File:Capsaicin NMR.jpg

2007-11-01T15:49:09Z

Ty506:

It07:Capsaicin

2007-11-01T15:48:56Z

Ty506:

==Capsacin==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Capsaicin.jpg|200px|Capsaicin]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 8-Methyl-N-vanillyl-trans-6-nonenamide

|-
| Other names
| Capsaicin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C18H27NO3
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 305.42
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 404-86-4
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in liqiud carbon dioxide]
| 0.543648gl<sup>-1</sup> (35°C)
pressure dependent
|-
<>>


| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339.25K in petroleum ether solvent
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 483.15-483.15K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| Monoclinic 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Capsaicin is a colourless crystalline alkaloid and also one of the most pungent compounds. Capsaicin is irritant to skin and mucous membrane. This compound is slightly soluble in water but is very soluble in organic solvents such as alcohol and fats. It is a part of capsaicinoid which is an active component of capsicum (chilli pepper’s biological name). Capsaicin of capsaicinoid is the main source for the chilli peppers being hot. Natural occurring capsaicinoid consists of six different compounds, capsaicin, dihydrocapsaicin which are the main components. The minor components of capsaicinoid are nordihydrocapsaicin, homocapsaicin and homodihydrocapsaicin.

<jmol>
<jmolApplet>
<size>200</size>
<color>blue</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Capsaicin.mol
title1
title2
49 49 0 0 1 V2000
-5.6000 2.1800 1.5960 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.2920 0.9360 1.4840 O 0 0 0 0 0 0 0 0 0 0 0 0
-5.5760 0.1600 0.6280 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.4120 0.6520 0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.6800 -0.1360 -0.8080 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4160 0.3960 -1.4240 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2760 0.0680 -0.5640 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0320 0.4480 -0.9160 C 0 0 0 0 0 0 0 0 0 0 0 0
0.1400 1.0640 -1.9480 O 0 0 0 0 0 0 0 0 0 0 0 0
1.1360 0.1120 -0.0280 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4240 0.6520 -0.6560 C 0 0 0 0 0 0 0 0 0 0 0 0
3.6120 0.3120 0.2440 C 0 0 0 0 0 0 0 0 0 0 0 0
4.8960 0.8520 -0.3800 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0680 0.5160 0.5040 C 0 0 0 0 0 0 0 0 0 0 0 0
7.0960 -0.1320 0.0160 C 0 0 0 0 0 0 0 0 0 0 0 0
8.2640 -0.4680 0.9040 C 0 0 0 0 0 0 0 0 0 0 0 0
8.4480 -1.9880 0.9520 C 0 0 0 0 0 0 0 0 0 0 0 0
9.5320 0.1760 0.3400 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1120 -1.4120 -1.1160 C 0 0 0 0 0 0 0 0 0 0 0 0
-5.2760 -1.9080 -0.5520 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.0080 -1.1240 0.3240 C 0 0 0 0 0 0 0 0 0 0 0 0
-7.1480 -1.6080 0.8800 O 0 0 0 0 0 0 0 0 0 0 0 0
-4.5960 2.0040 1.9840 H 0 0 0 0 0 0 0 0 0 0 0 0
-5.5360 2.6480 0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0
-6.1400 2.8360 2.2760 H 0 0 0 0 0 0 0 0 0 0 0 0
-4.0720 1.6480 0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.2680 -0.0520 -2.4080 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.4920 1.4800 -1.5320 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.4200 -0.4200 0.2600 H 0 0 0 0 0 0 0 0 0 0 0 0
0.9920 0.5640 0.9480 H 0 0 0 0 0 0 0 0 0 0 0 0
1.2120 -0.9680 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0
2.5680 0.2000 -1.6360 H 0 0 0 0 0 0 0 0 0 0 0 0
2.3480 1.7360 -0.7600 H 0 0 0 0 0 0 0 0 0 0 0 0
3.4640 0.7640 1.2240 H 0 0 0 0 0 0 0 0 0 0 0 0
3.6880 -0.7680 0.3480 H 0 0 0 0 0 0 0 0 0 0 0 0
5.0440 0.4000 -1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0
4.8200 1.9360 -0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0
6.0600 0.8120 1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0
7.1000 -0.4280 -1.0200 H 0 0 0 0 0 0 0 0 0 0 0 0
8.0800 -0.0920 1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0
8.6320 -2.3640 -0.0520 H 0 0 0 0 0 0 0 0 0 0 0 0
9.2920 -2.2320 1.5920 H 0 0 0 0 0 0 0 0 0 0 0 0
7.5440 -2.4480 1.3480 H 0 0 0 0 0 0 0 0 0 0 0 0
9.4040 1.2560 0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0
10.3800 -0.0640 0.9840 H 0 0 0 0 0 0 0 0 0 0 0 0
9.7200 -0.1960 -0.6600 H 0 0 0 0 0 0 0 0 0 0 0 0
-3.5400 -2.0240 -1.7960 H 0 0 0 0 0 0 0 0 0 0 0 0
-5.6080 -2.9040 -0.7920 H 0 0 0 0 0 0 0 0 0 0 0 0
-6.8960 -2.0480 1.7000 H 0 0 0 0 0 0 0 0 0 0 0 0
22 49 1 0
21 22 1 0
20 48 1 0
20 21 1 0
19 47 1 0
19 20 1 0
18 46 1 0
18 45 1 0
18 44 1 0
17 43 1 0
17 42 1 0
17 41 1 0
16 40 1 0
16 18 1 0
16 17 1 0
15 39 1 0
15 16 1 0
14 38 1 0
14 15 1 0
13 37 1 0
13 36 1 0
13 14 1 0
12 35 1 0
12 34 1 0
12 13 1 0
11 33 1 0
11 32 1 0
11 12 1 0
10 31 1 0
10 30 1 0
10 11 1 0
8 10 1 0
8 9 1 0
7 29 1 0
7 8 1 0
6 28 1 0
6 27 1 0
6 7 1 0
5 19 1 0
5 6 1 0
4 26 1 0
4 5 1 0
3 4 1 0
3 21 1 0
2 3 1 0
1 25 1 0
1 24 1 0
1 23 1 0
1 2 1 0
M END</inlineContents>
</jmolApplet>
</jmol>

==Capsaicinoid==
As it is stated above, the capsaicinoid in chilli pepper consists of six natural occurring compounds. All of which are pungent but each compound has different level of pungency and irritations.
Nordihydrocapsaicin is class as the least irritating and least pungent out of all six.
The most irritating and pungent molecule is homodihydrocapsaicin. This compound is said to cause burning sensations which is so strong that you even feel your tongue.
Rest of them are rated midst, however, since capsaicin and dihydrocapsaicin have the highest composition of capasnoid, they are rated very irritating on overall effect.

==Toxicity and lethal dose==
Pure capsaicin needs to be handled with extreme care in the labs. Due to irritating nature of capsaicin, it needs to be handled in air filtered room and the person handling it needs to wear full body protection in order to prevent the inhalation of capsain. When a person inhales it, the person would suffer from severe burning and irritation. At high concentration of capsaicin, it disturbs the cells from producing neurotransmitters which causes the feeling of numbness and eventually the cells will be damaged or destroyed at very high concentration. In the guinea pig experiment, it is found out that the lethal dose varies depending on the way capsaicin is taken in to body. When it is given by injection, the lethal dose is 56 milligram. When it is given by consumption, 190 milligram is the lethal dose. When it is absorbed through skin, the lethal dose is 512 milligrams. It is found that different animals have different capacity of capsaicin dose.

==Spectrum Data==
===Mass Spectrum===
[[image:Capsaicin_mass_spec.jpg|400px]]<ref>WSS: Spectral data were obtained from Wiley Subscription Services, Inc. (US)</ref>

===UV Spectrum===
[[Image:Capsaicin_UV_spectrum.jpg]]<ref>Chem. Res. Toxicol., 16 (3), 336 -349, 2003 {{DOI|10.1021/tx025599q S0893-228x(02)05599-6}}</ref>
==Reference==
<references/>

2007-11-01T15:03:59Z

Ty506:

It07:Capsaicin

2007-11-01T15:03:44Z

Ty506:

==Capsacin==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Capsaicin.jpg|200px|Capsaicin]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 8-Methyl-N-vanillyl-trans-6-nonenamide

|-
| Other names
| Capsaicin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C18H27NO3
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 305.42
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 404-86-4
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in liqiud carbon dioxide]
| 0.543648gl<sup>-1</sup> (35°C)
pressure dependent
|-
<>>


| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339.25K in petroleum ether solvent
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 483.15-483.15K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| Monoclinic 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Capsaicin is a colourless crystalline alkaloid and also one of the most pungent compounds. Capsaicin is irritant to skin and mucous membrane. This compound is slightly soluble in water but is very soluble in organic solvents such as alcohol and fats. It is a part of capsaicinoid which is an active component of capsicum (chilli pepper’s biological name). Capsaicin of capsaicinoid is the main source for the chilli peppers being hot. Natural occurring capsaicinoid consists of six different compounds, capsaicin, dihydrocapsaicin which are the main components. The minor components of capsaicinoid are nordihydrocapsaicin, homocapsaicin and homodihydrocapsaicin.

