Nicotine
C₁₀H₁₄N₂·162.236 g/mol·Pharmaceutical·CID 89594
DrugAlkaloid
The primary addictive compound in tobacco. A nicotinic acetylcholine receptor agonist that triggers dopamine release. Acts as both a stimulant and relaxant depending on dose. Named after Jean Nicot, who introduced tobacco to France.
IUPAC: 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
Also known as: L-Nicotine, 54-11-5, (-)-Nicotine, (S)-Nicotine, (S)-3-(1-methylpyrrolidin-2-yl)pyridine (+14 more)
Molecular Structure
Molecular Propertiesmass · H-bonds · stereo
Molecular Weight
162.230g/mol
Exact Mass
162.115698Da
Monoisotopic Mass
162.115698Da
XLogP
1.2
Polar Surface Area
16.1Ų
Complexity
147
Formal Charge
0
H-Bond Donors
0
H-Bond Acceptors
2
Rotatable Bonds
1
Heavy Atoms
12
Stereo Centers
1
Bond Stereo
0
Drug-Likeness (Lipinski's Rule of Five)
✓ 162.2 g/mol
MW ≤ 500
✓ 1.2
LogP ≤ 5
✓ 0
H-bond donors ≤ 5
✓ 2
H-bond acceptors ≤ 10
Passes all rules — good oral bioavailability predicted
GHS Hazard Classification
Danger
Hazards
H300Fatal if swallowedH310Fatal in contact with skinH330Fatal if inhaledH411Toxic to aquatic life with long lasting effectsH301Toxic if swallowedH315Causes skin irritationH318Causes serious eye damageH400Very toxic to aquatic lifeH341Suspected of causing genetic defectsH361Suspected of damaging fertility or the unborn child
Source: PubChem GHS Classification. Always consult the SDS for handling.
Chemical IdentifiersSMILES · InChI
InChI
InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1
Constituent Elements
Isomers8 compounds with formula C₁₀H₁₄N₂
3-[(2S)-piperidin-2-yl]pyridine
CID 205586 · 162.2 g/mol
3-(1-methylpyrrolidin-2-yl)pyridine
CID 942 · 162.2 g/mol
3-piperidin-2-ylpyridine
CID 2181 · 162.2 g/mol
1-phenylpiperazine
CID 7096 · 162.2 g/mol
(E)-N-methyl-4-pyridin-3-ylbut-3-en-1-amine
CID 5310967 · 162.2 g/mol
N-(2,4-dimethylphenyl)-N'-methylmethanimidamide
CID 36326 · 162.2 g/mol
3-[(2R)-1-methylpyrrolidin-2-yl]pyridine
CID 157672 · 162.2 g/mol
3-[(2R)-piperidin-2-yl]pyridine
CID 641266 · 162.2 g/mol