Minor phytocannabinoid
CBNDCannabinodiol
2-(5-methyl-2-prop-1-en-2-ylphenyl)-5-pentylbenzene-1,3-diol
Aliases.Cannabinodiol · CBND · CBND-C5 · cannabidinodiol
A fully aromatised analogue of CBD, present in trace amounts.
Updated on
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.
Identifiers
- Formula
- C₂₁H₂₆O₂
- Molar mass
- 310.40 g·mol⁻¹
- CAS
- 39624-81-2
- PubChem CID
- 11551346
- First described
- Décrit dans les années 1970 parmi les constituants mineurs du cannabis, notamment dans certains haschichs vieillis.
- Origin
- Cannabis sativa (a minor constituent); mainly a conversion product of CBD and CBN.
- InChIKey
- TWKHUZXSTKISQC-UHFFFAOYSA-N
In plain terms
Cannabinodiol is a minor cannabinoid, a fully aromatised cousin of CBD, found in trace amounts in hemp, especially in aged material.
Receptors and activity
- CB1Modulator
- CB2Modulator
- 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.
- Calm30
- Clarity15
- Sleep25
- Appetite15
- High12
Editorial estimate, not clinical.
Pharmacology
Cannabinodiol (CBND) is a minor cannabinoid corresponding to the fully aromatised form of cannabidiol: the terpene ring of CBD has become aromatic, which makes it a biphenyl molecule. It is not produced directly by hemp but appears as a conversion product of CBD (aromatisation by photo-oxidation or by oxidation under basic conditions) and can also derive from cannabinol. Its pharmacology is very little studied: no reliable affinity for the CB1 or CB2 receptors is documented, and it does not belong to the structural family of THC. It is among the trace constituents isolated from certain aged cannabis and hashish samples.
Biosynthetic pathway
Cannabinodiol is not made directly by an enzyme of hemp: it appears as a conversion product, through aromatisation of the cyclohexene ring of CBD (photo-oxidation, or oxidation under basic conditions in air), a route by which it can also derive from the rearrangement of cannabinol (CBN). It is therefore found above all in aged plant material or material heavily exposed to light.
Legal framework
France
In France, cannabinodiol is not listed by name on the list of narcotics. Being a CBD-type analogue (a biphenyl core, and not the benzo[c]chromene core of the THC derivatives), it is not covered by the generic clause relating to derivatives of tetrahydrocannabinol. It is a poorly characterised minor cannabinoid: its status is not explicitly settled and the general regime applicable to hemp extracts should be applied (with the THC content strictly regulated).
European Union
No harmonised status at European Union level: cannabinodiol is not specifically regulated, each Member State applying its own approach to minor cannabinoids. Certain non-EU countries do regulate it (Canada: Schedule II; United Kingdom: Psychoactive Substances Act 2016).
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Minor phytocannabinoid
- Origin
- Cannabis sativa (a minor constituent); mainly a conversion product of CBD and CBN.
Cannabinoïde de type biphényle : deux noyaux aromatiques reliés, dont un cycle résorcinol pentylé, correspondant à la forme entièrement aromatisée du cannabidiol (le cycle terpénique du CBD y est devenu aromatique).
References
Structured data
- InChIKey
- TWKHUZXSTKISQC-UHFFFAOYSA-N
- SMILES
- CCCCCC1=CC(=C(C(=C1)O)C2=C(C=CC(=C2)C)C(=C)C)O
- Formula
- C21H26O2
- Molar mass
- 310.40 g·mol⁻¹
- CAS
- 39624-81-2
- PubChem CID
- 11551346
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.