<jmol>
<jmolApplet>
<size>200</size>
<color>blue</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Capsaicin.mol
title1
title2
49 49 0 0 1 V2000
-5.6000 2.1800 1.5960 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.2920 0.9360 1.4840 O 0 0 0 0 0 0 0 0 0 0 0 0
-5.5760 0.1600 0.6280 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.4120 0.6520 0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.6800 -0.1360 -0.8080 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4160 0.3960 -1.4240 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2760 0.0680 -0.5640 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0320 0.4480 -0.9160 C 0 0 0 0 0 0 0 0 0 0 0 0
0.1400 1.0640 -1.9480 O 0 0 0 0 0 0 0 0 0 0 0 0
1.1360 0.1120 -0.0280 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4240 0.6520 -0.6560 C 0 0 0 0 0 0 0 0 0 0 0 0
3.6120 0.3120 0.2440 C 0 0 0 0 0 0 0 0 0 0 0 0
4.8960 0.8520 -0.3800 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0680 0.5160 0.5040 C 0 0 0 0 0 0 0 0 0 0 0 0
7.0960 -0.1320 0.0160 C 0 0 0 0 0 0 0 0 0 0 0 0
8.2640 -0.4680 0.9040 C 0 0 0 0 0 0 0 0 0 0 0 0
8.4480 -1.9880 0.9520 C 0 0 0 0 0 0 0 0 0 0 0 0
9.5320 0.1760 0.3400 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1120 -1.4120 -1.1160 C 0 0 0 0 0 0 0 0 0 0 0 0
-5.2760 -1.9080 -0.5520 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.0080 -1.1240 0.3240 C 0 0 0 0 0 0 0 0 0 0 0 0
-7.1480 -1.6080 0.8800 O 0 0 0 0 0 0 0 0 0 0 0 0
-4.5960 2.0040 1.9840 H 0 0 0 0 0 0 0 0 0 0 0 0
-5.5360 2.6480 0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0
-6.1400 2.8360 2.2760 H 0 0 0 0 0 0 0 0 0 0 0 0
-4.0720 1.6480 0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.2680 -0.0520 -2.4080 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.4920 1.4800 -1.5320 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.4200 -0.4200 0.2600 H 0 0 0 0 0 0 0 0 0 0 0 0
0.9920 0.5640 0.9480 H 0 0 0 0 0 0 0 0 0 0 0 0
1.2120 -0.9680 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0
2.5680 0.2000 -1.6360 H 0 0 0 0 0 0 0 0 0 0 0 0
2.3480 1.7360 -0.7600 H 0 0 0 0 0 0 0 0 0 0 0 0
3.4640 0.7640 1.2240 H 0 0 0 0 0 0 0 0 0 0 0 0
3.6880 -0.7680 0.3480 H 0 0 0 0 0 0 0 0 0 0 0 0
5.0440 0.4000 -1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0
4.8200 1.9360 -0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0
6.0600 0.8120 1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0
7.1000 -0.4280 -1.0200 H 0 0 0 0 0 0 0 0 0 0 0 0
8.0800 -0.0920 1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0
8.6320 -2.3640 -0.0520 H 0 0 0 0 0 0 0 0 0 0 0 0
9.2920 -2.2320 1.5920 H 0 0 0 0 0 0 0 0 0 0 0 0
7.5440 -2.4480 1.3480 H 0 0 0 0 0 0 0 0 0 0 0 0
9.4040 1.2560 0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0
10.3800 -0.0640 0.9840 H 0 0 0 0 0 0 0 0 0 0 0 0
9.7200 -0.1960 -0.6600 H 0 0 0 0 0 0 0 0 0 0 0 0
-3.5400 -2.0240 -1.7960 H 0 0 0 0 0 0 0 0 0 0 0 0
-5.6080 -2.9040 -0.7920 H 0 0 0 0 0 0 0 0 0 0 0 0
-6.8960 -2.0480 1.7000 H 0 0 0 0 0 0 0 0 0 0 0 0
22 49 1 0
21 22 1 0
20 48 1 0
20 21 1 0
19 47 1 0
19 20 1 0
18 46 1 0
18 45 1 0
18 44 1 0
17 43 1 0
17 42 1 0
17 41 1 0
16 40 1 0
16 18 1 0
16 17 1 0
15 39 1 0
15 16 1 0
14 38 1 0
14 15 1 0
13 37 1 0
13 36 1 0
13 14 1 0
12 35 1 0
12 34 1 0
12 13 1 0
11 33 1 0
11 32 1 0
11 12 1 0
10 31 1 0
10 30 1 0
10 11 1 0
8 10 1 0
8 9 1 0
7 29 1 0
7 8 1 0
6 28 1 0
6 27 1 0
6 7 1 0
5 19 1 0
5 6 1 0
4 26 1 0
4 5 1 0
3 4 1 0
3 21 1 0
2 3 1 0
1 25 1 0
1 24 1 0
1 23 1 0
1 2 1 0
M END</inlineContents>
</jmolApplet>
</jmol>

==Capsaicinoid==
As it is stated above, the capsaicinoid in chilli pepper consists of six natural occurring compounds. All of which are pungent but each compound has different level of pungency and irritations.
Nordihydrocapsaicin is class as the least irritating and least pungent out of all six.
The most irritating and pungent molecule is homodihydrocapsaicin. This compound is said to cause burning sensations which is so strong that you even feel your tongue.
Rest of them are rated midst, however, since capsaicin and dihydrocapsaicin have the highest composition of capasnoid, they are rated very irritating on overall effect.

==Toxicity and lethal dose==
Pure capsaicin needs to be handled with extreme care in the labs. Due to irritating nature of capsaicin, it needs to be handled in air filtered room and the person handling it needs to wear full body protection in order to prevent the inhalation of capsain. When a person inhales it, the person would suffer from severe burning and irritation. At high concentration of capsaicin, it disturbs the cells from producing neurotransmitters which causes the feeling of numbness and eventually the cells will be damaged or destroyed at very high concentration. In the guinea pig experiment, it is found out that the lethal dose varies depending on the way capsaicin is taken in to body. When it is given by injection, the lethal dose is 56 milligram. When it is given by consumption, 190 milligram is the lethal dose. When it is absorbed through skin, the lethal dose is 512 milligrams. It is found that different animals have different capacity of capsaicin dose.

==Spectrum Data==
Mass Spectrum
[[Image:Example.jpg]]

It07:Capsaicin

2007-11-01T14:54:13Z

Ty506:

==Capsacin==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Capsaicin.jpg|200px|Capsaicin]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 8-Methyl-N-vanillyl-trans-6-nonenamide

|-
| Other names
| Capsaicin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C18H27NO3
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 305.42
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 404-86-4
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in liqiud carbon dioxide]
| 0.543648gl<sup>-1</sup> (35°C)
pressure dependent
|-
<>>


| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339.25K in petroleum ether solvent
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 483.15-483.15K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| Monoclinic 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Capsaicin is a colourless crystalline alkaloid and also one of the most pungent compounds. Capsaicin is irritant to skin and mucous membrane. This compound is slightly soluble in water but is very soluble in organic solvents such as alcohol and fats. It is a part of capsaicinoid which is an active component of capsicum (chilli pepper’s biological name). Capsaicin of capsaicinoid is the main source for the chilli peppers being hot. Natural occurring capsaicinoid consists of six different compounds, capsaicin, dihydrocapsaicin which are the main components. The minor components of capsaicinoid are nordihydrocapsaicin, homocapsaicin and homodihydrocapsaicin.

<jmol>
<jmolApplet>
<size>200</size>
<color>blue</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Capsaicin.mol
title1
title2
49 49 0 0 1 V2000
-5.6000 2.1800 1.5960 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.2920 0.9360 1.4840 O 0 0 0 0 0 0 0 0 0 0 0 0
-5.5760 0.1600 0.6280 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.4120 0.6520 0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.6800 -0.1360 -0.8080 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4160 0.3960 -1.4240 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2760 0.0680 -0.5640 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0320 0.4480 -0.9160 C 0 0 0 0 0 0 0 0 0 0 0 0
0.1400 1.0640 -1.9480 O 0 0 0 0 0 0 0 0 0 0 0 0
1.1360 0.1120 -0.0280 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4240 0.6520 -0.6560 C 0 0 0 0 0 0 0 0 0 0 0 0
3.6120 0.3120 0.2440 C 0 0 0 0 0 0 0 0 0 0 0 0
4.8960 0.8520 -0.3800 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0680 0.5160 0.5040 C 0 0 0 0 0 0 0 0 0 0 0 0
7.0960 -0.1320 0.0160 C 0 0 0 0 0 0 0 0 0 0 0 0
8.2640 -0.4680 0.9040 C 0 0 0 0 0 0 0 0 0 0 0 0
8.4480 -1.9880 0.9520 C 0 0 0 0 0 0 0 0 0 0 0 0
9.5320 0.1760 0.3400 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1120 -1.4120 -1.1160 C 0 0 0 0 0 0 0 0 0 0 0 0
-5.2760 -1.9080 -0.5520 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.0080 -1.1240 0.3240 C 0 0 0 0 0 0 0 0 0 0 0 0
-7.1480 -1.6080 0.8800 O 0 0 0 0 0 0 0 0 0 0 0 0
-4.5960 2.0040 1.9840 H 0 0 0 0 0 0 0 0 0 0 0 0
-5.5360 2.6480 0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0
-6.1400 2.8360 2.2760 H 0 0 0 0 0 0 0 0 0 0 0 0
-4.0720 1.6480 0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.2680 -0.0520 -2.4080 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.4920 1.4800 -1.5320 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.4200 -0.4200 0.2600 H 0 0 0 0 0 0 0 0 0 0 0 0
0.9920 0.5640 0.9480 H 0 0 0 0 0 0 0 0 0 0 0 0
1.2120 -0.9680 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0
2.5680 0.2000 -1.6360 H 0 0 0 0 0 0 0 0 0 0 0 0
2.3480 1.7360 -0.7600 H 0 0 0 0 0 0 0 0 0 0 0 0
3.4640 0.7640 1.2240 H 0 0 0 0 0 0 0 0 0 0 0 0
3.6880 -0.7680 0.3480 H 0 0 0 0 0 0 0 0 0 0 0 0
5.0440 0.4000 -1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0
4.8200 1.9360 -0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0
6.0600 0.8120 1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0
7.1000 -0.4280 -1.0200 H 0 0 0 0 0 0 0 0 0 0 0 0
8.0800 -0.0920 1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0
8.6320 -2.3640 -0.0520 H 0 0 0 0 0 0 0 0 0 0 0 0
9.2920 -2.2320 1.5920 H 0 0 0 0 0 0 0 0 0 0 0 0
7.5440 -2.4480 1.3480 H 0 0 0 0 0 0 0 0 0 0 0 0
9.4040 1.2560 0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0
10.3800 -0.0640 0.9840 H 0 0 0 0 0 0 0 0 0 0 0 0
9.7200 -0.1960 -0.6600 H 0 0 0 0 0 0 0 0 0 0 0 0
-3.5400 -2.0240 -1.7960 H 0 0 0 0 0 0 0 0 0 0 0 0
-5.6080 -2.9040 -0.7920 H 0 0 0 0 0 0 0 0 0 0 0 0
-6.8960 -2.0480 1.7000 H 0 0 0 0 0 0 0 0 0 0 0 0
22 49 1 0
21 22 1 0
20 48 1 0
20 21 1 0
19 47 1 0
19 20 1 0
18 46 1 0
18 45 1 0
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17 41 1 0
16 40 1 0
16 18 1 0
16 17 1 0
15 39 1 0
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12 13 1 0
11 33 1 0
11 32 1 0
11 12 1 0
10 31 1 0
10 30 1 0
10 11 1 0
8 10 1 0
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7 8 1 0
6 28 1 0
6 27 1 0
6 7 1 0
5 19 1 0
5 6 1 0
4 26 1 0
4 5 1 0
3 4 1 0
3 21 1 0
2 3 1 0
1 25 1 0
1 24 1 0
1 23 1 0
1 2 1 0
M END</inlineContents>
</jmolApplet>
</jmol>

==Capsaicinoid==
As it is stated above, the capsaicinoid in chilli pepper consists of six natural occurring compounds. All of which are pungent but each compound has different level of pungency and irritations.
Nordihydrocapsaicin is class as the least irritating and least pungent out of all six.
The most irritating and pungent molecule is homodihydrocapsaicin. This compound is said to cause burning sensations which is so strong that you even feel your tongue.
Rest of them are rated midst, however, since capsaicin and dihydrocapsaicin have the highest composition of capasnoid, they are rated very irritating on overall effect.

