140111-52-0

Basic information

• Product Name: (+/-)-EPIBATIDINE
• Synonyms: (+/-)-EPIBATIDINE;(+-)-EPIBATIDINE DIHYDROCHLORIDE SYNTHET IC >99%;(+/-)-EpibatidineHCl;(±)-exo-2-(6-Chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane;7-Azabicyclo(2.2.1)heptane, 2-(6-chloro-3-pyridinyl)-, (1R,2R,4S)-;7-Azabicyclo(2.2.1)heptane, 2-(6-chloro-3-pyridinyl)-, exo-;(2R,4S)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane;2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane
• CAS NO: 140111-52-0
• Molecular Formula: C₁₁H₁₃ClN₂
• Molecular Weight: 208.69
• Product Categories: Miscellaneous Natural Products;Alkaloids;Acetylcholine receptor
• Mol File: 140111-52-0.mol

Chemical Properties

• Boiling Point: 336.7°Cat760mmHg
• Flash Point: 157.4°C
• Appearance: /
• Density: 1.223g/cm³
• Vapor Pressure: 0.00011mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Desiccate at +4°C
• PKA: 10.07±0.40(Predicted)
• CAS DataBase Reference: (+/-)-EPIBATIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-EPIBATIDINE(140111-52-0)
• EPA Substance Registry System: (+/-)-EPIBATIDINE(140111-52-0)

Safety Data

• Hazardous Substances Data: 140111-52-0(Hazardous Substances Data)

Usage

Uses

(+)-Epibatidine has binding affinities for α4β2 and α3β4 nicotinic receptors.

Biological Activity

Very potent nicotinic agonist (K i values are 0.02 and 233 nM for α 4 β 2 and α 7 nicotinic receptors respectively). Analgesic.

InChI:InChI=1/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2/t8-,9+,10+/m1/s1

Upstream product

• 868528-89-6 (1S,2R,4S)-methanesulfonic acid 4-amino-2-(6-chloropyridin-3-yl)cyclohexyl ester 
• 217323-82-5 (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine 
• 159153-42-1 2-chloro-5-trans-(β-nitrovinyl)pyridine 
• 53939-30-3 5-bromo-2-chloropyridine 
• 179321-49-4 N-(tert-butoxycarbonyl)-4-aminocyclohexanone 
• 371247-39-1 3-[(2E)-3-(6-chloro(3-pyridyl))prop-2-enoyl](4R)-4-benzyl-1,3-oxazolidin-2-one 
• 23100-12-1 6-chloronicotinylaldehyde 
• 21543-49-7 2-Chloro-5-hydroxymethylpyridine 
• 162809-79-2 (1R,4S,4aR,8R,8aS)-8-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-4,4a,8,8a-tetrahydro[1,4]methanonaphthalen-5(1H)-one 
• 163517-83-7 (1R,2R,4S)-2-(6-Methoxy-pyridin-3-yl)-7-aza-bicyclo[2.2.1]heptane 
• 249552-19-0 (1S,2R,4S)-4-Azido-2-(6-methoxy-pyridin-3-yl)-cyclohexanol 
• 249552-17-8 5-[(1R,2S,5S)-5-Azido-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-2-methoxy-pyridine 
• 249552-15-6 Methanesulfonic acid (1R,3R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-(6-methoxy-pyridin-3-yl)-cyclohexyl ester 
• 69045-79-0 2-choro-5-iodopyridine 

Relevant articles and documents

Stereoselective Conjugate Addition of the Lithium Anion of N-Allyl Imine to Unsaturated Esters: Application to the Enantiospecific Total Synthesis of (-)-Epibatidine

A regio- and diastereoselective conjugate addition of the lithium anion of N-allyl imine (prepared from allylamine and benzophenone) to α,β-unsaturated esters in good yields is reported. The reaction was general and provided the γ-amino esters resulting from the regioselective C-C bond formation between the α-carbon to the nitrogen in the imine and the β-carbon of the unsaturated ester. Synthetic utility of the formed products was illustrated in the nonracemic total synthesis of the bioactive alkaloid (-)-epibatidine.

