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Minor phytocannabinoid

CBGBCannabigerobutol

Butyl homologue of CBG, a main impurity of cannabigerol extracted from hemp.

Unscheduled
Level of detail

Harm-reduction warning

No characterised human dose: animal / in vitro data only. Effect profile, safety margin and acute toxicity are not documented in human clinical practice. Extremely potent compound: severe effects, seizures and deaths reported in the literature.

Receptors and activity

  1. CB1Modulatoraucune constante d'affinité publiée5 out of 100
  2. CB2Modulatoraucune constante d'affinité publiée5 out of 100
Bar length shows the relative strength of the interaction, as an indication.

Subjective signature

Calm
6 out of 100
Relaxation of body and mind; reduced mental noise without marked drowsiness.
Clarity
4 out of 100
Sustained attention and clear thinking; functional lucidity, not euphoria.
High
2 out of 100
Euphoria and sensory intensity; altered perception of time and space.
Appetite
4 out of 100
Stimulation of hunger and of taste appreciation (the “munchies” effect).
Sleep
4 out of 100
Sedative effect: aids sleep onset and the continuity of deep sleep.
Editorial estimate, not clinical.

Pharmacology

Cannabigerobutol (CBGB) is the butyl side-chain homologue of cannabigerol. It was identified in 2021 by Cannazza and Citti's team as one of the two main impurities of commercial cannabigerol extracted from hemp, together with cannabigerovarin, by high-resolution mass spectrometry and then comparison with the synthetic standard; the same study provides its full spectroscopic characterisation and an assay validated between 0.01 and 1.00 µg/mL. A 2022 study prepared a series of CBG homologues by synthesis: in mice, all of them attenuated chemotherapy-induced neuropathic pain to a similar extent at 10 mg/kg, and the short chains, CBGV and CBGB, reduced the viability of colorectal cancer cells more strongly. No CB1 or CB2 affinity and no human data have been published.

Key sources.

History

Source
Cannabis sativa L. (hemp): identified as one of the two main impurities of cannabigerol extracted from hemp, alongside cannabigerovarin.

Biosynthetic pathway

Biosynthetic pathway: CBGB belongs to the butyl series of cannabinoids, in which the olivetolic acid type precursor carries a four-carbon chain. Its geranylation leads to cannabigerobutolic acid, whose decarboxylation releases CBGB. Because cannabigerol and its homologues are the precursors of the other cannabinoids, they are rapidly converted in the plant and persist there only in small amounts.

References

  1. Tolomeo et coll., analyse HPLC-UV-HRMS du cannabigérovarine et du cannabigérobutol, les deux impuretés du cannabigérol extrait du chanvre, Journal of Pharmaceutical and Biomedical Analysis 2021 (new tab)PMID 34153935
  2. Raup-Konsavage et coll., synthèse efficace pour modifier la longueur de chaîne latérale des cannabinoïdes et effets sur la chimiothérapie et la douleur neuropathique induite, Biomolecules 2022 (new tab)PMID 36551296
  3. Légifrance, annexe IV de l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants (new tab)
  4. PubChem CID 131973883 : cannabigérobutol (identifiants) (new tab)

Structured data

SMILES
CCCCC1=CC(=C(C(=C1)O)C/C=C(\C)/CCC=C(C)C)O
InChIKey
LXMICYYYVWWGAM-LFIBNONCSA-N

Machine-readable entry (JSON)

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