Cotinine

Title: Cotinine
CAS Registry Number: 486-56-6
CAS Name: 1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone
Additional Names: N-methyl-2-(3-pyridyl)-5-pyrrolidone
Molecular Formula: C10H12N2O
Molecular Weight: 176.22
Percent Composition: C 68.16%, H 6.86%, N 15.90%, O 9.08%
Literature References: Nicotine metabolite first described by Pinner, Arch. Pharm. 231, 378 (1893). Isolated from autoxidized nicotine, nicotine treated with hydrogen peroxide, from nicotine irradiated with ultraviolet light: Frankenburg, Vaitekunas, J. Am. Chem. Soc. 79, 149 (1957).
Properties: Viscous oil, bp6 210-211°. Absorption spectra: Frankenburg, Vaitekunas, loc. cit.
Boiling point: bp6 210-211°
Derivative Type: Fumarate
CAS Registry Number: 5695-98-7
Trademarks: Scotine (Unimed)
Molecular Formula: (C10H12N2O)2.C4H4O4
Molecular Weight: 468.50
Percent Composition: C 61.53%, H 6.02%, N 11.96%, O 20.49%
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Pyrrolidones.
Cotoin Cotton-root Bark Cottonseed Oil Coumachlor Coumafuryl

Cotinine
Cotinine Structural Formulae.png
Systematic (IUPAC) name
(5S)-1-methyl-5-(3-pyridyl)pyrrolidin-2-one
Clinical data
Legal status Prescription only
Routes Oral, Smoked
Pharmacokinetic data
Half-life 20 hours
Identifiers
CAS number 486-56-6 YesY
ATC code None
PubChem CID 854019
ChemSpider 746405 YesY
UNII K5161X06LL YesY
ChEMBL CHEMBL578211 YesY
Chemical data
Formula C10H12N2O 
Mol. mass 176.22 g/mol
 YesY (what is this?)  (verify)

Cotinine is an alkaloid found in tobacco and is also a metabolite of nicotine.[1][2] The word "cotinine" is an anagram of "nicotine". Cotinine is used as a biomarker for exposure to tobacco smoke and has also been sold as an antidepressant under the brand name Scotine.[1]

Similarly to nicotine, cotinine binds to, activates, and desensitizes neuronal nicotinic acetylcholine receptors, though at much lower potency in comparison.[2][3][4][5] It has demonstrated nootropic and antipsychotic-like effects in animal models.[6][7] Direct administration of high levels of cotinine resulted in no significant physiologic, subjective, or performance effects.[8]