Drugs derived from cannabinoids. 2. Basic esters of nitrogen and carbocyclic analogs.

Journal Article (Journal Article)

Various basic esters of nitrogen (2) and carbocyclic (3 and 4) analogs of cannabinoids were synthesized using dicyclohexylcarbodiimide in methylene chloride. The compounds in the three series werw studied in selected pharmacological tests in mice, rats, dogs, and cats. It was shown that making the basic ester from the phenol retains biological activity and can lead to a greater selectivity of action, particularly the antinociceptive activity. The most interesting esters were 5, 6, 10, and 14 in the nitrogen analogs series and 19 and 20 in the carbocyclic series. Compound 5 was more potent than codeine in the writhing, hot-plate, and tail-flick tests and is at present undergoing clinical testing. Compound 20 was very potent in the mouse audiogenic seizure test and is of interest as an anticovulsant agent.

Full Text

Duke Authors

Cited Authors

  • Razdan, RK; Terris, BZ; Pars, HG; Plotnikoff, NP; Dodge, PW; Dren, AT; Kyncl, J; Somani, P

Published Date

  • April 1, 1976

Published In

Volume / Issue

  • 19 / 4

Start / End Page

  • 454 - 461

PubMed ID

  • 817020

Electronic International Standard Serial Number (EISSN)

  • 1520-4804

International Standard Serial Number (ISSN)

  • 0022-2623

Digital Object Identifier (DOI)

  • 10.1021/jm00226a002


  • eng