U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N2O
Molecular Weight 176.2151
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COTININE

SMILES

CN1[C@@H](CCC1=O)C2=CN=CC=C2

InChI

InChIKey=UIKROCXWUNQSPJ-VIFPVBQESA-N
InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H12N2O
Molecular Weight 176.2151
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://cancercontrol.cancer.gov/brp/tcrb/monographs/7/m7_7.pdf | https://www.ncbi.nlm.nih.gov/pubmed/26972290

Cotinine is a product formed after the chemical nicotine enters the body. Measuring cotinine in people’s blood is the most reliable way to determine exposure to nicotine for both smokers and nonsmokers exposed to environmental tobacco smoke. Cotinine is safe, non-addictive and has pharmacokinetic properties adequate for therapeutic use. Research has shown that cotinine has antipsychotic, anxiolytic, and antidepressant properties and modulates the serotonergic, cholinergic and dopaminergic systems. Cotinine behaves as a positive allosteric modulator of the nicotinic acetylcholine receptors and has anti-inflammatory effects. Cotinine is under investigation as an agent for the treatment of depression, PTSD, schizophrenia, Alzheimer's disease and Parkinson's disease.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.

Originator

Sources: DOI: 10.1002/cber.18930260165

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Nicotinic acetylcholine receptors alpha3/alpha6/beta2 (Saimiri sciureus)
236.0 µM [EC50]
Target ID: Nicotinic acetylcholine receptors alpha4/beta2 (Saimiri sciureus)
495.0 µM [EC50]
175.0 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Urine test for the assessment of smoking status.
2001
The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age.
2001
[Prevalence of cannabis and tobacco use in patients attending a methadone center. Evaluation by urinary biomarkers].
2001 Apr
Determination of coumarin metabolism in Turkish population.
2001 Apr
Accuracy of self-reported cigarette smoking among pregnant women in the 1990s.
2001 Apr
Infant exposure to environmental tobacco smoke: a prevalence study in Australia.
2001 Apr
Rebuttal to: Passive smoking adversely affects the haemostasis/fibrinolytic parameters in healthy non-smoker offspring of healthy smokers.
2001 Apr
Effectiveness of a high school smoking cessation program.
2001 Apr
Novel liquid chromatographic-tandem mass spectrometric methods using silica columns and aqueous-organic mobile phases for quantitative analysis of polar ionic analytes in biological fluids.
2001 Apr 25
Osteogenic protein-1 overcomes the inhibitory effect of nicotine on posterolateral lumbar fusion.
2001 Aug 1
Smoking reduction in smokers compliant to a smoking cessation trial with nicotine patch.
2001 Feb
Assessment of prenatal smoke exposure by determining nicotine and its metabolites in maternal and neonatal urine.
2001 Jan
High-performance liquid chromatographic determination of pyridostigmine bromide, nicotine, and their metabolites in rat plasma and urine.
2001 Jul
A simple high-pressure liquid chromatography cotinine assay: validation of smoking status in pregnant women.
2001 Jul
Single-dose pharmacokinetics of bupropion in adolescents: effects of smoking status and gender.
2001 Jul
Oltipraz chemoprevention trial in Qidong, People's Republic of China: results of urine genotoxicity assays as related to smoking habits.
2001 Jul
Saliva cotinine as indicator of cigarette smoking in pregnant women.
2001 Jul
Trends in the smoking habits of young adults with diabetes.
2001 Jul
Correlation between nicotine-induced inhibition of hematopoiesis and decreased CD44 expression on bone marrow stromal cells.
2001 Jul 15
Prevalence of nicotine consumption in drug deaths.
2001 Jul 15
The effect of tobacco smoke, nicotine, and cotinine on the mutagenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL).
2001 Jul 25
Nicotine produces selective degeneration in the medial habenula and fasciculus retroflexus.
2001 Jul 6
An integrated approach to prenatal smoking cessation interventions.
2001 Jul-Aug
Nicotine metabolism and CYP2A6 allele frequencies in Koreans.
2001 Jun
Gender differences in autoantibodies to oxidative DNA base damage in cigarette smokers.
2001 Jun
Individual differences in urinary cotinine levels in Japanese smokers: relation to genetic polymorphism of drug-metabolizing enzymes.
2001 Jun
Biomarkers of polycyclic aromatic hydrocarbon-DNA damage and cigarette smoke exposures in paired maternal and newborn blood samples as a measure of differential susceptibility.
2001 Jun
Dose-years as an improved index of cumulative tobacco smoke exposure.
2001 Jun
Heavily smoking women who cannot quit in pregnancy: evidence of pharmacokinetic predisposition.
2001 Jun
CYP1B1 expression in human lung.
2001 Jun
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro.
2001 Jun
Effect of cigarette smoking on levels of bioavailable testosterone in healthy men.
2001 Jun
Regional cerebral blood flow effects of nicotine in overnight abstinent smokers.
2001 Jun 1
Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography.
2001 Jun 15
A prospective study of insulin-like growth factor-I, IGF-binding proteins-1, -2 and -3 and lung cancer risk in women.
2001 Jun 15
Cluster randomised controlled trial to compare three methods of promoting secondary prevention of coronary heart disease in primary care.
2001 Jun 2
Cost effectiveness of computer tailored and non-tailored smoking cessation letters in general practice: randomised controlled trial.
2001 Jun 9
Cotinine binding to nicotinic acetylcholine receptors in bovine chromaffin cell and rat brain membranes.
2001 May
CDC unveils body burden.
2001 May
Lung cancer due to passive smoking--a review.
2001 May
Household smoking and bronchial hyperresponsiveness in children with asthma.
2001 May
Effects of smoking cessation and nicotine substitution on systemic eicosanoid production in man.
2001 May
Preparation of pyridine-N-glucuronides of tobacco-specific nitrosamines.
2001 May
Science is changing! 300 chemicals and each chemical will have a fingerprint.
2001 May
Metropolitan home living conditions associated with indoor endotoxin levels.
2001 May
Measures of maternal tobacco exposure and infant birth weight at term.
2001 May 15
Drop in cotinine levels signals less smoke exposure, experts say.
2001 May 2
Bacterial mutagenicity of some tobacco aromatic nitrogen bases and their mixtures.
2001 May 31
Systemic nicotine exposure in tobacco harvesters.
2001 May-Jun
Personal exposures to PM(2.5) and polycyclic aromatic hydrocarbons and their relationship to environmental tobacco smoke at two locations in Greece.
2001 May-Jun
Patents

