3-(pyrrolidin-2-yl)pyridine

• ChemBase ID: 12357
• Molecular Formular: C9H12N2
• Molecular Mass: 148.20498
• Monoisotopic Mass: 148.10004839
• SMILES: c1cncc(c1)C1CCCN1
• Canonical SMILES: C1CNC(C1)c1cccnc1
• InChI: InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2
• InChIKey: MYKUKUCHPMASKF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(pyrrolidin-2-yl)pyridine
• IUPAC Traditional name: pyridine, 3-(2-pyrrolin-2-yl); (+-)-nornicotine; 2-(3-pyridyl)pyrrolidine
• Synonyms: DL-Nornicotine; 2-(3-Pyridyl)pyrrolidine; (±)-Nornicotine; 3-(2S)-2-Pyrrolidinylpyridine; 1'-Demethylnicotine; (-)-(S)-Nornicotine; (-)-Nornicotine; (S)-(-)-Nornicotine; (S)-2-(3-Pyridyl)pyrrolidine; Nornicotin; Nornicotine; l-Nornicotine; (S)-Nornicotine; (±)-1'-Demethylnicotine; (±)-3-(2-Pyrrolidinyl)pyridine; (±)-Nornicotine; 2-(3-Pyridinyl)pyrrolidine; 3-(Pyrrolidin-2-yl)pyridine; (RS)-Nornicotine; DL-2-(3-Pyridyl)pyrrolidine; DL-Nornicotine; 3-(2-Pyrrolidinyl)pyridine; (±)-NORNICOTINE; 2-(Pyridin-3-yl)pyrrolidine; 3-(Pyrrolidin-2-yl)pyridine; 3-pyrrolidin-2-ylpyridine; DL-降烟碱

Database IDs

• CAS Number: 494-97-3; 5746-86-1
• MDL Number: MFCD00016913
• Beilstein Number: 81968
• Merck Index: 146712
• PubChem SID: 24897615; 160975664
• PubChem CID: 412

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -2.4496567
• LogD (pH = 7.4): -1.8956487
• Log P: 0.7794868
• Molar Refractivity: 44.3603 cm^3
• Polarizability: 17.60328 Å^3
• Polar Surface Area: 24.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Acetone; Chloroform; DMSO; H2O: soluble50 mg/mL; H2O: soluble50 mg/mL, clear, faintly yellow; Water
• Apperance: Colourless Oil; Pale Yellow to Reddish Brown Oil; yellow liquid
• Boiling Point: 107-108°C/2mm; 107-108°C/2mm; 107-108-2mm°C; 108-110°C/0.5 mm
• Flash Point: 101°C; 101°C(213°F)
• Density: 1.074
• Refractive Index: 1.5400; 1.5490
• Hydrophobicity(logP): 0.437

Safety Information

• Storage Condition: 0°C; Refrigerator; Refrigerator, under inert atmosphere
• Storage Warning: Harmful/Irritant; IRRITANT, IRRITANT-HARMFUL, KEEP COLD
• RTECS: QS6350000; QS6405000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: UN2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 20/21/22-36/37/38; 20/21/22-36/38
• Safety Statements: 26-36/37; 9-26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335; H331-H302-H312-H315-H319
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: mouse ... Chrna1(11435), Chrna7(11441)rat ... Chrna4(25590)

Product Information

• Purity: ≥98% (TLC); ≥98.0% (GC); 95%; 98%
• Empirical Formula (Hill Notation): C9H12N2

DETAILS

MP Biomedicals - 02155954

(3-(2-Pyrrolidinyl)pyridine) Purity: 98%

Sigma Aldrich - N3018

Biochem/physiol Actions
Nicotinic acetylcholine receptor agonist; active metabolite of nicotine; tobacco alkaloid.

Toronto Research Chemicals - N757000

(RS)-Nornicotine is a tobacco alkaloid and the major Nicotine (N412420) metabolite in brain. Nornicotine appears to activate different nAChR subtypes, has a better pharmacokinetic profile, and produces less toxicity than Nicotine. Nornicotine shows a sign

Toronto Research Chemicals - N756995

(S)-Nornicotine is a metabolite of Nicotine (N412420). Can catalyze aqueous aldol reactions.

REFERENCES

• Hecht, S., et al.: Carcinogenesis, 9, 875 (1988)
• Rivenson, A., et al.: Cancer Res., 48, 6912 (1988)
• Hoffmann, D., et al.: Chem. Res. Toxicol., 14, 767 (1988)
• Kool, J., et al.: J. Med. Chem., 49, 3287 (1988)
• Kool, J., et al.: Drug Metab. Dispos., 35, 6
• Wynder, E.L., et al.: Tobacco and Tobacco Smoke, Studies in Experimental Carcinogenesis Academic Press, Inc., New York, 377 (1968)
• Kool, J., et al.: J. Med. Chem., 49, 3287 (1968)
• Kool, J., et al.: Drug Metab. Dispos., 35, 640 (1968)