(5S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

• ChemBase ID: 61941
• Molecular Formular: C10H12N2O
• Molecular Mass: 176.21508
• Monoisotopic Mass: 176.09496301
• SMILES: C1CC(=O)N([C@@H]1c1cnccc1)C
• Canonical SMILES: O=C1CC[C@H](N1C)c1cccnc1
• 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
• InChIKey: UIKROCXWUNQSPJ-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
• IUPAC Traditional name: cotinine; (5S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
• Synonyms: Cotinine; (-)-Cotinine; (-)-Cotinine solution; (-)-Cotinine; (S)-1-Methyl-5-(3-pyridyl)-2-pyrrolidinone; S(-)-1-Methyl-5-(3-pyridyl)-2-pyrrolidone; Cotinine; (5S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone; (S)-(-)-1-Methyl-5-(3-pyridiyl)-2-pyrrolidinone; (-)-Cotinine; (S)-Cotinine; NIH 10498; S-(-)-Cotinine; (S)-1-甲基-5-(3-吡啶基)-2-吡咯烷酮; S(-)-1-甲基-5-(3-吡啶基)-2-吡咯烷酮; (-)-可替宁; (-)-可替宁 溶液

Database IDs

• CAS Number: 486-56-6
• EC Number: 200-659-6; 207-634-9
• MDL Number: MFCD00077696
• Beilstein Number: 83099
• PubChem SID: 24892255; 24856726; 24278324; 162027680
• PubChem CID: 854019
• CHEMBL: 578211
• Chemspider ID: 746405
• Unique Ingredient Identifier: K5161X06LL
• Wikipedia Title: Cotinine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.14203912
• LogD (pH = 7.4): 0.20968148
• Log P: 0.21063453
• Molar Refractivity: 49.2805 cm^3
• Polarizability: 19.111326 Å^3
• Polar Surface Area: 33.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Methanol; Water
• Apperance: White to Off-White Low-Melting Solid
• Melting Point: 35-37°C; 40-42 °C(lit.)
• Boiling Point: 145-150°C/3 mm; 250 °C/150 mmHg(lit.)
• Flash Point: 11 °C; 110 °C; 230 °F; 51.8 °F
• Optical Rotation: [α]20/D -21°, c = 1 in ethanol

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: IRRITANT
• RTECS: GN1925500
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1230
• German water hazard class: 1; 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25; 22-36/37/38
• Safety Statements: 26-36; 7-16-36/37-45
• TSCA Listed: false
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H301-H311-H331-H370; H302-H315-H319-H335
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral, Smoked
• Half Life: 20 hours
• Legal Status: Rx-only
• Gene Information: human ... CYP1A2(1544), CYP2A6(1548)mouse ... Cyp2a5(13087)
• Mechanism of Action: Prevents neuron death

Product Information

• Purity: ≥96.0% (TLC); ≥98%; 97%; 98%
• Concentration: 1.0 mg/mL±5% in methanol
• Grade: drug standard; purum
• Suitability: suitable for 1694 per US EPA
• Biological Source: Alkaloid from leaf tobacco (Nicotiana tabacum), also detected in Duboisia hopwoodii (Solanaceae)
• Application(s): Antidepressant; Improves mental function in treating schizophrenia, Alzheimer's and Parkinson's diseases; Psychostimulant
• Empirical Formula (Hill Notation): C10H12N2O

DETAILS

Sigma Aldrich - C5923

Biochem/physiol Actions
尼古丁在人体内的主要代谢物。

Sigma Aldrich - 284718

Biochem/physiol Actions
Major metabolite of nicotine in humans.

Sigma Aldrich - 27699

Biochem/physiol Actions
Major metabolite of nicotine in humans.

Toronto Research Chemicals - C725000

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

REFERENCES

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