Cannabinoid class metabolites

Direct HPLC analysis of urine extracts appears feasible for A -THC. 215nm is the optimum wavelength for detection of THC-class compounds. Dual wavelength at 215 and 280nm serves as a valuable check on cannabinoid retention assignment and as a screen for unknown THC or CBN-class metabolites. The latter feature was demonstrated in the observance of CBN-class peaks in both hexane and E-I extracts. This observation suggests a CBN-metabolic route of A -THC. Evidence of a CBN-metabolic route for A -THC has been reported by McCallum (8) and Green (6) for humans and by Ben Zvi et al (9) for rhesus monkeys. 

Up to 16 illicit drugs and metabolites belonging to five different chemical classes (cocainics, cannabinoids, opioids, amphetamine-like, and lysergic compounds) were analyzed in the collected samples. High purity (>97%) standard solutions... 

Semiplenamides A 359 to G 365, a series of new anandamide-like fatty acid amides, were isolated from a 1997 Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena, and all these new metabolites displayed toxicity in the brine shrimp model system. Only semiplenamides A 359, B 360, and G 365 showed weak affinity for the rat cannabinoid CBl receptor. Semiplenamide A 364 was also a moderate inhibitor (IC50 = 18.1 pM) of the anandamide membrane transporter (AMT). Novel 5y -aldol/dehydration methodology was developed for the stereoselective synthesis of the core ( )-a, P-unsaturated amide functionality of this class of natural product, and employed for the efficient synthesis of semiplenamide... 

The phytochemical diversity of C. saliva is well illustrated by more than 500 com-potmds isolated from this plant, encompassing all major classes of phytochemicals (polyketides, terpenoids, alkaloids, flavonoids, stilbenoids, oxylipins). Undoubtedly, the most important and peculiar secondary metabolites of C. saliva are cannabinoids, a class of mono- to tetracyclic C21 (or C22) meroterpenoids encompassing more than 100 members. These compounds are synthesized in secretory cells of glandular trichomes, most concentrated in unfertilized female cannabis flowers prior to senescence. A number of detailed accounts on the cannabinoid chemistry have been reported in the literature [6-8], also recently by Appendino et al. [9]. In this paragraph, we will provide an updated, although not comprehensive, account of the chemistry of this fascinating class of secondary metabolites. 

---