A’-tetrahydro cannabinol

Hively RL, Mosher WA, Hoffmann FW, Isolation of tn7 t-A -tetrahydro-cannabinol from marijuana,Chem Soc 88 1832—1833, 1966. 

Tashkin, D.P., Shapiro, B.J., and Frank, I.M. Acute pulmonary physiologic effects of smoked marijuana and oral A -tetrahydro-cannabinol in healthy young men. N. Engl. J. Med. 289 336-341, 1973. 

N.A. Tetrahydro-cannabinols, thiamine protein. Seeds contain choline, inositol, xylose, phytosterols, trigonelline.100102 Induce euphoria and exhilaration, sedative, antispasmodic. 

Berdyshev EV, Boichot E, Germain N, AUain N, Anger J-P, Lagente V (1997) Influence of fatty acid ethanolamides and A -tetrahydro-cannabinol on cytokine and arachidonate release by mononuclear cells. Eur J Pharmacol 330 231-240. 

Fischer-Stenger K, Dove Pettit DA, Cabral GA (1993) A -tetrahydro-cannabinol inhibition of tumor necrosis factor-a Suppression of post-translational events. J Pharmacol Exp Ther 267 1558-1565. 

Immunoassay. THC is extensively metabolized to a large number of compounds, most of which are inactive. The principal urinary metabolite is U -nor-A -tetrahydro-cannabinol-9" carboxylic acid (THC-COOH) and its glucuronide conjugate (see Figure 34-30). Immunoassays designed to screen urine samples for marijuana use measure this and other THC metabolites. These assays are calibrated with THC-COOH, but because of cross-reactivity with many other THC metabolites, quantitative results based on them are 1.5 to 8 times greater than the actual concentration of THC-COOH as determined by GC-MS. Therefore... 

Bell R, Taylor EH, Ackerman B, Pappas AA. Interpretation of urine quantitative 11-nor-A -tetrahydro-cannabinol-9-carboxylic acid to determine abstinence from marijuana smoking. Clin Toxicol 1989 27 109-15. 

Jones AB, ElSohly HN, Aragat ES, ElSohly MA. Analysis of the major metabolite of A -tetrahydro-cannabinol in urine IV. A comparison of five methods. J Anal Toxicol 1984 8 249-51. 

Garcfa-Gil L, de Miguel R, Ramos JA, Ferndndez-Ruiz JJ (1996) Perinatal A -tetrahydro-cannabinol exposure in rats modifies the responsiveness of midbrain dopaminergic neurons in adulthood to a variety of challenges with dopaminergic drugs. Drug Alcohol Depend 42 155-166... 

Surprisingly, the rearrangement of dihydropyran 6 used in the synthesis of trans-A -tetrahydro-cannabinole (8) from 5 can be carried out at room temperature177. The ability to use these mild reaction conditions is probably a result of the donor effect of the aromatic ring. 

Pistis, M., Ferraro, L., Pira, L., Flore, G., Tanganelli, S., Gessa, G.L. and Devoto, P. (2002) A -Tetrahydro-cannabinol decreases extracellular GABA and increases extracellular glutamate and dopamine levels in the rat prefrontal cortex an in vivo microdialysis study, Brain Res, 948 155-158. 

Rivas, J.F. and Garcia, R. (1980) Inhibition of histamine-stimulated gastric acid secretion by A -tetrahydro-cannabinol in rat isolated stomach, Eur. J. Pharmacol. 65 317-318. 

Smith CG, Almirez RG, Scher PM, Asch RH. 1984. Tolerance to the reproductive effects of A -tetrahydro-cannabinol. Comparison of the acute, short-term, and drug chronic effects on menstrual cycle hormones, in Agurell S, Dewey W, Willette R., Eds. The Cannabinoids Chemical, Pharmacologic and Therapeutic Aspects. New York Academic Press, pp. 471 485. 

Tyre L, Murphy L. 1988. Inhibition of suckling-induced milk ejections in the lactating rat by A -tetrahydro-cannabinol. Endocrinology 123 469-472. 

Starting from the thought that a lock had been discovered, there came now the question of the endogenous key . Altough A -tetrahydrocannabinol from hemp fits nicely into this lock it could be mere serendipity the more so as THC, unlike morphine, had not been detected in the human body as an endogenous compound. In 1992, Raphael Mechoulam (Fig. 5.67), at the Hebrew University in Jerusalem, discovered the first endocannabinoid, which he extracted from a pig s brain he demonstrated its affinity to the CBl-receptor by classical displacement studies. Mechoulam named it anandamide" (Sanskrit, ananda bliss). In chemical terms it is arachidonoylethanolamide (Fig. 5.68). Anandamide (Kj 52 nM) has practically the same affinity as A -tetrahydro-cannabinol (Kj 41 nM) at the CBl-receptor, but in contrast to THC, the former is rapidly deactivated hydrolytically by the enzyme anandamide amidohydro-lase. 

The careful use of mixtures of closely related silyl derivatives can assist in resolving problems arising in GC—MS analyses where spectra lack diagnostic fragmentations or where co-elutions mask compounds of interest [387]. For example, the number of trimethylsilyl groups in the TMS derivative of butyl-A -tetrahydro-cannabinolic add was determined by comparison of the mass spectra of the TMS and TMS-d9 derivatives [387). As part of the same investigation, an interfering peak... 

Cannabinoids in cannabis preparations have been measured using an ODS-modified silica column with ED (presumably GCE, +1.2V vs Ag/AgCl). " The eluent was acetonitrile-methanol-aq. sulfuric acid (10mmolL ) (16 + 7 + 6). Bourquin and Brenneisen used a similar system to measure 11-carboxy-A -tetrahydro-cannabinol (THC-COOH) in hydrolysed urine. Cannabinol was the internal standard. The reason such a high potential was used in these reports is not clear (no voltammogram was given) since THC-COOH contains a phenolic hydroxyl... 

Quantitation of A -Tetrahydrocannabinol and ll-Nor-A -tetrahydro-cannabinol-9-carboxylic Acid in Body Fluids by GC/CI-MS ACS Symp. Ser. 98(Cannabinoid Anal. Physiol. Fluids) 59-71 (1979) CA 91 32563f... 

The principal active ingredient of concern in marijuana is A -tetrahydro-cannabinol (A THC, or just THC). THC is acidic and has an ionizable center and a pKg of 10.6. THC also has a logP value of 6.97, which reflects the insolubility of oils in water. The typical concentration of THC in the leaves is between 1 and 5%, and much higher values are found in the oily resin on the flowering... 

Cannabis THC-COOH (ll-nor-9- carboxy-A - tetrahydro- cannabinol) Major metabolite ofTHC (cannabis active principle) 0.6 0.91 152... 

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