ChemWiki - User contributions [en]

It:Theobromine

2006-12-15T11:22:40Z

Nc305: added synthesis

== Introduction ==
Theobromine is an alkyloid of the methylxanthine family. It is a common stimulant similar in structure to caffine. It is found in the cacoa plant, Theobroma Cacao, in bean form. It is abundant in between 1.5%-3% in cacao while caffine is between 0.2%-0.4% abundant. Counterintuitivly theobromine doesn't contain any bromine, the name of the compound comes from the name of the tree Theobroma Cacao.

Theobromine is also the key ingredient of all chocolate!!!

== Effects ==
Theobromine has the following effects:

-Weak adenosine receptor antagonist

-Phosphosdiesterase inhibitor

-Smooth muscle relaxant

-Diuretic.

== Uses ==
Theobromine is used in all chocolate; dark chocolate (or better quality chocolate) contains a higher proportion of theobromine than milk chocolate (or lower quality choclate). Production of chocolate is the primary use of theobromine, but not the only one.

Theobromine has been used to help those with high blood pressure as it dilates the blood vessels.

It has also been used as a diuretic as it increases urine production in the body. It is especially useful for those who have experianced heart failure, as heart failure can lead to biuld up of bodily fluids.

== Chemical Information==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data'''
|-
| Names
| align="center"|3,7-dimethylxanthine,
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione (IUPAC)
|-
| Chemical formula
| align="center"|C7H8N4O2
|-
| Molecular Mass
| align="center"|180.16
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Properties'''
|-
| Melting Point
| align="center"|618-623 K
|-
| Form
| align="center"|Solid
|-
| Colour
| align="center"|White
|-
| Flavour
| align="center"|Bitter
|-
| Solubility
| align="center"|H2O: slightly soluble
aqueous base: moderately soluble

ethanol: slightly soluble
|-
| Reference
| align="center"| http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4500
|-
|}

== Structure ==

[[Image:Theobromine 2d gif.jpg|thumb|left|200|2D structure of Theobromine]][[Image:Theobromine 3d gif.jpg|thumb|left|200|3D structure of Theobromine (ball and stick)]]

<jmol>
<jmolApplet>
<title>Theobromine</title><color>white</color>
<uploadedFileContents>Theobroming 3d mol.mol</uploadedFileContents>
</jmolApplet>
</jmol>

<jmol>
<jmolApplet>
<size>200</size>
<color>red</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>theobromine.mol
title 1
title 2
21 22 0 0 0 0 0 0 0 0999 V2000
-2.9570 0.5579 0.0190 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.9381 -0.8174 0.0043 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6994 -1.4147 -0.0177 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.4902 -0.7238 -0.0371 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.5756 0.6680 -0.0180 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.8591 1.3844 0.0146 C 0 0 0 0 0 0 0 0 0 0 0 0
0.8192 -1.1102 -0.0682 N 0 0 0 0 0 0 0 0 0 0 0 0
1.5488 0.0077 -0.0650 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7397 1.0782 -0.0328 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.0024 2.5989 0.0352 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.9994 -1.4328 0.0132 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.6001 -2.8850 -0.0126 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2217 2.4580 -0.0132 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.8607 1.0016 0.0361 H 0 0 0 0 0 0 0 0 0 0 0 0
2.6412 0.0740 -0.0829 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.5883 -3.3946 -0.0071 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.0515 -3.2359 -0.9163 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.0481 -3.2258 0.8932 H 0 0 0 0 0 0 0 0 0 0 0 0
0.3902 3.1943 0.0022 H 0 0 0 0 0 0 0 0 0 0 0 0
1.8411 2.6607 -0.9160 H 0 0 0 0 0 0 0 0 0 0 0 0
1.8455 2.6302 0.8932 H 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
6 1 1 0
1 14 1 0
2 3 1 0
2 11 2 0
3 4 1 0
3 12 1 0
4 5 2 0
4 7 1 0
5 6 1 0
9 5 1 0
6 10 2 0
7 8 2 0
8 9 1 0
8 15 1 0
9 13 1 0
12 16 1 0
12 17 1 0
12 18 1 0
13 19 1 0
13 20 1 0
13 21 1 0
M END</inlineContents>
</jmolApplet>
</jmol>

==Synthesis==

[[Image:Synthesis of Theobromine.jpg|Synthesis of Theobromine]]

Indian Journal of Heterocyclic Chemistry, 14(4), 301-306; 2005

== References ==

Pages that I used to research this tiopic:

http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T4500

http://chemistry.about.com/library/weekly/aa090301a.htm

http://www.3dchem.com/molecules.asp?ID=155

http://www.greatvistachemicals.com/proteins-sugars-nucleotides/theobromine.html

http://www.xocoatl.org/caffeine.htm

File:Synthesis of Theobromine.jpg

2006-12-15T11:20:10Z

Nc305:

