ChemWiki - User contributions [en]

It07:Dopamine

2007-12-06T21:09:43Z

Hkc06: /* References */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Dopamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:dopamine.png|200px|Dopamine]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 1,2-Benzenediol, 4-(2-aminoethyl)-

|-
| Other names
| Pyrocatechol, 4-(2-aminoethyl)- (8CI); .alpha.-(3,4-Dihydroxyphenyl)-.beta.-aminoethane; 2-(3,4-Dihydroxyphenyl)ethylamine; 3,4-Dihydroxyphenethylamine; 3,4-Dihydroxyphenylethylamine; 3-Hydroxytyramine; 4-(2-Aminoethyl)-1,2-benzenediol; 4-(2-Aminoethyl)catechol; 4-(2-Aminoethyl)pyrocatechol; DA; Dopamin; Dopamine; Dophamine; Hydroxytyramin; NSC 173182; Oxytyramine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>8</sub>H<sub>11</sub>NO<sub>2</sub>
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| C1=CC(=C(C=C1CCN)O)O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 153.178
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 51-61-6
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| 60.0 g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 128°C 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 227°C
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[http://redpoll.pharmacy.ualberta.ca/drugbank/drugBank/drugFile/msds/APRD00085.pdf L-Dopamine]] 
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: 36/37/38 <br /> [[List of S-phrases|S]]: 26-36
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

==Dopamine==
--[[User:Hkc06|Hkc06]] 15:58, 5 December 2007 (UTC)

Dopamine, a phenethylamine, is also known as 1,2-Benzenediol, 4-(2-aminoethyl)-. It is a hormone and a neurotransmitter in the brain. It gives the feeling of "being doped" and is linked to drug abuse and addiction. Dopamine plays a big role in addiction as it affects the part of the brain that controls movement, emotional response and also the feelings of pleasure and pain.

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HEADER NONAME 05-Dec-07 NONE 1
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AUTHOR WWW daemon apache NONE 3
REVDAT 1 05-Dec-07 0 NONE 4
ATOM 1 C 0 0.153 -1.456 -0.249 0.00 0.00 C+0
ATOM 2 C 0 -1.199 -1.594 0.008 0.00 0.00 C+0
ATOM 3 C 0 -2.006 -0.471 0.093 0.00 0.00 C+0
ATOM 4 C 0 -1.453 0.794 -0.082 0.00 0.00 C+0
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ATOM 10 O 0 -2.242 1.899 0.000 0.00 0.00 O+0
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ATOM 12 H 0 0.781 -2.332 -0.311 0.00 0.00 H+0
ATOM 13 H 0 -1.625 -2.577 0.143 0.00 0.00 H+0
ATOM 14 H 0 0.333 1.906 -0.475 0.00 0.00 H+0
ATOM 15 H 0 2.531 -0.933 -1.242 0.00 0.00 H+0
ATOM 16 H 0 2.344 0.836 -1.308 0.00 0.00 H+0
ATOM 17 H 0 2.580 0.954 1.157 0.00 0.00 H+0
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CONECT 7 6 8 15 16 NONE 33
CONECT 8 7 9 17 18 NONE 34
CONECT 9 8 19 20 0 NONE 35
CONECT 10 4 21 0 0 NONE 36
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==Reaction==
Below is one of the many reaction schemes for the formation of dopamine.

[[Image:dopamine_rxn.png|500px|Dopamine]]

This reaction produces a 100% yield.

==Uses==

Dopamine is as a catecholamine. A catecholamine is the group of molecules that are neurotransmitters as well as hormones. It is also a monoamine. Adrenalin is a very similar molecule to dopamine. Dopamine is formed when a carboxyl group is removed from dopa, (3,4-dihydroxy-L-phenylalanine).

Dopamine can be used as a medicine, increasing heart rates and blood pressure. However, for some diseases, dopa has to be used instead of dopamine because dopamine is unable to cross the blood brain barrier, where as dopa can.

