What is CBV (cannabivarin)? Effects, legality, buying

Identifiers

Formula: C₁₉H₂₂O₂
Molar mass: 282.40 g·mol⁻¹
CAS: 33745-21-0
PubChem CID: 622545
First described: La cannabivarine a été décrite en 1971 par F. W. H. M. Merkus, qui a signalé dans Nature la présence conjointe de cannabivarine et de tétrahydrocannabivarine dans du haschisch. Une méthode de chromatographie en phase gazeuse permettant de la distinguer du cannabidiol et du cannabichromène a été publiée en 1975 par Bailey et Gagné. Sa caractérisation pharmacologique n'a réellement commencé qu'à partir de 2018.
Origin: A minor cannabinoid of Cannabis sativa, present in trace amounts in inflorescences, resins and hashish. Its content rises with the ageing and oxidation of the plant material, so that it gives information on the age and storage conditions of a batch, in the same way as CBN. It appears only in the chemotypes that actually express the propyl pathway, a minority among cultivated varieties.
InChIKey: SVTKBAIRFMXQQF-UHFFFAOYSA-N

In plain terms

Cannabivarin is a cannabinoid present in very small amounts in hemp. It forms slowly when another molecule of the plant, THCV, ages in contact with air, heat and light, rather as CBN forms from THC. Nothing indicates that it is intoxicating, and human data are lacking to say what it does in the body.

Receptors and activity

TRPA1
Agonist
TRPV2
Agonist
TRPM8
Antagonist
P2X4
Modulator

Agonist
Partial agonist
Antagonist
Modulator
Inverse agonist

Hover over a row for the precise value (Ki, EC50…)

Subjective signature

Hover over an axis to read its definition.

Calm
6
Clarity
5
Sleep
6
Appetite
5
High
5

Editorial estimate, not clinical.

Pharmacology

CBV is the propyl homologue of cannabinol: the same fully aromatised benzochromene tricycle, but a three-carbon side chain instead of five. It is not produced as such by the plant; it results from the progressive oxidation and aromatisation of THCV, as CBN results from those of THC. Its pharmacology is documented only very partially. No affinity constant for the CB1 and CB2 receptors has been published for this molecule, the reference screens not having included it, so that its status as a cannabinoid agonist or antagonist remains undetermined. The available work concerns ion channels: activation of TRPA1 at submicromolar concentrations, inhibition of TRPM8, marked activation of TRPV2, and competitive binding to the purinergic P2X4 receptor. These results come from cellular or cell-free systems, with no follow-up in animals or in humans. No pharmacokinetic, metabolic or toxicological data specific to CBV have been published, and no therapeutic benefit can be attributed to it in the present state of knowledge. Its current interest is above all analytical: its presence signals oxidised or aged plant material.

Key sources.

Biosynthetic pathway

CBV is not assembled directly by the plant. It belongs to the propyl series, known as the varin series: divarinolic acid, formed from butyryl-CoA and malonyl-CoA, is prenylated to cannabigerovarinic acid (CBGVA), which THCA synthase cyclises to tetrahydrocannabivarinic acid (THCVA). After decarboxylation, the THCV thus obtained slowly oxidises and aromatises under the effect of oxygen, heat and light, which produces CBV. The relationship is the same as that between THC and CBN, transposed to the propyl chain. The corresponding acid form, cannabivarinic acid (CBVA), is described in the same series.

Legal framework

France

In France, cannabivarin is not listed by name on the narcotics list. Annex IV of the decree of 22 February 1990 classifies tetrahydrocannabinols, their esters, their ethers, their salts as well as the salts of the aforementioned derivatives: this generic clause covers the THC family. CBV does not fall under it, since its terminal ring is fully aromatised and it is neither a tetrahydrocannabinol, nor an ester, ether or salt of tetrahydrocannabinol. It is therefore in the position of an unclassified substance, unlike the synthetic and semi-synthetic cannabinoids that the ANSM has listed one by one since 2023. Products containing it remain subject to the ceiling of 0.30 per cent delta-9-THC set by the decree of 30 December 2021, and food uses fall in addition under the novel foods regulations.

European Union

No Union text covers cannabivarin as such. It appears neither in the schedules of the 1961 Single Convention nor in those of the 1971 Convention on psychotropic substances. Minor cannabinoids are the subject of no European harmonisation: each Member State retains control of its own narcotics list, and national differences are real. The agricultural threshold of 0.30 per cent delta-9-THC applies to hemp grown in the Union. For any product intended to be ingested, the question of novel food status arises and is unsettled for cannabinoids other than CBD.

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

Structural classification

Class: Minor phytocannabinoid
Origin: A minor cannabinoid of Cannabis sativa, present in trace amounts in inflorescences, resins and hashish. Its content rises with the ageing and oxidation of the plant material, so that it gives information on the age and storage conditions of a batch, in the same way as CBN. It appears only in the chemotypes that actually express the propyl pathway, a minority among cultivated varieties.
Status: Unscheduled

Cannabinoïde de type cannabinol (CBN) : tricycle benzochroménique dont le cycle terminal est entièrement aromatisé, porteur d'une chaîne latérale propyle à trois carbones au lieu du pentyle habituel. Le CBV est donc l'homologue varine du cannabinol, sans double liaison isomère ni stéréoisomère possible.

Pharmacokinetics

Aucune étude d'absorption, de distribution ou d'élimination n'a été publiée pour la cannabivarine, ni chez l'animal ni chez l'humain. Sa forte lipophilie et sa parenté structurale avec le cannabinol laissent supposer un comportement voisin, avec accumulation dans les tissus adipeux, mais il s'agit d'une extrapolation et non d'une mesure.

Metabolism

Aucune voie métabolique n'a été caractérisée expérimentalement pour le CBV. Les isoformes du cytochrome P450 qui hydroxylent les cannabinoïdes voisins n'ont pas été évaluées sur cette molécule, et aucun métabolite n'a été identifié dans un fluide biologique.

Toxicology and risks

Aucune étude de toxicité aiguë ou répétée ne porte spécifiquement sur la cannabivarine. La littérature chimique la qualifie de composé non narcotique, mais cette mention traduit l'absence d'effet de type THC et ne constitue pas une évaluation de sécurité. En l'absence de données humaines, aucune conclusion sur l'innocuité ne peut être formulée, en particulier pour la grossesse, l'allaitement ou les interactions médicamenteuses.

Detection and analysis

La cannabivarine se dose par chromatographie en phase gazeuse ou liquide couplée à la spectrométrie de masse, et un matériau de référence certifié est commercialisé pour l'étalonnage des laboratoires. La première méthode de séparation, publiée en 1975, reposait sur une chromatographie en phase gazeuse avec méthylation en colonne, afin de la distinguer du cannabidiol et du cannabichromène. En criminalistique, elle figure parmi les composés visualisés par spectrométrie de masse d'ions secondaires à temps de vol sur des empreintes digitales contaminées par du cannabis. Elle sert aussi de repère de vieillissement, sa présence traduisant l'oxydation de la fraction propyle du matériel végétal.

References

Structured data

InChIKey: SVTKBAIRFMXQQF-UHFFFAOYSA-N
SMILES: CCCC1=CC(=C2C(=C1)OC(C3=C2C=C(C=C3)C)(C)C)O
Formula: C19H22O2
Molar mass: 282.40 g·mol⁻¹
CAS: 33745-21-0
PubChem CID: 622545

Machine-readable entry (JSON)

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

CBVCannabivarin