==Toxicity and lethal dose==
Pure capsaicin needs to be handled with extreme care in the labs. Due to irritating nature of capsaicin, it needs to be handled in air filtered room and the person handling it needs to wear full body protection in order to prevent the inhalation of capsain. When a person inhales it, the person would suffer from severe burning and irritation. At high concentration of capsaicin, it disturbs the cells from producing neurotransmitters which causes the feeling of numbness and eventually the cells will be damaged or destroyed at very high concentration. In the guinea pig experiment, it is found out that the lethal dose varies depending on the way capsaicin is taken in to body. When it is given by injection, the lethal dose is 56 milligram. When it is given by consumption, 190 milligram is the lethal dose. When it is absorbed through skin, the lethal dose is 512 milligrams. It is found that different animals have different capacity of capsaicin dose.

It07:Capsaicin

2007-11-01T12:19:08Z

Ty506: /* Capsacin */

==Capsacin==
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Capsaicin.jpg|200px|Capsaicin]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 8-Methyl-N-vanillyl-trans-6-nonenamide

|-
| Other names
| Capsaicin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C18H27NO3
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 305.42
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 404-86-4
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| {{{Mp}}} K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Capsaicin is a colourless crystalline alkaloid and also one of the most pungent compounds. Capsaicin is irritant to skin and mucous membrane. This compound is slightly soluble in water but is very soluble in organic solvents such as alcohol and fats. It is a part of capsaicinoid which is an active component of capsicum (chilli pepper’s biological name). Capsaicin of capsaicinoid is the main source for the chilli peppers being hot. Natural occurring capsaicinoid consists of six different compounds, capsaicin, dihydrocapsaicin which are the main components. The minor components of capsaicinoid are nordihydrocapsaicin, homocapsaicin and homodihydrocapsaicin.

<jmol>
<jmolApplet>
<size>200</size>
<color>blue</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Capsaicin.mol
title1
title2
49 49 0 0 1 V2000
-5.6000 2.1800 1.5960 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.2920 0.9360 1.4840 O 0 0 0 0 0 0 0 0 0 0 0 0
-5.5760 0.1600 0.6280 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.4120 0.6520 0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.6800 -0.1360 -0.8080 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4160 0.3960 -1.4240 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.2760 0.0680 -0.5640 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0320 0.4480 -0.9160 C 0 0 0 0 0 0 0 0 0 0 0 0
0.1400 1.0640 -1.9480 O 0 0 0 0 0 0 0 0 0 0 0 0
1.1360 0.1120 -0.0280 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4240 0.6520 -0.6560 C 0 0 0 0 0 0 0 0 0 0 0 0
3.6120 0.3120 0.2440 C 0 0 0 0 0 0 0 0 0 0 0 0
4.8960 0.8520 -0.3800 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0680 0.5160 0.5040 C 0 0 0 0 0 0 0 0 0 0 0 0
7.0960 -0.1320 0.0160 C 0 0 0 0 0 0 0 0 0 0 0 0
8.2640 -0.4680 0.9040 C 0 0 0 0 0 0 0 0 0 0 0 0
8.4480 -1.9880 0.9520 C 0 0 0 0 0 0 0 0 0 0 0 0
9.5320 0.1760 0.3400 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1120 -1.4120 -1.1160 C 0 0 0 0 0 0 0 0 0 0 0 0
-5.2760 -1.9080 -0.5520 C 0 0 0 0 0 0 0 0 0 0 0 0
-6.0080 -1.1240 0.3240 C 0 0 0 0 0 0 0 0 0 0 0 0
-7.1480 -1.6080 0.8800 O 0 0 0 0 0 0 0 0 0 0 0 0
-4.5960 2.0040 1.9840 H 0 0 0 0 0 0 0 0 0 0 0 0
-5.5360 2.6480 0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0
-6.1400 2.8360 2.2760 H 0 0 0 0 0 0 0 0 0 0 0 0
-4.0720 1.6480 0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.2680 -0.0520 -2.4080 H 0 0 0 0 0 0 0 0 0 0 0 0
-2.4920 1.4800 -1.5320 H 0 0 0 0 0 0 0 0 0 0 0 0
-1.4200 -0.4200 0.2600 H 0 0 0 0 0 0 0 0 0 0 0 0
0.9920 0.5640 0.9480 H 0 0 0 0 0 0 0 0 0 0 0 0
1.2120 -0.9680 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0
2.5680 0.2000 -1.6360 H 0 0 0 0 0 0 0 0 0 0 0 0
2.3480 1.7360 -0.7600 H 0 0 0 0 0 0 0 0 0 0 0 0
3.4640 0.7640 1.2240 H 0 0 0 0 0 0 0 0 0 0 0 0
3.6880 -0.7680 0.3480 H 0 0 0 0 0 0 0 0 0 0 0 0
5.0440 0.4000 -1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0
4.8200 1.9360 -0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0
6.0600 0.8120 1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0
7.1000 -0.4280 -1.0200 H 0 0 0 0 0 0 0 0 0 0 0 0
8.0800 -0.0920 1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0
8.6320 -2.3640 -0.0520 H 0 0 0 0 0 0 0 0 0 0 0 0
9.2920 -2.2320 1.5920 H 0 0 0 0 0 0 0 0 0 0 0 0
7.5440 -2.4480 1.3480 H 0 0 0 0 0 0 0 0 0 0 0 0
9.4040 1.2560 0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0
10.3800 -0.0640 0.9840 H 0 0 0 0 0 0 0 0 0 0 0 0
9.7200 -0.1960 -0.6600 H 0 0 0 0 0 0 0 0 0 0 0 0
-3.5400 -2.0240 -1.7960 H 0 0 0 0 0 0 0 0 0 0 0 0
-5.6080 -2.9040 -0.7920 H 0 0 0 0 0 0 0 0 0 0 0 0
-6.8960 -2.0480 1.7000 H 0 0 0 0 0 0 0 0 0 0 0 0
22 49 1 0
21 22 1 0
20 48 1 0
20 21 1 0
19 47 1 0
19 20 1 0
18 46 1 0
18 45 1 0
18 44 1 0
17 43 1 0
17 42 1 0
17 41 1 0
16 40 1 0
16 18 1 0
16 17 1 0
15 39 1 0
15 16 1 0
14 38 1 0
14 15 1 0
13 37 1 0
13 36 1 0
13 14 1 0
12 35 1 0
12 34 1 0
12 13 1 0
11 33 1 0
11 32 1 0
11 12 1 0
10 31 1 0
10 30 1 0
10 11 1 0
8 10 1 0
8 9 1 0
7 29 1 0
7 8 1 0
6 28 1 0
6 27 1 0
6 7 1 0
5 19 1 0
5 6 1 0
4 26 1 0
4 5 1 0
3 4 1 0
3 21 1 0
2 3 1 0
1 25 1 0
1 24 1 0
1 23 1 0
1 2 1 0
M END</inlineContents>
</jmolApplet>
</jmol>

==Capsaicinoid==
As it is stated above, the capsaicinoid in chilli pepper consists of six natural occurring compounds. All of which are pungent but each compound has different level of pungency and irritations.
Nordihydrocapsaicin is class as the least irritating and least pungent out of all six.
The most irritating and pungent molecule is homodihydrocapsaicin. This compound is said to cause burning sensations which is so strong that you even feel your tongue.
Rest of them are rated midst, however, since capsaicin and dihydrocapsaicin have the highest composition of capasnoid, they are rated very irritating on overall effect.

==Toxicity and lethal dose==
Pure capsaicin needs to be handled with extreme care in the labs. Due to irritating nature of capsaicin, it needs to be handled in air filtered room and the person handling it needs to wear full body protection in order to prevent the inhalation of capsain. When a person inhales it, the person would suffer from severe burning and irritation. At high concentration of capsaicin, it disturbs the cells from producing neurotransmitters which causes the feeling of numbness and eventually the cells will be damaged or destroyed at very high concentration. In the guinea pig experiment, it is found out that the lethal dose varies depending on the way capsaicin is taken in to body. When it is given by injection, the lethal dose is 56 milligram. When it is given by consumption, 190 milligram is the lethal dose. When it is absorbed through skin, the lethal dose is 512 milligrams. It is found that different animals have different capacity of capsaicin dose.

File:Capsaicin.jpg

2007-11-01T12:18:15Z

Ty506:

2007-10-29T15:00:26Z

Ty506:

==Nicotine==

===A three dimesional representation of nicotine===

<jmol>
<jmolApplet>
<title>Nicotine</title><color>black</color><size>200</size>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents>
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<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>
<jmol><jmolAppletButton><title>Show Nicotine_3-d.pdb in popup window</title><color>cyan</color>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents></jmolAppletButton>
</jmol>

===A three dimensional representation of the crystal structure of a unit cell of nicotine iodide===
<jmol>
<jmolApplet>
<title>nicotine iodide</title><color>black</color>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DOXSIScell.cif</uploadedFileContents>
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<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
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<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
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</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Nicotine.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-[(2S)-1-methyl-2-pyrrolidinyl]Pyridine

|-
| Other names
| Nicotine, L-Nicotine, .beta.-Pyridyl-.alpha.-N-methylpyrrolidine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C10H14N2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN1CCC[S@H]1[C@]2=CC=CN=C2
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 162.23
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 54-11-5
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 1.0068 g/cm³
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 496-497 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 521 K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| Dynamic Viscosity at 20°C 
|0.04536 gcm<sup>-1</sup>s<sup>-1</sup><ref>Journal:Z.Phys.Chem.Stoechiom.Verwandtschaftsl, Page37, Volume 68, 1909</ref>

|-
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Nicotine is an alkaloid. The compound is famously known for being contained in the tabacco products. This compound is also contained in some of the vegetables such as totato, potato and green pepper. This can be proven by carrying out GLC, TLC or CC-mass spectrometry. However the amount of nicotine contained in those vegetables is very small compare to the amount in tabacco product. In those vegitables, upto about 23ppm of nicotine is present. On the other hand, a typical pack of cigarette contains around 1mg of nicotine.