Parkinson’s disease can be treated using dopa. Parkinson’s disease is caused by low levels of dopamine in the brain. To treat this, dopa is taken by mouth and it crosses the blood brain barrier. When it goes into the brain, it converts into dopamine. This increases the levels of dopamine in the brain which then improves the nerve conduction. The use of dopa was approved in 1970 in the US for the treatment of Parkinson’s disease.

==History==

Dopamine was discovered in 1952 in Sweden by Arvid Carlsson and Nils-Ake Hillarp. The name of dopamine arose from the fact that dopamine was a monoamine and dopamine came from L-DOPA. In 2000, Arvid Carlsson was awarded the Nobel Prize in Physiology or Medicine for discovering that dopamine is a neurotransmitter as well.

==Functions==

In the brain, dopamine controls movement, behaviour, sleep, moods and learning. It functions as a neurotransmitter i.e. a messenger and activates the five types of dopamine receptors; D1, D2, D3, D4, D5. It’s also a hormone, whose main function is to stall the release of prolactin from the pituitary.

Dopamine is released by the brain when the person experiences pleasure for example, food, drugs, sex etc. With drugs, the dopamine levels increase which can lead to addiction. Cocaine increases the lifetime of dopamine, increasing the levels of dopamine up to 150%. Amphetamines also increase the concentration of dopamine.

Dopamine is also linked to behaviour disorders. By blocking the dopamine receptors, desire decreases but an increase in drug taking is seen – this is because since the feeling of desire is blocked, there is a psychological effect seen where the person wants to “feel something.”
Low dopamine levels are linked to ADHD – attention-deficit hyperactivity disorder. Very high levels of dopamine are linked to diseases such as psychosis and schizophrenia.

==References==
<references/>
# SciFinder
# http://redpoll.pharmacy.ualberta.ca/drugbank/drugBank/drugFile/msds/APRD00085.pdf
# http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00085.txt
# http://www.mol-net.com/tmp/11511.pdb
# http://www.medterms.com/script/main/art.asp?articlekey=14345
# http://en.wikipedia.org/wiki/Dopamine

It07:Dopamine

2007-12-06T20:57:12Z

Hkc06: /* Functions */

It07:Dopamine

2007-12-06T15:27:49Z

Hkc06: /* Functions */

2007-12-05T17:50:23Z

Hkc06: /* Dopamine */

==Dopamine==
--[[User:Hkc06|Hkc06]] 15:58, 5 December 2007 (UTC)

Dopamine, a phenethylamine, is also known as 1,2-Benzenediol, 4-(2-aminoethyl)-. It is a hormone and a neurotransmitter in the brain. It gives the feeling of "being doped" and is linked to drug abuse and addiction. Dopamine plays a big role in addiction as it affects the part of the brain that controls movement, emotional response and also the feelings of pleasure and pain.

