Semi-synthetic cannabinoid
UnscheduledCBD-DACannabidiol diacetate
[3-acetyloxy-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylphenyl] acetate
Aliases.cannabidiol diacetate · CBD diacétate · CBD-DA · ALL00142 · diacétate de CBD
The acetic diester of CBD, a presumed prodrug found in grey-market products.
Updated on
Level of detail
Identifiers
- Formula
- C₂₅H₃₄O₄
- Molar mass
- 398.50 g·mol⁻¹
- CAS
- -
- PubChem CID
- 15139512
- Origin
- A semi-synthetic compound, absent from cannabis. It is obtained by acetylation of the two hydroxyl groups of cannabidiol. It is encountered today in two distinct contexts: pharmaceutical research on transdermal prodrugs, and grey-market products where it is added outside any regulatory framework.
- InChIKey
- UCYSPYOYJNVCAI-FCHUYYIVSA-N
In plain terms
Cannabidiol diacetate is CBD in which two points of the molecule have been masked by an acetate group. The idea is that it turns back into CBD once in the body. It is found in vaping liquids and foods sold outside any regulatory framework.
Receptors and activity
- CB1Partial agonist
- CB2Partial agonist
- 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.
- Calm25
- Clarity15
- Sleep20
- Appetite5
- High5
Editorial estimate, not clinical.
Pharmacology
Cannabidiol diacetate is the acetic diester of cannabidiol, in which the two phenol functions of the resorcinol ring are masked by acetyl groups. The logic is that of a prodrug: cannabidiol distributes rapidly into adipose tissue and undergoes substantial first-pass metabolism carried by CYP3A and CYP2C, so that increasing its lipophilicity and protecting its phenols may favourably modify its kinetics, the acetate groups then being cleaved by esterases to restore the active molecule. That is the route explored by the company AllTranz, which became Zynerba, in a series of derivatives intended for transdermal administration. The compound has since migrated out of the laboratory: it has been identified as a constituent of grey-market products, electronic cigarette liquids and infused foods. That displacement deserves to be flagged, because a derivative designed for controlled transdermal absorption has been the subject of no assessment for inhalation, a route that raises its own questions, notably about the fate of heated esters. No pharmacokinetic or human safety data are published for this compound.
Route of preparation (chemical process)
No plant route. The diacetate is the acetic diester of cannabidiol: the two phenol functions of the resorcinol ring are esterified by acetic acid, which removes the two free hydroxyls and strongly increases the lipophilicity of the molecule. It is described here by chemical class only.
Legal framework
France
Cannabidiol is not a narcotic in France and its diacetate is named in no text. It falls neither under the heading of tetrahydrocannabinols and their esters, cannabidiol not being a tetrahydrocannabinol, nor under the generic clause targeting derivatives of the benzo[c]chromene core, a skeleton that cannabidiol does not possess. Its presence in consumer products does, however, raise a question of food safety and novel food regulation, distinct from narcotics law.
European Union
No control under the international conventions. The status of an acetylated derivative of cannabidiol in food or vaping falls under the regimes applicable to novel foods and vaping products, where the absence of assessment is the main obstacle: no safety dossier has been submitted for this compound.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Semi-synthetic cannabinoid
- Origin
- A semi-synthetic compound, absent from cannabis. It is obtained by acetylation of the two hydroxyl groups of cannabidiol. It is encountered today in two distinct contexts: pharmaceutical research on transdermal prodrugs, and grey-market products where it is added outside any regulatory framework.
- Status
- Unscheduled
References
Structured data
- InChIKey
- UCYSPYOYJNVCAI-FCHUYYIVSA-N
- SMILES
- CCCCCC1=CC(=C(C(=C1)OC(=O)C)[C@@H]2C=C(CC[C@H]2C(=C)C)C)OC(=O)C
- Formula
- C25H34O4
- Molar mass
- 398.50 g·mol⁻¹
- PubChem CID
- 15139512
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.