JWH-193

Formula

C₂₆H₂₆N₂O₂

Molar mass

398.50 g·mol⁻¹

CAS

133438-58-1

PubChem CID

10250276

Origin

A wholly synthetic compound. It has no natural occurrence, is found in no plant and is not a product of metabolism. Its production belongs to the laboratory, for pharmacological research purposes, and to clandestine manufacture intended for the synthetic cannabinoid market.

InChIKey

ICKWPPYMDARCKJ-UHFFFAOYSA-N

Editorial estimate, not clinical.

JWH-193 belongs to the naphthoylindole family, those synthetic cannabinoids built on an indole core linked by a ketone to a naphthalene, whose leader JWH-018 opened the market in products sold under the misleading label of incense or smoking mixtures. It is distinguished by its morpholinoethyl chain borne by the indole nitrogen, inherited from JWH-200, and by a methyl at position 4 of the naphthalene. That last modification is the compound's reason for existing within the series: it multiplies by about seven the affinity for the CB1 receptor, which stands around 6 nanomolar, far above that of Δ9-THC. The structure-activity relationship work of Huffman and his team, covering dozens of analogues, served precisely to map the effect of naphthalene substituents and of N-alkyl chain length on CB1 affinity and on CB2 selectivity, and to identify along the way several highly selective CB2 agonists. What this entry cannot say must be stressed. No specific functional efficacy study, no pharmacokinetic, metabolic or human toxicology data are published for this compound. The risks documented for the whole class of synthetic CB1 agonists, most of which are full agonists where THC is only a partial agonist, cannot be quantified for it in particular, but they apply by construction: agitation, tachycardia, convulsions and acute psychiatric disturbances have been reported for this entire family.

An entirely chemical route, described here by class only. The molecule combines three elements assembled by synthesis: an indole core, a ketone function linking position 3 of that indole to a methylated naphthalene, and a morpholinoethyl chain borne by the indole nitrogen. It does not exist in nature and proceeds from no enzymatic route.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Class

ECS modulator (research)

Origin

A wholly synthetic compound. It has no natural occurrence, is found in no plant and is not a product of metabolism. Its production belongs to the laboratory, for pharmacological research purposes, and to clandestine manufacture intended for the synthetic cannabinoid market.

Status

Narcotic: generic clause

1. 1.Huffman et Padgett 2005 : développements récents en chimie médicinale des indoles, pyrroles et indènes cannabimimétiquesPMID 15974991
2. 2.Huffman et coll. 2005 : relations structure-activité des 1-alkyl-3-(1-naphtoyl)indoles sur les récepteurs CB1 et CB2PMID 15582455