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
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
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 |
DescriptionSources: www.inchem.org/documents/pims/chemical/nicotine.htmCurator'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/
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443 |
7.9 null [pKi] | ||
Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22148173 |
260.0 nM [Ki] | ||
Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443 |
3.0 µM [Ki] | ||
Target ID: CHEMBL2109238 |
|||
Target ID: Nicotinic acetylcholine receptors |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | NICORETTE Approved UseReduces withdrawal symptoms, including nicotine craving associated with quitting smoking Launch Date1984 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 245.0 |
minor | |||
Page: 245.0 |
minor | |||
Sources: https://molpharm.aspetjournals.org/content/72/3/761 Page: - |
no | |||
Page: - |
yes | |||
Page: 245.0 |
yes | |||
Page: - |
yes | |||
Page: 60.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/17909004/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: - |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22148173
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
Edited
Wed Apr 02 11:21:42 GMT 2025
by
admin
on
Wed Apr 02 11:21:42 GMT 2025
|
Record UNII |
8XAS3GPB3T
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|