An improved synthesis of the enantiomers of BM-5 and their effects on the central in vivo release of acetylcholine.

Abstract:

:Racemic N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5), a putative postsynaptic agonist and presynaptic antagonist at muscarinic receptors, was resolved into the enantiomers by a new method suitable for large scale preparation. The method involves a chemoselective N-debenzylation as the key step. The enantiomers of BM-5 were obtained after six separate steps in 25% overall yield. The ability of the enantiomers to release acetylcholine was evaluated in vivo by use of brain dialysis. (R)-BM-5 was the more potent enantiomer in this assay.

journal_name

Chirality

journal_title

Chirality

authors

Nilsson BM,De Boer P,Grol CJ,Hacksell U

doi

10.1002/chir.530040607

subject

Has Abstract

pub_date

1992-01-01 00:00:00

pages

367-76

issue

6

eissn

0899-0042

issn

1520-636X

journal_volume

4

pub_type

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