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Semi-synthetic cannabinoid

CBDDCannabidiol dimethyl ether

Dimethyl ether of CBD, a potent and selective inhibitor of 15-lipoxygenase.

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. 15-lipoxygénaseAntagonist85 out of 100

    CI50 0,28 µM (2,56 µM pour le CBD) ; rapport de sélectivité 5-LOX/15-LOX supérieur à 700 (Takeda et coll., 2009)

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

Cannabidiol-2',6'-dimethyl ether (CBDD) is the cannabidiol derivative whose two phenolic hydroxyls are methylated. In 2009 Takeda's team showed that this methylation strengthens the inhibition of 15-lipoxygenase: the IC50 falls from 2.56 µM for CBD to 0.28 µM for CBDD, with a selectivity above 700 over 5-lipoxygenase. Because 15-lipoxygenase takes part in the formation of oxidised LDL, CBDD was proposed as a prototype for atherosclerosis research, and a 2011 study confirms that it selectively blocks this pathway in vitro. In apolipoprotein E-deficient mice, however, it stimulated body weight gain. Its metabolism in the guinea pig goes through an epoxide, 1S,2R-epoxy-CBDD. No human data exist.

Key sources.

History

Source
A derivative of cannabidiol in which the two phenolic hydroxyls are masked by methyl groups. It is studied as a research tool, mainly by the Japanese team of Shuso Takeda and Kazuhito Watanabe.

Route of preparation (chemical process)

Route of preparation: CBDD is obtained by methylation of the two phenol groups of cannabidiol, itself extracted from hemp. This is a chemical transformation of the etherification class, with no enzymatic equivalent described in the plant for the dimethylated derivative.

References

  1. Takeda et coll., le cannabidiol-2',6'-diméthyl éther, dérivé du cannabidiol, est un inhibiteur puissant et sélectif de la 15-lipoxygénase, Drug Metabolism and Disposition 2009 (new tab)PMID 19406952
  2. Takeda et coll., le cannabidiol-2',6'-diméthyl éther protège efficacement de l'oxydation des lipoprotéines de basse densité par la 15-lipoxygénase in vitro, Biological and Pharmaceutical Bulletin 2011 (new tab)PMID 21804214
  3. Takeda et coll., le cannabidiol-2',6'-diméthyl éther stimule la prise de poids chez des souris déficientes en apolipoprotéine E, Journal of Toxicological Sciences 2015 (new tab)PMID 26558454
  4. Gohda et coll., métabolisme in vivo et in vitro de l'éther monométhylique et de l'éther diméthylique du cannabidiol chez le cobaye, Chemical and Pharmaceutical Bulletin 1990 (new tab)PMID 2208386
  5. Légifrance, annexe IV de l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants (new tab)
  6. PubChem CID 3081957 : cannabidiol diméthyl éther (identifiants) (new tab)

Structured data

SMILES
CCCCCC1=CC(=C(C(=C1)OC)[C@@H]2C=C(CC[C@H]2C(=C)C)C)OC
InChIKey
UYBGHBAVRNATET-VQTJNVASSA-N

Machine-readable entry (JSON)

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