Conversion of cannabidiol to Δ9-tetrahydrocannabinol and related cannabinoids in artificial gastric juice, and their pharmacological effects in mice

Abstract

sleeping time by 1.8 to 8.0 times as compared with the control solution with 1% Tween 80-saline. The ED 50 values (mg/kg, i.v.) of 9α-OH-HHC and 8-OH-iso-HHC for the antinociceptive effect were 14.1 and 39.4, respectively. The present study demonstrated that CBD can be converted to ∆ 9 -THC and its related cannabinoids, 9α-OH-HHC and 8-OH-iso-HHC, in artifi cial gastric juice, and that these HHCs show ∆ 9 -THC-like effects in mice, although their pharmacological effects were less potent than those of ∆ 9 -THC.

Δ9-Tetrahydrocannabinol and Its Major Metabolite Δ9-Tetrahydrocannabinol-11-oic Acid as 15-Lipoxygenase Inhibitors

“…27,35-39 Furthermore, we have reported that CBD can be converted into 9 -THC in acidic conditions that are mimicked by stomach acid. 40 In acidic conditions, 9 -THC can be isomerized to 8 -THC. 41 If this is the case with 9 -THC-11-oic acid, the metabolic fate and action might be modulated by its administration route (i.e., oral vs. intravenous administration).…”

Flax straw char‐CO2 gasification kinetics and its inhibition studies with CO

“…9,10‐α‐epoxyhexahydrocannabinol (9,10‐α‐EHHC) was found to be formed from Δ 9 ‐tetrahydrocannabinol (Δ 9 ‐THC) 48. Further, pharmacological effects of 9,10‐α‐EHHC in mice, were compared with those of Δ 9 ‐THC in catalepsy, hypothermia, pentobarbital‐induced sleep prolongation and anticonvulsant activity against pentylenetetrazol (PTZ) 48, 49. 9,10‐α‐EHHC was approximately as equipotent as THC in the pharmacological indexes except for catalepsy.…”

Possible involvement of Cyp3a enzymes in the metabolism of tetrahydrocannabinols by mouse brain microsomes

“…The mixture was extracted with 4 ml of ethyl acetate after addition of 0.5 ml of 1 M KH 2 PO 4 , and 5 0 -nor-D 8 -THC-4 0 -oic acid methyl ester (0.5 lg) as an internal standard. After evaporation of the organic solvent, the residue was trimethylsilylated as described previously [14][15][16] and subjected to gas chromatography-mass spectrometry (GC-MS) under the following conditions: instrument, Shimadzu GCMS-QP2010 (Shimadzu, Kyoto, Japan); column, DB-1 (0.25 mm 9 30 m, film thickness 0.25 lm, Agilent, Santa Clara, CA, USA); column temperatures, 50°C (1-min hold), 25°C/min (6 min), 10°C/min (10 min), and 300°C (5-min hold); ion source temperature, 250°C; interface temperature 280°C; ionization energy, 70 eV; emission current, 60 lA; carrier gas, He at flow rate of 2.04 ml/min. Under these conditions, the retention times of the trimethylsilyl (TMS) derivatives of the THC metabolites were: 4 0 -hydroxy-D 8 -THC, 15.14 min; 5 0 -hydroxy-D 8 -THC, 15.76 min; 4 0 -hydroxy-D 9 -THC, 15.21 min; 5 0 -hydroxy-D 9 -THC, 15.84 min.…”

“…These retention times were very similar to those of the authentic standards for 4 0 -and 5 0 -hydroxy metabolites of THCs.In GC-MS analyses, all of the metabolites showed molecular ions at m/z 474, and a fragment ion at m/z 391 that is a typical diagnostic ion of pentyl side chain hydroxylated metabolites of THCs(Fig. 2)[15,16]; the mass spectra of these metabolites were almost identical with those of synthetic standards or…”