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).
References
Dewey, W. L., Martin, B. R., and May, E. L., in: Handbook of Stereoisomers: Drugs in Psychopharmacology, pp. 317–348. Ed. D. F. Smith. CRC Press, Boca Raton, Fla. 1984; Mechoulam, R., Lander, N., Varkony, T. H., Kimmel, I., Becker, O., Ben-Zvi, Z., Edery, H., and Porath, G., J. med. Chem.23 (1980) 1068.
Martin, B. R., Pharmac. Rev.38 (1986) 45.
Mechoulam, R., Braun, P., and Gaoni, Y., J. Am. Chem. Soc.89 (1967) 4552;94 (1972) 6159.
Hiltunen, A. J., and Järbe, T. U. C., Neuropharmacology25 (1986) 133.
Järbe, T. U. C., Swedberg, M. D. B., and Mechoulam, R., Psychopharmacology75 (1981) 152.
Ferster, C. B., and Skinner, B. F., Schedules of Reinforcement. Appleton-Century-Crofts, New York 1957.
Järbe, T. U. C., Hiltunen, A. J., Lander, N., and Mechoulam, R., Pharmac. Biochem. Behav.25 (1986) 393.
Consroe, P., and Wolkin, A., J. Pharmac. exp. Ther.201 (1977) 26.
Consroe, P., Martin, A., and Mechoulam, R., in: Marihuana '84, Proceed. Oxford Symp. Cannabis, pp. 705–712. Ed. D. J. Harvey. IRL Press, Oxford 1985.
Pertwee, R. G., Br. J. Pharmac.46 (1972) 753.
Razdan, R. K., Pharmac. Rev.38 (1986) 75; Mechoulam, R., and Feigenbaum, J. J., Progr. med. Chem.24 (1987) 159.
Harvey, D. J., and Paton, W. D. M., Rev. Biochem. Toxic.6 (1984) 221.
Dewey, W. L., Pharmac. Rev.38 (1986) 151.
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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