ChemicalBook Product Catalog Natural Products Alkaloids 3-(2-Pyrrolidinyl)pyridine

3-(2-Pyrrolidinyl)pyridine

3-(2-Pyrrolidinyl)pyridine Basic information
Product Name:3-(2-Pyrrolidinyl)pyridine
Synonyms:NORNICOTINE, DL-;(+/-)-NORNICOTINE;(R,S)-NORNICOTINE;(+-)-1’-demethylnicotine;beta-dl-nornicotine;3-PYRROLIDIN-2-YLPYRIDINE;DL-NORNICOTINE;2-[3-PYRIDYL]PYRROLIDINE
CAS:5746-86-1
MF:C9H12N2
MW:148.21
EINECS:637-353-0
Product Categories:Metabolites & Impurities;Aromatics;pharmacetical;Chiral Reagents;Heterocycles;Mutagenesis Research Chemicals;Alkaloids;Nicotine Derivatives;Benzenes;Heterocycle-Pyridine series
Mol File:5746-86-1.mol
3-(2-Pyrrolidinyl)pyridine Structure
3-(2-Pyrrolidinyl)pyridine Chemical Properties
Melting point 235-236 °C(Solv: ethanol (64-17-5))
Boiling point 107-108°C 2mm
density 1,074 g/cm3
refractive index 1.54
Fp 101°C
storage temp. 2-8°C
solubility H2O: 50 mg/mL
pka9.09±0.10(Predicted)
form liquid
color yellow
Specific Gravity1.074
Water Solubility Soluble in acetone, chloroform and water (50mg/ml).
Merck 14,6712
BRN 81968
Stability:Hygroscopic, Light Sensitive, Moisture Sensitive
CAS DataBase Reference5746-86-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi,T,F
Risk Statements 20/21/22-36/37/38-39/23/24/25-23/24/25-11
Safety Statements 26-36/37-45-16-7
RIDADR 2810
WGK Germany 3
RTECS QS6350000
F 3-10
HazardClass 6.1
PackingGroup III
HS Code 29399990
ToxicityLDLo ipr-rat: 6 mg/kg AJEBAK 25,83,47
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
3-(2-Pyrrolidinyl)pyridine Usage And Synthesis
Description(±)-Nornicotine is a metabolite of nicotine that acts as a neuronal nicotinic acetylcholine receptor (nAChR) agonist. The α6 and α7 subunit-containing neuronal nAChRs are particularly responsive to nornicotine with EC50 values of approximately 4 and 17 μM, respectively, when expressed in Xenopus oocytes. Nornicotine promotes cell migration and destabilizes cell-cell junctions in an endothelial cell line. It is generally thought to be free from abuse potential, but it has been self-administered by rats. It can be detected in urine.
Chemical PropertiesColourless Oil
UsesA metabolite of Nicotine ((N412420). Can catalyze aqueous aldol reactions.
Uses

3-(2-Pyrrolidinyl)pyridine 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 significant analgesic activity. Nicotine USP Related Compound F (3-(pyrrolidine-2-yl)pyridine).

UsesA metabolite of Nicotine. Can catalyze aqueous aldol reactions
Synthesis Reference(s)Tetrahedron Letters, 37, p. 1137, 1996 DOI: 10.1016/0040-4039(96)00002-0
Safety ProfilePoison by intraperitoneal route.When heated to decomposition it emits very toxic fumesof NOx and HCl. See also NORNICOTINE
3-(2-Pyrrolidinyl)pyridine Preparation Products And Raw materials
Preparation ProductsLY-2795050-->NORNICOTINE, DL-(RG)-->(+/-)-NICOTINE
Povidone iodine N-Methyl-2-pyrrolidone N-Vinyl-2-pyrrolidone (+/-)-NICOTINE-D3 SALICYLATE SALT Polyvinylpyrrolidone 3-(2-Pyrrolidinyl)pyridine NICOTINE, D [N-METHYL 14C] NICOTINE, L-, [N-METHYL-3H] (+/-)-COTININE-D3 METHYL-2-PYRROLIDONE (-)-COTININE rac trans-4-Cotininecarboxylic Acid 3-(N-METHYL-2-PYRROLIDINYL)PYRIDINE SULFATE Pyridine NICOTINE SALICYLATE (+/-)-NICOTINE-METHYL-D3 (+)-NICOTINE (+)-DI-P-TOLUOYLTARTRATE SALT Pyrrolidine
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