% H=6% N=5%
Type of Bonding: Piperine has predominantly covalent bonds. However, with its large amount of hydrogen atoms it has been hydrogen bonds as well.

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-30T11:05:02Z

Chl105: /* History of Piperine */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

==Background==

The familiar spicy flavor of peppers that is black spicy, making you sneeze comes from the molecule piperine. Piperine, with the chemical formula C17H19NO3, primarily comes from the Asian vine Piper Nigrum. Pepper have played a large role in the history of the world. Explorers once searched the globe for this tangy spicy that was perfect for the seasoning of their food. But pepper and piperine has far more uses then just for flavoring. Piperine has a wide-range of uses, from pesticides to medical treatments.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==History of Piperine==
Before the invention of processed foods and refrigerators, food could only be preserved by drying. If this did not occur then the food would simply go bad. In order to mask the taste seasonings and spices were added for flavor. Pepper, with piperine's tangy and spicy taste, was one such spice. The Romans traveled the silk road to obtain it from the Middle East and Asia, while from the 1600's to the 1800's the Dutch and English fought over trade routes and land. Although piperine has been used in peppers for thousands of years, however, it was not truly discovered into 1820. Danish physicist, Chemist and professor at the University of Copenhagen, Hans Christian Orsted was the first to identify the compound piperine. The chemical makeup of piperine was later isolated during laboratory synthesis in 1882 and 1894.

==Characteristics of Piperine==
Piperine is a member of the Lipids family. Lipids are a group defined as consisting of fats or fat like substances. However, Piperine is also characterized as a member of the alkaloids. Alkaloids are similar in the fact that they are all nitrogenous.

Purity in Nature: 98% in piper nigrum. Can only be attained in 100% purity through processing in the laboratory.

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-30T11:04:23Z

Chl105: /* 3D Image of Piperine */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Piperine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:piperine.png|Piperine]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"| 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl]piperidine
|-
| colspan="1" |Auto name
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C17H19NO3
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O=C(N2CCCCC2)/C=C/C=C/C1=CC(OCO3)=C3C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |285.34
|-
| colspan="1" |Appearance
| colspan="2" |Yellow/Green Powder
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |90741
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-62-2, 495-91-0, 7780-20-3, 30511-76-3, 30511-77-4
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)| Solubility in Water
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |131-135oC
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |Decomposes
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine] 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[http://www.sigmaaldrich.com/spectra/fnmr/FNMR011260.PDF NMR]], [[Mass spectrometry|MS]], [[Isotope Distribution Pattern|IDP]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==

'''Piperine''' is a substance found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper.

Piperine can be extracted directly from black pepper by using ethanol. At first, piperine is tasteless but a burning sensation on the tongue is felt soon after ingestion. Other less common names for piperine include piperoylpiperidine, piperylpiperidine, and piperoylpiperidin. The color of piperine varies according to whether it is found naturally or synthesized. It is naturally yellow, whereas it is green if synthesized.

==Background==

The familiar spicy flavor of peppers that is black spicy, making you sneeze comes from the molecule piperine. Piperine, with the chemical formula C17H19NO3, primarily comes from the Asian vine Piper Nigrum. Pepper have played a large role in the history of the world. Explorers once searched the globe for this tangy spicy that was perfect for the seasoning of their food. But pepper and piperine has far more uses then just for flavoring. Piperine has a wide-range of uses, from pesticides to medical treatments.

== 3D Image of Piperine ==

<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 O 0 3.507 -2.115 -0.157 0.00 0.00 O+0
ATOM 2 C 0 3.446 -0.904 -0.277 0.00 0.00 C+0
ATOM 3 N 0 4.578 -0.181 -0.385 0.00 0.00 N+0
ATOM 4 C 0 4.521 1.265 -0.642 0.00 0.00 C+0
ATOM 5 C 0 5.340 1.989 0.430 0.00 0.00 C+0
ATOM 6 C 0 6.757 1.412 0.460 0.00 0.00 C+0
ATOM 7 C 0 6.697 -0.074 0.821 0.00 0.00 C+0
ATOM 8 C 0 5.893 -0.821 -0.242 0.00 0.00 C+0
ATOM 9 C 0 2.187 -0.258 -0.309 0.00 0.00 C+0
ATOM 10 C 0 1.052 -0.972 -0.096 0.00 0.00 C+0
ATOM 11 C 0 -0.203 -0.328 -0.128 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.040 0.084 0.00 0.00 C+0
ATOM 13 C 0 -2.641 -0.370 0.051 0.00 0.00 C+0
ATOM 14 C 0 -3.813 -1.104 0.270 0.00 0.00 C+0
ATOM 15 C 0 -5.039 -0.468 0.238 0.00 0.00 C+0
ATOM 16 O 0 -6.306 -0.943 0.415 0.00 0.00 O+0
ATOM 17 C 0 -7.174 0.067 -0.133 0.00 0.00 C+0
ATOM 18 O 0 -6.418 1.283 0.009 0.00 0.00 O+0
ATOM 19 C 0 -5.108 0.903 -0.013 0.00 0.00 C+0
ATOM 20 C 0 -3.945 1.631 -0.230 0.00 0.00 C+0
ATOM 21 C 0 -2.718 1.007 -0.194 0.00 0.00 C+0
ATOM 22 H 0 4.938 1.477 -1.627 0.00 0.00 H+0
ATOM 23 H 0 3.485 1.602 -0.601 0.00 0.00 H+0
ATOM 24 H 0 5.386 3.053 0.196 0.00 0.00 H+0
ATOM 25 H 0 4.870 1.850 1.403 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.530 -0.520 0.00 0.00 H+0
ATOM 27 H 0 7.350 1.943 1.206 0.00 0.00 H+0
ATOM 28 H 0 7.708 -0.479 0.865 0.00 0.00 H+0
ATOM 29 H 0 6.214 -0.194 1.790 0.00 0.00 H+0
ATOM 30 H 0 5.763 -1.860 0.061 0.00 0.00 H+0
ATOM 31 H 0 6.419 -0.779 -1.195 0.00 0.00 H+0
ATOM 32 H 0 2.130 0.803 -0.502 0.00 0.00 H+0
ATOM 33 H 0 1.110 -2.033 0.097 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.733 -0.321 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.101 0.277 0.00 0.00 H+0
ATOM 36 H 0 -3.759 -2.165 0.463 0.00 0.00 H+0
ATOM 37 H 0 -7.381 -0.135 -1.184 0.00 0.00 H+0
ATOM 38 H 0 -8.102 0.124 0.436 0.00 0.00 H+0
ATOM 39 H 0 -4.003 2.692 -0.423 0.00 0.00 H+0
ATOM 40 H 0 -1.817 1.577 -0.363 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 19 0 NONE 59
CONECT 16 15 17 0 0 NONE 60
CONECT 17 16 18 37 38 NONE 61
CONECT 18 17 19 0 0 NONE 62
CONECT 19 15 18 20 0 NONE 63
CONECT 20 19 21 39 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
</jmol>

==History of Piperine==
Before the invention of processed foods and refrigerators, food could only be preserved by drying. If this did not occur then the food would simply go bad. In order to mask the taste seasonings and spices were added for flavor. Pepper, with piperine's tangy and spicy taste, was one such spice. The Romans traveled the silk road to obtain it from the Middle East and Asia, while from the 1600's to the 1800's the Dutch and English fought over trade routes and land. Although piperine has been used in peppers for thousands of years, however, it was not truly discovered into 1820. Danish physicist, Chemist and professor at the University of Copenhagen, Hans Christian Orsted was the first to identify the compound piperine. The chemical makeup of piperine was later isolated during laboratory synthesis in 1882 and 1894.

