Separation of the discriminative stimulus effects of stereoisomers of Δ2- and Δ3-tetrahydrocannabinols in pigeons

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Abstract

Pigeons, trained to discriminate between the presence or absence of Δ1-tetrahydrocannabinol (THC) (I) (0.56 mg/kg), were tested with (1S,4R)-Δ2-THC (II) (1–17.5 mg/kg), with the C-1 epimers of (4R)-Δ2-THC acetate, namely (1S,4R)-Δ2-THC acetate (IIIA) (3–17.5 mg/kg) and (1R,4R)-Δ2-THC acetate (IIIB) (1–17.5 mg/kg) and with the enantiomers of Δ3-THC acetate, namely (1S)-Δ3-THC acetate (IVA) (1–10 mg/kg) and (1R)-Δ3-THC acetate (IVB) (3–30 mg/kg). The results indicated that (I) was considerably more potent than any of the other compounds evaluated (ED50 of compound I = 0.18 and 0.25 mg/kg at the two post-injection intervals examined, 90 and 270 min, respectively). Furthermore, of the two Δ2-THC acetates, compound (IIIB) was active whereas compound (IIIA) was not in comparable doses. The parent phenol of compound (IIIA), namely (II),was also inactive. Comparison of the pair of enantiomers, (IVA) and (IVB), showed the former to be significantly more potent than the latter. We have thus shown that the Δ1-THC-like cue properties are separated in the stereoisomers of Δ2- and Δ3-THC.

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A brief account of these data was communicated in a poster session at the First Meeting of the Center for Neuroscience Research in Uppsala, Sweden, December 9, 1987.

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