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An improved synthesis of the enantiomers of bm‐5 and their effects on the central in vivo release of acetylcholine
Author(s) -
Nilsson Björn M.,
De Boer Peter,
Grol Cor. J.,
Hacksell Uli
Publication year - 1992
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530040607
Subject(s) - chemistry , enantiomer , in vivo , acetylcholine , pharmacology , stereochemistry , microbiology and biotechnology , medicine , biology
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. © 1992 Wiley‐Liss, Inc.