Synthesis of (-)-epibatidine

An asymmetric synthesis to the dendrobatid alkaloid (-)-epibatidine has been described, featuring chiral resolution of both optically pure 7-azabicyclo[2.2.1]heptanecarboxylic acid, and subsequent transformations to (-)-epibatidine. The methodology provides a flexible access to various substituted chiral epibatidine analogues.

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

Enantioselective tandem Michael reaction to nitroalkene catalyzed by bifunctional thiourea: Total synthesis of (-)-epibatidine

Successive treatment of γ,δ-unsaturated β-ketoesters and nitroalkenes with a bifunctional thiourea and TMG promoted the tandem Michael addition, giving rise to highly functionalized cyclohexanones in good yields. The three contiguous stereogenic centers o

Enantioselective α-arylation of cyclohexanones with diaryl iodonium salts: Application to the synthesis of (-)-epibatidine

(Chemical Equation Presented) Short cut: Direct asymmetric α-arylation of prochiral ketones has been effected using chiral lithium amide bases and diaryl iodonium salts. The methodology has been employed in a short total synthesis of the alkaloid (-)-epibatidine (see scheme).

LIGANDS FOR NICOTINIC ACETYLCHOLINE RECEPTORS, AND METHODS OF MAKING AND USING THEM

One aspect of the present invention relates to heterocyclic compounds that are ligands for nicotinic acetylcholine receptors. A second aspect of the invention relates to the use of a compound of the invention for modulation of a mammalian nicotinic acetylcholine receptor. The present invention also relates to the use of a compound of the invention for treating a mammal suffering from Alzheimer's disease, Parkinson's disease, dyskinesias, Tourette's syndrome, schizophrenia, attention deficit disorder, anxiety, pain, depression, obsessive compulsive disorder, chemical substance abuse, alcoholism, memory deficit, pseudodementia, Ganser's syndrome, migraine pain, bulimia, obesity, premenstrual syndrome or late luteal phase syndrome, tobacco abuse, post-traumatic syndrome, social phobia, chronic fatigue syndrome, premature ejaculation, erectile difficulty, anorexia nervosa, disorders of sleep, autism, mutism or trichtillomania.

Bifunctional thiourea-catalyzed enantioselective double Michael reaction of γ,δ-unsaturated β-ketoester to nitroalkene: Asymmetric synthesis of (-)-epibatidine

The asymmetric synthesis of 4-nitrocyclohexanone derivatives has been accomplished by enantioselective double Michael additions of γ,δ-unsaturated β-ketoesters to nitroalkenes using a catalytic amount of bifunctional thiourea and TMG. The three contiguous

Synthesis of (-)-epibatidine

matrix presented The synthesis of (-)-epibatidine has been accomplished utilizing a highly exo-selective asymmetric hetero Diels-Alder reaction. The key steps employed to transform the resulting bicycle into the natural product include a fluoride-promoted fragmentation and a Hofmann rearrangement.

A stereocontrolled route to (-)-epibatidine using a chiral cis-cy clohexadiene-1, 4-diol equivalent

A concise diastereo- and enantio-controlled synthesis of (-)-epibatidine, the potent analgesic alkaloid from an Ecuadoran poison frog, Epipedobates tricolor, has been developed starting with a synthetic equivalent of chiral cw-cyclohexadiene-1, 4-diol. Th

Asymmetric total synthesis of (-)-epibatidine

An enantioselective approach to (-)-epibatidine based on asymmetric hetero Diels-Alder cycloaddition with an N-acylnitroso dienophile bearing 8- (2-naphthyl)menthol as a chiral source, wherein π-π stacking interaction between the naphthyl and nitrosocarbonyl groups may contribute to facial control, is described.