It:DEET

2006-12-08T15:25:07Z

Nc305: added spectra

DEET is the active ingredient in all common insect repellents. Its name is an anacronym of N,N-Diethyl-meta-Toluamide 1, however this is not its systematic IUPAC name which is N,N-diethyl-3-methyl-benzamide 2. It is estimated that at least half the population of the US uses DEET every year. It is very important in stopping the spread of diseases such as West Nile virus, Eastern Equine Encephalitis, Rickets, Malaria and Dengue fever which are carried by mosquitoes.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of DEET
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:DEET.gif|Structure of DEET]]
|-
! {{chembox header}} colspan="3" |3D structure 3
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 150; cpk off;frame 100; move 100 -10 10 10 0 0 0 10 31; delay 1;</script>
<inlineContents>REMARK This PDB file is created by CS Chem3D
REMARK
COMPND DEET.pdb
HETATM 1 C UNK 0 3.619 0.570 -0.492 C
HETATM 2 C UNK 0 5.121 0.560 -0.282 C
HETATM 3 C UNK 0 5.822 1.791 -0.207 C
HETATM 4 C UNK 0 5.807 -0.677 -0.160 C
HETATM 5 C UNK 0 7.228 1.792 -0.005 C
HETATM 6 C UNK 0 7.212 -0.675 0.040 C
HETATM 7 C UNK 0 7.974 3.087 0.080 C
HETATM 8 C UNK 0 7.918 0.556 0.118 C
HETATM 9 C UNK 0 3.574 -1.824 -1.140 C
HETATM 10 C UNK 0 1.819 -0.961 0.280 C
HETATM 11 C UNK 0 2.669 -3.025 -0.904 C
HETATM 12 C UNK 0 1.987 -0.646 1.761 C
HETATM 13 H UNK 0 5.278 2.742 -0.303 H
HETATM 14 H UNK 0 5.255 -1.627 -0.220 H
HETATM 15 H UNK 0 9.007 0.552 0.275 H
HETATM 16 H UNK 0 7.755 -1.627 0.137 H
HETATM 17 H UNK 0 4.600 -2.053 -0.774 H
HETATM 18 H UNK 0 3.611 -1.595 -2.229 H
HETATM 19 H UNK 0 1.565 -2.038 0.157 H
HETATM 20 H UNK 0 1.000 -0.336 -0.141 H
HETATM 21 H UNK 0 1.037 -0.849 2.302 H
HETATM 22 H UNK 0 2.257 0.426 1.895 H
HETATM 23 H UNK 0 2.793 -1.279 2.196 H
HETATM 24 H UNK 0 3.076 -3.917 -1.430 H
HETATM 25 H UNK 0 1.647 -2.813 -1.290 H
HETATM 26 H UNK 0 2.606 -3.245 0.186 H
HETATM 27 H UNK 0 8.594 3.107 1.004 H
HETATM 28 H UNK 0 7.256 3.937 0.109 H
HETATM 29 H UNK 0 8.638 3.203 -0.805 H
HETATM 30 N UNK 0 3.054 -0.676 -0.424 N
HETATM 31 O UNK 0 2.981 1.575 -0.697 O
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3"| Properties
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| Molecular Formula
| C12H17NO
|-
| Molecular Weight
|191.27
|-
| Boiling Point 4
|286 oC
|-
| Density 5
| 0.996 g/cm3
|-
| Refractive index 6
| 1.5205
|-
| CAS registry number
| 134-62-3
|-
| Appearance
| colourless liquid
|-
|}

==History and information==

Traditionally methods such as smoke and various natural oils were employed to repel insects. After several previous attempts to make succesful synthetic repellents, prompted by the experience of jungle warfare, the US military developed DEET in 1946.
Over half a centuary later DEET is still the most commonly used insect repellent. Its success can be attributed to its effectiveness at relatively low concentrations and its harmlessness to humans. Only in rare cases will DEET cause skin or eye irritation. Care should however be taken when applying DEET near various plastics and other materials as these may be dissolved by the repellent. Recently however a new compound, known as IBI-246 and discoverd at North Carolina State University, which is extracted from tomatoes could provide a safer and more effective repellent.

==How does DEET work?==

Insects are sensitive to the lactic acid secreted by all mammals. DEET is thought to bind to the insect's lactic acid receptors, thereby obscuring the whereabouts of any real lactic acid. Thus the insect is unable to locate its victim.

