8-OH-HHC.8-hydroxyhexahydrocannabinol

8-Hydroxyhexahydrocannabinol is a metabolite of HHC, hydroxylated at position 8 of the saturated ring; its two centres at C8 and C9 give four stereoisomers. Harvey and Brown (1991) showed in liver microsomes that this route exists in several mammals, with high concentrations of 8α-OH-HHC in mice and of 8β-OH-HHC in hamsters, whereas C11 hydroxylation predominates in most species. In humans, Lindbom et al. (2024) place 11-OH-HHC and 5'-OH-HHC among the only metabolites present in all 16 authentic urine samples studied, and Höfert et al. (2026) followed 8-OH-HHC in the serum and urine of six volunteers after oral (25 mg) or inhaled HHC, proposing it as a marker of HHC use unlikely to derive from THC. The four stereoisomers were synthesised and their configurations confirmed in 2026 (Ieuji et al.). No receptor affinity or activity has been published for this molecule.

Source

No presence in cannabis is established: Wikipedia calls it a trace phytocannabinoid, without a source, and no publication of isolation or detection in the plant was found. 8-OH-HHC is a metabolite of HHC: described as early as 1991 in animal liver microsomes, it has been found in humans in urine from users and in serum and urine from volunteers after controlled HHC intake (Höfert et al. 2026). The HHC it derives from is a semi-synthetic cannabinoid, the first reported on the European market, in May 2022.

No known plant pathway. In the body, the molecule results from hydroxylation of HHC at position 8 by hepatic cytochromes P450; Harvey and Brown (1991) showed that the weight of this route, alongside C11 hydroxylation, varies strongly between species, and attributed this to the orientation of the molecule in the enzyme's active site rather than to the reactivity of the C-H bond. The human isoforms involved have not been identified. Standards of the four stereoisomers are obtained by chemical synthesis from Δ8-THC (Ieuji et al. 2026).

European Union

8-hydroxy-HHC is not the subject of any European measure naming it. The relevant framework is that of HHC: the first semi-synthetic cannabinoid reported in the Union, monitored by the early warning system since October 2022, it was controlled in at least twenty-two member states according to the European drug report 2025. At international level, the United Nations Commission on Narcotic Drugs listed HHC in Schedule II of the 1971 Convention at its 68th session, in March 2025, a decision that entered into force on 6 December 2025. Hydroxylated derivatives such as 8-hydroxy-HHC are treated variously depending on the state, often through generic chemical-family clauses.

France

8-hydroxyhexahydrocannabinol is not named individually on the list of substances classified as narcotics published by the ANSM. It falls under the generic clause entered in annex IV of the decree of 22 February 1990 by the decision of 22 May 2024, which covers any substance derived from the benzo[c]chromene nucleus, whether that nucleus is non-, partially or fully hydrogenated on ring A, apart from expressly provided exclusions (cannabinol, cannabinolic acid, and, subject to content conditions, THCV, THCVA and THCA). The HHC from which it derives is, for its part, classified as a narcotic by name since the decision of 12 June 2023, alongside HHC acetate and HHCP. HHC has been listed in annex III of the decree since the ANSM decision of 16 January 2026. Production, sale and use therefore fall under the narcotics regime.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Family

Metabolite

Chemistry

C5 side chain · neutral form

Parent molecule

HHC

Natural trace reported

Natural trace reported, unverified: the Wikipedia article calls the 8-OH-HHCs « trace phytocannabinoids » without a reference, and no publication of isolation or detection in Cannabis was found.

Wikipedia (en), 8-Hydroxyhexahydrocannabinol, revid 1370714682 (new tab)

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

8-Hydroxyhexahydrocannabinol (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

1. 1Ieuji K, Nakamura K, Takahashi H. Stereoselective Synthesis and Structural Confirmation of All Four 8-Hydroxyhexahydrocannabinol Stereoisomers. Molecules. 2026;31(2):289. (new tab)PMID 41599339
2. 2Harvey DJ, Brown NK. Comparative in vitro metabolism of the cannabinoids. Pharmacol Biochem Behav. 1991;40(3):533-540. Identification of 8-alpha-OH-HHC in the mouse and 8-beta-OH-HHC in the hamster. (new tab)
3. 3Lindbom K, Norman C, Baginski S, et al. Human metabolism of the semi-synthetic cannabinoids hexahydrocannabinol, hexahydrocannabiphorol and their acetates using hepatocytes and urine samples. Drug Test Anal. 2025;17(3):372-386. (new tab)
4. 4Synthesis and pharmacological activity of the epimers of hexahydrocannabinol (HHC). Scientific Reports, 2023. Reference data on the parent HHC (CB1 partial agonism, 9R and 9S epimers). (new tab)
5. 5ANSM. Consolidated list of substances classified as narcotics, updated 16 February 2026 (annex IV, generic benzo[c]chromene clause). (new tab)
6. 6ANSM. Decision of 22 May 2024 amending the list of substances classified as narcotics (generic benzo[c]chromene clause). (new tab)
7. 7ANSM. Decision of 12 June 2023 amending the list of substances classified as narcotics (HHC, HHC-acetate, HHCP). (new tab)
8. 8ANSM. Decision of 16/01/2026 amending the list of substances classified as narcotics (HHC listed in annex III) (new tab)
9. 9UNODC. CND decision on international control of hexahydrocannabinol (HHC) enters into force, 6 December 2025 (Schedule II, 1971 Convention). (new tab)
10. 10EUDA. Hexahydrocannabinol (HHC) and related substances, technical report. (new tab)

SMILES

OC=1C=C(C=C2OC(C)(C)C3CC(O)C(C)CC3C12)CCCCC

Machine-readable entry (JSON)

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