==Uses of Piperine==
As well as its most common use as a flavouring agent in pepper, piperine can be used in everything from pesticides to medical treatments. Some studies have shown that piperine can be helpful in increasing the absorption of certain vitamins such as Vitamin B and Beta-Carotene. Piperine can also increase the body's normal thermogenic activities. [http://en.wikipedia.org/wiki/Thermogenesis Thermogenesis] is the process of generating energy in the cell. Piperine increases thermogenesis and creates a demand for necessary nutrients of the metabolism.

==Synthesis of Piperine==
The synthesis of piperine occurs by the following mechanism:

[[Image:piperine2.gif]]

==Spectra of Piperine==
[[Image:cbook.gif]]

==Safety==

Piperine is a harmful substance and the dust/vapour should not be inhaled. As with most chemicals, contact with the skin and eyes should be avoided.

==External Links==

*[http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for Piperine]
*[http://www.uni-bayreuth.de/departments/oc1/Publications/ref09.pdf Three-component synthesis of (''E'')-(α,β)- unsaturated amides of the piperine family]

==References==

*[http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm Piperine Home Page]
*[http://http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml Piperine]
*[http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp?MW=285.341 National Library of Medicine, Specialised Information Services]
*[http://www.sigmaaldrich.com/Area_of_Interest/Europe_Home/UK.html Sigma-Alrich UK website]
*http://www2.ups.edu/faculty/hanson/c251lab.01/piperine.htm

[[Further Abstract]]

It:Piperine

2006-10-30T11:03:47Z

Chl105: /* Introduction */

It:Gentamycin

2006-10-26T10:55:49Z

Chl105: /* Before taking Gentamycin, */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

==Before taking Gentamycin,==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
<jmol>
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<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Gentamycin

2006-10-26T10:55:22Z

Chl105: /* Before taking Gentamycin, */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

==Before taking Gentamycin,==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: The Dangers of Gentamycin by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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11 10 1 0 0 0
11 12 1 0 0 0
14 13 1 0 0 0
14 47 1 0 0 0
14 48 1 0 0 0
17 16 1 0 0 0
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22 21 1 0 0 0
22 57 1 0 0 0
24 23 1 0 0 0
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24 59 1 0 0 0
27 26 1 0 0 0
27 64 1 0 0 0
29 28 1 0 0 0
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31 30 1 0 0 0
31 68 1 0 0 0
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3 36 1 0 0 0
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20 21 1 0 0 0
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25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Gentamycin

2006-10-26T10:55:08Z

Chl105: /* Before taking Gentamycin, */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

==Before taking Gentamycin,==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: The Dangers of Gentamycin, By Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
<jmol>
<jmolApplet>
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68 70 0 0 0 0 0 0 0 0999 V2000
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-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4
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-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16
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1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19
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4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29
-0.1580 -2.2980 1.2370 C 0 0 2 0 0 0 0 0 0 30
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-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45
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-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
1 2 1 0 0 0
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11 10 1 0 0 0
11 12 1 0 0 0
14 13 1 0 0 0
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14 48 1 0 0 0
17 16 1 0 0 0
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17 53 1 0 0 0
19 18 1 0 0 0
19 20 1 0 0 0
22 21 1 0 0 0
22 57 1 0 0 0
24 23 1 0 0 0
24 25 1 0 0 0
24 59 1 0 0 0
27 26 1 0 0 0
27 64 1 0 0 0
29 28 1 0 0 0
29 20 1 0 0 0
31 30 1 0 0 0
31 68 1 0 0 0
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2 35 1 0 0 0
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2 3 1 0 0 0
3 36 1 0 0 0
3 4 1 0 0 0
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6 8 1 0 0 0
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12 13 1 0 0 0
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26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Gentamycin

2006-10-26T10:53:27Z

Chl105: /* Before taking Gentamycin, */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

==Before taking Gentamycin,==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: The Dangers of Gentamycin ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
</inlineContents>
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</jmol>
<jmol>
<jmolApplet>
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WLViewer 3D 0

68 70 0 0 0 0 0 0 0 0999 V2000
-4.8690 -0.2540 2.7230 O 0 0 0 0 0 0 0 0 0 1
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-4.2080 0.6690 0.5900 C 0 0 1 0 0 0 0 0 0 3
-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4
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-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9
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-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11
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-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16
2.4450 -3.4250 -1.2820 N 0 0 0 0 0 0 0 0 0 17
1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19
2.6860 -0.6020 0.2110 C 0 0 1 0 0 0 0 0 0 20
3.0880 0.5730 -0.6830 C 0 0 2 0 0 0 0 0 0 21
2.1790 1.6580 -0.4840 O 0 0 0 0 0 0 0 0 0 22
4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29
-0.1580 -2.2980 1.2370 C 0 0 2 0 0 0 0 0 0 30
-0.1450 -1.2630 2.2230 O 0 0 0 0 0 0 0 0 0 31
-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32
-5.2540 -0.0280 3.5810 H 0 0 0 0 0 0 0 0 0 33
-5.8170 1.3580 1.8450 H 0 0 0 0 0 0 0 0 0 34
-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
1 2 1 0 0 0
1 33 1 0 0 0
5 4 1 0 0 0
5 38 1 0 0 0
7 6 1 0 0 0
7 40 1 0 0 0
9 8 1 0 0 0
9 42 1 0 0 0
9 43 1 0 0 0
11 10 1 0 0 0
11 12 1 0 0 0
14 13 1 0 0 0
14 47 1 0 0 0
14 48 1 0 0 0
17 16 1 0 0 0
17 52 1 0 0 0
17 53 1 0 0 0
19 18 1 0 0 0
19 20 1 0 0 0
22 21 1 0 0 0
22 57 1 0 0 0
24 23 1 0 0 0
24 25 1 0 0 0
24 59 1 0 0 0
27 26 1 0 0 0
27 64 1 0 0 0
29 28 1 0 0 0
29 20 1 0 0 0
31 30 1 0 0 0
31 68 1 0 0 0
32 10 1 0 0 0
32 3 1 0 0 0
2 35 1 0 0 0
2 34 1 0 0 0
2 3 1 0 0 0
3 36 1 0 0 0
3 4 1 0 0 0
4 37 1 0 0 0
4 6 1 0 0 0
6 8 1 0 0 0
6 39 1 0 0 0
8 10 1 0 0 0
8 41 1 0 0 0
10 44 1 0 0 0
12 30 1 0 0 0
12 45 1 0 0 0
12 13 1 0 0 0
13 15 1 0 0 0
13 46 1 0 0 0
15 16 1 0 0 0
15 50 1 0 0 0
15 49 1 0 0 0
16 51 1 0 0 0
16 18 1 0 0 0
18 30 1 0 0 0
18 54 1 0 0 0
20 55 1 0 0 0
20 21 1 0 0 0
21 56 1 0 0 0
21 23 1 0 0 0
23 58 1 0 0 0
23 26 1 0 0 0
25 60 1 0 0 0
25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Gentamycin

2006-10-26T10:49:30Z

Chl105: /* Symptoms of overdose */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

==Before taking Gentamycin,==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Molecule-1
WLViewer 3D 0