==Synthesis==

[[Image:syn1.gif]]

Synthesis, (2), 272-276; 2003

[[Image:syn2.gif]]

Shanxi Daxue Xuebao, Ziran Kexueban, 25(1), 43-44; 2002

==IR Spectrum of DEET7==

[[Image:deetir.jpeg|IR Spectrum of DEET]]

==NMR Spectrum of DEET7==

[[Image:deetnmr.jpeg|NMR Spectrum of DEET]]

==References==

1http://acronyms.thefreedictionary.com/DEET

2Substance Identification (Beilstein(2006/03): BRN 2046711)

3http://chemfinder.cambridgesoft.com

4Journal; Journal; Vekki, A. V. de; Mozzhukhina, T. N.; PECHAM; Pet.Chem.USSR (Engl.Transl.); EN; 37; 4; 1997; 320-331; NEFTAH; Neftekhimiya; RU; 37; 4; 1997; 326-336.

5Journal; Maxim; Chem.Abstr.; 24; 1930; 94.

6Journal; Naumov et al.; JOCYA9; J.Org.Chem.USSR (Engl.Transl.); 9; 1973; 600; ZORKAE; Zh. Org. Khim.; 9; 1973; 591.

7http://www.sigmaaldrich.com

http://news.bbc.co.uk/1/hi/sci/tech/2037822.stm

http://www.fides.org/eng/sanita/insetti_180203.html

File:Deetnmr.jpeg

2006-12-08T15:24:52Z

Nc305:

File:Deetir.jpeg

2006-12-08T15:24:31Z

Nc305:

It:DEET

2006-12-08T15:02:04Z

Nc305: added syntheses

DEET is the active ingredient in all common insect repellents. Its name is an anacronym of N,N-Diethyl-meta-Toluamide 1, however this is not its systematic IUPAC name which is N,N-diethyl-3-methyl-benzamide 2. It is estimated that at least half the population of the US uses DEET every year. It is very important in stopping the spread of diseases such as West Nile virus, Eastern Equine Encephalitis, Rickets, Malaria and Dengue fever which are carried by mosquitoes.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of DEET
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:DEET.gif|Structure of DEET]]
|-
! {{chembox header}} colspan="3" |3D structure 3
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 150; cpk off;frame 100; move 100 -10 10 10 0 0 0 10 31; delay 1;</script>
<inlineContents>REMARK This PDB file is created by CS Chem3D
REMARK
COMPND DEET.pdb
HETATM 1 C UNK 0 3.619 0.570 -0.492 C
HETATM 2 C UNK 0 5.121 0.560 -0.282 C
HETATM 3 C UNK 0 5.822 1.791 -0.207 C
HETATM 4 C UNK 0 5.807 -0.677 -0.160 C
HETATM 5 C UNK 0 7.228 1.792 -0.005 C
HETATM 6 C UNK 0 7.212 -0.675 0.040 C
HETATM 7 C UNK 0 7.974 3.087 0.080 C
HETATM 8 C UNK 0 7.918 0.556 0.118 C
HETATM 9 C UNK 0 3.574 -1.824 -1.140 C
HETATM 10 C UNK 0 1.819 -0.961 0.280 C
HETATM 11 C UNK 0 2.669 -3.025 -0.904 C
HETATM 12 C UNK 0 1.987 -0.646 1.761 C
HETATM 13 H UNK 0 5.278 2.742 -0.303 H
HETATM 14 H UNK 0 5.255 -1.627 -0.220 H
HETATM 15 H UNK 0 9.007 0.552 0.275 H
HETATM 16 H UNK 0 7.755 -1.627 0.137 H
HETATM 17 H UNK 0 4.600 -2.053 -0.774 H
HETATM 18 H UNK 0 3.611 -1.595 -2.229 H
HETATM 19 H UNK 0 1.565 -2.038 0.157 H
HETATM 20 H UNK 0 1.000 -0.336 -0.141 H
HETATM 21 H UNK 0 1.037 -0.849 2.302 H
HETATM 22 H UNK 0 2.257 0.426 1.895 H
HETATM 23 H UNK 0 2.793 -1.279 2.196 H
HETATM 24 H UNK 0 3.076 -3.917 -1.430 H
HETATM 25 H UNK 0 1.647 -2.813 -1.290 H
HETATM 26 H UNK 0 2.606 -3.245 0.186 H
HETATM 27 H UNK 0 8.594 3.107 1.004 H
HETATM 28 H UNK 0 7.256 3.937 0.109 H
HETATM 29 H UNK 0 8.638 3.203 -0.805 H
HETATM 30 N UNK 0 3.054 -0.676 -0.424 N
HETATM 31 O UNK 0 2.981 1.575 -0.697 O
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3"| Properties
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| Molecular Formula
| C12H17NO
|-
| Molecular Weight
|191.27
|-
| Boiling Point 4
|286 oC
|-
| Density 5
| 0.996 g/cm3
|-
| Refractive index 6
| 1.5205
|-
| CAS registry number
| 134-62-3
|-
| Appearance
| colourless liquid
|-
|}

==History and information==

Traditionally methods such as smoke and various natural oils were employed to repel insects. After several previous attempts to make succesful synthetic repellents, prompted by the experience of jungle warfare, the US military developed DEET in 1946.
Over half a centuary later DEET is still the most commonly used insect repellent. Its success can be attributed to its effectiveness at relatively low concentrations and its harmlessness to humans. Only in rare cases will DEET cause skin or eye irritation. Care should however be taken when applying DEET near various plastics and other materials as these may be dissolved by the repellent. Recently however a new compound, known as IBI-246 and discoverd at North Carolina State University, which is extracted from tomatoes could provide a safer and more effective repellent.

