152378-30-8

Basic information

• Product Name: (-)-epibatidine-l-tartrate
• Synonyms: 7-Azabicyclo[2.2.1]heptane,2-(6-chloro-3-pyridinyl)-, (1S-exo)-; (-)-Epibatidine; (1S,2S,4R)-Epibatidine;(1S-exo)-2-(6-Chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane; CMI 477
• CAS NO: 152378-30-8
• Molecular Formula: C11H13ClN2.C4H6O6
• Molecular Weight: 358.776
• Mol File: 152378-30-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 61-62 °C
• Boiling Point: 336.7°Cat760mmHg
• Flash Point: 157.4°C
• Appearance: /
• Density: 1.223g/cm³
• Storage Temp.: −20°C
• PKA: 10.07±0.40(Predicted)
• CAS DataBase Reference: (-)-epibatidine-l-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-epibatidine-l-tartrate(152378-30-8)
• EPA Substance Registry System: (-)-epibatidine-l-tartrate(152378-30-8)

Safety Data

• Hazard Codes: T+
• Statements: 27/28
• Safety Statements: 28-36/37-45
• RIDADR: UN 2811 6.1/PG 1
• Hazardous Substances Data: 152378-30-8(Hazardous Substances Data)

Usage

General Description

(-)-Epibatidine-l-tartrate is a chemical compound that is a synthetic analog of epibatidine, a potent neurotoxin found in the skin of the Ecuadorian frog Epipedobates tricolor. It acts as a selective agonist for nicotinic acetylcholine receptors in the central nervous system, specifically at the α4β2 subtype. (-)-epibatidine-l-tartrate has received interest in scientific research for its potential medical applications, particularly in the field of pain management. However, it is also known to be highly toxic and can be lethal if ingested, making it important to handle and use with extreme caution. Overall, (-)-epibatidine-l-tartrate is a complex and potent compound that has both potential therapeutic benefits and significant risks associated with its use.

Upstream product

• 159153-42-1 2-chloro-5-trans-(β-nitrovinyl)pyridine 
• 875553-03-0 (4S,5R,6S)-6-(6-chloropyridin-3-yl)-2-hydroxy-4-methoxy-5-nitrocyclohex-1-enecarboxylic acid allyl ester 
• 875553-02-9 allyl (4E)-2-[(1R)-1-(6-chloropyridin-3-yl)-2-nitroethyl]-5-methoxy-3-oxo-4-pentenoate 
• 151885-30-2 (-)-N-(Trifluoroacetyl)epibatidine 
• 765-87-7 cyclohexane-1,2-dione 
• 21543-49-7 2-Chloro-5-hydroxymethylpyridine 
• 23100-12-1 6-chloronicotinylaldehyde 
• 5326-23-8 6-Chloro-3-pyridinecarboxylic acid 
• 154905-37-0 (1S,2R,4R)-2-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 163513-99-3 (1S,4R)-7-(tert-Butoxycarbonyl)-7-azabicyclo<2.2.1>heptan-2-one 
• 152533-46-5 (±)-tert-butyl-(1SR,2RS,4RS)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 154905-38-1 (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol 

Relevant articles and documents

The amino thiourea-catalyzed asymmetric nucleophilic reactions

Bifunctional amino thiourea-catalyzed asymmetric additions of several nucleophiles into electron-deficient unsaturated compounds such as nitroolefins, α,β-unsaturated imides, imines, and azodicarboxylates are described. We discovered that bifunctional thi

7-azabicyclo[2.2.1]-heptane and -heptene derivatives as cholinergic receptor ligands

7-Azabicyclo[2.2.1]-heptane and -heptene derivatives are disclosed that can be administered to a mammal, including a human, to treat disorders associated with a decrease or increase in cholinergic activity.

Process for the preparation of epibatidine

A novel 6-chloro-3-vinyl-pyridine of formula STR1 where X represents -H, -SO2 Ph, -CO2 Et, -COCH3 and -CHO; which is used for the synthesis of Epibatidine of formula STR2 by reacting said 6-chloro-3-vinyl pyridine with N-1-alkyl-2,5-di(trialkyl silyl) pyrrolidine of formula STR3 to obtain N-alkyl Epibatidine which is hydrogenated to obtain the Epibatidine.