68 70 0 0 0 0 0 0 0 0999 V2000
-4.8690 -0.2540 2.7230 O 0 0 0 0 0 0 0 0 0 1
-4.8110 0.9570 1.9660 C 0 0 0 0 0 0 0 0 0 2
-4.2080 0.6690 0.5900 C 0 0 1 0 0 0 0 0 0 3
-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4
-3.4860 2.9650 0.3570 O 0 0 0 0 0 0 0 0 0 5
-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6
-3.5880 2.8380 -2.4090 O 0 0 0 0 0 0 0 0 0 7
-2.2910 1.0170 -1.4800 C 0 0 1 0 0 0 0 0 0 8
-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9
-2.3880 -0.1830 -0.5340 C 0 0 1 0 0 0 0 0 0 10
-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11
-1.2960 -2.0440 0.2460 C 0 0 1 0 0 0 0 0 0 12
-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16
2.4450 -3.4250 -1.2820 N 0 0 0 0 0 0 0 0 0 17
1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19
2.6860 -0.6020 0.2110 C 0 0 1 0 0 0 0 0 0 20
3.0880 0.5730 -0.6830 C 0 0 2 0 0 0 0 0 0 21
2.1790 1.6580 -0.4840 O 0 0 0 0 0 0 0 0 0 22
4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29
-0.1580 -2.2980 1.2370 C 0 0 2 0 0 0 0 0 0 30
-0.1450 -1.2630 2.2230 O 0 0 0 0 0 0 0 0 0 31
-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32
-5.2540 -0.0280 3.5810 H 0 0 0 0 0 0 0 0 0 33
-5.8170 1.3580 1.8450 H 0 0 0 0 0 0 0 0 0 34
-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
1 2 1 0 0 0
1 33 1 0 0 0
5 4 1 0 0 0
5 38 1 0 0 0
7 6 1 0 0 0
7 40 1 0 0 0
9 8 1 0 0 0
9 42 1 0 0 0
9 43 1 0 0 0
11 10 1 0 0 0
11 12 1 0 0 0
14 13 1 0 0 0
14 47 1 0 0 0
14 48 1 0 0 0
17 16 1 0 0 0
17 52 1 0 0 0
17 53 1 0 0 0
19 18 1 0 0 0
19 20 1 0 0 0
22 21 1 0 0 0
22 57 1 0 0 0
24 23 1 0 0 0
24 25 1 0 0 0
24 59 1 0 0 0
27 26 1 0 0 0
27 64 1 0 0 0
29 28 1 0 0 0
29 20 1 0 0 0
31 30 1 0 0 0
31 68 1 0 0 0
32 10 1 0 0 0
32 3 1 0 0 0
2 35 1 0 0 0
2 34 1 0 0 0
2 3 1 0 0 0
3 36 1 0 0 0
3 4 1 0 0 0
4 37 1 0 0 0
4 6 1 0 0 0
6 8 1 0 0 0
6 39 1 0 0 0
8 10 1 0 0 0
8 41 1 0 0 0
10 44 1 0 0 0
12 30 1 0 0 0
12 45 1 0 0 0
12 13 1 0 0 0
13 15 1 0 0 0
13 46 1 0 0 0
15 16 1 0 0 0
15 50 1 0 0 0
15 49 1 0 0 0
16 51 1 0 0 0
16 18 1 0 0 0
18 30 1 0 0 0
18 54 1 0 0 0
20 55 1 0 0 0
20 21 1 0 0 0
21 56 1 0 0 0
21 23 1 0 0 0
23 58 1 0 0 0
23 26 1 0 0 0
25 60 1 0 0 0
25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Gentamycin

2006-10-26T10:49:24Z

Chl105: /* Side Effects */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

==Before taking Gentamycin,==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

===Symptoms of overdose ===

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Gentamycin

2006-10-26T10:48:39Z

Chl105: /* Before taking Gentamycin */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

==Before taking Gentamycin,==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

====Side Effects====
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

===Symptoms of overdose ===

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
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<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
</inlineContents>
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M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Gentamycin

2006-10-26T10:48:27Z

Chl105: /* Before taking Gentamycin */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

==Before taking Gentamycin==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

====Side Effects====
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

===Symptoms of overdose ===

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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M END

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</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Gentamycin

2006-10-26T10:47:16Z

Chl105: /* Gentamycin A */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

===Before taking Gentamycin===

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

====Side Effects====
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

===Symptoms of overdose ===

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
1 2 1 0 0 0
1 33 1 0 0 0
5 4 1 0 0 0
5 38 1 0 0 0
7 6 1 0 0 0
7 40 1 0 0 0
9 8 1 0 0 0
9 42 1 0 0 0
9 43 1 0 0 0
11 10 1 0 0 0
11 12 1 0 0 0
14 13 1 0 0 0
14 47 1 0 0 0
14 48 1 0 0 0
17 16 1 0 0 0
17 52 1 0 0 0
17 53 1 0 0 0
19 18 1 0 0 0
19 20 1 0 0 0
22 21 1 0 0 0
22 57 1 0 0 0
24 23 1 0 0 0
24 25 1 0 0 0
24 59 1 0 0 0
27 26 1 0 0 0
27 64 1 0 0 0
29 28 1 0 0 0
29 20 1 0 0 0
31 30 1 0 0 0
31 68 1 0 0 0
32 10 1 0 0 0
32 3 1 0 0 0
2 35 1 0 0 0
2 34 1 0 0 0
2 3 1 0 0 0
3 36 1 0 0 0
3 4 1 0 0 0
4 37 1 0 0 0
4 6 1 0 0 0
6 8 1 0 0 0
6 39 1 0 0 0
8 10 1 0 0 0
8 41 1 0 0 0
10 44 1 0 0 0
12 30 1 0 0 0
12 45 1 0 0 0
12 13 1 0 0 0
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13 46 1 0 0 0
15 16 1 0 0 0
15 50 1 0 0 0
15 49 1 0 0 0
16 51 1 0 0 0
16 18 1 0 0 0
18 30 1 0 0 0
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20 55 1 0 0 0
20 21 1 0 0 0
21 56 1 0 0 0
21 23 1 0 0 0
23 58 1 0 0 0
23 26 1 0 0 0
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25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Gentamycin

2006-10-26T10:42:22Z

Chl105: /* Side Effects */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram[http://en.wikipedia.org/wiki/Gram]negative infections.

It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

====Side Effects====
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness
*loss of equilibrium

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

===Symptoms of overdose ===

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] 
<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
</inlineContents>
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</jmol>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Molecule-1
WLViewer 3D 0

68 70 0 0 0 0 0 0 0 0999 V2000
-4.8690 -0.2540 2.7230 O 0 0 0 0 0 0 0 0 0 1
-4.8110 0.9570 1.9660 C 0 0 0 0 0 0 0 0 0 2
-4.2080 0.6690 0.5900 C 0 0 1 0 0 0 0 0 0 3
-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4
-3.4860 2.9650 0.3570 O 0 0 0 0 0 0 0 0 0 5
-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6
-3.5880 2.8380 -2.4090 O 0 0 0 0 0 0 0 0 0 7
-2.2910 1.0170 -1.4800 C 0 0 1 0 0 0 0 0 0 8
-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9
-2.3880 -0.1830 -0.5340 C 0 0 1 0 0 0 0 0 0 10
-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11
-1.2960 -2.0440 0.2460 C 0 0 1 0 0 0 0 0 0 12
-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16
2.4450 -3.4250 -1.2820 N 0 0 0 0 0 0 0 0 0 17
1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19
2.6860 -0.6020 0.2110 C 0 0 1 0 0 0 0 0 0 20
3.0880 0.5730 -0.6830 C 0 0 2 0 0 0 0 0 0 21
2.1790 1.6580 -0.4840 O 0 0 0 0 0 0 0 0 0 22
4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29
-0.1580 -2.2980 1.2370 C 0 0 2 0 0 0 0 0 0 30
-0.1450 -1.2630 2.2230 O 0 0 0 0 0 0 0 0 0 31
-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32
-5.2540 -0.0280 3.5810 H 0 0 0 0 0 0 0 0 0 33
-5.8170 1.3580 1.8450 H 0 0 0 0 0 0 0 0 0 34
-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
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25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C18H36N4O10
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm3mol-1(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| Boiling point
| align="center"| °C
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O- [3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin

