ContaminantDB: Nicotine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (22)XML

Record Information

Version

1.0

Creation Date

2009-06-01 22:04:25 UTC

Update Date

2026-05-14 16:24:32 UTC

Accession Number

CHEM000712

Identification

Common Name

Nicotine

Class

Small Molecule

Description

Nicotine is only found in individuals that have used or taken this drug. It is a highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke. [PubChem]Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed up of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible the euphoric and addictive properties of nicotine.Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing influx of sodium, causing depolarization of the cell, which activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar.

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anti-Craving Agent
Appetite Depressant
Autonomic Agent
Central Nervous System Agent
Drug
Food Toxin
Ganglionic Stimulant
Household Toxin
Human Neurotoxin
Insecticide
Metabolite
Natural Compound
Nicotinic Agonist
Organic Compound
PFAS
Pesticide
Phytotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-3-(1-Methyl-2-pyrrolidinyl)pyridine	Kegg
(+-)-Nicotine	HMDB
(R,S)-Nicotine	HMDB
(RS)-Nicotine	HMDB
Nicotin	HMDB
Nikotin	HMDB
L-Nicotine	HMDB
Nicotine alkaloid	HMDB

Chemical Formula

C₁₀H₁₄N₂

Average Molecular Mass

162.232 g/mol

Monoisotopic Mass

162.116 g/mol

CAS Registry Number

54-11-5

IUPAC Name

3-[(2S)-1-methylpyrrolidin-2-yl]pyridine

Traditional Name

nicotine

SMILES

CN1CCCC1C1=CN=CC=C1

InChI Identifier

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

InChI Key

SNICXCGAKADSCV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyrrolidinylpyridines

Direct Parent

Pyrrolidinylpyridines

Alternative Parents

Substituents

Pyrrolidinylpyridine
Alkaloid or derivatives
Aralkylamine
N-alkylpyrrolidine
Heteroaromatic compound
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrrolidine alkaloid (CHEBI:18723 )
pyridine alkaloid (CHEBI:18723 )
N-alkylpyrrolidine (CHEBI:18723 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-79°C
Boiling Point	247°C
Solubility	1E+006 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	93.3 g/L	ALOGPS
logP	0.87	ALOGPS
logP	1.16	ChemAxon
logS	-0.24	ALOGPS
pKa (Strongest Basic)	8.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.66 m³·mol⁻¹	ChemAxon
Polarizability	18.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9800000000-e2da519a4fcd1232adad	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-03di-1900000000-857425bc16c796bf0300	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-7900000000-a874f46eadd0eba440d0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03di-3900000000-e16953a6ae58e6dbf414	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03e9-0900000000-2136090ec9c3fd3eafad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03e9-0900000000-2653170118c64eb33be4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-bf73c660c9fef052a3e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-317ad58e8bc4c3092420	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053u-9400000000-ea4895202e26a55d8a9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ed813017157d07798ea2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1900000000-02ba66ba693d048f19ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-442e757e1da476d883af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-f3be6a7a178ad995ccc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-2900000000-8e7cb15e223d1455b015	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01po-9700000000-c940c6d9f118d7bd2e57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-4900000000-f46a350ab4b3f0a0cf22	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-6900000000-04b0561e6d267153f2a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-5fccbd13ba25ff51dd04	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (5) ; Inhalation (5) Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.

Mechanism of Toxicity

Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed up of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible the euphoric and addictive properties of nicotine. Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing influx of sodium, causing depolarization of the cell, which activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar.

Metabolism

As nicotine enters the body, it is distributed quickly through the bloodstream and can cross the blood-brain barrier. On average it takes about seven seconds for the substance to reach the brain when inhaled. The half life of nicotine in the body is around two hours. Nicotine is metabolized in the liver by cytochrome P450 enzymes (mostly CYP2A6, and also by CYP2B6). A major metabolite is cotinine. Other primary metabolites include nicotine N'-oxide, nornicotine, nicotine isomethonium ion, 2-hydroxynicotine and nicotine glucuronide. (5) Route of Elimination: About 10% of the nicotine absorbed is excreted unchanged in the urine. Half Life: Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours

Toxicity Values

LD50: 140 mg/kg (Dermal, Rat) LD50: 25 mg/kg (Subcutaneous, Rat) LD50: 5900 ug/kg (Intraperitoneal, Mouse) LD50: 2.8 mg/kg (Intravenous, Rat) (13) LD50: 24 mg/kg (Oral, Mouse) (11)

Lethal Dose

40 to 60 mg (<1 mg/kg) for an adult human. (12)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Nicotine is highly toxic alkaloid found in the nightshade family of plants (Solanaceae). (5) NICOTROL Inhaler is indicated as an aid to smoking cessation for the relief of nicotine withdrawal symptoms. NICOTROL Inhaler therapy is recommended for use as part of a comprehensive behavioral smoking cessation program. It is used for the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.

Minimum Risk Level

Not Available

Health Effects

Nicotine has mood-altering effects that may include relaxation, sharpness, calmness, and alertness. It may act as a stimulant or sedative/pain killer, depending on the dosage. (5)

Symptoms

Symptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension.

Treatment

Other supportive measures include diazepam or barbiturates for seizures, atropine for excessive bronchial secretions or diarrhea, respiratory support for respiratory failure, and vigorous fluid support for hypotension and cardiovascular collapse. (8)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0243542

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Charles G. Chavdarian, Edward B. Sanders, “Process for the preparation of optically active nicotine analogs.” U.S. Patent US4321387, issued September, 1959.

MSDS

Link

General References

1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.

Nicotine (CHEM000712)

Structure for CHEM000712: Nicotine