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From the plant

CBDMCannabidiol monomethyl ether

Methyl ether of CBD isolated from hemp in 1972; weak THC-like activity in animals.

Unscheduled
Level of detail

C₂₂H₃₂O₂

CAS 1972-05-0

Family
PhytocannabinoidMinor
Origin
Origin not established
Molar mass
328.50 g/mol

Updated on

In plain terms

CBDM is a CBD in which one of the two hydroxyl groups carries a methyl. It was isolated from hemp leaves in 1972, without anyone knowing how the plant forms it. In rats and pigeons it barely reproduced the effects of THC, and no human data exist.

Receptors and activity

Target network

  • Blocks or inhibits

The lower the cited value, the closer the target sits to CBDM: one ring per factor of 100. A target with no measured value stays on the edge.

Cited values

  1. CYP2C19InhibitorIC50 = 1.9 µM · human29 out of 100

    Jiang et al. 2013, Drug Metab Pharmacokinet (new tab) · Catalytic activity of recombinant human CYP2C19 (structure-activity series around CBD)

  2. 15-lipoxygenaseInhibitorno measured value cited

    Stronger inhibition than that of CBD (CBD IC50: 2.56 µM); the CBDM-specific value is not reproduced here (Takeda et al. 2009)

Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Measured effects

Not characterised. No placebo-controlled human trial has measured the effects of CBDM, so no level is shown.

Levels computed from placebo-controlled human trials: difference from placebo on 100, at the dose and route stated. Read the method

Pharmacology

Cannabidiol monomethyl ether (CBDM) is a CBD-type cannabinoid in which one of the two phenolic hydroxyls carries a methyl. Described in 1972 by Shoyama et al., it was isolated from the decarboxylated ethanolic extract of hemp leaves (Radwan 2021); its origin in the plant is not established, as no methylating enzyme has been described. In rats and pigeons trained to recognise Δ9-THC, it produced only vehicle-appropriate responding at 3 and 10 mg/kg; at 17.5 mg/kg, tested in pigeons only, 30% of responses were THC-appropriate, with a depressant effect on response rate (Järbe 1986). No CB1 or CB2 affinity constant has been published. In vitro, it inhibited recombinant human CYP2C19 (IC50 = 1.88 µM, comparable to CBD; Jiang 2013) and inhibited 15-lipoxygenase more strongly than CBD (Takeda 2009). In the guinea pig, liver microsomes convert it into cannabielsoin monomethyl ether through the cytochrome P450 system (Gohda 1990). No human data are available.

Key sources.

History

Source
Cannabis sativa L.: isolated from hemp leaves after decarboxylation of the extract (Shoyama et al. 1972, per Radwan et al. 2021). Origin not established: no enzyme able to methylate CBD or its acid has been described.

Biosynthetic pathway

Origin not established. No methyltransferase forming CBDM has been described in the sources consulted. Linciano et al. (2020) note that the literature also reports a corresponding acid, cannabidiolic acid monomethyl ether (CBDMA), of which CBDM would be the decarboxylated form; this relationship has not been demonstrated.

Classification

Family, origin and source verification

Family

Phytocannabinoid › Minor

Presence in the plant

Present in the plant; origin not established

Chemistry

Type CBD · C5 side chain · neutral form

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

No dedicated article.

References

  1. Shoyama Y., Kuboe K., Nishioka I., Yamauchi T. 1972, Chem Pharm Bull 20:2072: cannabidiol monomethyl ether, a new neutral cannabinoid (new tab)DOI 10.1248/cpb.20.2072
  2. Radwan M.M. et al. 2021, Molecules 26:2774: inventory of cannabinoids, CBD-type subclass (new tab)PMID 34066753
  3. Järbe T.U. et al. 1986, Pharmacol Biochem Behav: cannabimimetic activity (Δ1-THC cue) of CBDM in rats and pigeons (new tab)PMID 3020594
  4. Gohda H. et al. 1990, Chem Pharm Bull: metabolism of CBDM and CBD dimethyl ether in the guinea pig (new tab)PMID 2208386
  5. Jiang R. et al. 2013, Drug Metab Pharmacokinet: inhibition of CYP2C19 by CBD and its methyl ethers (new tab)PMID 23318708
  6. Takeda S. et al. 2009, Drug Metab Dispos: inhibition of 15-lipoxygenase by CBD methyl ethers (new tab)PMID 19406952
  7. Linciano P. et al. 2020, Sci Rep: identification of CBDH, an isomer of CBDM (new tab)PMID 33328530
  8. PubChem CID 164905: cannabidiol monomethyl ether (identifiers) (new tab)
  9. ANSM, consolidated list of substances classified as narcotics, updated 26/06/2026 (new tab)

Identifiers

Names

Common name
Cannabidiol monomethyl ether
IUPAC name
3-methoxy-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylphenol
Other names
CBDM

Identifiers

Formula
C₂₂H₃₂O₂
CAS
1972-05-0
PubChem CID
164905(new tab)
InChIKey
IPGGELGANIXRSX-RBUKOAKNSA-N
SMILES
CCCCCC1=CC(=C(C(=C1)OC)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O

Machine-readable entry (JSON)

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