==Biosynthesis of Nicotine in Tabacco plant==
Nicotine is synthesized from a protein chain called polyamine putrescine at the root of tabacco plant. The nicotine would then be transferred to the shoot of the plant and stored. Polyamine putrescine can be synthesised from ornithine with a presence of ornithine decarboxylate as a catalyst. On this pathway, CO2 is produced as a by-product. Another pathway is to react arginine in a presence of arginine dacarboxylate as a catalyst via forming agmatine. This pathway has three stages of reaction in order to get a desired product. The pathway is shown below.
[[Image:Polyamine_putrescine_production.gif|500px|]]
After the formation of polyamine purtrescine, the product is deaminated with putrescine N-methyltransferase enzyme (PMT) to form N-methylputrescine. Then Diamine oxdase(DAO) reacts with N-methylputrescine to form methyl pyrrolinium cation. This cation part will form the pyrrolidine part of the final molecule. Pyridine part of nicotine is formed in following. Aspartate molecule undergoes the NAD biosynthesis pathway to form 3-pyridine carboxylic acid (nicotinic acid). At this moment it is not know that either 3-pyrodine acid or its metabolised derivative react with methyl pyrrolinium cation to form nicotine.
[[Image:Nicotine_biosynthesis_pathway.jpg|500px|]]
A diagram of biosynthetic pathway

==Transportation process and defence mechanism involving nicotine in nicotine plant==
Nicotine is biosynthesised in the root of the tobacco plant. After the production, nicotine is transferred to xylem which transports nicotine up to aerial parts of the plant such as leaf and lateral buds. Vacuoles in these parts of the plant accumulate the nicotine. Nicotine is produced as a defence mechanism against herbivores. There is evidence which suggests the damage on the plant effects the amount of nicotine produced and accumulated in tobacco plant. When the plant is damaged by insect herbivores, the plant increases concentration of Jasmonates (JA) which is a group of plant hormone. Jasmonic acid in JA acts on the enzymes to producing more nicotine. Hence more nicotine would be accumulated in vacuoles. This is experimentally proved. However, the concentration rise depends on the position of the damage. Puncturing the leaves has less effect on concentration of nicotine relative to removal of shoot apex. Tobacco plant without the damages accumulates 0.1-1% of its dry mass. However, damaging the plant could increase the concentration up to around 4% of its dry mass.
[[Image:Nicotine_plant.jpg]]<ref>Plant Biotechnology 22, 389–392 (2005) "Molecular regulation of nicotine biosynthesis", Akira Katoh, Hiroyuki Ohki, Koji Inai, Takashi Hashimoto http://db1.wdc-jp.com/pdf_store/jspcmb/pdf/pb22_5/22_389.pdf</ref>

Diagram of nicotine production process

==Nicotine in the body==

''Entry and lifetime''

Nicotine can get into the body in various ways, the main channels into the body include:
*Skin
*Membranes (including the lining of the lungs and gums)

The diffusion into the body and hence time to get to the brain is quickest through the lungs which has an extremely high diffusion rate due to:
Large surface area, moist lining, extremely thin lining and a good blood supply.

Once in the body nicotine is broken down mainly in the liver by conversion into cotinine through an enzyme pathway. It can also be metabolised in the lungs again to cotinine as well as nicotine oxide which is then excreted, along with remaining nicotine filtered in the kidneys, in the form of urine. These processes amount to the nicotine being reduced in amount by 97% in just 360 minutes after smoking the cigarette. Some people do have a natural genetic defect however which means the enzyme that breaks down nicotine is not as effective as it could be as so the nicotine remains in the blood a lot longer and so reduces the need for a nicotine "top-up" during the day.
[http://health.howstuffworks.com/nicotine2.htm]

''Effects whilst in the body''

Whist nicotine is in the body it has many immediate effects. It has a biphasic nature in which it can either have a positive or negative effect on the general mood of the consumer. The way in which this effect swings is dependant on ''how much'' and ''how often'' nicotine is being given to the body.[http://health.howstuffworks.com/nicotine3.htm]

When nicotine enters the body it causes a sudden release of adrenaline. This adrenaline has the effect of increasing blood flow rate as well as decreasing the size of the arteries. This has an overall effect of increasing blood pressure in the smoker. Adrenaline also lowers the amount of the hormone insulin in the blood which causes to some extent a hypoglycemic effect. This is thought to be a reason for a suppression in appetite prevalent in the smoker because the brain can detect the large amount of glucose and then slows down release of hormones telling the body it needs food.

Also intake of nicotine can result in an increase in LDL(low density lipoproteins) and decrease in HDL (high density lipoproteins), shown by experimental evidence. [http://www.springerlink.com/content/x034836182u68752/fulltext.pdf]{{DOI|10.1007/BF00190750}} {{DOI|10.1007/BF00190750}}

*Control: LDL= 140 mg/dl HDL 48.8 mg/dl
*Nicotine: LDL= 168 mg/dl HDL 27.8 mg/dl

This effect can in turn can lead to an elevation in concentration of triglycerides and cholesterol in the body and also an to an increase in plaques in the arteries. This leads to an increased chance of atherosclerosis, myocardial infarction or cerebral infarction.

[[Image:Atherosclerosis pic.jpg|thumb|400|left|Severe athero sclerosis: This image is a work of the Centers for Disease Control and Prevention, part of the United States Department of Health and Human Services, taken or made during the course of an employee's official duties. As a work of the U.S. federal government, the image is in the public domain.]]

[[Image:Nicotine metabolic.jpg|thumb|left|Nicotine metabolic pathways[http://jpet.aspetjournals.org/cgi/content/full/291/3/1196?ck=nck]]]

<jmol>
<jmolApplet>
<title>Cytochrome P450 2A6 (CYP2A6)</title><color>white</color>
<size>500</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicprotein.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

The above protein (Cytochrome P450 2A6) [http://www.rcsb.org/pdb/static.do?p=explorer/viewers/jmol.jsp]is one of the most important enzymes in human nicotine metabolism.[http://www.cogsci.ecs.soton.ac.uk/cgi/psyc/ptopic?topic=nicotine-addiction ]

[[Image:IR nicotine.JPG|thumb|300|left|IR spectrum for nicotine]]
[[Image:NMRnicotine.JPG|thumb|300|left|NMR spectrum for nicotine {{DOI|10.1016/0022-2364(89)90324-7}}]]
[[Image:Mass_spectrum_of_nicotine.jpg|thumb|300|left|Mass spectrum for nicotine<ref>Anal. Chem.; 1956; 28(3) pp 306 - 316, "Mass Spectrometric Analysis Broad Applicability to Chemical Research", F. W. McLafferty, {{DOI|10.1021/ac60111a005}}</ref>]]
==Reference==
<references/>

2.Journal of Experimental Botany Page2899-2907 Volume57 Number 11 August 2006, "Nicotine synthesis in Nicotiana tabacum L. induced by mechanical wounding is regulated by auxin", Qiumei Shi, Chunjian Li, and Fusuo Zhang
{{DOI|10.1093/jxb/erl051}}
3.Journal of Food Science, Volume 53 Issue 5 Page 1572-1573, September 1988,"Abstract
Detection of Nicotine in Foods and Plant Materials", Shun J. Sheen, {{DOI|10.1111/j.1365-2621.1988.tb09328.x}}
4. Journal:Z.Phys.Chem.Stoechiom.Verwandtschaftsl, Page37, Volume 68, 1909

File:Mass spectrum of nicotine.jpg

2007-10-29T14:34:02Z

Ty506:

It07:Nicotine

2007-10-26T12:39:54Z

Ty506:

==Nicotine==

===A three dimesional representation of nicotine===

<jmol>
<jmolApplet>
<title>Nicotine</title><color>black</color><size>200</size>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>
<jmol><jmolAppletButton><title>Show Nicotine_3-d.pdb in popup window</title><color>cyan</color>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents></jmolAppletButton>
</jmol>

===A three dimensional representation of the crystal structure of a unit cell of nicotine iodide===
<jmol>
<jmolApplet>
<title>nicotine iodide</title><color>black</color>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DOXSIScell.cif</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Nicotine.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-[(2S)-1-methyl-2-pyrrolidinyl]Pyridine

|-
| Other names
| Nicotine, L-Nicotine, .beta.-Pyridyl-.alpha.-N-methylpyrrolidine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C10H14N2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN1CCC[S@H]1[C@]2=CC=CN=C2
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 162.23
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 54-11-5
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 1.0068 g/cm³
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 496-497 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 521 K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| Dynamic Viscosity at 20°C 
|0.04536 gcm<sup>-1</sup>s<sup>-1</sup><ref>Journal:Z.Phys.Chem.Stoechiom.Verwandtschaftsl, Page37, Volume 68, 1909</ref>

|-
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Nicotine is an alkaloid. The compound is famously known for being contained in the tabacco products. This compound is also contained in some of the vegetables such as totato, potato and green pepper. This can be proven by carrying out GLC, TLC or CC-mass spectrometry. However the amount of nicotine contained in those vegetables is very small compare to the amount in tabacco product. In those vegitables, upto about 23ppm of nicotine is present. On the other hand, a typical pack of cigarette contains around 1mg of nicotine.

==Biosynthesis of Nicotine in Tabacco plant==
Nicotine is synthesized from a protein chain called polyamine putrescine at the root of tabacco plant. The nicotine would then be transferred to the shoot of the plant and stored. Polyamine putrescine can be synthesised from ornithine with a presence of ornithine decarboxylate as a catalyst. On this pathway, CO2 is produced as a by-product. Another pathway is to react arginine in a presence of arginine dacarboxylate as a catalyst via forming agmatine. This pathway has three stages of reaction in order to get a desired product. The pathway is shown below.
[[Image:Polyamine_putrescine_production.gif|500px|]]
After the formation of polyamine purtrescine, the product is deaminated with putrescine N-methyltransferase enzyme (PMT) to form N-methylputrescine. Then Diamine oxdase(DAO) reacts with N-methylputrescine to form methyl pyrrolinium cation. This cation part will form the pyrrolidine part of the final molecule. Pyridine part of nicotine is formed in following. Aspartate molecule undergoes the NAD biosynthesis pathway to form 3-pyridine carboxylic acid (nicotinic acid). At this moment it is not know that either 3-pyrodine acid or its metabolised derivative react with methyl pyrrolinium cation to form nicotine.
[[Image:Nicotine_biosynthesis_pathway.jpg|500px|]]
A diagram of biosynthetic pathway

==Transportation process and defence mechanism involving nicotine in nicotine plant==
Nicotine is biosynthesised in the root of the tobacco plant. After the production, nicotine is transferred to xylem which transports nicotine up to aerial parts of the plant such as leaf and lateral buds. Vacuoles in these parts of the plant accumulate the nicotine. Nicotine is produced as a defence mechanism against herbivores. There is evidence which suggests the damage on the plant effects the amount of nicotine produced and accumulated in tobacco plant. When the plant is damaged by insect herbivores, the plant increases concentration of Jasmonates (JA) which is a group of plant hormone. Jasmonic acid in JA acts on the enzymes to producing more nicotine. Hence more nicotine would be accumulated in vacuoles. This is experimentally proved. However, the concentration rise depends on the position of the damage. Puncturing the leaves has less effect on concentration of nicotine relative to removal of shoot apex. Tobacco plant without the damages accumulates 0.1-1% of its dry mass. However, damaging the plant could increase the concentration up to around 4% of its dry mass.
[[Image:Nicotine_plant.jpg]]

Diagram of nicotine production process

==Nicotine in the body==

''Entry and lifetime''

Nicotine can get into the body in various ways, the main channels into the body include:
*Skin
*Membranes (including the lining of the lungs and gums)

The diffusion into the body and hence time to get to the brain is quickest through the lungs which has an extremely high diffusion rate due to:
Large surface area, moist lining, extremely thin lining and a good blood supply.

