182137-57-1

Usage

Type of Compound

Chemical compound

Application

Used in scientific research as a competitive antagonist for GABAA receptors

Derivative of

Bicuculline, a potent convulsant alkaloid

Source of Bicuculline

Primarily found in plants of the buckwheat family

Utilization

Commonly used to study the role and function of GABAA receptors in the central nervous system

Relevance

Particularly in relation to epilepsy and other neurological disorders

Laboratory Use

Often used in laboratory settings to manipulate and investigate GABAA receptor function

Additional Studies

Has been used in studies exploring the mechanisms of drug addiction and dependence

Upstream product

• 182137-51-5 7-(tert-butyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]heptane benzyl ester 

Downstream Products

• 441353-52-2 Boc-Ach-OH 

Relevant academic research and scientific papers

Chirospecific synthesis of conformationally constrained 7-azabicycloheptane amino acids by transannular alkylation

A new method is reported for the chirospecific preparation of optically pure 1-carboxy-7-azabicycloheptane amino acids for the generation of peptidomimetics as conformational probes. The method allows for the multigram preparation of these amino acid analogues through use of a thiolactam sulfide contraction and a transannular alkylation sequence as the key C-C bond-forming steps, starting from L-glutamic acid. The route provides access to two common intermediates, 7-(benzyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]-3-heptane and (1S,4R)-7-(benzyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]-3-heptanon e tert-butyl ester, for elaboration to symmetrical and chiral amino acid homologues, respectively. Decarboxylation of the C-1 carboxy unit of the latter intermediate also demonstrated the applicability of the method for a short, chirospecific preparation of a (+)-epibatidine intermediate, (1S,4R)-7-(tert-butyloxycarbonyl)-1-carboxy-7-azabicyclo[2.2.1]3-hepta none.