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JWH-139

1-deoxy Δ8-THC analogue of the JWH series, with high CB2 affinity and low CB1 affinity.

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.

C₂₁H₃₀O

CID 58683014

Family
Synthetic cannabinoid (SCRA)
Molar mass
298.50 g/mol

Updated on

In plain terms

JWH-139 is a synthetic molecule close to THC, created in the laboratory as a research tool for the CB2 receptor. In the published measurements it binds CB2 far more strongly than CB1, and no human use is established. In France it is not named in the list of narcotics, but it falls under the generic clause for derivatives of the benzo[c]chromene nucleus.

Receptors and activity

  1. CB1Modulator27 out of 100

    Ki 2 290 nM sur CB1 de rat (Mangiatordi et coll., 2020, via ChEMBL) ; série de Huffman et coll., 1999 : Ki supérieur à 295 nM pour les termes n = 1 à 4

  2. CB2Modulator82 out of 100

    Ki 14,0 nM sur CB2 humain (Mangiatordi et coll., 2020, via ChEMBL) ; série de Huffman et coll., 1999 : Ki inférieur à 20 nM pour les termes n = 1 à 5

Bar length shows the relative strength of the interaction, as an indication; its colour, the mode of action: pink for an agonist, ink for an antagonist, grey for a modulator.

Pharmacology

JWH-139 is a 1-deoxy analogue of Δ8-THC, part of the series by Huffman et al. (1999) devoted to the search for selective CB2 receptor ligands. In the reported measurements, its affinity is high for CB2 (Ki of 14.0 nM according to the ChEMBL database) and low for CB1 (Ki of 2 290 nM at the rat receptor), while the abstract of the article reports, for the analogues of the series with n from 1 to 4, a Ki above 295 nM at CB1. No functional efficacy, pharmacokinetic or human trial data were found in the sources consulted. In France it is not named in the list of narcotics, but it falls under the generic clause for the benzo[c]chromene nucleus (decision of 22 May 2024).

History

Source
A synthetic molecule with no known plant origin. It was designed as a research tool for cannabinoid receptors, not as a medicine.

Origin

Pharmaceutical research → illicit market

No biosynthetic pathway: JWH-139 is produced by no living organism. It belongs to synthetic chemistry alone, within the chemistry of THC analogues.

References

Identifiers

Names

IUPAC name
(6aR,10aR)-6,6,9-trimethyl-3-(2-methylbutan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene
Other names
910865DJI7 · 3-(1',1'-Dimethylpropyl)-1-deoxy-delta8-THC

Identifiers

Formula
C₂₁H₃₀O
InChIKey
YSHKYTNQWIZJFW-ZWKOTPCHSA-N
SMILES
CCC(C)(C)C1=CC2=C(C=C1)[C@@H]3CC(=CC[C@H]3C(O2)(C)C)C

Machine-readable entry (JSON)

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