Sample Use Guides

Mouse: 5 mg/kg during 37 days
Route of Administration: Oral
In Vitro Use Guide
High (190 ug/ml) concentration of Cotinine significantly altered all the sperm kinetic variables in relation to the time of incubation (forward motility, velocity, linearity and beat cross-frequency). Despite the impact seen on these parameters, there was still 30% forward motility after 24 h of incubation.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:37:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:37:35 GMT 2023
Record UNII
K5161X06LL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COTININE
HSDB   INN   MI  
INN  
Official Name English
COTININE [MI]
Common Name English
1-METHYL-5-(3-PYRIDINYL)-2-PYRROLIDINONE
Systematic Name English
2-PYRROLIDINONE, 1-METHYL-5-(3-PYRIDINYL)-, (S)-
Systematic Name English
NICOTINE RELATED COMPOUND C [USP-RS]
Common Name English
NICOTINE IMPURITY C [EP IMPURITY]
Common Name English
NICOTINE RESINATE IMPURITY C [EP IMPURITY]
Common Name English
(-)-1-METHYL-5-(3-PYRIDYL)-2-PYRROLIDINONE
Systematic Name English
NICOTINE RELATED COMPOUND C [USP IMPURITY]
Common Name English
N-METHYL-2-(3-PYRIDYL)-5-PYRROLIDONE
Systematic Name English
cotinine [INN]
Common Name English
NICOTINE DITARTRATE DIHYDRATE IMPURITY C [EP IMPURITY]
Common Name English
COTININE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C73579
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
Code System Code Type Description
DRUG CENTRAL
737
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
WIKIPEDIA
COTININE
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
HSDB
7805
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID1047576
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
PUBCHEM
854019
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-634-9
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
MESH
D003367
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
CAS
486-56-6
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
SMS_ID
100000084251
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
CHEBI
68641
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
FDA UNII
K5161X06LL
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
INN
1625
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
RS_ITEM_NUM
1463348
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
MERCK INDEX
m3811
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C70941
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL578211
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
EVMPD
SUB06811MIG
Created by admin on Fri Dec 15 15:37:36 GMT 2023 , Edited by admin on Fri Dec 15 15:37:36 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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Mediator Substance is AOX1
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ACTIVE MOIETY
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