Structure via PubChem · Public domain (PubChem)
cotinine
Sign in to saveAlso known as (S)-Cotinine, (S)-(-)-Cotinine, (S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone, (5S)-1-methyl-5-(3-pyridyl)-2-pyrrolidinone, (5S)-1-methyl-5-(3-pyridyl)pyrrolidin-2-one, (5S)-1-methyl-5-(3-pyridyl)-2-pyrrolidone, (5S)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one, (5S)-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one
Cotinine is an alkaloid found in tobacco and is also the predominant metabolite of nicotine, typically used as a biomarker for exposure to tobacco smoke. Cotinine is currently being studied as a treatment for depression, post-traumatic stress disorder (PTSD), schizophrenia, Alzheimer's disease and Parkinson's disease. Cotinine was developed as an antidepressant as a fumaric acid salt, cotinine fumarate, to be sold under the brand name Scotine, but it was never marketed.
In the Vinony graph
Vinony's link graph records 805 inbound references to cotinine, and connects out to passive smoking, nicotinic acetylcholine receptor and allosteric modulator.
It is catalogued under topics including 3-Pyridyl compounds, Alkaloids found in Nicotiana and Biomarkers.
Vinony links it to 20 Wikipedia language editions.
Chemical data
- Formula
- C10H12N2O
- Molecular weight
- 176.21 g/mol
- IUPAC name
- (5S)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one
- SMILES
- CN1[C@@H](CCC1=O)C2=CN=CC=C2
- InChIKey
- UIKROCXWUNQSPJ-VIFPVBQESA-N
- XLogP
- -0.3
- Polar surface area
- 33.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- nicotine dependence
via ChEMBL · EBI
Research
7,841 papers- [Cotinine].Nihon rinsho. Japanese journal of clinical medicine · 1999
- [Cotinine--metabolism, application as a biomarker and the effects on the organism].Postepy higieny i medycyny doswiadczalnej (Online) · 2012
- Overview of Cotinine Cutoff Values for Smoking Status Classification.International journal of environmental research and public health · 2016
- Cotinine: a potential new therapeutic agent against Alzheimer's disease.CNS neuroscience & therapeutics · 2012
- Cotinine as a biomarker of environmental tobacco smoke exposure.Epidemiologic reviews · 1996
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 176.094963
Show 6 more facts
- chemical formula
- C₁₀H₁₂N₂O
- canonical SMILES
- CN1C(CCC1=O)C2=CN=CC=C2
- isomeric SMILES
- CN1[C@@H](CCC1=O)C2=CN=CC=C2
- found in taxon
- Duboisia hopwoodii
- World Health Organisation international non-proprietary name
- cotinine
- Commons category
- Cotinine
via Wikidata · CC0
~6 min read
Encyclopedic overview
4 sectionsContents
- Pharmacology
- Pharmacokinetics
- Detection in body fluids
- References
Cotinine is an alkaloid found in tobacco and is also the predominant metabolite of nicotine, typically used as a biomarker for exposure to tobacco smoke. Cotinine is currently being studied as a treatment for depression, post-traumatic stress disorder (PTSD), schizophrenia, Alzheimer's disease and Parkinson's disease. Cotinine was developed as an antidepressant as a fumaric acid salt, cotinine fumarate, to be sold under the brand name Scotine, but it was never marketed.
Similarly to nicotine, cotinine binds to, activates, and desensitizes neuronal nicotinic acetylcholine receptors, though at much lower potency in comparison. It has demonstrated nootropic and antipsychotic-like effects in animal models. Cotinine treatment has also been shown to reduce depression, anxiety, and fear-related behavior as well as memory impairment in animal models of depression, post-traumatic stress disorder, and Alzheimer's disease. Nonetheless, treatment with cotinine in humans was reported to have no significant physiologic, subjective, or performance effects in one study, though others suggest that this may not be the case.
Excerpted from Wikipedia’s “cotinine” article, available under the CC BY-SA 4.0 licence.