Δ6-Tetrahydrocannabinol-7-oic acid, a urinary Δ6-THC metabolite: Isolation and synthesis

Mechoulam, Raphael; Ben‐Zvi, Zvi; Agurell, Stig; Nilsson, Inger; Nilsson, Jonas; Edery, H.; Grunfeld, Yona

doi:10.1007/bf01935065

Cited by 55 publications

(27 citation statements)

References 12 publications

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“…Oxidation of the psychoactive 11-OH-THC produces the inactive metabolite THC-COOH [64] [94]. THC-COOH and its glucuronide conjugate are the major end products of biotransformation in most species, including man [91] [95].…”

Section: Metabolismmentioning

confidence: 99%

Human Cannabinoid Pharmacokinetics

Huestis

2007

Chemistry & Biodiversity

910

775

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Section: Metabolismmentioning

confidence: 99%

Human Cannabinoid Pharmacokinetics

Huestis

2007

Chemistry & Biodiversity

910

775

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“…Although a number of cannabinoids of this series have been synthesized and examined by the Mechoulam group [e.g. [50][51][52], it is little known about structural requirements and the mechanism of receptor binding of non-psychotropic cannabinoids. Such a study has been initiated.…”

Section: Novelmentioning

confidence: 99%

Nonpsychotropic Synthetic Cannabinoids

Pop

2000

CPD

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Unlike natural cannabinoids which belong to the 6aR - trans series, the synthetic dexanabinol (HU-211), a 6aS-trans enantiomer, does not have affinity toward cannabinoid receptors and is devoid of cannabimimetic activity. On the other hand, dexanabinol demonstrated significant neuroprotective properties which prompted its development as a therapeutic agent. We now present the extension of a series of 6aS-trans cannabinoids with novel derivatives, including water soluble derivatives and congeners of dexanabinol.

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“…Cannabinoids and other chemicals: 11-Oxo-D 8 -THC, 15) D 8 -THC-11-oic acid 16) and 5?-nor-D 8 -THC-4?-oic acid 17) were prepared by the methods described previously. The purities of these cannabinoids were determined to be at least 95z by gas chromatography.…”

Section: Methodsmentioning

confidence: 99%

“…Enzyme source: Hepatic microsomes were prepared from the human livers of a 57-year-old woman (HL-1) and 16 year-old man (HL-2) who were killed in tra‹c accidents. The use of the human liver for experiments was approved by Ethics Committee of Kanazawa University, Faculty of Medicine.…”

Section: Methodsmentioning

confidence: 99%

Major Cytochrome P450 Enzymes Responsible for Microsomal Aldehyde Oxygenation of 11-Oxo-Δ8-tetrahydrocannabinol and 9-Anthraldehyde in Human Liver

Watanabe

Matsunaga

Kimura

et al. 2002

Drug Metabolism and Pharmacokinetics

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Hepatic microsomes from human liver catalyzed oxidation of the allyl aldehydes such as 11-oxo-Delta(8)-tetrahydrocannabinol and 9-anthraldehyde to the corresponding carboxylic acid metabolites. The oxygenation mechanism was confirmed by GC-MS that molecular oxygen was exclusively incorporated into Delta(8)-tetrahydrocannabinol-11-oic acid and 9-anthracene carboxylic acid formed under oxygen-18 gas. The microsomal aldehyde oxygenase (named MALDO) activities of 11-oxo-Delta(8)-tetrahydrocannabinol and 9-anthraldehyde were significantly inhibited by the antibody against CYP2C and CYP3A, respectively. MALDO activity for 11-oxo-Delta(8)-tetrahydrocannabinol was significantly inhibited by sulfaphenazole whereas that for 9-anthraldehyde was markedly inhibited by troleandomycin, but not by sulfaphenazole. CYP2C9 expressed in human B-lymphoblastoid cells catalyzed efficiently the MALDO activity for 11-oxo-Delta(8)-tetrahydrocannabinol (10.1 nmol/min/nmol P450), while the catalytic activities of other human CYPs expressed in the cells were lesser extents. In MALDO activity for 9-anthraldehyde, CYP3A4 expressed in the cells had the highest catalytic activity (7.72 nmol/min/nmol P450). These results indicate that CYP2C9 and CYP3A4 are major enzymes responsible for the MALDO activity in human liver for 11-oxo-Delta(8)-tetrahydrocannabinol and 9-anthraldehyde, respectively.

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Δ6-Tetrahydrocannabinol-7-oic acid, a urinary Δ6-THC metabolite: Isolation and synthesis

Cited by 55 publications

References 12 publications

Human Cannabinoid Pharmacokinetics

Human Cannabinoid Pharmacokinetics

Nonpsychotropic Synthetic Cannabinoids

Major Cytochrome P450 Enzymes Responsible for Microsomal Aldehyde Oxygenation of 11-Oxo-Δ8-tetrahydrocannabinol and 9-Anthraldehyde in Human Liver

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