It:Schwartz

2006-10-26T10:29:10Z

Chl105: /* References */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Schwartz Reagent
|-
! {{chembox header}} colspan="3" |Structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 120; wireframe on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
title1
title2
23 32 0 0 0 0 0 0 0 0999 V2000
0.4968 2.4426 -1.8773 Zr 0 0 0 0 0 0 0 0 0 1
2.1386 2.5155 -0.0069 C 0 0 1 0 0 0 0 0 0 2
0.8893 2.8016 0.5785 C 0 0 1 0 0 0 0 0 0 3
0.4392 4.0345 0.0856 C 0 0 1 0 0 0 0 0 0 4
1.4009 4.5239 -0.7980 C 0 0 1 0 0 0 0 0 0 5
2.4581 3.6019 -0.8408 C 0 0 1 0 0 0 0 0 0 6
1.3075 2.1266 -4.2373 C 0 0 1 0 0 0 0 0 0 7
2.3637 1.7885 -3.4062 C 0 0 2 0 0 0 0 0 0 8
2.0155 0.6537 -2.7061 C 0 0 2 0 0 0 0 0 0 9
0.7446 0.2636 -3.1093 C 0 0 2 0 0 0 0 0 0 10
0.3198 1.1821 -4.0620 C 0 0 2 0 0 0 0 0 0 11
-1.3981 1.1750 -0.8823 Cl 0 0 0 0 0 0 0 0 0 12
-0.4999 3.6324 -2.6415 H 0 0 0 0 0 0 0 0 0 13
2.7373 1.6100 0.1615 H 0 0 0 0 0 0 0 0 0 14
0.3782 2.1727 1.3172 H 0 0 0 0 0 0 0 0 0 15
-0.5084 4.5050 0.3479 H 0 0 0 0 0 0 0 0 0 16
1.3481 5.4625 -1.3655 H 0 0 0 0 0 0 0 0 0 17
3.3834 3.6763 -1.4290 H 0 0 0 0 0 0 0 0 0 18
1.2659 3.0120 -4.9152 H 0 0 0 0 0 0 0 0 0 19
3.3152 2.3417 -3.3261 H 0 0 0 0 0 0 0 0 0 20
2.6389 0.1300 -1.9509 H 0 0 0 0 0 0 0 0 0 21
0.1603 -0.6100 -2.7365 H 0 0 0 0 0 0 0 0 0 22
-0.6338 1.1620 -4.5991 H 0 0 0 0 0 0 0 0 0 23
1 2 1 0 0 0
2 3 4 0 0 0
3 1 1 0 0 0
4 1 1 0 0 0
5 1 1 0 0 0
6 1 1 0 0 0
7 1 1 0 0 0
8 1 1 0 0 0
9 1 1 0 0 0
10 1 1 0 0 0
11 1 1 0 0 0
12 1 1 0 0 0
13 1 1 0 0 0
14 2 1 0 0 0
15 3 1 0 0 0
16 4 1 0 0 0
17 5 1 0 0 0
18 6 1 0 0 0
19 7 1 0 0 0
20 8 1 0 0 0
21 9 1 0 0 0
22 10 1 0 0 0
23 11 1 0 0 0
2 6 4 0 0 0
3 4 4 0 0 0
4 5 4 0 0 0
5 6 4 0 0 0
7 8 4 0 0 0
7 11 4 0 0 0
8 9 4 0 0 0
9 10 4 0 0 0
10 11 4 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Off-white solid
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
| colspan="1" |[http://en.wikipedia.org/wiki/EC-No EC number]
| colspan="2" |253-479-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase]
| colspan="2" |g/cm3, solid
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [http://en.wikipedia.org/wiki/Water_%28molecule%29 water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Standard_enthalpy_change_of_formation Δ''H''''f''<s>o</s>solid]
| colspan="2" |-314.8 ± 3.9 kJ/mol
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water
liberates flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

The first organochlorobis(cyclopentadienyl)zirconium(W)complex was prepared by Wailes, Weigold and Bell 25 years ago. Ever since, these organometallics have become important members in the field of synthetic strategy and tactics.because of the formations of carbon-carbon and carbon-heteroatom bond.Although the polarization of the carbon-zirconium bond is similar to Grignard reagents, the bulky cyclopentadienyl groups prevent the attack of many organic electrophiles due to steric crowding around the Zr atom. The resulting functional group tolerance of organozirconocenes is useful for the preparation of the organometallic species, but this low reactivity must be overcome for subsequent selective carbon-carbon bond formations. Therefore, much of the development of organozirconocenes focuses on indirect reaction pathways involving transmetalation or activation by ligand.

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

Zirconocene dichloride is added under argon to a flask equipped with a magnetic stirring bar, followed by addition of dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether is added dropwise. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The suspension is then stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in Organic Synthesis==

===Triethylborane-induced radical reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and regiocontrolled synthesis of branched trisubstituted conjugated dienes by palladium(0)-catalyzed cross-coupling reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:

[[Image:Hydrozirconation.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]

These are the thermodynamic products of the reaction and arise primarily from steric interaction with the Cp ring.

=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

==Hydrozirconation of 1-alkynes==

This reaction is important in chemistry because the product that is synthesised from the acetylene (e.g. 1-alkynes) is regioselectively controlled. This gives rise to greater yields of products with the selectively required stereochemistry. So a range of diverse compounds can be derived from mono-substitued acetylenes, via this reaction.

[[Image:Vlzirconation.gif]]

The above reaction scheme [[1]] requires 4 steps. The second and third steps require a very cool temperature of -78oC, to prevent unwanted side reactions which would produce unwanted products.

==References==

1. http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1990/112/i20/f-pdf/f_ja00176a079.pdf?sessid=6006l3

2. http://people.bu.edu/jaylowe/Named%20reagents/S/Schwartz/Schwartz.htm

3. http://orgchem.chem.uconn.edu/namereact/schwartz.html

4. http://www.answers.com/topic/schwartz-s-reagent

5. http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV9P0162

6. http://pubs.acs.org/cen/nlw/8216sci1.html

It:Schwartz

2006-10-26T10:28:36Z

Chl105: /* References */

It:Lignocaine

2006-10-26T10:24:58Z

Chl105: /* References */

Lignocaine is a local anaesthetic drug especially used in dentistry. Discovered by N.Lofgren and B.Lundqvist in the 1940s, it has been very successful due to it's low neurotoxicity when compared with other local anaesthetics.
It has found uses also in the treatment of Arrhythmias eg: problems of the electrical system of the heart, causing it to pump less efficiently.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Lignocaine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Lignocaine.gif|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Fri Oct 20 12:51:30 GMT Standard Time 2006
ATOM 1 N1 MOL 1 16.171 14.259 -0.113 1.00 0.00
ATOM 2 C2 MOL 1 15.015 15.193 -0.048 1.00 0.00
ATOM 3 C3 MOL 1 16.350 12.740 -0.084 1.00 0.00
ATOM 4 C4 MOL 1 13.631 14.760 0.341 1.00 0.00
ATOM 5 O5 MOL 1 15.239 16.388 -0.269 1.00 0.00
ATOM 6 C6 MOL 1 17.620 12.369 0.089 1.00 0.00
ATOM 7 C7 MOL 1 15.303 11.593 -0.240 1.00 0.00
ATOM 8 N8 MOL 1 12.525 15.630 -0.076 1.00 0.00
ATOM 9 C9 MOL 1 18.684 13.420 0.225 1.00 0.00
ATOM 10 C10 MOL 1 18.006 10.961 0.175 1.00 0.00
ATOM 11 C11 MOL 1 13.855 11.750 -0.564 1.00 0.00
ATOM 12 C12 MOL 1 15.713 10.329 -0.151 1.00 0.00
ATOM 13 C13 MOL 1 11.298 14.808 0.242 1.00 0.00
ATOM 14 C14 MOL 1 12.596 16.947 0.673 1.00 0.00
ATOM 15 C15 MOL 1 17.099 9.998 0.079 1.00 0.00
ATOM 16 C16 MOL 1 9.983 15.249 -0.446 1.00 0.00
ATOM 17 C17 MOL 1 11.626 18.047 0.168 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[CA Index Name]]
| colspan="2"| Acetamide,
2-(diethylamino)-N-(2,6-dimethylphenyl)- (9CI)
|-
| [[Commercial Names]]
|colspan="2"| Xylocaine (Astra)
Emla (Astra)

