| Identification | Back Directory | [Name]
(-)-COTININE | [CAS]
486-56-6 | [Synonyms]
COTININE
NIH 10498
L-COTININE
(-)-COTININE
COTININE(RG)
S-(-)-COTININE
(-)-Cotinine,98%
(s)-2-pyrrolidinon
(?)-Cotinine solution
Nicotine Related Compound C
(-)COTININE METHANOL SOLUTION
CREATINE ETHYL ESTER ANALYSIS KIT
S-(-)-Cotinine (1.0 Mg/ML in Methanol)
1-METHYL-5-[3-PYRIDYL]-2-PYRROLIDINONE
1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone
1-methyl-5-pyridin-3-yl-pyrrolidin-2-one
S(-)-1-METHYL-5-(3-PYRIDYL)-2-PYRROLIDONE
[S]-1-METHYL-5-[3-PYRIDYL]-2-PYRROLIDINONE
(5S)-1-Methyl-5-(3-pyridyl)pyrrolidin-2-one
(s)-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone
(5S)-1-Methyl-5-(3-pyridinyl)pyrrolidin-2-one
(5S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone
S-(-)-1-Methyl-5-(pyridin-3yl)pyrrolidin-2-one
(S)-(-)-1-METHYL-5-(3-PYRIDIYL)-2-PYRROLIDINONE
2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (S)-
(5S)-(-)-1-Methyl-5-(pyridin-3-yl)pyrrolidin-2-one
CHROMIUM POTASSIUM SULFATE*DODECAHYDRATE ACS REAGENT
Inchi=1/C10H12N2o/C1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/H2-3,6-7,9H,4-5H2,1h
(S)-1-Methyl-5-(3-pyridyl)-2-pyrrolidinone, S(-)-1-Methyl-5-(3-pyridyl)-2-pyrrolidone
()-Cotinine,(S)-1-Methyl-5-(3-pyridyl)-2-pyrrolidinone, S()-1-Methyl-5-(3-pyridyl)-2-pyrrolidone
(5S)-(-)-1-Methyl-5-(pyridin-3-yl)pyrrolidin-2-one, 3-[(2S)-(-)-1-Methyl-5-oxopyrrolidin-2-yl]pyridine, (5S)-(-)-1-Methyl-2-oxo-5-(pyridin-3-yl)pyrrolidine | [EINECS(EC#)]
207-634-9 | [Molecular Formula]
C10H12N2O | [MDL Number]
MFCD00077696 | [MOL File]
486-56-6.mol | [Molecular Weight]
176.22 |
| Chemical Properties | Back Directory | [Appearance]
Colourless to Light Brown Solid | [Melting point ]
40-42 °C(lit.)
| [alpha ]
[α]D20 -18～-22° (c=1, C2H5OH) | [Boiling point ]
250 °C150 mm Hg(lit.)
| [density ]
1.1102 (rough estimate) | [refractive index ]
1.7110 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
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 | [Stability:]
Stable. Incompatible with strong oxidizing agents. May be heat sensitive-store cold. | [Optical Rotation]
[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 | [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 | [InChIKey]
UIKROCXWUNQSPJ-VIFPVBQESA-N | [SMILES]
CN1[C@@H](CCC1=O)c2cccnc2 | [EPA Substance Registry System]
Cotinine (486-56-6) |
| Hazard Information | Back Directory | [Chemical Properties]
Colourless to Light Brown Solid | [Uses]
A major metabolite of Nicotine (N412450) in humans. Carcinogen. | [Uses]
A major metabolite of nicotine in humans | [Uses]
antidepressant | [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. | [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 . | [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. | [Synthesis Reference(s)]
Synthetic Communications, 18, p. 1331, 1988 DOI: 10.1080/00397918808078800 | [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. |
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