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)

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

Toxicity

LDLo ipr-rat: 6 mg/kg AJEBAK 25,83,47

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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

3-(2-Pyrrolidinyl)pyridine(5746-86-1)Related Product Information

• Pyridine
• Polyvinylpyrrolidone
• Pyrrolidine
• Povidone iodine
• N-Methyl-2-pyrrolidone
• N-Vinyl-2-pyrrolidone
• 3-(Pyrrolidin-2-yl)pyridine hydrochloride
• 3-(pyrrolidin-2-yl)pyridine dihydrochloride
• Nicotine
• (+/-)-COTININE-D3
• (-)-COTININE
• (+/-)-NICOTINE-METHYL-D3
• (+)-3-[(2R)-1-Methyl-2-pyrrolidinyl]pyridine,3-[(2R)-1-Methyl-2-pyrrolidinyl]pyridine
• (+/-)-COTININE-D3
• NICOTINE DITARTRATE DIHYDRATE
• (S)-3-(1-METHYL-2-PYRROLIDINYL)PYRIDINE, DI-D-TARTRATE,(S)-3-(1-METHYL-2-PYRROLIDINYL)PYRIDINE TARTRATE SALT
• 4-(2-PYRROLIDINYL)PYRIDINE
• METHYL-2-PYRROLIDONE