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Stereoselectivity of Some Muscarinic and Antimuscarinic Agents Related to Oxotremorine

  • R. Dahlbom
  • B. Ringdahl
  • B. Resul
  • D. J. Jenden
Part of the Advances in Behavioral Biology book series (ABBI, volume 30)

Abstract

Oxotremorine, N-(4-pyrrolidino-2-butynyl)-2-pyrrolidone ([1]), is a muscarinic agent equal in potency to acetylcholine (3, 7). Its extraordinary potency is surprising in view of its structural dissimilarity to other muscarinic agents. Whereas most powerful muscarinic agents possess a quaternary trimethyl ammonium group, oxotremorine is a tertiary amine with no N-methyl groups at all. Moreover, it contains an acetylenic bond at the position in the molecule where strong muscarinic agents have an oxygen atom. The structural requirements for muscarinic activity are rather specific and even slight changes in the structure lead to loss of the muscarinic activity or to a change of the type of activity from agonistic to antagonistic (4, 14). The only amino congeners which show agonistic activity of the same order of magnitude as oxotremorine are the dimethylamino ([2]) and the azetidino ([3]) analogs. Compound [3] is in fact the most potent tertiary muscarinic agent known to date (see structures on next page).

Keywords

Tertiary Amine Pharmacological Data Pyrrolidine Ring Opposite Configuration Agonist Binding Site 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Press, New York 1986

Authors and Affiliations

  • R. Dahlbom
    • 1
  • B. Ringdahl
    • 2
  • B. Resul
    • 1
  • D. J. Jenden
    • 2
  1. 1.Department of Organic Pharmaceutical Chemistry, Biomedical CenterUppsala UniversityUppsalaSweden
  2. 2.Department of Pharmacology, School of MedicineUniversity of CaliforniaLos AngelesUSA

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