==How does DEET work?==

Insects are sensitive to the lactic acid secreted by all mammals. DEET is thought to bind to the insect's lactic acid receptors, thereby obscuring the whereabouts of any real lactic acid. Thus the insect is unable to locate its victim.

==Synthesis==

[[Image:syn1.gif|Structure of DEET]]

Synthesis, (2), 272-276; 2003

[[Image:syn2.gif|Structure of DEET]]

Shanxi Daxue Xuebao, Ziran Kexueban, 25(1), 43-44; 2002

==References==

1http://acronyms.thefreedictionary.com/DEET

2Substance Identification (Beilstein(2006/03): BRN 2046711)

3http://chemfinder.cambridgesoft.com

4Journal; Journal; Vekki, A. V. de; Mozzhukhina, T. N.; PECHAM; Pet.Chem.USSR (Engl.Transl.); EN; 37; 4; 1997; 320-331; NEFTAH; Neftekhimiya; RU; 37; 4; 1997; 326-336.

5Journal; Maxim; Chem.Abstr.; 24; 1930; 94.

6Journal; Naumov et al.; JOCYA9; J.Org.Chem.USSR (Engl.Transl.); 9; 1973; 600; ZORKAE; Zh. Org. Khim.; 9; 1973; 591.

http://news.bbc.co.uk/1/hi/sci/tech/2037822.stm

http://www.fides.org/eng/sanita/insetti_180203.html

File:Syn2.gif

2006-12-08T15:01:28Z

Nc305:

File:Syn1.gif

2006-12-08T15:01:09Z

Nc305:

It:DEET

2006-12-07T13:50:23Z

Nc305: extended history and how does deet work

DEET is the active ingredient in all common insect repellents. Its name is an anacronym of N,N-Diethyl-meta-Toluamide 1, however this is not its systematic IUPAC name which is N,N-diethyl-3-methyl-benzamide 2. It is estimated that at least half the population of the US uses DEET every year. It is very important in stopping the spread of diseases such as West Nile virus, Eastern Equine Encephalitis, Rickets, Malaria and Dengue fever which are carried by mosquitoes.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of DEET
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:DEET.gif|Structure of DEET]]
|-
! {{chembox header}} colspan="3" |3D structure 3
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 150; cpk off;frame 100; move 100 -10 10 10 0 0 0 10 31; delay 1;</script>
<inlineContents>REMARK This PDB file is created by CS Chem3D
REMARK
COMPND DEET.pdb
HETATM 1 C UNK 0 3.619 0.570 -0.492 C
HETATM 2 C UNK 0 5.121 0.560 -0.282 C
HETATM 3 C UNK 0 5.822 1.791 -0.207 C
HETATM 4 C UNK 0 5.807 -0.677 -0.160 C
HETATM 5 C UNK 0 7.228 1.792 -0.005 C
HETATM 6 C UNK 0 7.212 -0.675 0.040 C
HETATM 7 C UNK 0 7.974 3.087 0.080 C
HETATM 8 C UNK 0 7.918 0.556 0.118 C
HETATM 9 C UNK 0 3.574 -1.824 -1.140 C
HETATM 10 C UNK 0 1.819 -0.961 0.280 C
HETATM 11 C UNK 0 2.669 -3.025 -0.904 C
HETATM 12 C UNK 0 1.987 -0.646 1.761 C
HETATM 13 H UNK 0 5.278 2.742 -0.303 H
HETATM 14 H UNK 0 5.255 -1.627 -0.220 H
HETATM 15 H UNK 0 9.007 0.552 0.275 H
HETATM 16 H UNK 0 7.755 -1.627 0.137 H
HETATM 17 H UNK 0 4.600 -2.053 -0.774 H
HETATM 18 H UNK 0 3.611 -1.595 -2.229 H
HETATM 19 H UNK 0 1.565 -2.038 0.157 H
HETATM 20 H UNK 0 1.000 -0.336 -0.141 H
HETATM 21 H UNK 0 1.037 -0.849 2.302 H
HETATM 22 H UNK 0 2.257 0.426 1.895 H
HETATM 23 H UNK 0 2.793 -1.279 2.196 H
HETATM 24 H UNK 0 3.076 -3.917 -1.430 H
HETATM 25 H UNK 0 1.647 -2.813 -1.290 H
HETATM 26 H UNK 0 2.606 -3.245 0.186 H
HETATM 27 H UNK 0 8.594 3.107 1.004 H
HETATM 28 H UNK 0 7.256 3.937 0.109 H
HETATM 29 H UNK 0 8.638 3.203 -0.805 H
HETATM 30 N UNK 0 3.054 -0.676 -0.424 N
HETATM 31 O UNK 0 2.981 1.575 -0.697 O
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3"| Properties
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| Molecular Formula
| C12H17NO
|-
| Molecular Weight
|191.27
|-
| Boiling Point 4
|286 oC
|-
| Density 5
| 0.996 g/cm3
|-
| Refractive index 6
| 1.5205
|-
| CAS registry number
| 134-62-3
|-
| Appearance
| colourless liquid
|-
|}

