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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2.C7H6O3
Molecular Weight 300.3523
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICOTINE SALICYLATE

SMILES

OC(=O)C1=C(O)C=CC=C1.CN2CCC[C@H]2C3=CN=CC=C3

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 C7H6O3
Molecular Weight 138.1207
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
n = 44
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 49 years
Sex: M+F
Population Size: 44
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
n = 44
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 49 years
Sex: M+F
Population Size: 44
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
n = 50
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 50 years
Sex: M+F
Population Size: 50
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
n = 50
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 50 years
Sex: M+F
Population Size: 50
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
n = 1
Health Status: healthy
Condition: adult smoker
Age Group: 41 years
Sex: M
Population Size: 1
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
n = 36
Health Status: healthy
Condition: adult smokers
Age Group: adult
Sex: unknown
Population Size: 36
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
n = 44
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 49 years
Sex: M+F
Population Size: 44
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
n = 44
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 49 years
Sex: M+F
Population Size: 44
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
n = 50
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 50 years
Sex: M+F
Population Size: 50
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
n = 50
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 50 years
Sex: M+F
Population Size: 50
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
n = 50
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 50 years
Sex: M+F
Population Size: 50
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
n = 50
Health Status: healthy
Condition: adult smokers
Age Group: 19 - 50 years
Sex: M+F
Population Size: 50
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
n = 1
Health Status: healthy
Condition: adult smoker
Age Group: 41 years
Sex: M
Population Size: 1
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
n = 36
Health Status: healthy
Condition: adult smokers
Age Group: adult
Sex: unknown
Population Size: 36
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cow's urine poisoning in Nigeria. Experimental observations in mice.
1975 Jun
Nicotine potentiates sulpiride-induced catalepsy in mice.
1998
Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice.
1999 Nov 15
Mimicking gene defects to treat drug dependence.
2000
Analgesic and toxic effects of ABT-594 resemble epibatidine and nicotine in rats.
2000 Apr
Potential role of the alpha4 and alpha6 nicotinic receptor subunits in regulating nicotine-induced seizures.
2000 Apr
Genetic and pharmacological strategies identify a behavioral function of neuronal nicotinic receptors.
2000 Aug
Antioxidant effect of onion oil (Allium cepa. Linn) on the damages induced by nicotine in rats as compared to alpha-tocopherol.
2000 Jul 27
Nicotine switches the form of H(2)O(2)-induced cell death from apoptosis to necrosis in U937 cells.
2000 Jun 1
Regional and cellular induction of nicotine-metabolizing CYP2B1 in rat brain by chronic nicotine treatment.
2000 Jun 15
Neurobiological mechanisms by which nicotine mediates different types of anxiety.
2000 Mar 30
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
Prenatal nicotine exposure is associated with an increase in [125I]epibatidine binding in discrete cortical regions in rats.
2000 Oct
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
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
Variable CYP2A6-mediated nicotine metabolism alters smoking behavior and risk.
2001 Apr
Tolerance to nicotine's effects in the elevated plus-maze and increased anxiety during withdrawal.
2001 Feb
Nicotine self-administration and withdrawal: modulation of anxiety in the social interaction test in rats.
2001 Jan
Relationship between interindividual differences in nicotine metabolism and CYP2A6 genetic polymorphism in humans.
2001 Jan
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
An immunotherapeutic program for the treatment of nicotine addiction: hapten design and synthesis.
2001 Jun 15
A novel single nucleotide polymorphism altering stability and activity of CYP2a6.
2001 Mar 2
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
Chronic ethanol and nicotine interaction on rat tissue antioxidant defense system.
2001 Oct
Acute myocardial infarction soon after nicotine replacement therapy.
2001 Sep
Nornicotine, a nicotine metabolite and tobacco alkaloid: desensitization of nicotinic receptor-stimulated dopamine release from rat striatum.
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
Mechanisms of cytotoxicity of nicotine in human periodontal ligament fibroblast cultures in vitro.
2002 Aug
The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines.
2002 Aug
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
An in vivo pilot study characterizing the new CYP2A6*7, *8, and *10 alleles.
2002 Jan 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
Nicotine potentiation of morphine-induced catalepsy in mice.
2002 May
Nicotine's oxidative and antioxidant properties in CNS.
2002 Nov 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
Lobeline attenuates locomotor stimulation induced by repeated nicotine administration in rats.
2003 Jan
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 Fri Dec 15 16:48:41 GMT 2023
Edited
by admin
on Fri Dec 15 16:48:41 GMT 2023
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 Fri Dec 15 16:48:41 GMT 2023 , Edited by admin on Fri Dec 15 16:48:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
249-852-7
Created by admin on Fri Dec 15 16:48:41 GMT 2023 , Edited by admin on Fri Dec 15 16:48:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID5075319
Created by admin on Fri Dec 15 16:48:41 GMT 2023 , Edited by admin on Fri Dec 15 16:48:41 GMT 2023
PRIMARY
MERCK INDEX
m7879
Created by admin on Fri Dec 15 16:48:41 GMT 2023 , Edited by admin on Fri Dec 15 16:48:41 GMT 2023
PRIMARY Merck Index
PUBCHEM
20056613
Created by admin on Fri Dec 15 16:48:41 GMT 2023 , Edited by admin on Fri Dec 15 16:48:41 GMT 2023
PRIMARY
FDA UNII
744Q1CL77H
Created by admin on Fri Dec 15 16:48:41 GMT 2023 , Edited by admin on Fri Dec 15 16:48:41 GMT 2023
PRIMARY
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