Compositions useful as a cannabinoid receptor probe

Details Compositions useful as a cannabinoid receptor probe Compositions useful as a cannabinoid receptor probe

1993-08-06

1995-08-08

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31180

Patent

active

054400520

ABSTRACT:
A composition of matter, comprising a cannabinol compound having the structure ##STR1## wherein, Q is --C(R.sup.1) (Y.sup.1)--(CH.sub.2).sub.n ----Z.sup.1 ; R.sup.1 is --H or --CH.sub.3 ; Y.sup.1 is --CH.sub.3 or Y.sup.2 ; Y.sup.2 is --N.sub.3 or --NCS; n is 4 or 6; Z.sup.1 is --H, when Y.sup.1 is Y.sup.2, or is Z.sup.2, when Y.sup.1 is --CH.sub.3 ; and Z.sup.2 is --N.sub.3 or --NCS.
This composition has good binding affinity to the cannabinoid receptor and therefore, is useful as a receptor probe.

REFERENCES:
patent: 3897306 (1975-07-01), Vidic et al.
Reggio, P. H., et al., "Characterization of a Region of Steric Interference at the Cannabinoid Receptor Using the Active Analog Approach," J. Med. Chem. United States, 36(12):1761-1771, (Jun. 11, 1993).
Gold, L. H., et al., "A Comparison of the Discriminative Stimulus Properties of .DELTA..sup.9 -Tetrahydrocannabinol and CP 55, 940 in Rats and Rhesus Monkeys," J. Pharmacol. Exp. Ther., 262(2):479-486.
Charalambous A., et al., "Pharmacological Evaluation of Halogenated .DELTA..sup.8 -THC Analogs," Pharmacol. Biochem. Behav., 40(3):509-512 (Nov. 1991).
Martin, B. R., et al., "Behavioral, Biochemical, and Molecular Modeling Evaluations of Cannabinoid Analogs," Pharmacol. Biochem. Behav., 40(3):471-478 (Nov. 1991).
Compton D. R., et al., "Synthesis and Pharmacological Evaluation of Ether and Related Analogues of .DELTA..sup.8 -, and .DELTA..sup.9 -, and .DELTA..sup.9,11 -Tetrahydrocannabinol," J. Med. Chem., 34(11):3310-3316 (Nov. 1991).
Burstein, S. H. et al., "Detection of Cannabinoid Receptors by Photoaffinity Labelling," Biochem. Biophys. Res. Commun., 176(1):492-497 (Apr. 15, 1991).
Howlett, A. C., et al., "Stereochemical Effects of 11-OH-.DELTA..sup.8 -Tetrahydrocannabinol-Dimethylheptyl to Inhibit Adenylate Cyclase and Bind to the Cannabinoid Receptor," Neuropharmacology, 29(2):161-165 (Feb. 1990).
Nye, J. S., et al., "High-Affinity Cannabinoid Binding Sites in Brain Membranes Labeled with (.sup.3 H)-5'-Trimethylammonium .DELTA..sup.8 -Tetrahydrocannabinol," J. Pharmacol. Exp. Ther., 234(3):784-791 (1985).
J. Med. Chem., 35:3076-3079, Communications to the Editor, (1992).
The Merck Index, Eleventh Edition, Compound No. 9142 (1989).

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