==History and information==

Traditionally methods such as smoke and various natural oils were employed to repel insects. After several previous attempts to make succesful synthetic repellents, prompted by the experience of jungle warfare, the US military developed DEET in 1946.
Over half a centuary later DEET is still the most commonly used insect repellent. Its success can be attributed to its effectiveness at relatively low concentrations and its harmlessness to humans. Only in rare cases will DEET cause skin or eye irritation. Care should however be taken when applying DEET near various plastics and other materials as these may be dissolved by the repellent. Recently however a new compound, known as IBI-246 and discoverd at North Carolina State University, which is extracted from tomatoes could provide a safer and more effective repellent.

==How does DEET work?==

Insects are sensitive to the lactic acid secreted by all mammals. DEET is thought to bind to the insect's lactic acid receptors, thereby obscuring the whereabouts of any real lactic acid. Thus the insect is unable to locate its victim.

==References==

1http://acronyms.thefreedictionary.com/DEET

2Substance Identification (Beilstein(2006/03): BRN 2046711)

3http://chemfinder.cambridgesoft.com

4Journal; Journal; Vekki, A. V. de; Mozzhukhina, T. N.; PECHAM; Pet.Chem.USSR (Engl.Transl.); EN; 37; 4; 1997; 320-331; NEFTAH; Neftekhimiya; RU; 37; 4; 1997; 326-336.

5Journal; Maxim; Chem.Abstr.; 24; 1930; 94.

6Journal; Naumov et al.; JOCYA9; J.Org.Chem.USSR (Engl.Transl.); 9; 1973; 600; ZORKAE; Zh. Org. Khim.; 9; 1973; 591.

http://news.bbc.co.uk/1/hi/sci/tech/2037822.stm

http://www.fides.org/eng/sanita/insetti_180203.html

It:DEET

2006-12-07T13:33:34Z

Nc305:

DEET is the active ingredient in all common insect repellents. Its name is an anacronym of N,N-Diethyl-meta-Toluamide 1, however this is not its systematic IUPAC name which is N,N-diethyl-3-methyl-benzamide 2. It is estimated that at least half the population of the US uses DEET every year. It is very important in stopping the spread of diseases such as West Nile virus, Eastern Equine Encephalitis, Rickets, Malaria and Dengue fever which are carried by mosquitoes.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of DEET
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:DEET.gif|Structure of DEET]]
|-
! {{chembox header}} colspan="3" |3D structure 3
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 150; cpk off;frame 100; move 100 -10 10 10 0 0 0 10 31; delay 1;</script>
<inlineContents>REMARK This PDB file is created by CS Chem3D
REMARK
COMPND DEET.pdb
HETATM 1 C UNK 0 3.619 0.570 -0.492 C
HETATM 2 C UNK 0 5.121 0.560 -0.282 C
HETATM 3 C UNK 0 5.822 1.791 -0.207 C
HETATM 4 C UNK 0 5.807 -0.677 -0.160 C
HETATM 5 C UNK 0 7.228 1.792 -0.005 C
HETATM 6 C UNK 0 7.212 -0.675 0.040 C
HETATM 7 C UNK 0 7.974 3.087 0.080 C
HETATM 8 C UNK 0 7.918 0.556 0.118 C
HETATM 9 C UNK 0 3.574 -1.824 -1.140 C
HETATM 10 C UNK 0 1.819 -0.961 0.280 C
HETATM 11 C UNK 0 2.669 -3.025 -0.904 C
HETATM 12 C UNK 0 1.987 -0.646 1.761 C
HETATM 13 H UNK 0 5.278 2.742 -0.303 H
HETATM 14 H UNK 0 5.255 -1.627 -0.220 H
HETATM 15 H UNK 0 9.007 0.552 0.275 H
HETATM 16 H UNK 0 7.755 -1.627 0.137 H
HETATM 17 H UNK 0 4.600 -2.053 -0.774 H
HETATM 18 H UNK 0 3.611 -1.595 -2.229 H
HETATM 19 H UNK 0 1.565 -2.038 0.157 H
HETATM 20 H UNK 0 1.000 -0.336 -0.141 H
HETATM 21 H UNK 0 1.037 -0.849 2.302 H
HETATM 22 H UNK 0 2.257 0.426 1.895 H
HETATM 23 H UNK 0 2.793 -1.279 2.196 H
HETATM 24 H UNK 0 3.076 -3.917 -1.430 H
HETATM 25 H UNK 0 1.647 -2.813 -1.290 H
HETATM 26 H UNK 0 2.606 -3.245 0.186 H
HETATM 27 H UNK 0 8.594 3.107 1.004 H
HETATM 28 H UNK 0 7.256 3.937 0.109 H
HETATM 29 H UNK 0 8.638 3.203 -0.805 H
HETATM 30 N UNK 0 3.054 -0.676 -0.424 N
HETATM 31 O UNK 0 2.981 1.575 -0.697 O
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3"| Properties
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| Molecular Formula
| C12H17NO
|-
| Molecular Weight
|191.27
|-
| Boiling Point 4
|286 oC
|-
| Density 5
| 0.996 g/cm3
|-
| Refractive index 6
| 1.5205
|-
| CAS registry number
| 134-62-3
|-
| Appearance
| colourless liquid
|-
|}