Once in the body nicotine is broken down mainly in the liver by conversion into cotinine through an enzyme pathway. It can also be metabolised in the lungs again to cotinine as well as nicotine oxide which is then excreted, along with remaining nicotine filtered in the kidneys, in the form of urine. These processes amount to the nicotine being reduced in amount by 97% in just 360 minutes after smoking the cigarette. Some people do have a natural genetic defect however which means the enzyme that breaks down nicotine is not as effective as it could be as so the nicotine remains in the blood a lot longer and so reduces the need for a nicotine "top-up" during the day.
[http://health.howstuffworks.com/nicotine2.htm]

''Effects whilst in the body''

Whist nicotine is in the body it has many immediate effects. It has a biphasic nature in which it can either have a positive or negative effect on the general mood of the consumer. The way in which this effect swings is dependant on ''how much'' and ''how often'' nicotine is being given to the body.[http://health.howstuffworks.com/nicotine3.htm]

When nicotine enters the body it causes a sudden release of adrenaline. This adrenaline has the effect of increasing blood flow rate as well as decreasing the size of the arteries. This has an overall effect of increasing blood pressure in the smoker. Adrenaline also lowers the amount of the hormone insulin in the blood which causes to some extent a hypoglycemic effect. This is thought to be a reason for a suppression in appetite prevalent in the smoker because the brain can detect the large amount of glucose and then slows down release of hormones telling the body it needs food.

Also intake of nicotine can result in an increase in LDL(low density lipoproteins) and decrease in HDL (high density lipoproteins), shown by experimental evidence. [http://www.springerlink.com/content/x034836182u68752/fulltext.pdf]{{DOI|10.1007/BF00190750}} {{DOI|10.1007/BF00190750}}

*Control: LDL= 140 mg/dl HDL 48.8 mg/dl
*Nicotine: LDL= 168 mg/dl HDL 27.8 mg/dl

This effect can in turn can lead to an elevation in concentration of triglycerides and cholesterol in the body and also an to an increase in plaques in the arteries. This leads to an increased chance of atherosclerosis, myocardial infarction or cerebral infarction.

[[Image:Atherosclerosis pic.jpg|thumb|400|left|Severe athero sclerosis: This image is a work of the Centers for Disease Control and Prevention, part of the United States Department of Health and Human Services, taken or made during the course of an employee's official duties. As a work of the U.S. federal government, the image is in the public domain.]]

[[Image:Nicotine metabolic.jpg|thumb|left|Nicotine metabolic pathways[http://jpet.aspetjournals.org/cgi/content/full/291/3/1196?ck=nck]]]

<jmol>
<jmolApplet>
<title>Cytochrome P450 2A6 (CYP2A6)</title><color>white</color>
<size>500</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicprotein.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

The above protein (Cytochrome P450 2A6) [http://www.rcsb.org/pdb/static.do?p=explorer/viewers/jmol.jsp]is one of the most important enzymes in human nicotine metabolism.[http://www.cogsci.ecs.soton.ac.uk/cgi/psyc/ptopic?topic=nicotine-addiction ]

[[Image:IR nicotine.JPG|thumb|300|left|IR spectrum for nicotine]]
[[Image:NMRnicotine.JPG|thumb|300|left|NMR spectrum for nicotine {{DOI|10.1016/0022-2364(89)90324-7}}]]
==Reference==
<references/>

1.Journal: Plant Biotechnology 22, 389–392 (2005) "Molecular regulation of nicotine biosynthesis", Akira Katoh, Hiroyuki Ohki, Koji Inai, Takashi Hashimoto http://db1.wdc-jp.com/pdf_store/jspcmb/pdf/pb22_5/22_389.pdf
2.Journal of Experimental Botany Page2899-2907 Volume57 Number 11 August 2006, "Nicotine synthesis in Nicotiana tabacum L. induced by mechanical wounding is regulated by auxin", Qiumei Shi, Chunjian Li, and Fusuo Zhang
{{DOI|10.1093/jxb/erl051}}
3.Journal of Food Science, Volume 53 Issue 5 Page 1572-1573, September 1988,"Abstract
Detection of Nicotine in Foods and Plant Materials", Shun J. Sheen, {{DOI|10.1111/j.1365-2621.1988.tb09328.x}}
4. Journal:Z.Phys.Chem.Stoechiom.Verwandtschaftsl, Page37, Volume 68, 1909

It07:Nicotine

2007-10-26T12:05:35Z

Ty506:

==Nicotine==

===A three dimesional representation of nicotine===

<jmol>
<jmolApplet>
<title>Nicotine</title><color>black</color><size>200</size>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>
<jmol><jmolAppletButton><title>Show Nicotine_3-d.pdb in popup window</title><color>cyan</color>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents></jmolAppletButton>
</jmol>

===A three dimensional representation of the crystal structure of a unit cell of nicotine iodide===
<jmol>
<jmolApplet>
<title>nicotine iodide</title><color>black</color>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DOXSIScell.cif</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Nicotine.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-[(2S)-1-methyl-2-pyrrolidinyl]Pyridine

|-
| Other names
| Nicotine, L-Nicotine, .beta.-Pyridyl-.alpha.-N-methylpyrrolidine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C10H14N2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN1CCC[S@H]1[C@]2=CC=CN=C2
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 162.23
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 54-11-5
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 1.0068 g/cm³
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 496-497 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 521 K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Nicotine is an alkaloid. The compound is famously known for being contained in the tabacco products. This compound is also contained in some of the vegetables such as totato, potato and green pepper. This can be proven by carrying out GLC, TLC or CC-mass spectrometry. However the amount of nicotine contained in those vegetables is very small compare to the amount in tabacco product. In those vegitables, upto about 23ppm of nicotine is present. On the other hand, a typical pack of cigarette contains around 1mg of nicotine.

==Biosynthesis of Nicotine in Tabacco plant==
Nicotine is synthesized from a protein chain called polyamine putrescine at the root of tabacco plant. The nicotine would then be transferred to the shoot of the plant and stored. Polyamine putrescine can be synthesised from ornithine with a presence of ornithine decarboxylate as a catalyst. On this pathway, CO2 is produced as a by-product. Another pathway is to react arginine in a presence of arginine dacarboxylate as a catalyst via forming agmatine. This pathway has three stages of reaction in order to get a desired product. The pathway is shown below.
[[Image:Polyamine_putrescine_production.gif|500px|]]
After the formation of polyamine purtrescine, the product is deaminated with putrescine N-methyltransferase enzyme (PMT) to form N-methylputrescine. Then Diamine oxdase(DAO) reacts with N-methylputrescine to form methyl pyrrolinium cation. This cation part will form the pyrrolidine part of the final molecule. Pyridine part of nicotine is formed in following. Aspartate molecule undergoes the NAD biosynthesis pathway to form 3-pyridine carboxylic acid (nicotinic acid). At this moment it is not know that either 3-pyrodine acid or its metabolised derivative react with methyl pyrrolinium cation to form nicotine.
[[Image:Nicotine_biosynthesis_pathway.jpg|500px|]]
A diagram of biosynthetic pathway

==Transportation process and defence mechanism involving nicotine in nicotine plant==
Nicotine is biosynthesised in the root of the tobacco plant. After the production, nicotine is transferred to xylem which transports nicotine up to aerial parts of the plant such as leaf and lateral buds. Vacuoles in these parts of the plant accumulate the nicotine. Nicotine is produced as a defence mechanism against herbivores. There is evidence which suggests the damage on the plant effects the amount of nicotine produced and accumulated in tobacco plant. When the plant is damaged by insect herbivores, the plant increases concentration of Jasmonates (JA) which is a group of plant hormone. Jasmonic acid in JA acts on the enzymes to producing more nicotine. Hence more nicotine would be accumulated in vacuoles. This is experimentally proved. However, the concentration rise depends on the position of the damage. Puncturing the leaves has less effect on concentration of nicotine relative to removal of shoot apex. Tobacco plant without the damages accumulates 0.1-1% of its dry mass. However, damaging the plant could increase the concentration up to around 4% of its dry mass.
[[Image:Nicotine_plant.jpg]]

Diagram of nicotine production process

==Nicotine in the body==

''Entry and lifetime''

Nicotine can get into the body in various ways, the main channels into the body include:
*Skin
*Membranes (including the lining of the lungs and gums)

The diffusion into the body and hence time to get to the brain is quickest through the lungs which has an extremely high diffusion rate due to:
Large surface area, moist lining, extremely thin lining and a good blood supply.

Once in the body nicotine is broken down mainly in the liver by conversion into cotinine through an enzyme pathway. It can also be metabolised in the lungs again to cotinine as well as nicotine oxide which is then excreted, along with remaining nicotine filtered in the kidneys, in the form of urine. These processes amount to the nicotine being reduced in amount by 97% in just 360 minutes after smoking the cigarette. Some people do have a natural genetic defect however which means the enzyme that breaks down nicotine is not as effective as it could be as so the nicotine remains in the blood a lot longer and so reduces the need for a nicotine "top-up" during the day.
[http://health.howstuffworks.com/nicotine2.htm]

''Effects whilst in the body''

Whist nicotine is in the body it has many immediate effects. It has a biphasic nature in which it can either have a positive or negative effect on the general mood of the consumer. The way in which this effect swings is dependant on ''how much'' and ''how often'' nicotine is being given to the body.[http://health.howstuffworks.com/nicotine3.htm]

When nicotine enters the body it causes a sudden release of adrenaline. This adrenaline has the effect of increasing blood flow rate as well as decreasing the size of the arteries. This has an overall effect of increasing blood pressure in the smoker. Adrenaline also lowers the amount of the hormone insulin in the blood which causes to some extent a hypoglycemic effect. This is thought to be a reason for a suppression in appetite prevalent in the smoker because the brain can detect the large amount of glucose and then slows down release of hormones telling the body it needs food.

Also intake of nicotine can result in an increase in LDL(low density lipoproteins) and decrease in HDL (high density lipoproteins), shown by experimental evidence. [http://www.springerlink.com/content/x034836182u68752/fulltext.pdf]{{DOI|10.1007/BF00190750}} {{DOI|10.1007/BF00190750}}

*Control: LDL= 140 mg/dl HDL 48.8 mg/dl
*Nicotine: LDL= 168 mg/dl HDL 27.8 mg/dl

This effect can in turn can lead to an elevation in concentration of triglycerides and cholesterol in the body and also an to an increase in plaques in the arteries. This leads to an increased chance of atherosclerosis, myocardial infarction or cerebral infarction.

[[Image:Atherosclerosis pic.jpg|thumb|400|left|Severe athero sclerosis: This image is a work of the Centers for Disease Control and Prevention, part of the United States Department of Health and Human Services, taken or made during the course of an employee's official duties. As a work of the U.S. federal government, the image is in the public domain.]]

