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Enantiomeric cannabinoids: stereospecificity of psychotropic activity

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Summary

The 1,1-dimethylheptyl homolog of (−)-(3R,4R)-7-hydroxy-delta-6-tetrahydrocannabinol (compoundII) is highly psychotropic in mice, rats and pigeons. The (+)-(3S,4S) enantiomer (III) was found to be psychotropically inactive at doses up to several thousand times those of the ED50 of (II).

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Authors and Affiliations

  1. Brettler Medical Research Center, Faculty of Medicine, Hebrew University, 91120, Jerusalem, Israel

    R. Mechoulam, J. J. Feigenbaum, N. Lander, M. Segal, T. U. C. Järbe, A. J. Hiltunen & P. Consroe

  2. Departments of Psychology and Applied Psychology, University of Uppsala, Box 227, S-75104, Uppsala, Sweden

    R. Mechoulam, J. J. Feigenbaum, N. Lander, M. Segal, T. U. C. Järbe, A. J. Hiltunen & P. Consroe

  3. Department of Pharmacology and Toxicology, College of Pharmacy, University of Arizona, 85721, Tucson, Arizona, USA

    R. Mechoulam, J. J. Feigenbaum, N. Lander, M. Segal, T. U. C. Järbe, A. J. Hiltunen & P. Consroe

Authors
  1. R. Mechoulam
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  2. J. J. Feigenbaum
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  3. N. Lander
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  4. M. Segal
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  5. T. U. C. Järbe
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  6. A. J. Hiltunen
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  7. P. Consroe
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Additional information

We thank Dr A. Breuer and Mrs H. Amsalem for help with the syntheses. The research reported above was supported in Tucson by NIH grant NS 15441; in Uppsala by grants from the Swedish Medical Research Council (5757) and the Swedish Council for the Planning and Coordination of Research (84/208∶2); in Jerusalem by the Szold Foundation.

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Mechoulam, R., Feigenbaum, J.J., Lander, N. et al. Enantiomeric cannabinoids: stereospecificity of psychotropic activity. Experientia 44, 762–764 (1988). https://doi.org/10.1007/BF01959156

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  • DOI: https://doi.org/10.1007/BF01959156

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