Instillagel (Cliniflex)

Laryng-o-jet (IMS)
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C14H22N2O
|-
| [[Molar mass]]
| colspan="2" |234.2 g/mol
|-
| [[CAS registry number|CAS number]]
| colspan="2" | 137-58-6
|-
| [[Appearance]]
| colspan="2" | colourless crystalline powder
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | g/cm
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | Soluble (15 g/L)
|-
| [[Melting point]]
| colspan="2" | 159-160 °C
|-
| [[Boiling point]]
| colspan="2" | 68.5 °C
|-
| [[Acid dissociation constant|Acidity]] (p''Ka'') 
| colspan="2" | 7.8
|-
| [[Flash Point]]
| colspan="2" | 166.0±24.6 °C
|-
| [[Enthalpy of Vaporization]]
| colspan="2" | 59.55±3.0 kJ/mol
|-
! {{chembox header}} colspan="3"| Structure
|-
| [[Crystal structure]] 
| colspan="2"|
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| colspan="2" |? [[Debye|D]]
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}

==Synthesis==
[[Image:synthesisoflinocaine.gif|200px{{PAGENAME}}]]

==IR spectrum of lidocaine==
[[Image:vlirlidocaine.gif]]

Above: The IR spectrum of lidocaine

==Mass spectrum of lidocaine==

[[Image:vlmasslidocaine.gif]]

Above: The mass spectrum of lidocaine

==What does Lignocaine do?==
• Stabilises neuronal membrane, prevents the initiation and transmission of nerve impulses

• Antiarrhythmic effect by increasing the electrical stimulation threshold of the ventricle during diastole

• Depresses slow spontaneous depolarisation (ie decreases automaticity)

• Increases period of effective refractory period

• Potent suppressor of abnormal cardiac activity

• Blocks activated & inactivated sodium channels

• Suppresses activity of depolarised, arrhythmogenic tissues while minimally interfering with the electrical activity of normal tissues: therefore is effective in suppressing arrhythmias associated with depolarisation [eg ischaemia, digitalis toxicity] but is relatively ineffective against arrhythmias occurring in normally polarised cells [eg AF & Af]

==Uses==

Lignocaine acts by provisionally blocking conduction over the nerve fibers.

When used in concentrations of 2-4% it produces a surface anaesthesia. Commonly injected at 1%, it has a rapid onset and a half life of about 90- 120 minutes.
It is commonly mixed with adrenaline in order to limit the bleeding, thus becoming a good face or scalp anaesthetic.

Lignocaine is also classified as a Class Ib antiarrhythmic agent.

==Contraindications==

Possible side effects:

• visual disturbances

• convulsions

• hypotension

• agitation

• deteriorating conscious level

• heart failure - negatively inotropic

• bradycardia - asystole

• left ventricular failure

An overdosage of lignocaine can result in convulsions, twitching and psychosis.

== Symptoms of allergic reaction to Lignocaine==

• Cough

• Difficulty swallowing or tongue swelling

• Dizziness or fainting; hives or swelling of eyelids, face or lips

• Itching or skin rash

• Stuffy nose

• Chest tightness

• Shortness of breath

• Troubled breathing or wheezing

== Signs of too much medicine being absorbed into the body ==
• Blurred or double vision

• Confusion

• Dizziness

• Light-headedness or drowsiness

• Feeling hot, cold, or numb

• Muscle twitching or trembling

• Nausea or vomiting

• Ringing or buzzing in the ears

• Shortness of breath or trouble breathing

• Unusual excitement

• Nervousness or restlessness

• Unusual tiredness or weakness

(The above side effects may occur if the medicine is used too often, applied to broken or inflamed skin, applied to very large areas, or kept on the skin too long.)

==References==
http://www.themediweb.net/pharmacy/Lignocaine.htm

http://www.elephantcare.org/Drugs/lidocain.htm

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=IR&Large=on

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=Mass&Large=on

http://www.perfusion.com.au/CCP/Pharmacology/lignocaine.htm

http://pharmacypractice.netfirms.com/kinetics/19/

http://www.healthtouch.com/bin/EContent_HT/drugShowLfts.asp?fname=usp0778.htm&title=Lignocaine&cid=HT

It:Lignocaine

2006-10-26T10:20:04Z

Chl105: /* Uses */

It:Lignocaine

2006-10-26T10:15:58Z

Chl105: /* Symptoms of allergic reaction to Lignocaine */

Lignocaine is a local anaesthetic drug especially used in dentistry. Discovered by N.Lofgren and B.Lundqvist in the 1940s, it has been very successful due to it's low neurotoxicity when compared with other local anaesthetics.
It has found uses also in the treatment of Arrhythmias eg: problems of the electrical system of the heart, causing it to pump less efficiently.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Lignocaine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Lignocaine.gif|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Fri Oct 20 12:51:30 GMT Standard Time 2006
ATOM 1 N1 MOL 1 16.171 14.259 -0.113 1.00 0.00
ATOM 2 C2 MOL 1 15.015 15.193 -0.048 1.00 0.00
ATOM 3 C3 MOL 1 16.350 12.740 -0.084 1.00 0.00
ATOM 4 C4 MOL 1 13.631 14.760 0.341 1.00 0.00
ATOM 5 O5 MOL 1 15.239 16.388 -0.269 1.00 0.00
ATOM 6 C6 MOL 1 17.620 12.369 0.089 1.00 0.00
ATOM 7 C7 MOL 1 15.303 11.593 -0.240 1.00 0.00
ATOM 8 N8 MOL 1 12.525 15.630 -0.076 1.00 0.00
ATOM 9 C9 MOL 1 18.684 13.420 0.225 1.00 0.00
ATOM 10 C10 MOL 1 18.006 10.961 0.175 1.00 0.00
ATOM 11 C11 MOL 1 13.855 11.750 -0.564 1.00 0.00
ATOM 12 C12 MOL 1 15.713 10.329 -0.151 1.00 0.00
ATOM 13 C13 MOL 1 11.298 14.808 0.242 1.00 0.00
ATOM 14 C14 MOL 1 12.596 16.947 0.673 1.00 0.00
ATOM 15 C15 MOL 1 17.099 9.998 0.079 1.00 0.00
ATOM 16 C16 MOL 1 9.983 15.249 -0.446 1.00 0.00
ATOM 17 C17 MOL 1 11.626 18.047 0.168 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[CA Index Name]]
| colspan="2"| Acetamide,
2-(diethylamino)-N-(2,6-dimethylphenyl)- (9CI)
|-
| [[Commercial Names]]
|colspan="2"| Xylocaine (Astra)
Emla (Astra)

Instillagel (Cliniflex)

Laryng-o-jet (IMS)
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C14H22N2O
|-
| [[Molar mass]]
| colspan="2" |234.2 g/mol
|-
| [[CAS registry number|CAS number]]
| colspan="2" | 137-58-6
|-
| [[Appearance]]
| colspan="2" | colourless crystalline powder
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | g/cm
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | Soluble (15 g/L)
|-
| [[Melting point]]
| colspan="2" | 159-160 °C
|-
| [[Boiling point]]
| colspan="2" | 68.5 °C
|-
| [[Acid dissociation constant|Acidity]] (p''Ka'') 
| colspan="2" | 7.8
|-
| [[Flash Point]]
| colspan="2" | 166.0±24.6 °C
|-
| [[Enthalpy of Vaporization]]
| colspan="2" | 59.55±3.0 kJ/mol
|-
! {{chembox header}} colspan="3"| Structure
|-
| [[Crystal structure]] 
| colspan="2"|
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| colspan="2" |? [[Debye|D]]
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}

==Synthesis==
[[Image:synthesisoflinocaine.gif|200px{{PAGENAME}}]]

==IR spectrum of lidocaine==
[[Image:vlirlidocaine.gif]]

Above: The IR spectrum of lidocaine

==Mass spectrum of lidocaine==

[[Image:vlmasslidocaine.gif]]

Above: The mass spectrum of lidocaine

==Uses==

Lignocaine acts by provisionally blocking conduction over the nerve fibers.

