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HomeProduct name list(-)-COTININE

(-)-COTININE

Synonym(s):(−)-Cotinine;(S)-1-Methyl-5-(3-pyridyl)-2-pyrrolidinone;S(−)-1-Methyl-5-(3-pyridyl)-2-pyrrolidone

  • CAS NO.:486-56-6
  • Empirical Formula: C10H12N2O
  • Molecular Weight: 176.22
  • MDL number: MFCD00077696
  • EINECS: 207-634-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
(-)-COTININE Structural

What is (-)-COTININE?

Description

Cotinine is the major metabolite of nicotine. In the liver, nicotine is rapidly metabolized to cotinine (70–80%) by CYP2A6 and to nornicotine (5%) by CYP2A6 and CYP2B6. With a half-life about 10-fold longer than that of nicotine (15–19 h for cotinine versus 2–3 h for nicotine), cotinine induces plasma concentrations of 1–3 mM in smokers. After administration to rats, cotinine levels in the brain reach fourfold those of nicotine at 4 h following injection. Cotinine is not biotransformed in the brain, allowing accumulation of this substance to levels greater than that of nicotine.
Like nicotine, cotinine is able to induce dopamine release in smokers and in superfused rat striatal slices in a dose- and calcium-dependent manner via the nicotinic receptors, but only at concentrations higher than those normally seen in smokers. Indeed, administration of cotinine to smokers at levels 10-fold that is seen following smoking had no observable effect, suggesting that cotinine is not neuroactive at doses found in smokers. However, cotinine also acts as an inhibitor for nicotine binding in rat brain via desensitization of the nicotinic receptor.

Chemical properties

Colourless to Light Brown Solid

The Uses of (-)-COTININE

(-)-Cotinine is used to activate a subpopulation of α3/ α6β2 nAChRs in monkey striatum. It 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.

The Uses of (-)-COTININE

A major metabolite of nicotine in humans

The Uses of (-)-COTININE

A major metabolite of Nicotine (N412450) in humans. Carcinogen.

The Uses of (-)-COTININE

antidepressant

What are the applications of Application

(?)-Cotinine is a major nicotine metabolite

Definition

ChEBI: An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.

Synthesis Reference(s)

Synthetic Communications, 18, p. 1331, 1988 DOI: 10.1080/00397918808078800

Biological Activity

Major metabolite of nicotine. Shown to activate a subpopulation of α 3/ α 6 β 2 nAChRs in monkey striatum. Displays cognition-enhancing effects in vivo .

Environmental Fate

Cotinine stimulates dopamine release in the nigrostriatal pathway by activating nicotinic acetylcholine receptors. However, its lower EC50 prevents significant activation of this pathway in smokers.

Toxicity evaluation

Cotinine has a vapor pressure of 3.8×10-4mmHg at 25 °C. Cotinine will be photochemically degraded with a half-life of 15 h. In sediment, cotinine is completely degraded to carbon dioxide within 72 h. It is not expected to bioaccumulate in aquatic organisms.

Properties of (-)-COTININE

Melting point: 40-42 °C(lit.)
Boiling point: 250 °C150 mm Hg(lit.)
alpha  [α]D20 -18~-22° (c=1, C2H5OH)
Density  1.1102 (rough estimate)
refractive index  1.7110 (estimate)
Flash point: >230 °F
storage temp.  Sealed in dry,2-8°C
solubility  Chloroform (Sparingly), DMSO (Slightly), Methanol (Sparingly)
form  Solid
pka 4.72±0.12(Predicted)
color  Colourless to Very Dark Orange Oil
optical activity [α]/D -21±2°, c = 1 in ethanol
Water Solubility  Not miscible or difficult to mix in water. Soluble in dimethyl sulfoxide (100 mM), ethanol (50 mg/ml, yielding a clear, faint yellow to yellow solution), methanol and chloroform.
Merck  14,2553
BRN  83099
Stability: Stable. Incompatible with strong oxidizing agents. May be heat sensitive - store cold.
EPA Substance Registry System Cotinine (486-56-6)

Safety information for (-)-COTININE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for (-)-COTININE

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