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title1
title2
HEADER NONAME 05-Dec-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 05-Dec-07 0 NONE 4
ATOM 1 C 0 0.153 -1.456 -0.249 0.00 0.00 C+0
ATOM 2 C 0 -1.199 -1.594 0.008 0.00 0.00 C+0
ATOM 3 C 0 -2.006 -0.471 0.093 0.00 0.00 C+0
ATOM 4 C 0 -1.453 0.794 -0.082 0.00 0.00 C+0
ATOM 5 C 0 -0.098 0.925 -0.339 0.00 0.00 C+0
ATOM 6 C 0 0.702 -0.199 -0.423 0.00 0.00 C+0
ATOM 7 C 0 2.175 -0.055 -0.703 0.00 0.00 C+0
ATOM 8 C 0 2.935 0.075 0.619 0.00 0.00 C+0
ATOM 9 N 0 4.372 0.216 0.345 0.00 0.00 N+0
ATOM 10 O 0 -2.242 1.899 0.000 0.00 0.00 O+0
ATOM 11 O 0 -3.335 -0.605 0.345 0.00 0.00 O+0
ATOM 12 H 0 0.781 -2.332 -0.311 0.00 0.00 H+0
ATOM 13 H 0 -1.625 -2.577 0.143 0.00 0.00 H+0
ATOM 14 H 0 0.333 1.906 -0.475 0.00 0.00 H+0
ATOM 15 H 0 2.531 -0.933 -1.242 0.00 0.00 H+0
ATOM 16 H 0 2.344 0.836 -1.308 0.00 0.00 H+0
ATOM 17 H 0 2.580 0.954 1.157 0.00 0.00 H+0
ATOM 18 H 0 2.766 -0.815 1.224 0.00 0.00 H+0
ATOM 19 H 0 4.492 1.101 -0.124 0.00 0.00 H+0
ATOM 20 H 0 4.831 0.298 1.240 0.00 0.00 H+0
ATOM 21 H 0 -2.236 2.179 0.926 0.00 0.00 H+0
ATOM 22 H 0 -3.441 -0.581 1.306 0.00 0.00 H+0
CONECT 1 6 2 12 0 NONE 27
CONECT 2 1 3 13 0 NONE 28
CONECT 3 2 4 11 0 NONE 29
CONECT 4 3 5 10 0 NONE 30
CONECT 5 4 6 14 0 NONE 31
CONECT 6 5 1 7 0 NONE 32
CONECT 7 6 8 15 16 NONE 33
CONECT 8 7 9 17 18 NONE 34
CONECT 9 8 19 20 0 NONE 35
CONECT 10 4 21 0 0 NONE 36
CONECT 11 3 22 0 0 NONE 37
END
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==Reaction==
Below is one of the many reaction schemes for the formation of dopamine.

[[Image:dopamine_rxn.png|Dopamine]]

This reaction produces a 100% yield.

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Dopamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:dopamine.png|200px|Dopamine]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 1,2-Benzenediol, 4-(2-aminoethyl)-

|-
| Other names
| Pyrocatechol, 4-(2-aminoethyl)- (8CI); .alpha.-(3,4-Dihydroxyphenyl)-.beta.-aminoethane; 2-(3,4-Dihydroxyphenyl)ethylamine; 3,4-Dihydroxyphenethylamine; 3,4-Dihydroxyphenylethylamine; 3-Hydroxytyramine; 4-(2-Aminoethyl)-1,2-benzenediol; 4-(2-Aminoethyl)catechol; 4-(2-Aminoethyl)pyrocatechol; DA; Dopamin; Dopamine; Dophamine; Hydroxytyramin; NSC 173182; Oxytyramine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>8</sub>H<sub>11</sub>NO<sub>2</sub>
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| C1=CC(=C(C=C1CCN)O)O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 153.178
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 51-61-6
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| 60.0 g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 128°C 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 227°C
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[http://redpoll.pharmacy.ualberta.ca/drugbank/drugBank/drugFile/msds/APRD00085.pdf L-Dopamine]] 
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: 36/37/38 <br /> [[List of S-phrases|S]]: 26-36
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

File:Dopamine.PDB

2007-12-05T17:45:21Z

Hkc06:

It07:Dopamine

2007-12-05T17:25:27Z

Hkc06: /* Reaction */

File:Dopamine rxn.png

2007-12-05T17:23:16Z

Hkc06:

It07:Dopamine

2007-12-05T17:21:44Z

Hkc06: /* Dopamine */

Mass spectrometry

2007-12-05T16:58:15Z

Hkc06: /* Mass Spectrum of Angelic Acid */

==Mass Spectrum of Angelic Acid==
--[[User:Hkc06|Hkc06]] 16:54, 30 November 2007 (UTC)
[[Image:Ms_angelic_acid.gif]]

==Mass Spectrum of Dopamine==
--[[User:Hkc06|Hkc06]] 16:58, 5 December 2007 (UTC)
[[Image:Ms_dopamine.jpg]]

Mass Specrometry for the molecule Methoxsalen(molecular formula C<sub>12</sub>H<sub>8</sub>O<sub>4</sub>)

[[Image:mass_spec_methoxsalen_lmm06.png|700px|{{Methoxsalen}}]]