==History==

Traditionally methods such as smoke and various natural oils were employed to repel insects. After several previous attempts to make succesful synthetic repellents, prompted by the experience of jungle warfare, the US military developed DEET in 1946. Over half a centuary later DEET is still the most commonly used insect repellent. Its success can be attributed to its effectiveness at relatively low concentration and its low toxicity in humans.

==how does DEET work?==

Insects are sensitive to the lactic acid secreted by all mammals. DEET is thought to bind to the insect's lactic acid receptors, thereby obscuring the whereabouts of any real lactic acid. Thus the insect is unable to locate its victim.

==References==

1http://acronyms.thefreedictionary.com/DEET

2Substance Identification (Beilstein(2006/03): BRN 2046711)

3http://chemfinder.cambridgesoft.com

4Journal; Journal; Vekki, A. V. de; Mozzhukhina, T. N.; PECHAM; Pet.Chem.USSR (Engl.Transl.); EN; 37; 4; 1997; 320-331; NEFTAH; Neftekhimiya; RU; 37; 4; 1997; 326-336.

5Journal; Maxim; Chem.Abstr.; 24; 1930; 94.

6Journal; Naumov et al.; JOCYA9; J.Org.Chem.USSR (Engl.Transl.); 9; 1973; 600; ZORKAE; Zh. Org. Khim.; 9; 1973; 591.

It:DEET

2006-12-07T13:17:46Z

Nc305: added how does deet work?

DEET is the active ingredient in all common insect repellents. Its name is an anacronym of N,N-Diethyl-meta-Toluamide 1, however this is not its systematic IUPAC name which is N,N-diethyl-3-methyl-benzamide 2. It is estimated that at least half the population of the US uses DEET every year. It is very important in stopping the spread of diseases such as West Nile virus, Eastern Equine Encephalitis, malaria and dengue fever which are carried by mosquitos.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of DEET
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:DEET.gif|Structure of DEET]]
|-
! {{chembox header}} colspan="3" |3D structure 3
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 150; cpk off;frame 100; move 100 -10 10 10 0 0 0 10 31; delay 1;</script>
<inlineContents>REMARK This PDB file is created by CS Chem3D
REMARK
COMPND DEET.pdb
HETATM 1 C UNK 0 3.619 0.570 -0.492 C
HETATM 2 C UNK 0 5.121 0.560 -0.282 C
HETATM 3 C UNK 0 5.822 1.791 -0.207 C
HETATM 4 C UNK 0 5.807 -0.677 -0.160 C
HETATM 5 C UNK 0 7.228 1.792 -0.005 C
HETATM 6 C UNK 0 7.212 -0.675 0.040 C
HETATM 7 C UNK 0 7.974 3.087 0.080 C
HETATM 8 C UNK 0 7.918 0.556 0.118 C
HETATM 9 C UNK 0 3.574 -1.824 -1.140 C
HETATM 10 C UNK 0 1.819 -0.961 0.280 C
HETATM 11 C UNK 0 2.669 -3.025 -0.904 C
HETATM 12 C UNK 0 1.987 -0.646 1.761 C
HETATM 13 H UNK 0 5.278 2.742 -0.303 H
HETATM 14 H UNK 0 5.255 -1.627 -0.220 H
HETATM 15 H UNK 0 9.007 0.552 0.275 H
HETATM 16 H UNK 0 7.755 -1.627 0.137 H
HETATM 17 H UNK 0 4.600 -2.053 -0.774 H
HETATM 18 H UNK 0 3.611 -1.595 -2.229 H
HETATM 19 H UNK 0 1.565 -2.038 0.157 H
HETATM 20 H UNK 0 1.000 -0.336 -0.141 H
HETATM 21 H UNK 0 1.037 -0.849 2.302 H
HETATM 22 H UNK 0 2.257 0.426 1.895 H
HETATM 23 H UNK 0 2.793 -1.279 2.196 H
HETATM 24 H UNK 0 3.076 -3.917 -1.430 H
HETATM 25 H UNK 0 1.647 -2.813 -1.290 H
HETATM 26 H UNK 0 2.606 -3.245 0.186 H
HETATM 27 H UNK 0 8.594 3.107 1.004 H
HETATM 28 H UNK 0 7.256 3.937 0.109 H
HETATM 29 H UNK 0 8.638 3.203 -0.805 H
HETATM 30 N UNK 0 3.054 -0.676 -0.424 N
HETATM 31 O UNK 0 2.981 1.575 -0.697 O
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3"| Properties
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| Molecular Formula
| C12H17NO
|-
| Molecular Weight
|191.27
|-
| Boiling Point 4
|286 oC
|-
| Density 5
| 0.996 g/cm3
|-
| Refractive index 6
| 1.5205
|-
| CAS registry number
| 134-62-3
|-
| Appearance
| colourless liquid
|-
|}

