Human Liver Microsomal Oxidation of Δ8-Tetrahydrocannabinol

Ikuo Yamamoto; Shizuo Narimatsu; Kazuhito Watanabe; Tatsuyuki Shimonishi; Hidetoshi Yoshimura; Taizo Nagano

doi:10.1248/cpb.31.1784

Human Liver Microsomal Oxidation of Δ⁸-Tetrahydrocannabinol

Ikuo Yamamoto, Shizuo Narimatsu, Kazuhito Watanabe, Tatsuyuki Shimonishi, Hidetoshi Yoshimura, Taizo Nagano

Faculty of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

Human liver microsomal oxidation products of Δ8-tetrahydrocannabi-nol (THC) were isolated and identified by thin-layer chromatography, gas chromatography and gas chromatography-mass spectrometry. As the results, five monohydroxylated metabolites including 11-hydroxy-Δ8-THC, and 8β,9α-dihydroxyhexahydrocannabinol were identified as trimethyl-silyl derivatives. Isolation of the dihydroxylated metabolite suggests that epoxy metabolite(s) may be formed from A8-THC in humans.

Original language	English
Pages (from-to)	1784-1787
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	31
Issue number	5
DOIs	https://doi.org/10.1248/cpb.31.1784
Publication status	Published - Jan 1 1983

Keywords

11-hydroxy-Δ8-tetrahydrocannabi-nol
11-hydroxy-Δ8-tetrahydrocannabinol
3'-hydroxy-Δ8-tetra-hydrocannabinol
7α-hydroxy-Δ8-tetrahydrocannabinol
7β-hydroxy-Δ8-tetrahydro-cannabinol
8β,9α-dihydroxyhexahydrocannabinol
GC-MS
human liver microsomes
identification of metabolite
Δ8-tetrahydrocannabinol

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.31.1784

Cite this

@article{26f216d966764fae8f8acdac29739921,

title = "Human Liver Microsomal Oxidation of Δ8-Tetrahydrocannabinol",

abstract = "Human liver microsomal oxidation products of Δ8-tetrahydrocannabi-nol (THC) were isolated and identified by thin-layer chromatography, gas chromatography and gas chromatography-mass spectrometry. As the results, five monohydroxylated metabolites including 11-hydroxy-Δ8-THC, and 8β,9α-dihydroxyhexahydrocannabinol were identified as trimethyl-silyl derivatives. Isolation of the dihydroxylated metabolite suggests that epoxy metabolite(s) may be formed from A8-THC in humans.",

keywords = "11-hydroxy-Δ8-tetrahydrocannabi-nol, 11-hydroxy-Δ8-tetrahydrocannabinol, 3'-hydroxy-Δ8-tetra-hydrocannabinol, 7α-hydroxy-Δ8-tetrahydrocannabinol, 7β-hydroxy-Δ8-tetrahydro-cannabinol, 8β,9α-dihydroxyhexahydrocannabinol, GC-MS, human liver microsomes, identification of metabolite, Δ8-tetrahydrocannabinol",

author = "Ikuo Yamamoto and Shizuo Narimatsu and Kazuhito Watanabe and Tatsuyuki Shimonishi and Hidetoshi Yoshimura and Taizo Nagano",

year = "1983",

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doi = "10.1248/cpb.31.1784",

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T1 - Human Liver Microsomal Oxidation of Δ8-Tetrahydrocannabinol

AU - Yamamoto, Ikuo

AU - Narimatsu, Shizuo

AU - Watanabe, Kazuhito

AU - Shimonishi, Tatsuyuki

AU - Yoshimura, Hidetoshi

AU - Nagano, Taizo

PY - 1983/1/1

Y1 - 1983/1/1

N2 - Human liver microsomal oxidation products of Δ8-tetrahydrocannabi-nol (THC) were isolated and identified by thin-layer chromatography, gas chromatography and gas chromatography-mass spectrometry. As the results, five monohydroxylated metabolites including 11-hydroxy-Δ8-THC, and 8β,9α-dihydroxyhexahydrocannabinol were identified as trimethyl-silyl derivatives. Isolation of the dihydroxylated metabolite suggests that epoxy metabolite(s) may be formed from A8-THC in humans.

AB - Human liver microsomal oxidation products of Δ8-tetrahydrocannabi-nol (THC) were isolated and identified by thin-layer chromatography, gas chromatography and gas chromatography-mass spectrometry. As the results, five monohydroxylated metabolites including 11-hydroxy-Δ8-THC, and 8β,9α-dihydroxyhexahydrocannabinol were identified as trimethyl-silyl derivatives. Isolation of the dihydroxylated metabolite suggests that epoxy metabolite(s) may be formed from A8-THC in humans.

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KW - 11-hydroxy-Δ8-tetrahydrocannabinol

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KW - 8β,9α-dihydroxyhexahydrocannabinol

KW - GC-MS

KW - human liver microsomes

KW - identification of metabolite

KW - Δ8-tetrahydrocannabinol

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