Development of agonists, partial agonists and antagonists in the Delta(8)-tetrahydrocannabinol series

P J Crocker, B Saha, W J Ryan, J L Wiley, B R Martin, R A Ross, R G Pertwee, R K Razdan

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18 Citations (Scopus)

Abstract

Synthetic sequences were developed (Schemes 1 to 6) for the syntheses of various Delta(8)-THC analogs with either a rigid acetylenic linkage or a cis-double bond in different positions in the side chain. Various alkyne and cis-ene-Delta(8)-THC analogs were also synthesized carrying a functional group such as a cyano, isothiocyano, azido, amino, nitro, bromo, hydroxy, fluoro and a methoxy group at the chain terminal. The in vitro and in vivo pharmacology of these unique analogs have provided several ligands which are partial agonists or antagonists of the cannabinoid receptor CB1. The 2'-position in the side chain was found to be optimum for activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)13907-13926
Number of pages20
JournalTetrahedron
Volume55
Issue number49
DOIs
Publication statusPublished - 3 Dec 1999

Keywords

  • cannabinoids
  • alkynes
  • alkenes
  • pharmacologically active compounds
  • CANNABINOID RECEPTOR
  • SELECTIVE ANTAGONIST
  • POTENT
  • BRAIN
  • PHARMACOLOGY
  • ANANDAMIDE
  • CHEMISTRY
  • ALCOHOLS
  • ANALOGS
  • BINDS

Cite this

Crocker, P. J., Saha, B., Ryan, W. J., Wiley, J. L., Martin, B. R., Ross, R. A., Pertwee, R. G., & Razdan, R. K. (1999). Development of agonists, partial agonists and antagonists in the Delta(8)-tetrahydrocannabinol series. Tetrahedron, 55(49), 13907-13926. https://doi.org/10.1016/S0040-4020(99)00849-2