==History==

==how does DEET work?==

Insects are sensitive to the lactic acid secreted by all mammals. DEET is thought to bind to the insect's lactic acid receptors, thereby obscuring the whereabouts of any real lactic acid. Thus the insect is unable to locate its victim.

==References==

1http://acronyms.thefreedictionary.com/DEET

2Substance Identification (Beilstein(2006/03): BRN 2046711)

3http://chemfinder.cambridgesoft.com

4Journal; Journal; Vekki, A. V. de; Mozzhukhina, T. N.; PECHAM; Pet.Chem.USSR (Engl.Transl.); EN; 37; 4; 1997; 320-331; NEFTAH; Neftekhimiya; RU; 37; 4; 1997; 326-336.

5Journal; Maxim; Chem.Abstr.; 24; 1930; 94.

6Journal; Naumov et al.; JOCYA9; J.Org.Chem.USSR (Engl.Transl.); 9; 1973; 600; ZORKAE; Zh. Org. Khim.; 9; 1973; 591.

It:DEET

2006-12-06T19:01:38Z

Nc305: Adding table on right including structures (3D and 2D)

DEET is the active ingredient in all common insect repellents. Its name is an anacronym of N,N-Diethyl-meta-Toluamide 1, however this is not its systematic IUPAC name which is N,N-diethyl-3-methyl-benzamide 2.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of DEET
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:DEET.gif|Structure of DEET]]
|-
! {{chembox header}} colspan="3" |3D structure 3
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 150; cpk off;frame 100; move 100 -10 10 10 0 0 0 10 31; delay 1;</script>
<inlineContents>REMARK This PDB file is created by CS Chem3D
REMARK
COMPND DEET.pdb
HETATM 1 C UNK 0 3.619 0.570 -0.492 C
HETATM 2 C UNK 0 5.121 0.560 -0.282 C
HETATM 3 C UNK 0 5.822 1.791 -0.207 C
HETATM 4 C UNK 0 5.807 -0.677 -0.160 C
HETATM 5 C UNK 0 7.228 1.792 -0.005 C
HETATM 6 C UNK 0 7.212 -0.675 0.040 C
HETATM 7 C UNK 0 7.974 3.087 0.080 C
HETATM 8 C UNK 0 7.918 0.556 0.118 C
HETATM 9 C UNK 0 3.574 -1.824 -1.140 C
HETATM 10 C UNK 0 1.819 -0.961 0.280 C
HETATM 11 C UNK 0 2.669 -3.025 -0.904 C
HETATM 12 C UNK 0 1.987 -0.646 1.761 C
HETATM 13 H UNK 0 5.278 2.742 -0.303 H
HETATM 14 H UNK 0 5.255 -1.627 -0.220 H
HETATM 15 H UNK 0 9.007 0.552 0.275 H
HETATM 16 H UNK 0 7.755 -1.627 0.137 H
HETATM 17 H UNK 0 4.600 -2.053 -0.774 H
HETATM 18 H UNK 0 3.611 -1.595 -2.229 H
HETATM 19 H UNK 0 1.565 -2.038 0.157 H
HETATM 20 H UNK 0 1.000 -0.336 -0.141 H
HETATM 21 H UNK 0 1.037 -0.849 2.302 H
HETATM 22 H UNK 0 2.257 0.426 1.895 H
HETATM 23 H UNK 0 2.793 -1.279 2.196 H
HETATM 24 H UNK 0 3.076 -3.917 -1.430 H
HETATM 25 H UNK 0 1.647 -2.813 -1.290 H
HETATM 26 H UNK 0 2.606 -3.245 0.186 H
HETATM 27 H UNK 0 8.594 3.107 1.004 H
HETATM 28 H UNK 0 7.256 3.937 0.109 H
HETATM 29 H UNK 0 8.638 3.203 -0.805 H
HETATM 30 N UNK 0 3.054 -0.676 -0.424 N
HETATM 31 O UNK 0 2.981 1.575 -0.697 O
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3"| Properties
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| Molecular Formula
| C12H17NO
|-
| Molecular Weight
|191.27
|-
| Boiling Point 4
|286 oC
|-
| Density 5
| 0.996 g/cm3
|-
| Refractive index 6
| 1.5205
|-
| CAS registry number
| 134-62-3
|-
| Appearance
| colourless liquid
|-
|}