[[Image:Nicotine metabolic.jpg|thumb|left|Nicotine metabolic pathways[http://jpet.aspetjournals.org/cgi/content/full/291/3/1196?ck=nck]]]

<jmol>
<jmolApplet>
<title>Cytochrome P450 2A6 (CYP2A6)</title><color>white</color>
<size>500</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicprotein.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

The above protein (Cytochrome P450 2A6) [http://www.rcsb.org/pdb/static.do?p=explorer/viewers/jmol.jsp]is one of the most important enzymes in human nicotine metabolism.[http://www.cogsci.ecs.soton.ac.uk/cgi/psyc/ptopic?topic=nicotine-addiction ]

[[Image:IR nicotine.JPG|thumb|300|left|IR spectrum for nicotine]]
[[Image:NMRnicotine.JPG|thumb|300|left|NMR spectrum for nicotine {{DOI|10.1016/0022-2364(89)90324-7}}]]
==Reference==
<references/>1.Journal: Plant Biotechnology 22, 389–392 (2005) "Molecular regulation of nicotine biosynthesis", Akira Katoh, Hiroyuki Ohki, Koji Inai, Takashi Hashimoto http://db1.wdc-jp.com/pdf_store/jspcmb/pdf/pb22_5/22_389.pdf
<references/>2.Journal of Experimental Botany Page2899-2907 Volume57 Number 11 August 2006, "Nicotine synthesis in Nicotiana tabacum L. induced by mechanical wounding is regulated by auxin", Qiumei Shi, Chunjian Li, and Fusuo Zhang
{{DOI|10.1093/jxb/erl051}}
<references/>3.Journal of Food Science, Volume 53 Issue 5 Page 1572-1573, September 1988,"Abstract
Detection of Nicotine in Foods and Plant Materials", Shun J. Sheen, {{DOI|10.1111/j.1365-2621.1988.tb09328.x}}

It07:Nicotine

2007-10-25T16:33:10Z

Ty506:

==Nicotine==

===A three dimesional representation of nicotine===

<jmol>
<jmolApplet>
<title>Nicotine</title><color>black</color><size>200</size>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>
<jmol><jmolAppletButton><title>Show Nicotine_3-d.pdb in popup window</title><color>cyan</color>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents></jmolAppletButton>
</jmol>

===A three dimensional representation of the crystal structure of a unit cell of nicotine iodide===
<jmol>
<jmolApplet>
<title>nicotine iodide</title><color>black</color>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DOXSIScell.cif</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Nicotine.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-[(2S)-1-methyl-2-pyrrolidinyl]Pyridine

|-
| Other names
| Nicotine, L-Nicotine, .beta.-Pyridyl-.alpha.-N-methylpyrrolidine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C10H14N2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN1CCC[S@H]1[C@]2=CC=CN=C2
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 162.23
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 54-11-5
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 1.0068 g/cm³
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 496-497 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 521 K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Nicotine is famously known for being contained in the tabacco products. This compound is also contained in some of the vegetables such as totato, potato and green pepper. This can be proven by carrying out GLC, TLC or CC-mass spectrometry. However the amount of nicotine contained in those vegetables is very small compare to the amount in tabacco product. In those vegitables, upto about 23ppm of nicotine is present. On the other hand, a typical pack of cigarette contains around 1mg of nicotine.

==Biosynthesis of Nicotine in Tabacco plant==
Nicotine is synthesized from a protein chain called polyamine putrescine at the root of tabacco plant. The nicotine would then be transferred to the shoot of the plant and stored. Polyamine putrescine can be synthesised from ornithine with a presence of ornithine decarboxylate as a catalyst. On this pathway, CO2 is produced as a by-product. Another pathway is to react arginine in a presence of arginine dacarboxylate as a catalyst via forming agmatine. This pathway has three stages of reaction in order to get a desired product. The pathway is shown below.
[[Image:Polyamine_putrescine_production.gif|500px|]]
After the formation of polyamine purtrescine, the product is deaminated with putrescine N-methyltransferase enzyme (PMT) to form N-methylputrescine. Then Diamine oxdase(DAO) reacts with N-methylputrescine to form methyl pyrrolinium cation. This cation part will form the pyrrolidine part of the final molecule. Pyridine part of nicotine is formed in following. Aspartate molecule undergoes the NAD biosynthesis pathway to form 3-pyridine carboxylic acid (nicotinic acid). At this moment it is not know that either 3-pyrodine acid or its metabolised derivative react with methyl pyrrolinium cation to form nicotine.
[[Image:Nicotine_biosynthesis_pathway.jpg|500px|]]
A diagram of biosynthetic pathway

==Transportation process and defence mechanism involving nicotine in nicotine plant==
Nicotine is biosynthesised in the root of the tobacco plant. After the production, nicotine is transferred to xylem which transports nicotine up to aerial parts of the plant such as leaf and lateral buds. Vacuoles in these parts of the plant accumulate the nicotine. Nicotine is produced as a defence mechanism against herbivores. There is evidence which suggests the damage on the plant effects the amount of nicotine produced and accumulated in tobacco plant. When the plant is damaged by insect herbivores, the plant increases concentration of Jasmonates (JA) which is a group of plant hormone. Jasmonic acid in JA acts on the enzymes to producing more nicotine. Hence more nicotine would be accumulated in vacuoles. This is experimentally proved. However, the concentration rise depends on the position of the damage. Puncturing the leaves has less effect on concentration of nicotine relative to removal of shoot apex. Tobacco plant without the damages accumulates 0.1-1% of its dry mass. However, damaging the plant could increase the concentration up to around 4% of its dry mass.
[[Image:Nicotine_plant.jpg]]

Diagram of nicotine production process

==Nicotine in the body==

''Entry and lifetime''

Nicotine can get into the body in various ways, the main channels into the body include:
*Skin
*Membranes (including the lining of the lungs and gums)

The diffusion into the body and hence time to get to the brain is quickest through the lungs which has an extremely high diffusion rate due to:
Large surface area, moist lining, extremely thin lining and a good blood supply.

Once in the body nicotine is broken down mainly in the liver by conversion into cotinine through an enzyme pathway. It can also be metabolised in the lungs again to cotinine as well as nicotine oxide which is then excreted, along with remaining nicotine filtered in the kidneys, in the form of urine. These processes amount to the nicotine being reduced in amount by 97% in just 360 minutes after smoking the cigarette. Some people do have a natural genetic defect however which means the enzyme that breaks down nicotine is not as effective as it could be as so the nicotine remains in the blood a lot longer and so reduces the need for a nicotine "top-up" during the day.
[http://health.howstuffworks.com/nicotine2.htm]

''Effects whilst in the body''

Whist nicotine is in the body it has many immediate effects. It has a biphasic nature in which it can either have a positive or negative effect on the general mood of the consumer. The way in which this effect swings is dependant on ''how much'' and ''how often'' nicotine is being given to the body.[http://health.howstuffworks.com/nicotine3.htm]

When nicotine enters the body it causes a sudden release of adrenaline. This adrenaline has the effect of increasing blood flow rate as well as decreasing the size of the arteries. This has an overall effect of increasing blood pressure in the smoker. Adrenaline also lowers the amount of the hormone insulin in the blood which causes to some extent a hypoglycemic effect. This is thought to be a reason for a suppression in appetite prevalent in the smoker because the brain can detect the large amount of glucose and then slows down release of hormones telling the body it needs food.

Also intake of nicotine can result in an increase in LDL(low density lipoproteins) and decrease in HDL (high density lipoproteins), shown by experimental evidence. [http://www.springerlink.com/content/x034836182u68752/fulltext.pdf]{{DOI|10.1007/BF00190750}} {{DOI|10.1007/BF00190750}}

*Control: LDL= 140 mg/dl HDL 48.8 mg/dl
*Nicotine: LDL= 168 mg/dl HDL 27.8 mg/dl

This effect can in turn can lead to an elevation in concentration of triglycerides and cholesterol in the body and also an to an increase in plaques in the arteries. This leads to an increased chance of atherosclerosis, myocardial infarction or cerebral infarction.

[[Image:Atherosclerosis pic.jpg|thumb|400|left|Severe athero sclerosis: This image is a work of the Centers for Disease Control and Prevention, part of the United States Department of Health and Human Services, taken or made during the course of an employee's official duties. As a work of the U.S. federal government, the image is in the public domain.]]

[[Image:Nicotine metabolic.jpg|thumb|left|Nicotine metabolic pathways[http://jpet.aspetjournals.org/cgi/content/full/291/3/1196?ck=nck]]]

<jmol>
<jmolApplet>
<title>Cytochrome P450 2A6 (CYP2A6)</title><color>white</color>
<size>500</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicprotein.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

The above protein (Cytochrome P450 2A6) [http://www.rcsb.org/pdb/static.do?p=explorer/viewers/jmol.jsp]is one of the most important enzymes in human nicotine metabolism.[http://www.cogsci.ecs.soton.ac.uk/cgi/psyc/ptopic?topic=nicotine-addiction ]

[[Image:IR nicotine.JPG|thumb|300|left|IR spectrum for nicotine]]
[[Image:NMRnicotine.JPG|thumb|300|left|NMR spectrum for nicotine {{DOI|10.1016/0022-2364(89)90324-7}}]]
==Reference==
<references/>1.Journal: Plant Biotechnology 22, 389–392 (2005) "Molecular regulation of nicotine biosynthesis", Akira Katoh, Hiroyuki Ohki, Koji Inai, Takashi Hashimoto http://db1.wdc-jp.com/pdf_store/jspcmb/pdf/pb22_5/22_389.pdf
<references/>2.Journal of Experimental Botany Page2899-2907 Volume57 Number 11 August 2006, "Nicotine synthesis in Nicotiana tabacum L. induced by mechanical wounding is regulated by auxin", Qiumei Shi, Chunjian Li, and Fusuo Zhang
{{DOI|10.1093/jxb/erl051}}
<references/>3.Journal of Food Science, Volume 53 Issue 5 Page 1572-1573, September 1988,"Abstract
Detection of Nicotine in Foods and Plant Materials", Shun J. Sheen, {{DOI|10.1111/j.1365-2621.1988.tb09328.x}}

It07:Nicotine

2007-10-25T14:44:29Z

Ty506: /* Transportation process and defence mechanism involving nicotine in nicotine plant */

==Nicotine==

===A three dimesional representation of nicotine===

<jmol>
<jmolApplet>
<title>Nicotine</title><color>black</color><size>200</size>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>
<jmol><jmolAppletButton><title>Show Nicotine_3-d.pdb in popup window</title><color>cyan</color>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents></jmolAppletButton>
</jmol>

===A three dimensional representation of the crystal structure of a unit cell of nicotine iodide===
<jmol>
<jmolApplet>
<title>nicotine iodide</title><color>black</color>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DOXSIScell.cif</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Nicotine.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-[(2S)-1-methyl-2-pyrrolidinyl]Pyridine

|-
| Other names
| Nicotine, L-Nicotine, .beta.-Pyridyl-.alpha.-N-methylpyrrolidine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C10H14N2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN1CCC[S@H]1[C@]2=CC=CN=C2
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 162.23
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 54-11-5
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 1.0068 g/cm³
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 496-497 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 521 K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Nicotine is famously known for being contained in the tabacco products. This compound is also contained in some of the vegetables such as totato, potato and green pepper. This can be proven by carrying out GLC, TLC or CC-mass spectrometry. However the amount of nicotine contained in those vegetables is very small compare to the amount in tabacco product. In those vegitables, upto about 23ppm of nicotine is present. On the other hand, a typical pack of cigarette contains around 1mg of nicotine.

