5746-86-1

Basic information

• Product Name: 3-(2-Pyrrolidinyl)pyridine
• Synonyms: NORNICOTINE, DL-;(+/-)-NORNICOTINE;(R,S)-NORNICOTINE;(+-)-1’-demethylnicotine;beta-dl-nornicotine;2-[3-PYRIDYL]PYRROLIDINE;2-[3-PYRIDYL]PYRROLIDONE;(+/-)-3-(2-PYRROLIDINYL)PYRIDINE
• CAS NO: 5746-86-1
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.2
• EINECS: 200-659-6
• Product Categories: Alkaloids;pharmacetical;Nicotine Derivatives;Benzenes;Metabolites & Impurities;Aromatics;Chiral Reagents;Heterocycles;Mutagenesis Research Chemicals;Heterocycle-Pyridine series
• Mol File: 5746-86-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: 235-236 °C(Solv: ethanol (64-17-5))
• Boiling Point: 107-108°C 2mm
• Flash Point: 101°C
• Appearance: yellow/liquid
• Density: 1,074 g/cm3
• Vapor Pressure: 0.00702mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL
• PKA: 9.09±0.10(Predicted)
• Water Solubility: Soluble in acetone, chloroform and water (50mg/ml).
• Stability: Hygroscopic, Light Sensitive, Moisture Sensitive
• Merck: 14,6712
• BRN: 81968
• CAS DataBase Reference: 3-(2-Pyrrolidinyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Pyrrolidinyl)pyridine(5746-86-1)
• EPA Substance Registry System: 3-(2-Pyrrolidinyl)pyridine(5746-86-1)

Safety Data

• Hazard Codes: Xn,Xi,T,F
• 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
• Hazardous Substances Data: 5746-86-1(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 5746-86-1 differently. You can refer to the following data:
1. A metabolite of Nicotine ((N412420). Can catalyze aqueous aldol reactions.
2. 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).
3. A 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 Profile

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

InChI:InChI=1/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/p+1/t9-/m0/s1

Upstream product

• 17708-87-1 5-(pyridin-3-yl)pyrrolidin-2-one 
• 532-12-7 Myosmine 
• 1308392-26-8 1-(butenyl)-3-(pyridine-3-carbonyl)pyrrolidin-2-one 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 1076199-53-5 2-pyridin-3-ylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 123-75-1 pyrrolidine 
• 60573-68-4 3-pyridyllithium 
• 36740-10-0 4-oxo-4-(pyridin-3-yl)butanenitrile 
• 59578-62-0 4-(3-pyridyl)-4-oxobutanol 
• 76014-80-7 4-Oxo-1-(3-pyridyl)-1-butanone 
• 626-55-1 3-Bromopyridine 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 59-67-6 nicotinic acid 
• 1125-96-8 myosmine 

Downstream Products

• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 494-97-3 nornicotine 
• 7076-23-5 (+)-nornicotine 
• 3000-81-5 N'-formylnornicotine 
• 59-67-6 nicotinic acid 
• 54-11-5 nicotin 
• 1346133-08-1 3-chloro-4-[4-[ [ (2S)-2-(3-pyridyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide 
• 1346133-07-0 3-chloro-4-[4-[ [2-(3-pyridyl)pyrrolidin-1-yl]methyl]phenoxy]benzamide 
• 1346133-06-9 6-[4-[ [2-(3-pyridyl)pyrrolidin-1-yl]methyl]phenoxy]pyridine-3-carboxamide 
• 343244-02-0 1-[[7-(3,4-Dichloro-phenyl)-4,7-dihydro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]carbonyl]-2-(3-pyridinyl)pyrrolidine 
• 1185502-92-4 C₂₇H₃₀F₃N₅O 
• 459449-08-2 2-Methyl-5-[2-(2-pyridin-3-yl-pyrrolidin-1-yl)-ethoxy]-1H-indole-3-carboxylic acid benzyl ester 
• 86900-39-2 3-(1-ethylpyrrolidin-2-yl)pyridine 
• 110-86-1 pyridine 

Relevant articles and documents

Preparation method of nicotine and intermediate thereof

The invention relates to a preparation method of nicotine and an intermediate thereof, wherein the intermediate has a structure as shown in a formula (II), X1, X2 and X3 are respectively and independently CR2R3, R1 is a C1-6 alkyl group, and R2 and R3 are each independently H or a C1-6 alkyl group. According to the invention, the preparation method of the nicotine and the intermediate thereof has the advantages of simple operation, mild reaction conditions, easily available raw materials, and high conversion rate, can effectively reduce the production cost of the nicotine, and has the potential of industrial production, and each reaction can be directly post-fed through simple post-treatment basically.

Synthesis method of racemic nicotine

The invention discloses a synthesis method of racemic nicotine. The method comprises the following steps: S1, introducing 3-(1-pyrrolin-2-yl) pyridine, a solvent and hydrogen into a first fixed bed reactor filled with a metal catalyst, and cooling at an outlet to obtain a crude product 3-(1-pyrrolidin-2-yl) pyridine mixed solution; and S2, taking the crude product 3-(1-pyrrolidine-2-yl) pyridine and a methylation reagent to pass through a solid second fixed bed reactor filled with a solid base catalyst, and cooling at an outlet to obtain racemic nicotine. The continuous flow fixed bed method is used for preparing racemic nicotine so that the continuity of production is realized, the reaction time is shortened, the reaction operation is simplified, the solvent consumption is reduced, the discharge of waste water and waste liquid is reduced, and the catalyst is convenient to recover.

PREPARATION OF RACEMIC NICOTINE BY REACTION OF ETHYL NICOTINATE WITH N-VINYLPYRROLIDONE IN THE PRESENCE OF AN ALCOHOLATE BASE AND SUBSEQUENT PROCESS STEPS

The present invention relates to a method of preparing racemic nicotine comprising: (i) reacting ethyl nicotinate and N-vinylpyrrolidone in the presence of an alcoholate base to 3-nicotinoyl-1-vinylpyrrolidin-2-one; (ii) reacting the 3-nicotinoyl-1-vinylpyrrolidin-2-one with an acid to myosmine; (iii) reducing the myosmine to nornicotine using a reducing agent; and (iv) methylating the nornicotine to obtain the racemic nicotine.