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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

CNS Active
3828
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.

Originator

Pinner, A.
3
Sources: DOI: 10.1002/cber.18930260165

Approval Year

Unknown
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Nicotinic acetylcholine receptors alpha3/alpha6/beta2 (Saimiri sciureus)
Agonist
2662
 236.0 µM [EC50]
Target ID: Nicotinic acetylcholine receptors alpha4/beta2 (Saimiri sciureus)
Agonist
2662
 495.0 µM [EC50]
Agonist
2662
 175.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Preclinical
Unknown

Approved Use

Unknown
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
Palliative
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Determination of coumarin metabolism in Turkish population.
2001 Apr
Factors associated with discrepancies between self-reports on cigarette smoking and measured serum cotinine levels among persons aged 17 years or older: Third National Health and Nutrition Examination Survey, 1988-1994.
2001 Apr 15
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
Rationale and design of the LURIC study--a resource for functional genomics, pharmacogenomics and long-term prognosis of cardiovascular disease.
2001 Feb
[Smoking in adolescents, saliva cotinine concentrations and respiratory disease].
2001 Feb
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results.
2001 Feb
Tobacco hypersensitivity and environmental tobacco smoke exposure in a pediatric population.
2001 Jan
Pharmacokinetics of nicotine in healthy elderly people.
2001 Jan
Chronic maternal smoking and cord blood amino acid and enzyme levels at term.
2001 Jan
Does passive smoking increase the frequency of health service contacts in children with asthma?
2001 Jan
Effects of nicotine and cotinine on porcine arterial endothelial cell function.
2001 Jan
Nicotine yield from machine-smoked cigarettes and nicotine intakes in smokers: evidence from a representative population survey.
2001 Jan 17
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
Prevalence of nicotine consumption in drug deaths.
2001 Jul 15
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
CYP1B1 expression in human lung.
2001 Jun
Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography.
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
Exposure to ethanol and nicotine during the brain growth spurt: spatial DMP performance in male rats.
2001 Mar
The effect of stopping smoking on cervical Langerhans' cells and lymphocytes.
2001 Mar
Science is changing! 300 chemicals and each chemical will have a fingerprint.
2001 May
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

Patents

JP2006504654A
10
JP2010229131A
3
JPS5531005A
3

Sample Use Guides

In Vivo Use Guide
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 Wed Jul 05 23:06:52 UTC 2023
Edited
by admin
on Wed Jul 05 23:06:52 UTC 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 Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
Code System Code Type Description
DRUG CENTRAL
737
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
WIKIPEDIA
COTININE
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
HSDB
7805
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
EPA CompTox
DTXSID1047576
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
PUBCHEM
854019
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-634-9
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
MESH
D003367
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
CAS
486-56-6
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
SMS_ID
100000084251
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
CHEBI
68641
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
FDA UNII
K5161X06LL
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
INN
1625
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
RS_ITEM_NUM
1463348
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
MERCK INDEX
M3811
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C70941
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL578211
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
EVMPD
SUB06811MIG
Created by admin on Wed Jul 05 23:06:52 UTC 2023 , Edited by admin on Wed Jul 05 23:06:52 UTC 2023
PRIMARY
Related Record Type Details
Structure of COTININE FUMARATE
SALT/SOLVATE -> PARENT
Structure of COTININE TARTRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of NICOTINE
PARENT -> METABOLITE
Mediator Substance is AOX1
Related Record Type Details
Structure of NICOTINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of NICOTINE
PARENT -> IMPURITY
Structure of NICOTINE BITARTRATE
PARENT -> IMPURITY
Related Record Type Details
Structure of COTININE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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