==Biosynthesis of Nicotine in Tabacco plant==
Nicotine is synthesized from a protein chain called polyamine putrescine at the root of tabacco plant. The nicotine would then be transferred to the shoot of the plant and stored. Polyamine putrescine can be synthesised from ornithine with a presence of ornithine decarboxylate as a catalyst. On this pathway, CO2 is produced as a by-product. Another pathway is to react arginine in a presence of arginine dacarboxylate as a catalyst via forming agmatine. This pathway has three stages of reaction in order to get a desired product. The pathway is shown below.
[[Image:Polyamine_putrescine_production.gif|500px|]]
After the formation of polyamine purtrescine, the product is deaminated with putrescine N-methyltransferase enzyme (PMT) to form N-methylputrescine. Then Diamine oxdase(DAO) reacts with N-methylputrescine to form methyl pyrrolinium cation. This cation part will form the pyrrolidine part of the final molecule. Pyridine part of nicotine is formed in following. Aspartate molecule undergoes the NAD biosynthesis pathway to form 3-pyridine carboxylic acid (nicotinic acid). At this moment it is not know that either 3-pyrodine acid or its metabolised derivative react with methyl pyrrolinium cation to form nicotine.
[[Image:Nicotine_biosynthesis_pathway.jpg|500px|]]
A diagram of biosynthetic pathway

==Transportation process and defence mechanism involving nicotine in nicotine plant==
Nicotine is biosynthesised in the root of the tobacco plant. After the production, nicotine is transferred to xylem which transports nicotine up to aerial parts of the plant such as leaf and lateral buds. Vacuoles in these parts of the plant accumulate the nicotine. Nicotine is produced as a defence mechanism against herbivores. There is evidence which suggests the damage on the plant effects the amount of nicotine produced and accumulated in tobacco plant. When the plant is damaged by insect herbivores, the plant increases concentration of Jasmonates (JA) which is a group of plant hormone. Jasmonic acid in JA acts on the enzymes to producing more nicotine. Hence more nicotine would be accumulated in vacuoles. This is experimentally proved. However, the concentration rise depends on the position of the damage. Puncturing the leaves has less effect on concentration of nicotine relative to removal of shoot apex. Tobacco plant without the damages accumulates 0.1-1% of its dry mass. However, damaging the plant could increase the concentration up to around 4% of its dry mass.
[[Image:Nicotine_plant.jpg]]

Diagram of nicotine production process

==Nicotine in the body==

''Entry and lifetime''

Nicotine can get into the body in various ways, the main channels into the body include:
*Skin
*Membranes (including the lining of the lungs and gums)

The diffusion into the body and hence time to get to the brain is quickest through the lungs which has an extremely high diffusion rate due to:
Large surface area, moist lining, extremely thin lining and a good blood supply.

Once in the body nicotine is broken down mainly in the liver by conversion into cotinine through an enzyme pathway. It can also be metabolised in the lungs again to cotinine as well as nicotine oxide which is then excreted, along with remaining nicotine filtered in the kidneys, in the form of urine. These processes amount to the nicotine being reduced in amount by 97% in just 360 minutes after smoking the cigarette. Some people do have a natural genetic defect however which means the enzyme that breaks down nicotine is not as effective as it could be as so the nicotine remains in the blood a lot longer and so reduces the need for a nicotine "top-up" during the day.
[http://health.howstuffworks.com/nicotine2.htm]

''Effects whilst in the body''

Whist nicotine is in the body it has many immediate effects. It has a biphasic nature in which it can either have a positive or negative effect on the general mood of the consumer. The way in which this effect swings is dependant on ''how much'' and ''how often'' nicotine is being given to the body.[http://health.howstuffworks.com/nicotine3.htm]

When nicotine enters the body it causes a sudden release of adrenaline. This adrenaline has the effect of increasing blood flow rate as well as decreasing the size of the arteries. This has an overall effect of increasing blood pressure in the smoker. Adrenaline also lowers the amount of the hormone insulin in the blood which causes to some extent a hypoglycemic effect. This is thought to be a reason for a suppression in appetite prevalent in the smoker because the brain can detect the large amount of glucose and then slows down release of hormones telling the body it needs food.

Also intake of nicotine can result in an increase in LDL(low density lipoproteins) and decrease in HDL (high density lipoproteins), shown by experimental evidence. [http://www.springerlink.com/content/x034836182u68752/fulltext.pdf]{{DOI|10.1007/BF00190750}} {{DOI|10.1007/BF00190750}}

*Control: LDL= 140 mg/dl HDL 48.8 mg/dl
*Nicotine: LDL= 168 mg/dl HDL 27.8 mg/dl

This effect can in turn can lead to an elevation in concentration of triglycerides and cholesterol in the body and also an to an increase in plaques in the arteries. This leads to an increased chance of atherosclerosis, myocardial infarction or cerebral infarction.

[[Image:Atherosclerosis pic.jpg|thumb|400|left|Severe athero sclerosis: This image is a work of the Centers for Disease Control and Prevention, part of the United States Department of Health and Human Services, taken or made during the course of an employee's official duties. As a work of the U.S. federal government, the image is in the public domain.]]

[[Image:Nicotine metabolic.jpg|thumb|left|Nicotine metabolic pathways[http://jpet.aspetjournals.org/cgi/content/full/291/3/1196?ck=nck]]]

<jmol>
<jmolApplet>
<title>Cytochrome P450 2A6 (CYP2A6)</title><color>white</color>
<size>500</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicprotein.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

The above protein (Cytochrome P450 2A6) [http://www.rcsb.org/pdb/static.do?p=explorer/viewers/jmol.jsp]is one of the most important enzymes in human nicotine metabolism.[http://www.cogsci.ecs.soton.ac.uk/cgi/psyc/ptopic?topic=nicotine-addiction ]

[[Image:IR nicotine.JPG|thumb|300|left|IR spectrum for nicotine]]
[[Image:NMRnicotine.JPG|thumb|300|left|NMR spectrum for nicotine {{DOI|10.1016/0022-2364(89)90324-7}}]]

2007-10-23T16:27:57Z

Ty506:

It07:Nicotine

2007-10-23T16:26:37Z

Ty506:

==Nicotine==

===A three dimesional representation of nicotine===

<jmol>
<jmolApplet>
<title>Nicotine</title><color>black</color><size>200</size>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>
<jmol><jmolAppletButton><title>Show Nicotine_3-d.pdb in popup window</title><color>cyan</color>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents></jmolAppletButton>
</jmol>

===A three dimensional representation of the crystal structure of a unit cell of nicotine iodide===
<jmol>
<jmolApplet>
<title>nicotine iodide</title><color>black</color>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DOXSIScell.cif</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Nicotine.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-[(2S)-1-methyl-2-pyrrolidinyl]Pyridine

|-
| Other names
| Nicotine, L-Nicotine, .beta.-Pyridyl-.alpha.-N-methylpyrrolidine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C10H14N2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN1CCC[S@H]1[C@]2=CC=CN=C2
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 162.23
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 54-11-5
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 1.0068 g/cm³
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 496-497 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 521 K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Nicotine is famously known for being contained in the tabacco products. This compound is also contained in some of the vegetables such as totato, potato and green pepper. This can be proven by carrying out GLC, TLC or CC-mass spectrometry. However the amount of nicotine contained in those vegetables is very small compare to the amount in tabacco product. In those vegitables, upto about 23ppm of nicotine is present. On the other hand, a typical pack of cigarette contains around 1mg of nicotine.

==Biosynthesis of Nicotine in Tabacco plant==
Nicotine is synthesized from a protein chain called polyamine putrescine at the root of tabacco plant. The nicotine would then be transferred to the shoot of the plant and stored. Polyamine putrescine can be synthesised from ornithine with a presence of ornithine decarboxylate as a catalyst. On this pathway, CO2 is produced as a by-product. Another pathway is to react arginine in a presence of arginine dacarboxylate as a catalyst via forming agmatine. This pathway has three stages of reaction in order to get a desired product. The pathway is shown below.
[[Image:Polyamine_putrescine_production.gif|500px|]]
After the formation of polyamine purtrescine, the product is deaminated with putrescine N-methyltransferase enzyme (PMT) to form N-methylputrescine. Then Diamine oxdase(DAO) reacts with N-methylputrescine to form methyl pyrrolinium cation. This cation part will form the pyrrolidine part of the final molecule. Pyridine part of nicotine is formed in following. Aspartate molecule undergoes the NAD biosynthesis pathway to form 3-pyridine carboxylic acid (nicotinic acid). At this moment it is not know that either 3-pyrodine acid or its metabolised derivative react with methyl pyrrolinium cation to form nicotine.

A diagram of biosynthetic pathway
==Nicotine in the body==

''Entry and lifetime''

Nicotine can get into the body in various ways, the main channels into the body include:
*Skin
*Membranes (including the lining of the lungs and gums)

The diffusion into the body and hence time to get to the brain is quickest through the lungs which has an extremely high diffusion rate due to:
Large surface area, moist lining, extremely thin lining and a good blood supply.

Once in the body nicotine is broken down mainly in the liver by conversion into cotinine through an enzyme pathway. It can also be metabolised in the lungs again to cotinine as well as nicotine oxide which is then excreted, along with remaining nicotine filtered in the kidneys, in the form of urine. These processes amount to the nicotine being reduced in amount by 97% in just 360 minutes after smoking the cigarette. Some people do have a natural genetic defect however which means the enzyme that breaks down nicotine is not as effective as it could be as so the nicotine remains in the blood a lot longer and so reduces the need for a nicotine "top-up" during the day.
[http://health.howstuffworks.com/nicotine2.htm]

''Effects whilst in the body''

Whist nicotine is in the body it has many immediate effects. It has a biphasic nature in which it can either have a positive or negative effect on the general mood of the consumer. The way in which this effect swings is dependant on ''how much'' and ''how often'' nicotine is being given to the body.[http://health.howstuffworks.com/nicotine3.htm]

When nicotine enters the body it causes a sudden release of adrenaline. This adrenaline has the effect of increasing blood flow rate as well as decreasing the size of the arteries. This has an overall effect of increasing blood pressure in the smoker. Adrenaline also lowers the amount of the hormone insulin in the blood which causes to some extent a hypoglycemic effect. This is thought to be a reason for a suppression in appetite prevalent in the smoker because the brain can detect the large amount of glucose and then slows down release of hormones telling the body it needs food.

Also intake of nicotine can result in an increase in LDL(low density lipoproteins) and decrease in HDL (high density lipoproteins), shown by experimental evidence. [http://www.springerlink.com/content/x034836182u68752/fulltext.pdf]{{DOI|10.1007/BF00190750}} {{DOI|10.1007/BF00190750}}

*Control: LDL= 140 mg/dl HDL 48.8 mg/dl
*Nicotine: LDL= 168 mg/dl HDL 27.8 mg/dl

This effect can in turn can lead to an elevation in concentration of triglycerides and cholesterol in the body and also an to an increase in plaques in the arteries. This leads to an increased chance of atherosclerosis, myocardial infarction or cerebral infarction.

[[Image:Atherosclerosis pic.jpg|thumb|400|left|Severe athero sclerosis: This image is a work of the Centers for Disease Control and Prevention, part of the United States Department of Health and Human Services, taken or made during the course of an employee's official duties. As a work of the U.S. federal government, the image is in the public domain.]]

