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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2
Molecular Weight 162.2316
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICOTINE

SMILES

CN1CCC[C@H]1C2=CN=CC=C2

InChI

InChIKey=SNICXCGAKADSCV-JTQLQIEISA-N
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

HIDE SMILES / InChI

Molecular Formula C10H14N2
Molecular Weight 162.2316
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Nicotine is a natural alkaloid obtained from the dried leaves and stems of the nightshade family of pants, such as Nicotiana tabacum and Nicotiana rustica, where it occurs in concentrations of 0.5-8%. Cigarette tobacco varies in its nicotine content, but common blends contain 15-25 mg per cigarette, with a current trend towards lower levels. Nicotine is highly addictive substance, it exhibits a stimulant effect when adsorbed at 2 mg. Administration of higher doses could be harmful. Action of nicotine is mediated by nicotinic cholinergic receptors. Nicotine binds to the interface between two subunits of the receptors, opens the channel and allows the entry of sodium or calcium. The principal mediator of nicotine dependence is α4β2 nicotine receptor.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.9 null [pKi]
260.0 nM [Ki]
3.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
NICORETTE

Cmax

ValueDoseCo-administeredAnalytePopulation
12 ng/mL
1 mg single, nasal
NICOTINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
6 ng × h/mL
1 mg single, nasal
NICOTINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3 min
1 mg single, nasal
NICOTINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
95%
1 mg single, nasal
NICOTINE plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Reduces withdrawal symptoms, including nicotine craving associated with quitting smoking, nicotine is available as a chewing gum, and is administered according to a schedule at doses 2-4 mg once every 2-4 hours. Nicotine is also available as a transdermal patch.
Route of Administration: Other
In Vitro Use Guide
Functional activity of nicotine against hα4β2 nicotinic receptors was evaluated using the 86Rb+ ion flux assay in SH-EP1 cells, expressing hα4β2. The 86Rb+ efflux was measured using the “flip-plate” technique. Nicotine activated 86Rb+ efflux with EC50 of 290 nM.
Substance Class Chemical
Record UNII
6M3C89ZY6R
Record Status Validated (UNII)
Record Version