When used in concentrations of 2-4% it produces a surface anaesthesia. Commonly injected at 1%, it has a rapid onset and a half life of about 90- 120 minutes.
It is commonly mixed with adrenaline in order to limit the bleeding, thus becoming a good face or scalp anaesthetic.

Lignocaine is also classified as a Class Ib antiarrhythmic agent.

==Contraindications==

Possible side effects:

• visual disturbances

• convulsions

• hypotension

• agitation

• deteriorating conscious level

• heart failure - negatively inotropic

• bradycardia - asystole

• left ventricular failure

An overdosage of lignocaine can result in convulsions, twitching and psychosis.

== Symptoms of allergic reaction to Lignocaine==

• Cough

• Difficulty swallowing or tongue swelling

• Dizziness or fainting; hives or swelling of eyelids, face or lips

• Itching or skin rash

• Stuffy nose

• Chest tightness

• Shortness of breath

• Troubled breathing or wheezing

== Signs of too much medicine being absorbed into the body ==
• Blurred or double vision

• Confusion

• Dizziness

• Light-headedness or drowsiness

• Feeling hot, cold, or numb

• Muscle twitching or trembling

• Nausea or vomiting

• Ringing or buzzing in the ears

• Shortness of breath or trouble breathing

• Unusual excitement

• Nervousness or restlessness

• Unusual tiredness or weakness

(The above side effects may occur if the medicine is used too often, applied to broken or inflamed skin, applied to very large areas, or kept on the skin too long.)

==References==
http://www.themediweb.net/pharmacy/Lignocaine.htm

http://www.elephantcare.org/Drugs/lidocain.htm

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=IR&Large=on

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=Mass&Large=on

It:Lignocaine

2006-10-26T10:15:13Z

Chl105: /* Signs of too much medicine being absorbed into the body */

Lignocaine is a local anaesthetic drug especially used in dentistry. Discovered by N.Lofgren and B.Lundqvist in the 1940s, it has been very successful due to it's low neurotoxicity when compared with other local anaesthetics.
It has found uses also in the treatment of Arrhythmias eg: problems of the electrical system of the heart, causing it to pump less efficiently.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Lignocaine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Lignocaine.gif|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Fri Oct 20 12:51:30 GMT Standard Time 2006
ATOM 1 N1 MOL 1 16.171 14.259 -0.113 1.00 0.00
ATOM 2 C2 MOL 1 15.015 15.193 -0.048 1.00 0.00
ATOM 3 C3 MOL 1 16.350 12.740 -0.084 1.00 0.00
ATOM 4 C4 MOL 1 13.631 14.760 0.341 1.00 0.00
ATOM 5 O5 MOL 1 15.239 16.388 -0.269 1.00 0.00
ATOM 6 C6 MOL 1 17.620 12.369 0.089 1.00 0.00
ATOM 7 C7 MOL 1 15.303 11.593 -0.240 1.00 0.00
ATOM 8 N8 MOL 1 12.525 15.630 -0.076 1.00 0.00
ATOM 9 C9 MOL 1 18.684 13.420 0.225 1.00 0.00
ATOM 10 C10 MOL 1 18.006 10.961 0.175 1.00 0.00
ATOM 11 C11 MOL 1 13.855 11.750 -0.564 1.00 0.00
ATOM 12 C12 MOL 1 15.713 10.329 -0.151 1.00 0.00
ATOM 13 C13 MOL 1 11.298 14.808 0.242 1.00 0.00
ATOM 14 C14 MOL 1 12.596 16.947 0.673 1.00 0.00
ATOM 15 C15 MOL 1 17.099 9.998 0.079 1.00 0.00
ATOM 16 C16 MOL 1 9.983 15.249 -0.446 1.00 0.00
ATOM 17 C17 MOL 1 11.626 18.047 0.168 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[CA Index Name]]
| colspan="2"| Acetamide,
2-(diethylamino)-N-(2,6-dimethylphenyl)- (9CI)
|-
| [[Commercial Names]]
|colspan="2"| Xylocaine (Astra)
Emla (Astra)

Instillagel (Cliniflex)

Laryng-o-jet (IMS)
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C14H22N2O
|-
| [[Molar mass]]
| colspan="2" |234.2 g/mol
|-
| [[CAS registry number|CAS number]]
| colspan="2" | 137-58-6
|-
| [[Appearance]]
| colspan="2" | colourless crystalline powder
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | g/cm
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | Soluble (15 g/L)
|-
| [[Melting point]]
| colspan="2" | 159-160 °C
|-
| [[Boiling point]]
| colspan="2" | 68.5 °C
|-
| [[Acid dissociation constant|Acidity]] (p''Ka'') 
| colspan="2" | 7.8
|-
| [[Flash Point]]
| colspan="2" | 166.0±24.6 °C
|-
| [[Enthalpy of Vaporization]]
| colspan="2" | 59.55±3.0 kJ/mol
|-
! {{chembox header}} colspan="3"| Structure
|-
| [[Crystal structure]] 
| colspan="2"|
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| colspan="2" |? [[Debye|D]]
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}

==Synthesis==
[[Image:synthesisoflinocaine.gif|200px{{PAGENAME}}]]

==IR spectrum of lidocaine==
[[Image:vlirlidocaine.gif]]

Above: The IR spectrum of lidocaine

==Mass spectrum of lidocaine==

[[Image:vlmasslidocaine.gif]]

Above: The mass spectrum of lidocaine

==Uses==

Lignocaine acts by provisionally blocking conduction over the nerve fibers.

When used in concentrations of 2-4% it produces a surface anaesthesia. Commonly injected at 1%, it has a rapid onset and a half life of about 90- 120 minutes.
It is commonly mixed with adrenaline in order to limit the bleeding, thus becoming a good face or scalp anaesthetic.

Lignocaine is also classified as a Class Ib antiarrhythmic agent.

==Contraindications==

Possible side effects:

• visual disturbances

• convulsions

• hypotension

• agitation

• deteriorating conscious level

• heart failure - negatively inotropic

• bradycardia - asystole

• left ventricular failure

An overdosage of lignocaine can result in convulsions, twitching and psychosis.

== Symptoms of allergic reaction to Lignocaine==

• Cough
• Difficulty swallowing or tongue swelling
• Dizziness or fainting; hives or swelling of eyelids, face or lips
• Itching or skin rash
• Stuffy nose
• Chest tightness
• Shortness of breath
• Troubled breathing or wheezing

== Signs of too much medicine being absorbed into the body ==
• Blurred or double vision

• Confusion

• Dizziness

• Light-headedness or drowsiness

• Feeling hot, cold, or numb

• Muscle twitching or trembling

• Nausea or vomiting

• Ringing or buzzing in the ears

• Shortness of breath or trouble breathing

• Unusual excitement

• Nervousness or restlessness

• Unusual tiredness or weakness

(The above side effects may occur if the medicine is used too often, applied to broken or inflamed skin, applied to very large areas, or kept on the skin too long.)