==References==

1http://acronyms.thefreedictionary.com/DEET

2Substance Identification (Beilstein(2006/03): BRN 2046711)

3http://chemfinder.cambridgesoft.com

4Journal; Journal; Vekki, A. V. de; Mozzhukhina, T. N.; PECHAM; Pet.Chem.USSR (Engl.Transl.); EN; 37; 4; 1997; 320-331; NEFTAH; Neftekhimiya; RU; 37; 4; 1997; 326-336.

5Journal; Maxim; Chem.Abstr.; 24; 1930; 94.

6Journal; Naumov et al.; JOCYA9; J.Org.Chem.USSR (Engl.Transl.); 9; 1973; 600; ZORKAE; Zh. Org. Khim.; 9; 1973; 591.

File:DEET.gif

2006-12-06T18:03:04Z

Nc305: Structure of DEET.

Structure of DEET.

File:DEET.GIF

2006-12-06T17:58:26Z

Nc305: Structure of DEET

Structure of DEET

It:DEET

2006-12-06T17:47:57Z

Nc305: starting DEET

DEET is the active ingredient in all common insect repellents. Its name is an anacronym of N,N-Diethyl-meta-Toluamide1, however this is not its systematic IUPAC name which is N,N-diethyl-3-methyl-benzamide2.

==References==

1http://acronyms.thefreedictionary.com/DEET
2Substance Identification (Beilstein(2006/03): BRN 2046711)

It:projects

2006-12-06T17:12:44Z

Nc305: /* Supplemental Project Page */

__FORCETOC__

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! bgcolor="cyan" |Project Number
! bgcolor="cyan" |General Keywords
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| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]
|-
| bgcolor="#CCFF00" |03
| bgcolor="#CCFF00" | [[it:Rapamycin|Rapamycin (prevents transplant rejection)]]
|-
| bgcolor="#CCFF00" |04
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| bgcolor="#CCFF00" |14
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| bgcolor="#CCFF00" |20
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| bgcolor="#CCFF00" |21
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| bgcolor="#CCFF00" |22
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|bgcolor="#CCFF00" |23
| bgcolor="#CCFF00" | [[it:Vioxx|Vioxx (treatment of osteoarthritis symptoms and pain)]]
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| bgcolor="#CCFF00" |24
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| bgcolor="#CCFF00" |25
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| bgcolor="#CCFF00" |26
| bgcolor="#66FF99" | [[it:Zithromycin|Zithromycin (anti-infective)]]
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| bgcolor="#CCFF00" |27
| bgcolor="#CCFF00" | [[it:Lipitor|Lipitor (Cholesterol reducing agent)]]
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| bgcolor="#CCFF00" |28
| bgcolor="#66FF99" | [[it:Cyameluric Acid|Cyameluric acid (Linus Pauling's last idea!)]]
|}

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----
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'''PhenylButazone'''

[[Image:Example.jpg]]

''Medical applications''

Phenylbutazone has been used to treat serious pain in dogs due to osteoarthritis as it is a fast effective painkiller and also an anti-inflammatory. However dogs receiving intensive phenylbutazone therapy to tolerate the pain of osteoarthritis usually have regular blood work and renal monitoring to accompany this treatment. This is because an overdose of this drug is known to cause renal failure and liver injury.
This drug is also used to treat horses for such problems as musculoskeletal problems, soft tissue injury and bone and joint problems. Phenylbutazone is a nonsterodial drug which provides fast acting pain relief one to two hours after initial introduction into the body. The drug can be taken either orally or intravenously to the blood.

Safety

This drug is harmful of swallowed in excess of the dosage prescribed, it is also irritating to both the skin and eyes and respiratory system. Another precaution when dealing with phenylbutazone is that it should not be given to animals that are pregnant or nursing young as research has indicated it’s harmful to embryos and young.
This drug must not be injected into the muscles directly or under the skin.

IR spectrum of Phenylbutazone

[[Image:Example.jpg]]

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