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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2.C7H6O3
Molecular Weight 300.3529
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICOTINE SALICYLATE

SMILES

CN1CCC[C@@]1([H])c2cccnc2.c1ccc(c(c1)C(=O)O)O

InChI

InChIKey=AIBWPBUAKCMKNS-PPHPATTJSA-N
InChI=1S/C10H14N2.C7H6O3/c1-12-7-3-5-10(12)9-4-2-6-11-8-9;8-6-4-2-1-3-5(6)7(9)10/h2,4,6,8,10H,3,5,7H2,1H3;1-4,8H,(H,9,10)/t10-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C10H14N2
Molecular Weight 162.2319
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C7H6O3
Molecular Weight 138.121
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Sources: www.inchem.org/documents/pims/chemical/nicotine.htm
Curator's Comment:: 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

442713600000
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
Doses

Doses

DosePopulationAdverse events​
6 mg single, oral
Highest studied dose
Dose: 6 mg
Route: oral
Route: single
Dose: 6 mg
Sources:
healthy, 19 - 49 years
Health Status: healthy
Age Group: 19 - 49 years
Sex: M+F
Sources:
Disc. AE: Bradycardia...
AEs leading to
discontinuation/dose reduction:
Bradycardia (1 patient)
Sources:
4 mg single, oral
Studied dose
Dose: 4 mg
Route: oral
Route: single
Dose: 4 mg
Sources:
healthy, 19 - 49 years
Health Status: healthy
Age Group: 19 - 49 years
Sex: M+F
Sources:
Disc. AE: Allergic dermatitis...
AEs leading to
discontinuation/dose reduction:
Allergic dermatitis (1 patient)
Sources:
6 mg 1 times / hour steady, oral
Highest studied dose
Dose: 6 mg, 1 times / hour
Route: oral
Route: steady
Dose: 6 mg, 1 times / hour
Sources:
healthy, 19 - 50 years
Health Status: healthy
Age Group: 19 - 50 years
Sex: M+F
Sources:
Disc. AE: Hypersensitivity, Nausea...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity (1 patient)
Nausea (1 patient)
Sources:
8 mg 1 times / hour steady, oral
Highest studied dose
Dose: 8 mg, 1 times / hour
Route: oral
Route: steady
Dose: 8 mg, 1 times / hour
Sources:
healthy, 19 - 50 years
Health Status: healthy
Age Group: 19 - 50 years
Sex: M+F
Sources:
Disc. AE: Depression, Nausea...
AEs leading to
discontinuation/dose reduction:
Depression (1 patient)
Nausea (grade 2-3, 2 patients)
Sources:
111 mg single, transdermal
Overdose
Dose: 111 mg
Route: transdermal
Route: single
Dose: 111 mg
Sources:
healthy, 41 years
Health Status: healthy
Age Group: 41 years
Sex: M
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5, 1 patient)
Sources:
84 mg 1 times / day steady, transdermal
Highest studied dose
Dose: 84 mg, 1 times / day
Route: transdermal
Route: steady
Dose: 84 mg, 1 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Nausea...
AEs