==References==
http://www.themediweb.net/pharmacy/Lignocaine.htm

http://www.elephantcare.org/Drugs/lidocain.htm

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=IR&Large=on

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=Mass&Large=on

It:Lignocaine

2006-10-26T10:14:31Z

Chl105: /* Contraindications */

Lignocaine is a local anaesthetic drug especially used in dentistry. Discovered by N.Lofgren and B.Lundqvist in the 1940s, it has been very successful due to it's low neurotoxicity when compared with other local anaesthetics.
It has found uses also in the treatment of Arrhythmias eg: problems of the electrical system of the heart, causing it to pump less efficiently.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Lignocaine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Lignocaine.gif|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Fri Oct 20 12:51:30 GMT Standard Time 2006
ATOM 1 N1 MOL 1 16.171 14.259 -0.113 1.00 0.00
ATOM 2 C2 MOL 1 15.015 15.193 -0.048 1.00 0.00
ATOM 3 C3 MOL 1 16.350 12.740 -0.084 1.00 0.00
ATOM 4 C4 MOL 1 13.631 14.760 0.341 1.00 0.00
ATOM 5 O5 MOL 1 15.239 16.388 -0.269 1.00 0.00
ATOM 6 C6 MOL 1 17.620 12.369 0.089 1.00 0.00
ATOM 7 C7 MOL 1 15.303 11.593 -0.240 1.00 0.00
ATOM 8 N8 MOL 1 12.525 15.630 -0.076 1.00 0.00
ATOM 9 C9 MOL 1 18.684 13.420 0.225 1.00 0.00
ATOM 10 C10 MOL 1 18.006 10.961 0.175 1.00 0.00
ATOM 11 C11 MOL 1 13.855 11.750 -0.564 1.00 0.00
ATOM 12 C12 MOL 1 15.713 10.329 -0.151 1.00 0.00
ATOM 13 C13 MOL 1 11.298 14.808 0.242 1.00 0.00
ATOM 14 C14 MOL 1 12.596 16.947 0.673 1.00 0.00
ATOM 15 C15 MOL 1 17.099 9.998 0.079 1.00 0.00
ATOM 16 C16 MOL 1 9.983 15.249 -0.446 1.00 0.00
ATOM 17 C17 MOL 1 11.626 18.047 0.168 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[CA Index Name]]
| colspan="2"| Acetamide,
2-(diethylamino)-N-(2,6-dimethylphenyl)- (9CI)
|-
| [[Commercial Names]]
|colspan="2"| Xylocaine (Astra)
Emla (Astra)

Instillagel (Cliniflex)

Laryng-o-jet (IMS)
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C14H22N2O
|-
| [[Molar mass]]
| colspan="2" |234.2 g/mol
|-
| [[CAS registry number|CAS number]]
| colspan="2" | 137-58-6
|-
| [[Appearance]]
| colspan="2" | colourless crystalline powder
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | g/cm
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | Soluble (15 g/L)
|-
| [[Melting point]]
| colspan="2" | 159-160 °C
|-
| [[Boiling point]]
| colspan="2" | 68.5 °C
|-
| [[Acid dissociation constant|Acidity]] (p''Ka'') 
| colspan="2" | 7.8
|-
| [[Flash Point]]
| colspan="2" | 166.0±24.6 °C
|-
| [[Enthalpy of Vaporization]]
| colspan="2" | 59.55±3.0 kJ/mol
|-
! {{chembox header}} colspan="3"| Structure
|-
| [[Crystal structure]] 
| colspan="2"|
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| colspan="2" |? [[Debye|D]]
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}

==Synthesis==
[[Image:synthesisoflinocaine.gif|200px{{PAGENAME}}]]

==IR spectrum of lidocaine==
[[Image:vlirlidocaine.gif]]

Above: The IR spectrum of lidocaine

==Mass spectrum of lidocaine==

[[Image:vlmasslidocaine.gif]]

Above: The mass spectrum of lidocaine

==Uses==

Lignocaine acts by provisionally blocking conduction over the nerve fibers.

When used in concentrations of 2-4% it produces a surface anaesthesia. Commonly injected at 1%, it has a rapid onset and a half life of about 90- 120 minutes.
It is commonly mixed with adrenaline in order to limit the bleeding, thus becoming a good face or scalp anaesthetic.

Lignocaine is also classified as a Class Ib antiarrhythmic agent.

==Contraindications==

Possible side effects:

• visual disturbances

• convulsions

• hypotension

• agitation

• deteriorating conscious level

• heart failure - negatively inotropic

• bradycardia - asystole

• left ventricular failure

An overdosage of lignocaine can result in convulsions, twitching and psychosis.

== Symptoms of allergic reaction to Lignocaine==

• Cough
• Difficulty swallowing or tongue swelling
• Dizziness or fainting; hives or swelling of eyelids, face or lips
• Itching or skin rash
• Stuffy nose
• Chest tightness
• Shortness of breath
• Troubled breathing or wheezing

== Signs of too much medicine being absorbed into the body ==
• Blurred or double vision
• Confusion
• Dizziness
• Light-headedness or drowsiness
• Feeling hot, cold, or numb
• Muscle twitching or trembling
• Nausea or vomiting
• Ringing or buzzing in the ears
• Shortness of breath or trouble breathing
• Unusual excitement
• Nervousness or restlessness
• Unusual tiredness or weakness
(The above side effects may occur if the medicine is used too often, applied to broken or inflamed skin, applied to very large areas, or kept on the skin too long.)

==References==
http://www.themediweb.net/pharmacy/Lignocaine.htm

http://www.elephantcare.org/Drugs/lidocain.htm

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=IR&Large=on

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=Mass&Large=on

It:Schwartz

2006-10-26T10:07:35Z

Chl105: /* Preparation of Schwartz's Reagent */

It:Schwartz

2006-10-26T10:03:25Z

Chl105: /* Background */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Schwartz Reagent
|-
! {{chembox header}} colspan="3" |Structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 120; wireframe on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
title1
title2
23 32 0 0 0 0 0 0 0 0999 V2000
0.4968 2.4426 -1.8773 Zr 0 0 0 0 0 0 0 0 0 1
2.1386 2.5155 -0.0069 C 0 0 1 0 0 0 0 0 0 2
0.8893 2.8016 0.5785 C 0 0 1 0 0 0 0 0 0 3
0.4392 4.0345 0.0856 C 0 0 1 0 0 0 0 0 0 4
1.4009 4.5239 -0.7980 C 0 0 1 0 0 0 0 0 0 5
2.4581 3.6019 -0.8408 C 0 0 1 0 0 0 0 0 0 6
1.3075 2.1266 -4.2373 C 0 0 1 0 0 0 0 0 0 7
2.3637 1.7885 -3.4062 C 0 0 2 0 0 0 0 0 0 8
2.0155 0.6537 -2.7061 C 0 0 2 0 0 0 0 0 0 9
0.7446 0.2636 -3.1093 C 0 0 2 0 0 0 0 0 0 10
0.3198 1.1821 -4.0620 C 0 0 2 0 0 0 0 0 0 11
-1.3981 1.1750 -0.8823 Cl 0 0 0 0 0 0 0 0 0 12
-0.4999 3.6324 -2.6415 H 0 0 0 0 0 0 0 0 0 13
2.7373 1.6100 0.1615 H 0 0 0 0 0 0 0 0 0 14
0.3782 2.1727 1.3172 H 0 0 0 0 0 0 0 0 0 15
-0.5084 4.5050 0.3479 H 0 0 0 0 0 0 0 0 0 16
1.3481 5.4625 -1.3655 H 0 0 0 0 0 0 0 0 0 17
3.3834 3.6763 -1.4290 H 0 0 0 0 0 0 0 0 0 18
1.2659 3.0120 -4.9152 H 0 0 0 0 0 0 0 0 0 19
3.3152 2.3417 -3.3261 H 0 0 0 0 0 0 0 0 0 20
2.6389 0.1300 -1.9509 H 0 0 0 0 0 0 0 0 0 21
0.1603 -0.6100 -2.7365 H 0 0 0 0 0 0 0 0 0 22
-0.6338 1.1620 -4.5991 H 0 0 0 0 0 0 0 0 0 23
1 2 1 0 0 0
2 3 4 0 0 0
3 1 1 0 0 0
4 1 1 0 0 0
5 1 1 0 0 0
6 1 1 0 0 0
7 1 1 0 0 0
8 1 1 0 0 0
9 1 1 0 0 0
10 1 1 0 0 0
11 1 1 0 0 0
12 1 1 0 0 0
13 1 1 0 0 0
14 2 1 0 0 0
15 3 1 0 0 0
16 4 1 0 0 0
17 5 1 0 0 0
18 6 1 0 0 0
19 7 1 0 0 0
20 8 1 0 0 0
21 9 1 0 0 0
22 10 1 0 0 0
23 11 1 0 0 0
2 6 4 0 0 0
3 4 4 0 0 0
4 5 4 0 0 0
5 6 4 0 0 0
7 8 4 0 0 0
7 11 4 0 0 0
8 9 4 0 0 0
9 10 4 0 0 0
10 11 4 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Off-white solid
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
| colspan="1" |[http://en.wikipedia.org/wiki/EC-No EC number]
| colspan="2" |253-479-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase]
| colspan="2" |g/cm3, solid
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [http://en.wikipedia.org/wiki/Water_%28molecule%29 water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Standard_enthalpy_change_of_formation Δ''H''''f''<s>o</s>solid]
| colspan="2" |-314.8 ± 3.9 kJ/mol
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water
liberates flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

