(-)-Cotinine CAS: 486-56-6
MF: C10H12N2O
MW: 176.22
A major nicotine metabolite.

(-)-Cotinine (CAS 486-56-6)

(-)-Cotinine | CAS 486-56-6 is rated 5.0 out of 5 by 1.
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Synonym: (S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone
Application: A major nicotine metabolite
CAS Number: 486-56-6
Purity: ≥98%
Molecular Weight: 176.22
Molecular Formula: C10H12N2O
* Refer to Certificate of Analysis for lot specific data (including water content).
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(-)-Cotinine is a major nicotine metabolite. (-)-Cotinine has been shown to activate a subpopulation of α3/ α6β2 nAChRs in monkey striatum. It has a long pharmacological half-life (15-19 hours) compared to that of nicotine (2-3 hours). (-)-Cotinine binds nicotinic- and muscarinic-type acetylcholine receptors with minimal receptor desensitization and demonstrates antipsychotic drug-like properties in behavioral models, neuroprotective properties in neurodegenerative disease models, and enhances attention in a delayed matching-to-sample task.


References

Buccafusco and Terry (2003) The potential role of cotinine in the cognitive and neuroprotective actions of nicotine. Life sci. 72 2931. Terry et al (2005) Cotinine, a neuroactive metabolite of nicotine: potential for treating disorders of impaired cognition. CNS Drug Rev. 11 229. O'Leary et al (2008) Cotinine selectively activates a subpopulation of a3/a6b2 nicotinic receptors in monkey striatum. 325 646.

Physical State :
Low-Melting Solid
Solubility :
Soluble in water (partly), DMSO (100 mM), ethanol (50 mg/ml, yielding a clear, faint yellow to yellow solution), methanol, and chloroform.
Storage :
Desiccate at -20° C
Melting Point :
40-42° C (lit.)
Boiling Point :
250° C (lit.) at 150 mmHg
Refractive Index :
n20D 1.56 (Predicted)
Optical Activity :
α20/D -20°, c = 1 in ethanol; α20/D -20.3°, c = 1 in methanol
IC50 :
Plasmodium falciparum 3D7 : IC50 = 12.59 µM; Cytochrome P450 2A5: IC50 = 1.5 mM (mouse); CYP1A2: IC50 = 5.4 mM (human); CYP2A6: IC50 = 35 mM (human)
pK Values :
pKb: 4.72 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
GN1925500
PubChem CID :
21907
Merck Index :
14: 2553
MDL Number :
MFCD00077696
EC Number :
207-634-9
Beilstein Registry :
83099
SMILES :
CN1[[email protected]](CCC1=O)C2=CN=CC=C2

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Certificate of Analysis

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(-)-Cotinine  Product Citations

See how others have used (-)-Cotinine. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 25373622  Jacobson, GA. et al. 2014. Biomarkers. 19: 679-83.

PMID: # 25263812  Rodríguez-Álvarez, T. et al. 2014. Anal. Chem. 86: 10274-81.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from Smith Smith, D. et al. (PubMed 26372012) measured (-)-Cotinine, a major metabolite of nicotine, serum levels of pregnant C57BL/6J mice exposed to 2.4% nicotine in propylene glycol (PG) or 0% nicotine/PG once a day from gestational day 15 until delivery. After delivery, offspring and mothers were exposed to E-cigarette vapors for an additional 14 days from postnatal day 2 through 16. -SCBT Publication Review
Date published: 2015-03-18
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