<sub>http://www.chemcalc.org/</sub>

File:Ms dopamine.jpg

2007-12-05T16:57:05Z

Hkc06:

Nuclear magnetic resonance spectroscopy

2007-12-05T16:54:37Z

Hkc06: /* <sup>13</sup>C NMR of Angelic Acid */

File:13C nmr dopamine.jpg

2007-12-05T16:52:56Z

Hkc06:

It07:Dopamine

2007-12-05T16:50:17Z

Hkc06: /* Dopamine */

2007-12-05T16:23:23Z

Hkc06:

It07:Dopamine

2007-12-05T16:15:19Z

Hkc06: /* Dopamine */

2007-12-05T15:15:29Z

Hkc06: /* '''Angelic Acid''' */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Angelic Acid 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:angelic_acid.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| (Z)-2-methylbut-2-enoic acid

|-
| Other names
| 2-Butenoic acid, 2-methyl-, (Z)-; Angelic acid (6CI,7CI); Crotonic acid, 2-methyl-, (Z)- (8CI); cis-.alpha.,.beta.-Dimethylacrylic acid; cis-2-Methyl-2-butenoic acid
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>5</sub>H<sub>8</sub>O<sub>2</sub>
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CC=C(C)C(=O)O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 100.116g/mol
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 565-63-9
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.96 g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
|  45°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 183 - 185°C
|-
| Refractive Index
| 1.4430
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[http://www.chemblink.com/products/80-59-1.htm (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Harmful, Irritating to eyes, Irritating to respiratory system,

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
== '''Angelic Acid''' ==

Angelic acid is an organic, carboxylic acid, found in various plants. Despite its name, it is not "angelic" at all since it is used as a defence substance for beetles.
It is also known as "(Z)-2-Methyl-2-butenoic acid."
[[Image:angelic_acid.jpg|thumb|left|200|The Structure of Angelic Acid]]

<jmol>
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Angelic acid is the (Z) isomer. The other isomer, (E), is called "Tiglic Acid," and is also a beetle defence system. [[Image:Tiglicacid.jpg|thumb|left|200|The Structure of Tiglic Acid]]

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Angelic acid and tiglic acid are a pair of cis-trans isomers. Angelic acid is the (Z) isomer where as tiglic acid is the (E) isomer. Angelic acid has a pungent odour and a biting acid taste. It can also crystallise, giving colourless prisms. Angelic acid used to be used therapeutically as a sedative.

== Formation of Angelic Acid ==

Angelic Acid is found to occur naturally and can be made from many different reactions. Its isomer, Tiglic acid, however, is not naturally occurring and has to be synthesized.

Below is the reaction scheme for the formation of angelic acid.

[[Image:ang_rxn.png|Reaction Scheme]]

The reactant in this reaction is known as Methyl (Z)-2-methyl-2-butenoate. It has chemical formula
C<sub>6</sub>H<sub>10</sub>O<sub>2</sub>.
Essentially, what is happening here is a hydrolysis reaction. The ester is broken down by water, forming a carboxylic acid (angelic acid) and an alcohol should also form.
The reaction is carried out under reflux and produces a ~90% yield.

The reaction scheme for the formation of tiglic acid is shown below:

[[Image:tig_rxn.png|Reaction Scheme]]

This reaction should produce a 100% yield.

== NMR Spectrum ==
The <sup>13</sup>C NMR spectrum of Angelic Acid

[[Image:13C_NMR_angelic_acid.jpg|center|200|C Spectrum]]

The Predicted <sup>1</sup>H NMR spectrum of Angelic Acid is shown below.

[[Image:angelicacidnmr.jpg|center|200|Predicted NMR spectrum of Angelic Acid]]

It07:Angelic Acid

2007-12-05T15:08:32Z

Hkc06: /* Formation of Angelic Acid */

File:Tig rxn.png

2007-12-05T15:04:26Z

Hkc06:

It07:Angelic Acid

2007-12-05T14:53:57Z

Hkc06: /* Formation of Angelic Acid */