Evaluation of agonist-antagonist properties of nitrogen mustard and cyano derivatives of Δ8-tetrahydrocannabinol

Neuropharmacology

Volumn 35, Issue 12, 1996, Pages 1793-1804

  Wiley, Jenny L ^a   Compton, David R ^a   Gordon, Patrick M ^b   Siegel, Craig ^b   Singer, Michael ^b   Dutta, Aloke ^b   Lichtman, Aron H ^a   Balster, Robert L ^a   Razdan, Raj K ^b   Martin, Billy R ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b ORGANIX INC   (United States)

Author keywords

8 tetrahydrocannabinol; antagonist; behavior; cyano analog; nitrogen mustard analog; structure activity relationship

Indexed keywords

4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; CANNABINOID RECEPTOR; CANNABINOID RECEPTOR ANTAGONIST; CHLORMETHINE; TETRAHYDROCANNABINOL; TETRAHYDROCANNABINOL DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BEHAVIOR; BRAIN HOMOGENATE; CONTROLLED STUDY; INTRAVENOUS DRUG ADMINISTRATION; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; BODY TEMPERATURE REGULATION; CANNABINOIDS; CATALEPSY; CYCLOHEXANOLS; MALE; MAZE LEARNING; MICE; MICE, INBRED ICR; MOTOR ACTIVITY; NITROGEN MUSTARD COMPOUNDS; PAIN; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROCANNABINOL;

EID: 0030513691     PISSN: 00283908     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0028-3908(96)00120-7     Document Type: Article

References (32)

1. 9-Tetrahydrocannabinol discrimination in rats as a model for cannabis intoxication. Neurosci. Biobehav. Rev. 16:1992;55-62.
2. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:1976;248-254.
3. Carney J.M., Uwaydah I.M., Balster R.L. Evaluation of a suspension system for intravenous self-administration studies of water insoluble compounds in the rhesus monkey. Pharmacol. Biochem. Behav. 7:1977;357-364.
4. 8-THC analogs. Pharmacol. Biochem. Behav. 40:1991;509-512.
5. 50) on an enzymatic reaction. Biochem. Pharmacol. 22:1973;3099-3108.
6. Compton D.R., Dewey W.L., Martin B.R. Cannabis dependence and tolerance production. Adv. Alcohol Subst. Abuse. 9:1990;129-147.
7. Compton D.R., Johnson M.R., Melvin L.S., Martin B.R. Pharmacological profile of a series of bicyclic cannabinoid analogs: classification as cannabimimetic agents. J. Pharmacol. Exp. Ther. 260:1992;201-209.
8. 8-tetrahydrocannabinol. J. Med. Chem. 33:1990;1437-1443.
9. Compton D.R., Rice K.C., DeCosta B., Razdan R.K., Melvin L.S., Johnson M.R., Martin B.R. Cannabinoid structure-activity relationships: correlation of receptor binding and in vivo activities. J. Pharmacol. Exp. Ther. 265:1993;218-226.
10. Devane W.A., Dysarz F.A. III, Johnson M.R., Melvin L.S., Howlett A.C. Determination and characterization of a cannabinoid receptor in rat brain. Molec. Pharmacol. 34:1988;605-613.
11. Dewey W.L., Harris L.S., Howes J.F., Kennedy J.S., Granchelli F.E., Pars H.G., Razdan R.K. Pharmacology of some marijuana constituents and two heterocyclic analogues. Nature. 226:1970;1265-1267.
12. Dewey W.L., Harris L.S., Howes J.F., Nuite J.A. The effect of various neurohumoral modulators on the activity of morphine and the narcotic antagonists in the tail-flick and phenylquinone tests. J. Pharmacol. Exp. Ther. 175:1970;435-442.
13. Evans E.B., Wenger G.R. Effects of drugs of abuse on acquisition of behavioral chains in squirrel monkeys. Psychopharmacology. 107:1992;55-60.
14. 9-tetrahydrocannabinol and CP 55,940 in rats and rhesus monkeys. J. Pharmacol. Exp. Ther. 262:1992;479-486.
15. Heyser C.J., Hampson R.E., Deadwyler S.A. Effects of delta-9-tetrahydrocannabinol on delayed match to sample performance in rats: alterations in short-term memory associated with changes in task specific firing of hippocampal cells. J. Pharmacol. Exp. Ther. 264:1993;294-307.
16. 8-THC. Psychopharmacology. 75:1981;152-157.
17. Lichtman A.H., Dimen K.R., Martin B.R. Systemic or intrahippocampal cannabinoid administration impairs spatial memory in rats. Psychopharmacology. 119:1995;282-290.
18. Martin B.R., Compton D.R., Little P.J., Martin T.J., Beardsley P.M. Pharmacological evaluation of agonistic and antagonistic activity of cannabinoids. NIDA Res. Monogr. 79:1987;108-122.
19. 9-THC: reassessment of the putative three-point cannabinoid-receptor interaction. Drug Alcohol Depend. 37:1995;231-240.
20. Martin B.R., Compton D.R., Thomas B.F., Prescott W.R., Little P.J., Razdan R.K., Johnson M.R., Melvin L.S., Mechoulam R., Ward S.J. Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs. Pharmacol. Biochem. Behav. 40:1991;471-478.
21. 9-THC. Pharmacol. Biochem. Behav. 46:1993;295-301.
22. McPherson G.A. A practical computer-based approach to the analysis of radioligand binding experiments. Computer Programs Biomed. 17:1983;107-114.
23. 9-tetrahydrocannabinol in rats. Psychopharmacology. 67:1980;195-202.
24. Munson P.J., Rodbard D. LIGAND: a versatile computerized approach for characterization of ligand-binding systems. Anal. Biochem. 107:1980;220-239.
25. 9-tetrahydrocannabinol (THC) on memory in the rat. Drug Alcohol Depend. 28:1991;167-175.
26. Pertwee R.G. The ring test: a quantitative method for assessing the "cataleptic" effect of cannabis in mice. Br. J. Pharmacol. 46:1972;753-763.
27. Pertwee R.G., Stevenson L.A., Griffin G. Cross-tolerance between delta-9-tetrahydrocannabinol and the cannabimimetic agents, CP 55,940, WIN 55,212-2 and anandamide. Br. J. Pharmacol. 110:1993;1483-1490.
28. Portoghese P.S., Larson D.L., Sayre L.M., Fries D.S., Takemori A.E. A novel opioid receptor site directed alkylating agent with irreversible narcotic antagonistic and reversible agonistic activities. J. Med. Chem. 23:1980;233-235.
29. Rosenthal H.E. A graphic method for the determination and presentation of binding parameters in a complex system. Anal. Biochem. 20:1967;525-532.
30. Scatchard G. (1951) The attractions of proteins for small molecules and ions. Ann. N.Y. Acad. Sci. 51: 1951.
31. Tallarida R.J. and Murray R.B. (1987) Manual of Pharmacologic Calculations with Computer Programs, Second Edition, Springer, New York.
32. Wiley J.L., Barrett R.L., Lowe J., Balster R.L., Martin B.R. Discriminative stimulus effects of CP 55,940 and structurally dissimilar cananbinoids in rats. Neuropharmacology. 34:1995;669-676.