Cotinine

Cotinine

Clinical data
Routes of administration	Oral, Smoked, Insufflation
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Biological half-life	20 hours
Identifiers
IUPAC name (5S)-1-methyl-5-(3-pyridyl)pyrrolidin-2-one
CAS Number	486-56-6 Y
PubChem CID	854019
ChemSpider	746405 Y
UNII	K5161X06LL
ChEMBL	CHEMBL578211 Y
ECHA InfoCard	100.006.941
Chemical and physical data
Formula	C10H12N2O
Molar mass	176.22 g/mol
3D model (Jmol)	Interactive image
SMILES O=C2N(C)[C@H](c1cnccc1)CC2
InChI 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 Y Key:UIKROCXWUNQSPJ-VIFPVBQESA-N Y

Cotinine is an alkaloid found in tobacco and is also the predominant metabolite of nicotine. The word "cotinine" is an anagram of "nicotine". Cotinine is used as a biomarker for exposure to tobacco smoke. Cotinine is currently being studied as a treatment for depression, 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, PTSD, 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.

Because cotinine is the main metabolite to nicotine and has been shown to be pharmacologically active, it has been suggested that some of nicotine's effects in the nervous system may be mediated by cotinine and/or complex interactions with nicotine itself.