AEs

AESignificanceDosePopulation
Bradycardia 1 patient
Disc. AE
6 mg single, oral
Highest studied dose
Dose: 6 mg
Route: oral
Route: single
Dose: 6 mg
Sources:
healthy, 19 - 49 years
Health Status: healthy
Age Group: 19 - 49 years
Sex: M+F
Sources:
Allergic dermatitis 1 patient
Disc. AE
4 mg single, oral
Studied dose
Dose: 4 mg
Route: oral
Route: single
Dose: 4 mg
Sources:
healthy, 19 - 49 years
Health Status: healthy
Age Group: 19 - 49 years
Sex: M+F
Sources:
Hypersensitivity 1 patient
Disc. AE
6 mg 1 times / hour steady, oral
Highest studied dose
Dose: 6 mg, 1 times / hour
Route: oral
Route: steady
Dose: 6 mg, 1 times / hour
Sources:
healthy, 19 - 50 years
Health Status: healthy
Age Group: 19 - 50 years
Sex: M+F
Sources:
Nausea 1 patient
Disc. AE
6 mg 1 times / hour steady, oral
Highest studied dose
Dose: 6 mg, 1 times / hour
Route: oral
Route: steady
Dose: 6 mg, 1 times / hour
Sources:
healthy, 19 - 50 years
Health Status: healthy
Age Group: 19 - 50 years
Sex: M+F
Sources:
Depression 1 patient
Disc. AE
8 mg 1 times / hour steady, oral
Highest studied dose
Dose: 8 mg, 1 times / hour
Route: oral
Route: steady
Dose: 8 mg, 1 times / hour
Sources:
healthy, 19 - 50 years
Health Status: healthy
Age Group: 19 - 50 years
Sex: M+F
Sources:
Nausea grade 2-3, 2 patients
Disc. AE
8 mg 1 times / hour steady, oral
Highest studied dose
Dose: 8 mg, 1 times / hour
Route: oral
Route: steady
Dose: 8 mg, 1 times / hour
Sources:
healthy, 19 - 50 years
Health Status: healthy
Age Group: 19 - 50 years
Sex: M+F
Sources:
Death grade 5, 1 patient
Disc. AE
111 mg single, transdermal
Overdose
Dose: 111 mg
Route: transdermal
Route: single
Dose: 111 mg
Sources:
healthy, 41 years
Health Status: healthy
Age Group: 41 years
Sex: M
Sources:
Nausea
84 mg 1 times / day steady, transdermal
Highest studied dose
Dose: 84 mg, 1 times / day
Route: transdermal
Route: steady
Dose: 84 mg, 1 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Kynurenic acid does not protect against nicotine-induced seizures in mice.
2000 Nov-Dec
Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior.
2000 Oct
Effects of nicotine on the intervertebral disc: an experimental study in rabbits.
2001
Effect of nicotine on fibroblast beta 1 integrin expression and distribution in vitro.
2001 Apr
Contributory role for nornicotine in nicotine neuropharmacology: nornicotine-evoked [3H]dopamine overflow from rat nucleus accumbens slices.
2001 Dec 15
Nicotine inhibits UV-induced activation of the apoptotic pathway.
2001 Dec 15
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
Nicotinic regulation of c-fos and osteopontin expression in human-derived osteoblast-like cells and human trabecular bone organ culture.
2001 Jun
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro.
2001 Jun
An immunotherapeutic program for the treatment of nicotine addiction: hapten design and synthesis.
2001 Jun 15
Inhibition of nicotine-induced seizures in rats by combining vaccination against nicotine with chronic nicotine infusion.
2001 May
Smoking and balance: correlation of nicotine-induced nystagmus and postural body sway.
2001 May 8
Comparison of cytochrome P450 2A6 polymorphism frequencies in Caucasians and African-Americans using a new one-step PCR-RFLP genotyping method.
2001 Nov 30
Chronic ethanol and nicotine interaction on rat tissue antioxidant defense system.
2001 Oct
Nicotine affects the signaling of the death pathway, reducing the response of head and neck cancer cell lines to DNA damaging agents.
2001 Oct
Nicotine induced seizures blocked by mecamylamine and its stereoisomers.
2001 Oct 19
Activation of 5-HT(2C) receptors reduces the locomotor and rewarding effects of nicotine.
2001 Sep
Acute myocardial infarction soon after nicotine replacement therapy.
2001 Sep
Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco.
2001 Sep 21
Fetal and adolescent nicotine administration: effects on CNS serotonergic systems.
2001 Sep 28
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
The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines.
2002 Aug
Alcohol and nicotine reduce cell proliferation and enhance apoptosis in dentate gyrus.
2002 Aug 27
Microsomal N-glucuronidation of nicotine and cotinine: human hepatic interindividual, human intertissue, and interspecies hepatic variation.
2002 Dec
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
Enhancement of cocaine-seeking behavior by repeated nicotine exposure in rats.
2002 Jul
Involvement of human heat shock protein 90 alpha in nicotine-induced apoptosis.
2002 Jul 1
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
Up-regulation of L-type voltage-dependent calcium channels after long term exposure to nicotine in cerebral cortical neurons.
2002 Mar 8
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
Lack of CB1 cannabinoid receptors modifies nicotine behavioural responses, but not nicotine abstinence.
2002 Oct
beta 2 nicotinic acetylcholine receptor subunit modulates protective responses to stress: A receptor basis for sleep-disordered breathing after nicotine exposure.
2002 Oct 1
[Review of current etiopathogenic data of Buerger disease].
2002 Sep
N-glucuronidation of nicotine and cotinine in human: formation of cotinine glucuronide in liver microsomes and lack of catalysis by 10 examined UDP-glucuronosyltransferases.
2002 Sep
Lasting effects of adolescent nicotine exposure on the electroencephalogram, event related potentials, and locomotor activity in the rat.
2002 Sep 20
Lobeline attenuates locomotor stimulation induced by repeated nicotine administration in rats.
2003 Jan
Oral caffeine maintenance potentiates the reinforcing and stimulant subjective effects of intravenous nicotine in cigarette smokers.
2003 Jan
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
A functional role for nicotine in Bcl2 phosphorylation and suppression of apoptosis.
2003 Jan 17
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 Sat Jun 26 16:28:46 UTC 2021
Edited
by admin
on Sat Jun 26 16:28:46 UTC 2021
Record UNII
744Q1CL77H
Record Status Validated (UNII)
Record Version
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Name Type Language
NICOTINE SALICYLATE
MI   WHO-DD  
Systematic Name English
NICOTINE SALICYLATE [MI]
Common Name English
NICOTINE SALICYLATE [WHO-DD]
Common Name English
BENZOIC ACID, 2-HYDROXY-, COMPD. WITH 3-((2S)-1-METHYL-2-PYRROLIDINYL)PYRIDINE (1:1)
Common Name English
NICOTINE MONOSALICYLATE
Systematic Name English
Code System Code Type Description
CAS
29790-52-1
Created by admin on Sat Jun 26 16:28:46 UTC 2021 , Edited by admin on Sat Jun 26 16:28:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
249-852-7
Created by admin on Sat Jun 26 16:28:46 UTC 2021 , Edited by admin on Sat Jun 26 16:28:46 UTC 2021
PRIMARY
EPA CompTox
29790-52-1
Created by admin on Sat Jun 26 16:28:46 UTC 2021 , Edited by admin on Sat Jun 26 16:28:46 UTC 2021
PRIMARY
MERCK INDEX
M7879
Created by admin on Sat Jun 26 16:28:46 UTC 2021 , Edited by admin on Sat Jun 26 16:28:46 UTC 2021
PRIMARY Merck Index
PUBCHEM
20056613
Created by admin on Sat Jun 26 16:28:46 UTC 2021 , Edited by admin on Sat Jun 26 16:28:46 UTC 2021
PRIMARY
FDA UNII
744Q1CL77H
Created by admin on Sat Jun 26 16:28:46 UTC 2021 , Edited by admin on Sat Jun 26 16:28:46 UTC 2021
PRIMARY
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