[[Image:Nicotine metabolic.jpg|thumb|left|Nicotine metabolic pathways[http://jpet.aspetjournals.org/cgi/content/full/291/3/1196?ck=nck]]]

<jmol>
<jmolApplet>
<title>Cytochrome P450 2A6 (CYP2A6)</title><color>white</color>
<size>500</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicprotein.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

The above protein (Cytochrome P450 2A6) [http://www.rcsb.org/pdb/static.do?p=explorer/viewers/jmol.jsp]is one of the most important enzymes in human nicotine metabolism.[http://www.cogsci.ecs.soton.ac.uk/cgi/psyc/ptopic?topic=nicotine-addiction ]

[[Image:IR nicotine.JPG|thumb|300|left|IR spectrum for nicotine]]
[[Image:NMRnicotine.JPG|thumb|300|left|NMR spectrum for nicotine {{DOI|10.1016/0022-2364(89)90324-7}}]]

It07:Nicotine

2007-10-23T13:57:24Z

Ty506:

==Nicotine==
<jmol>
<jmolApplet>
<title>Nicotine</title><color>black</color><size>200</size>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>
<jmol><jmolAppletButton><title>Show Nicotine_3-d.pdb in popup window</title><color>cyan</color>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents></jmolAppletButton>
</jmol>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Nicotine.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-[(2S)-1-methyl-2-pyrrolidinyl]Pyridine

|-
| Other names
| Nicotine, L-Nicotine, .beta.-Pyridyl-.alpha.-N-methylpyrrolidine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C10H14N2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN1CCC[S@H]1[C@]2=CC=CN=C2
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 162.23
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 54-11-5
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 1.0068 g/cm³
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 496-497 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 521 K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Nicotine is famously known for being contained in the tabacco products. This compound is also contained in some of the vegetables such as totato, potato and green pepper. This can be proven by carrying out GLC, TLC or CC-mass spectrometry. However the amount of nicotine contained in those vegetables is very small compare to the amount in tabacco product. In those vegitables, upto about 23ppm of nicotine is present. On the other hand, a typical pack of cigarette contains around 1mg of nicotine.

==Synthesis of Nicotine in Tabacco plant==
Nicotine is synthesized from a protein chain called polyamine putrescine at the root of tabacco plant. The nicotine would then be transferred to the shoot of the plant and stored. Polyamine putrescine can be synthesised from ornithine with a presence of ornithine decarboxylate as a catalyst. On this pathway, CO2 is produced as a by-product. Another pathway is to react arginine in a presence of arginine dacarboxylate as a catalyst via forming agmatine. This pathway has three stages of reaction in order to get a desired product. The pathway is shown below.
[[Image:Polyamine_putrescine_production.gif|500px|]]
==Nicotine in the body==

''Entry and lifetime''

Nicotine can get into the body in various ways, the main channels into the body include:
*Skin
*Membranes (including the lining of the lungs and gums)

The diffusion into the body and hence time to get to the brain is quickest through the lungs which has an extremely high diffusion rate due to:
Large surface area, moist lining, extremely thin lining and a good blood supply.

Once in the body nicotine is broken down mainly in the liver by conversion into cotinine through an enzyme pathway. It can also be metabolised in the lungs again to cotinine as well as nicotine oxide which is then excreted, along with remaining nicotine filtered in the kidneys, in the form of urine. These processes amount to the nicotine being reduced in amount by 97% in just 360 minutes after smoking the cigarette. Some people do have a natural genetic defect however which means the enzyme that breaks down nicotine is not as effective as it could be as so the nicotine remains in the blood a lot longer and so reduces the need for a nicotine "top-up" during the day.
[http://health.howstuffworks.com/nicotine2.htm]

''Effects whilst in the body''

Whist nicotine is in the body it has many immediate effects. It has a biphasic nature in which it can either have a positive or negative effect on the general mood of the consumer. The way in which this effect swings is dependant on ''how much'' and ''how often'' nicotine is being given to the body.[http://health.howstuffworks.com/nicotine3.htm]

When nicotine enters the body it causes a sudden release of adrenaline. This adrenaline has the effect of increasing blood flow rate as well as decreasing the size of the arteries. This has an overall effect of increasing blood pressure in the smoker. Adrenaline also lowers the amount of the hormone insulin in the blood which causes to some extent a hypoglycemic effect. This is thought to be a reason for a suppression in appetite prevalent in the smoker because the brain can detect the large amount of glucose and then slows down release of hormones telling the body it needs food.

Also intake of nicotine can result in an increase in LDL(low density lipoproteins) and decrease in HDL (high density lipoproteins), shown by experimental evidence. [http://www.springerlink.com/content/x034836182u68752/fulltext.pdf]

*Control: LDL= 140 mg/dl HDL 48.8 mg/dl
*Nicotine: LDL= 168 mg/dl HDL 27.8 mg/dl

This effect can in turn can lead to an elevation in concentration of triglycerides and cholesterol in the body and also an to an increase in plaques in the arteries. This leads to an increased chance of atherosclerosis, myocardial infarction or cerebral infarction.

[[Image:Atherosclerosis pic.jpg|thumb|400|left|Severe athero sclerosis: This image is a work of the Centers for Disease Control and Prevention, part of the United States Department of Health and Human Services, taken or made during the course of an employee's official duties. As a work of the U.S. federal government, the image is in the public domain.]]

[[Image:Nicotine metabolic.jpg|thumb|left|Nicotine metabolic pathways[http://jpet.aspetjournals.org/cgi/content/full/291/3/1196?ck=nck]]]

<jmol>
<jmolApplet>
<title>Cytochrome P450 2A6 (CYP2A6)</title><color>white</color>
<size>500</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicprotein.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

The above protein (Cytochrome P450 2A6) [http://www.rcsb.org/pdb/static.do?p=explorer/viewers/jmol.jsp]is one of the most important enzymes in human nicotine metabolism.[http://www.cogsci.ecs.soton.ac.uk/cgi/psyc/ptopic?topic=nicotine-addiction ]

File:Polyamine putrescine production.gif

2007-10-23T13:52:31Z

Ty506:

It07:Nicotine

2007-10-23T13:52:06Z

Ty506: /* Nicotine */

==Nicotine==
<jmol>
<jmolApplet>
<title>Nicotine</title><color>black</color><size>200</size>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>
<jmol><jmolAppletButton><title>Show Nicotine_3-d.pdb in popup window</title><color>cyan</color>
<uploadedFileContents>Nicotine_3-d.pdb</uploadedFileContents></jmolAppletButton>
</jmol>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Nicotine.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-[(2S)-1-methyl-2-pyrrolidinyl]Pyridine

|-
| Other names
| Nicotine, L-Nicotine, .beta.-Pyridyl-.alpha.-N-methylpyrrolidine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C10H14N2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN1CCC[S@H]1[C@]2=CC=CN=C2
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 162.23
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 54-11-5
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 1.0068 g/cm³
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 496-497 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 521 K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{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>
|-
|}
{{Chem-Data_Structure}}

Nicotine is famously known for being contained in the tabacco products. This compound is also contained in some of the vegetables such as totato, potato and green pepper. This can be proven by carrying out GLC, TLC or CC-mass spectrometry. However the amount of nicotine contained in those vegetables is very small compare to the amount in tabacco product. In those vegitables, upto about 23ppm of nicotine is present. On the other hand, a typical pack of cigarette contains around 1mg of nicotine.

==Synthesis of Nicotine in Tabacco plant==
Nicotine is synthesized from a protein chain called polyamine putrescine at the root of tabacco plant. The nicotine would then be transferred to the shoot of the plant and stored. Polyamine putrescine can be synthesised from ornithine with a presence of ornithine decarboxylate as a catalyst. On this pathway, CO2 is produced as a by-product. Another pathway is to react arginine in a presence of arginine dacarboxylate as a catalyst via forming agmatine. This pathway has three stages of reaction in order to get a desired product. The pathway is shown below.

==Nicotine in the body==

''Entry and lifetime''

Nicotine can get into the body in various ways, the main channels into the body include:
*Skin
*Membranes (including the lining of the lungs and gums)

The diffusion into the body and hence time to get to the brain is quickest through the lungs which has an extremely high diffusion rate due to:
Large surface area, moist lining, extremely thin lining and a good blood supply.

Once in the body nicotine is broken down mainly in the liver by conversion into cotinine through an enzyme pathway. It can also be metabolised in the lungs again to cotinine as well as nicotine oxide which is then excreted, along with remaining nicotine filtered in the kidneys, in the form of urine. These processes amount to the nicotine being reduced in amount by 97% in just 360 minutes after smoking the cigarette. Some people do have a natural genetic defect however which means the enzyme that breaks down nicotine is not as effective as it could be as so the nicotine remains in the blood a lot longer and so reduces the need for a nicotine "top-up" during the day.
[http://health.howstuffworks.com/nicotine2.htm]

''Effects whilst in the body''

Whist nicotine is in the body it has many immediate effects. It has a biphasic nature in which it can either have a positive or negative effect on the general mood of the consumer. The way in which this effect swings is dependant on ''how much'' and ''how often'' nicotine is being given to the body.[http://health.howstuffworks.com/nicotine3.htm]

When nicotine enters the body it causes a sudden release of adrenaline. This adrenaline has the effect of increasing blood flow rate as well as decreasing the size of the arteries. This has an overall effect of increasing blood pressure in the smoker. Adrenaline also lowers the amount of the hormone insulin in the blood which causes to some extent a hypoglycemic effect. This is thought to be a reason for a suppression in appetite prevalent in the smoker because the brain can detect the large amount of glucose and then slows down release of hormones telling the body it needs food.

Also intake of nicotine can result in an increase in LDL(low density lipoproteins) and decrease in HDL (high density lipoproteins), shown by experimental evidence. [http://www.springerlink.com/content/x034836182u68752/fulltext.pdf]

*Control: LDL= 140 mg/dl HDL 48.8 mg/dl
*Nicotine: LDL= 168 mg/dl HDL 27.8 mg/dl

This effect can in turn can lead to an elevation in concentration of triglycerides and cholesterol in the body and also an to an increase in plaques in the arteries. This leads to an increased chance of atherosclerosis, myocardial infarction or cerebral infarction.

[[Image:Atherosclerosis pic.jpg|thumb|400|left|Severe athero sclerosis: This image is a work of the Centers for Disease Control and Prevention, part of the United States Department of Health and Human Services, taken or made during the course of an employee's official duties. As a work of the U.S. federal government, the image is in the public domain.]]

[[Image:Nicotine metabolic.jpg|thumb|left|Nicotine metabolic pathways[http://jpet.aspetjournals.org/cgi/content/full/291/3/1196?ck=nck]]]

<jmol>
<jmolApplet>
<title>Cytochrome P450 2A6 (CYP2A6)</title><color>white</color>
<size>500</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Nicprotein.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

The above protein (Cytochrome P450 2A6) [http://www.rcsb.org/pdb/static.do?p=explorer/viewers/jmol.jsp]is one of the most important enzymes in human nicotine metabolism.[http://www.cogsci.ecs.soton.ac.uk/cgi/psyc/ptopic?topic=nicotine-addiction ]

It07:Nicotine

2007-10-23T12:46:32Z

2007-10-22T14:52:30Z

Ty506: