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Details

Stereochemistry EPIMERIC
Molecular Formula C10H14N2.C3H6O3
Molecular Weight 252.3095
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICOTINE LACTATE

SMILES

CC(O)C(O)=O.CN1CCC[C@H]1C2=CN=CC=C2

InChI

InChIKey=VWTHFJXLFGINSW-PPHPATTJSA-N
InChI=1S/C10H14N2.C3H6O3/c1-12-7-3-5-10(12)9-4-2-6-11-8-9;1-2(4)3(5)6/h2,4,6,8,10H,3,5,7H2,1H3;2,4H,1H3,(H,5,6)/t10-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C3H6O3
Molecular Weight 90.0779
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Description
Sources: www.inchem.org/documents/pims/chemical/nicotine.htm
Curator's Comment: description was created based on several sources, including https://cancercontrol.cancer.gov/brp/tcrb/monographs/1/index.html https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2928221/

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
NICORETTE

Approved Use

Reduces withdrawal symptoms, including nicotine craving associated with quitting smoking

Launch Date

1984
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
12 ng/mL
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NICOTINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6 ng × h/mL
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NICOTINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 min
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NICOTINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
95%
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NICOTINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Modulation of phosphatidylinositol turnover on central nicotinic receptors.
1997 Jul
Nicotine potentiates sulpiride-induced catalepsy in mice.
1998
[Treatment outcome in tobacco dependence after nicotine replacement therapy and group therapy].
1999
Inducible, heterologous expression of human alpha7-nicotinic acetylcholine receptors in a native nicotinic receptor-null human clonal line.
1999 Apr 17
Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant.
1999 Feb 5
Transdermal nicotine mimics the smoking-induced endothelial dysfunction.
2000 Aug
Genetic and pharmacological strategies identify a behavioral function of neuronal nicotinic receptors.
2000 Aug
Chick optic lobe contains a developmentally regulated alpha2alpha5beta2 nicotinic receptor subtype.
2000 Aug
Regional and cellular induction of nicotine-metabolizing CYP2B1 in rat brain by chronic nicotine treatment.
2000 Jun 15
[A comparative study of the central H-cholinergic-blocking and NMDA-blocking actions of MK-801, memantin, amantadine, pyrilen and IEM-1754 in experiments on intact rats].
2000 Mar-Apr
Evidence that nicotinic alpha(7) receptors are not involved in the hyperlocomotor and rewarding effects of nicotine.
2000 Sep
Nicotine is a potent blocker of the cardiac A-type K(+) channels. Effects on cloned Kv4.3 channels and native transient outward current.
2000 Sep 5
Chronic nicotine exposure reduces N-methyl-D-aspartate receptor-mediated damage in the hippocampus without altering calcium accumulation or extrusion: evidence of calbindin-D28K overexpression.
2001
Nicotine inhibits UV-induced activation of the apoptotic pathway.
2001 Dec 15
Nicotine self-administration and withdrawal: modulation of anxiety in the social interaction test in rats.
2001 Jan
Cardiovascular effects of transdermal nicotine in mildly hypertensive smokers.
2001 Jul
Nicotine produces selective degeneration in the medial habenula and fasciculus retroflexus.
2001 Jul 6
Nicotine metabolism and CYP2A6 allele frequencies in Koreans.
2001 Jun
Comparison of cytochrome P450 2A6 polymorphism frequencies in Caucasians and African-Americans using a new one-step PCR-RFLP genotyping method.
2001 Nov 30
Nicotine affects the signaling of the death pathway, reducing the response of head and neck cancer cell lines to DNA damaging agents.
2001 Oct
Activation of 5-HT(2C) receptors reduces the locomotor and rewarding effects of nicotine.
2001 Sep
Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco.
2001 Sep 21
Molecular orbital calculations and nicotine metabolism: a rationale for experimentally observed metabolite ratios.
2002
Induction of CYP1A1 and CYP1A2 expressions by prototypic and atypical inducers in the human lung.
2002 Apr 8
Alcohol and nicotine reduce cell proliferation and enhance apoptosis in dentate gyrus.
2002 Aug 27
Genetic variation in CYP2A6-mediated nicotine metabolism alters smoking behavior.
2002 Feb
Increased sensitivity to nicotine-induced seizures in mice heterozygous for the L250T mutation in the alpha7 nicotinic acetylcholine receptor.
2002 Feb 11
Absence of alpha7-containing neuronal nicotinic acetylcholine receptors does not prevent nicotine-induced seizures.
2002 Jan 31
Enhancement of cocaine-seeking behavior by repeated nicotine exposure in rats.
2002 Jul
The selectively bred high alcohol sensitivity (HAS) and low alcohol sensitivity (LAS) rats differ in sensitivity to nicotine.
2002 Jun
N-n-alkylnicotinium analogs, a novel class of nicotinic receptor antagonist: inhibition of S(-)-nicotine-evoked [(3)H]dopamine overflow from superfused rat striatal slices.
2002 Jun
Increased sensitivity to nicotine-induced seizures in mice expressing the L250T alpha 7 nicotinic acetylcholine receptor mutation.
2002 Mar
Effects of whole deletion of CYP2A6 on nicotine metabolism in humans.
2002 May
Nicotine potentiation of morphine-induced catalepsy in mice.
2002 May
Genetic polymorphisms in human CYP2A6 gene causing impaired nicotine metabolism.
2002 Nov
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Nicotinic acetylcholine receptors and the regulation of neuronal signalling.
2004 Jun
Nicotine addiction.
2010 Jun 17
How much nicotine kills a human? Tracing back the generally accepted lethal dose to dubious self-experiments in the nineteenth century.
2014 Jan
Patents

Sample Use Guides

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
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
Created
by admin
on Wed Apr 02 11:21:42 GMT 2025
Edited
by admin
on Wed Apr 02 11:21:42 GMT 2025
Record UNII
8XAS3GPB3T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LACTIC ACID, COMPD. WITH NICOTINE
Preferred Name English
NICOTINE LACTATE
Common Name English
PROPANOIC ACID, 2-HYDROXY-, COMPD. WITH 3-((2S)-1-METHYL-2-PYRROLIDINYL)PYRIDINE (1:1)
Common Name English
LACTIC ACID, COMPOUND WITH (S)-3-(1-METHYLPYRROLIDIN-2-YL)PYRIDINE(1:1)
Systematic Name English
Code System Code Type Description
CAS
15197-02-1
Created by admin on Wed Apr 02 11:21:43 GMT 2025 , Edited by admin on Wed Apr 02 11:21:43 GMT 2025
NON-SPECIFIC STOICHIOMETRY
CAS
14474-00-1
Created by admin on Wed Apr 02 11:21:43 GMT 2025 , Edited by admin on Wed Apr 02 11:21:43 GMT 2025
PRIMARY
EPA CompTox
DTXSID80932395
Created by admin on Wed Apr 02 11:21:43 GMT 2025 , Edited by admin on Wed Apr 02 11:21:43 GMT 2025
PRIMARY
FDA UNII
8XAS3GPB3T
Created by admin on Wed Apr 02 11:21:43 GMT 2025 , Edited by admin on Wed Apr 02 11:21:43 GMT 2025
PRIMARY
PUBCHEM
44153120
Created by admin on Wed Apr 02 11:21:43 GMT 2025 , Edited by admin on Wed Apr 02 11:21:43 GMT 2025
PRIMARY
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