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3-(2-Pyrrolidinyl)pyridine

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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
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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
Flash point:
101°C
storage temp. 
2-8°C
solubility 
H2O: 50 mg/mL
form 
liquid
pka
9.09±0.10(Predicted)
Specific Gravity
1.074
color 
yellow
Water Solubility 
Soluble in acetone, chloroform and water (50mg/ml).
Merck 
14,6712
BRN 
81968
Stability:
Hygroscopic, Light Sensitive, Moisture Sensitive
CAS DataBase Reference
5746-86-1(CAS DataBase Reference)
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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
3-10
HazardClass 
6.1
PackingGroup 
III
HS Code 
29399990
Toxicity
LDLo ipr-rat: 6 mg/kg AJEBAK 25,83,47

MSDS

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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 Properties

Colourless Oil

Uses

A metabolite of Nicotine ((N412420). Can catalyze aqueous aldol reactions.

Uses

A metabolite of Nicotine. 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).

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 1137, 1996 DOI: 10.1016/0040-4039(96)00002-0

Safety Profile

Poison by intraperitoneal route.When heated to decomposition it emits very toxic fumesof NOx and HCl. See also NORNICOTINE

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