THC-C1.Tetrahydrocannabiorcol

Tetrahydrocannabiorcol (Δ9-THC-C1) is the methyl homologue of Δ9-THC: the same benzo[c]chromene skeleton with (6aR,10aR) configuration, but a side chain of a single carbon at position 3. It was reported by gas chromatography coupled with mass spectrometry in hashish (Vree et al. 1972), then in the pollen of male plants (Ross et al. 2005), without isolation from the plant. Andersson et al. (Nature Communications, 2011) found it devoid of agonist activity at the human CB1 and CB2 receptors and the most active of the cannabinoids screened at the human TRPA1 channel expressed in HEK293 cells, as potent and effective as allyl isothiocyanate, through a non-electrophilic mechanism. In cultured mouse sensory neurons, 20 µM triggered a calcium response in 38% of neurons versus 3% in mice lacking TRPA1, and intrathecal injection produced TRPA1-dependent antinociception in mice. It directly activates purified human TRPA1 (Moparthi et al. 2014) as well as TRPV2, in whose vanilloid pocket it sits, and human TRPV1 (Zhang et al. 2022); these activations lie in the micromolar range. No human data, no pharmacokinetics, no metabolism and no toxicology study have been published: it is a pharmacological tool for TRP channels, not a cannabinoid for consumption. In France, it falls within the generic class of benzo[c]chromene derivatives created by the ANSM in 2024.

Source

Cannabis sativa L.: tentative identification only, by gas chromatography coupled with mass spectrometry, in hashish (Vree et al. 1972), in Brazilian marijuana (1973, according to Radwan et al. 2021) and in the pollen of male plants (Ross et al. 2005); the molecule has not been isolated from the plant in the sources consulted. Origin not established. Pharmacological studies use synthetic compound.

No biosynthetic pathway has been demonstrated for the methyl-chain (C1) series. The corresponding acid form, Δ9-tetrahydrocannabiorcolic acid, was identified by GC-MS in cannabis samples (Radwan et al. 2021), but neither the starter unit nor the enzyme that would form it has been characterised.

European Union

Not listed by name in the schedules of the 1961 and 1971 United Nations conventions, according to annexes I to III of the ANSM consolidated list (26/06/2026). Checked on 20/10/2026.

France

Tetrahydrocannabiorcol is not named in the ANSM consolidated list (updated 26/06/2026). A derivative of the benzo[c]chromene nucleus, with a hydroxyl at position 1, an alkyl chain (a methyl) at 3, two alkyl groups at 6 and an alkyl at 9, it falls within the definition of the generic class created by the ANSM decisions of 22/05/2024 and 03/06/2024, and is not among its exclusions (CBN, CBNA, THCV and THCVA up to 0.3%, THCA subject to a content condition). It is therefore a controlled narcotic by generic capture and not by named listing; application to a given product is a matter for legal analysis. Checked on 20/10/2026.

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

Family

Phytocannabinoid › Minor

Presence in the plant

Tentative identification, never isolated

Chemistry

Type Δ9-THC · C1 side chain · neutral form

Verification

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

Wikipedia (English)

Tetrahydrocannabiorcol (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. 1Vree T. B. et al., identification in hashish of the methyl side-chain analogues of THC, CBD and CBN, J Pharm Pharmacol 1972, 24:7-12 (new tab)PMID 4401327
2. 2Radwan M. M. et al., Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis, Molecules 2021 (compounds 8 and 9) (new tab)PMID 34066753
3. 3Ross S. A. et al., flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L., Phytochem Anal 2005, 16:45-48 (new tab)PMID 15688956
4. 4Andersson D. A. et al., TRPA1 mediates spinal antinociception induced by acetaminophen and Δ9-tetrahydrocannabiorcol, Nat Commun 2011, 2:551 (new tab)PMID 22109525
5. 5Moparthi L. et al., human TRPA1 is intrinsically sensitive to cold and to chemical agents (direct activation by Δ9-tetrahydrocannabiorcol), PNAS 2014, 111:16901-16906 (new tab)PMID 25389312
6. 6Zhang L. et al., TRPV2 modulation by a cannabinoid site distinct from that of cannabidiol (Δ9-tetrahydrocannabiorcol, C16), Nat Commun 2022, 13:7483 (new tab)PMID 36470868
7. 7PubChem CID 22805649 and GSRS UNII 5D633LAJ19: Δ9-tetrahydrocannabiorcol (6aR,10aR), CAS 22972-65-2 (new tab)
8. 8ANSM, consolidated list of substances classified as narcotics, updated 26/06/2026 (benzo[c]chromene class and its exclusions) (new tab)

SMILES

CC1=C[C@@H]2[C@@H](CC1)C(OC3=C2C(=CC(=C3)C)O)(C)C

Machine-readable entry (JSON)

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