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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:: 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

4.42713604E11
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
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
Inhibitory effects of ginseng total saponin on nicotine-induced hyperactivity, reverse tolerance and dopamine receptor supersensitivity.
1999 Aug
Pharmacological characterization of nicotine-induced seizures in mice.
1999 Dec
Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant.
1999 Feb 5
Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice.
1999 Nov 15
Chronic nicotine pretreatment protects the blood-brain barrier against nicotine-induced seizures in the rat.
1999 Sep
CYP2A6 genetic polymorphisms and liver microsomal coumarin and nicotine oxidation activities in Japanese and Caucasians.
2000 Jan
Nicotinic receptor function: new perspectives from knockout mice.
2000 Jun
Involvement of 5-hydroxytryptamine(1A) receptors in nicotine-induced tail tremor in rats.
2000 Nov 10
Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior.
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
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
Formation of the quaternary ammonium-linked glucuronide of nicotine in human liver microsomes: identification and stereoselectivity in the kinetics.
2001 Dec
Tolerance to nicotine's effects in the elevated plus-maze and increased anxiety during withdrawal.
2001 Feb
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
An immunotherapeutic program for the treatment of nicotine addiction: hapten design and synthesis.
2001 Jun 15
Chronic ethanol and nicotine interaction on rat tissue antioxidant defense system.
2001 Oct
Mechanisms of cytotoxicity of nicotine in human periodontal ligament fibroblast cultures in vitro.
2002 Aug
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
An in vivo pilot study characterizing the new CYP2A6*7, *8, and *10 alleles.
2002 Jan 11
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
Nicotine potentiation of morphine-induced catalepsy in mice.
2002 May
Genetic polymorphisms in human CYP2A6 gene causing impaired nicotine metabolism.
2002 Nov
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
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
  • Download
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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