The first organochlorobis(cyclopentadienyl)zirconium(W)complex was prepared by Wailes, Weigold and Bell 25 years ago. Ever since, these organometallics have become important members in the field of synthetic strategy and tactics.because of the formations of carbon-carbon and carbon-heteroatom bond.Although the polarization of the carbon-zirconium bond is similar to Grignard reagents, the bulky cyclopentadienyl groups prevent the attack of many organic electrophiles due to steric crowding around the Zr atom. The resulting functional group tolerance of organozirconocenes is useful for the preparation of the organometallic species, but this low reactivity must be overcome for subsequent selective carbon-carbon bond formations. Therefore, much of the development of organozirconocenes focuses on indirect reaction pathways involving transmetalation or activation by ligand.

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in Organic Synthesis==

===Triethylborane-induced radical reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and regiocontrolled synthesis of branched trisubstituted conjugated dienes by palladium(0)-catalyzed cross-coupling reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:

[[Image:Hydrozirconation.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]

These are the thermodynamic products of the reaction and arise primarily from steric interaction with the Cp ring.

=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

==Hydrozirconation of 1-alkynes==

This reaction is important in chemistry because the product that is synthesised from the acetylene (e.g. 1-alkynes) is regioselectively controlled. This gives rise to greater yields of products with the selectively required stereochemistry. So a range of diverse compounds can be derived from mono-substitued acetylenes, via this reaction.

[[Image:Vlzirconation.gif]]

The above reaction scheme [[1]] requires 4 steps. The second and third steps require a very cool temperature of -78oC, to prevent unwanted side reactions which would produce unwanted products.

==References==

1. http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1990/112/i20/f-pdf/f_ja00176a079.pdf?sessid=6006l3

It:Schwartz

2006-10-23T15:28:14Z

Chl105: /* Selectivity: */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in Organic Synthesis==

===Triethylborane-induced radical reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and regiocontrolled synthesis of branched trisubstituted conjugated dienes by palladium(0)-catalyzed cross-coupling reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:

[[Image:Hydrozirconation.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]

These are the thermodynamic products of the reaction and arise primarily from steric interaction with the Cp ring.

=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

It:Schwartz

2006-10-23T15:27:16Z

Chl105: /* Triethylborane-Induced Radical Reaction with Schwartz Reagent: */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in Organic Synthesis==

===Triethylborane-induced radical reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and regiocontrolled synthesis of branched trisubstituted conjugated dienes by palladium(0)-catalyzed cross-coupling reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:

[[Image:Hydrozirconation.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

It:Schwartz

2006-10-23T15:26:55Z

Chl105: /* Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction: */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in Organic Synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and regiocontrolled synthesis of branched trisubstituted conjugated dienes by palladium(0)-catalyzed cross-coupling reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:

[[Image:Hydrozirconation.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

It:Schwartz

2006-10-23T15:26:13Z

Chl105: /* Examples in organic synthesis */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in Organic Synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:

[[Image:Hydrozirconation.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

It:Schwartz

2006-10-23T15:25:57Z

Chl105: /* Properties of Schwartz Reagent */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:

[[Image:Hydrozirconation.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

It:Schwartz

2006-10-23T15:25:40Z

Chl105: /* Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl) */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

It:Schwartz

2006-10-23T15:23:38Z

Chl105: /* Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl) */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:

[[Image:Hydrozirconation.gif]]

It:Schwartz

2006-10-23T15:21:29Z

Chl105: /* Electrophilic cleavage of alkyl zirconium bond: */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp2Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:
[[Image:Hydrozirconation.gif]]

File:Hydrozirconation.gif

2006-10-23T15:21:16Z

Chl105:

It:Schwartz

2006-10-23T15:19:27Z

Chl105: /* Mechanism of the Hydrozirconation reaction */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

==Mechanism of the Hydrozirconation reaction (reaction of an alkenes with Cp2ZrHCl)

It:Schwartz

2006-10-23T15:18:28Z

Chl105: /* Properties of Schwartz Reagent */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

==Mechanism of the Hydrozirconation reaction==

It:Schwartz

2006-10-23T15:12:48Z

Chl105: /* Electrophilic cleavage of alkyl zirconium bond */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

It:Schwartz

2006-10-23T15:12:37Z

Chl105: /* Electrophilic cleavage of alkyl zirconium bond */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

It:Schwartz

2006-10-23T15:12:25Z

Chl105: /* Electrophilic cleavage of alkyl zirconium bond is very facile and forms product in high yield: */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond ===
This reaction is very facile and forms product in high yield:===

[[Image:Picture3.png]]

It:Schwartz

2006-10-23T15:11:42Z

Chl105: /* Selectivity */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]
=== Electrophilic cleavage of alkyl zirconium bond is very facile and forms product in high yield:===

[[Image:Picture3.png]]

File:Picture3.png

2006-10-23T15:11:22Z

Chl105:

It:Schwartz

2006-10-23T15:08:02Z

Chl105: /* Examples in organic synthesis */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

===Triethylborane-Induced Radical Reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]

It:Schwartz

2006-10-23T15:07:42Z

Chl105: /* Properties of Schwartz Reagent */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

Triethylborane-Induced Radical Reaction with Schwartz Reagent:

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==

===Selectivity===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]

It:Schwartz

2006-10-23T15:06:34Z

Chl105: /* Examples in organic synthesis */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of the Schwartz Reagent
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |
*Bis(cyclopentadienyl)zirconium(IV)
chloride hydride
*Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H11ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase (matter)|phase]
| colspan="2" | g/cm
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [ http://en.wikipedia.org/wiki/Water_%28molecule%29 Water_(molecule)|water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water liberates
flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp2Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

To a dry, flask equipped with a magnetic stirring bar zirconocene dichloride is added under argon followed by dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C is added dropwise, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The resulting suspension is stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in organic synthesis==

Triethylborane-Induced Radical Reaction with Schwartz Reagent:

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

Stereo- and Regiocontrolled Synthesis of Branched Trisubstituted Conjugated Dienes by Palladium(0)-Catalyzed Cross-Coupling Reaction:

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Properties of Schwartz Reagent==
Selectivity:
Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end

[[Image:Picture2.png]]

File:Picture2.png

2006-10-23T15:05:14Z

Chl105: