Cannabisol.

Cannabisol is a dimer of Δ9-tetrahydrocannabinol: two THC units joined by a methylene bridge between their 2-positions, the first carbon-bridged dimeric cannabinoid described in the literature. Zulfiqar and colleagues isolated it in 2012 from 36 cannabis samples seized in the United States and rich in CBG, combined to reach 630 g of material, which yielded 10 mg of purified compound; the structure was established by high-resolution mass spectrometry, GC-MS and NMR. The authors propose a biogenesis through decarboxylation of Δ9-tetrahydrocannabinolic acid followed by enzymatic installation of the one-carbon bridge, without identifying an enzyme. In GC-MS the compound gave two peaks at m/z 314 and 328, assigned to Δ9-THC and 2-methyl-Δ9-THC. No pharmacology has been published: no binding assay, no activity measurement, no animal or human data.

Source

Present in trace amounts in cannabis: 36 samples seized in the United States, rich in CBG (1.4 to 3.8%) and combined (630 g), yielded 10 mg of purified product. The authors propose a plausible but unproven biogenesis: origin not established.

The molecule is a dimer: two units of Δ9-tetrahydrocannabinol linked by a methylene bridge between their positions 2, that is, on the aromatic ring of each unit. The authors of the isolation propose an initial decarboxylation of Δ9-tetrahydrocannabinolic acid, followed by nucleophilic attack of the resulting anion on the electrophilic carbonyl carbon of a coenzyme A ester, then an enzymatic reduction that installs the one-carbon bridge. This pathway is presented as plausible, not as demonstrated: no enzyme has been identified.

European Union

No EU instrument specific to the molecule; not named in the schedules of the 1961 and 1971 United Nations conventions.

France

Not named in the ANSM consolidated list (updated 26/06/2026). Each of its two units is a Δ9-THC (benzo[c]chromene nucleus, hydroxyl at 1, pentyl at 3, two methyls at 6, methyl at 9), but they are joined by a methylene bridge at position 2, where the text of the generic class (ANSM decisions of 22/05/2024 and 03/06/2024) only provides for a carboxyl. Cannabisol is not among the exclusions (CBN, CBNA, THCV and THCVA up to 0.3%, THCA subject to a content condition); its attachment to this class, or to the entry « Tétrahydrocannabinols, leurs esters, éthers, sels » (annex III since the ANSM decision of 06/02/2026), is a reading to be confirmed by a lawyer. Checked 20/10/2026.

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

Family

Phytocannabinoid › Minor

Presence in the plant

Present in the plant; origin not established

Chemistry

Δ9-THC type (dimer) · C5 side chain · neutral form

Verification

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

Wikipedia (English)

Cannabisol (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. 1Zulfiqar et al. 2012, Tetrahedron Lett 53(28):3560-3562: cannabisol, a methylene-bridged Δ9-THC dimer isolated from Cannabis sativa (new tab)PMID 27695140
2. 2Radwan et al. 2021, Molecules: inventory of cannabis cannabinoids (new tab)PMID 34066753
3. 3ANSM, decision of 22/05/2024 (benzo[c]chromene class) and consolidated list of 26/06/2026 (new tab)
4. 4PubChem CID 102487751: cannabisol (new tab)

SMILES

CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1CC4=C(C5=C(C=C4CCCCC)OC([C@H]6[C@H]5C=C(CC6)C)(C)C)O)O

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.