JWH-081 N-(4-hydroxypentyl)

Metabolite is a primary phase I metabolite of JWH-081, a synthetic cannabinoid. JWH-081 and its metabolites are studied for their interaction with the endocannabinoid system and are of interest in toxicology and forensic analysis, especially in the context of designer drug detection.

Parent Compound: JWH-081

Full Name: (4-Methoxynaphthalen-1-yl)(1-pentylindol-3-yl)methanone
Class: Synthetic cannabinoid (1-naphthoylindole family) Activity: Potent CB₁ receptor agonist (strong psychoactive effects)
Metabolite Identity and Formation

Name: JWH-081 N-(4-hydroxypentyl) metabolite
Chemical Nature: Phase I hydroxylation product Structure: Hydroxyl group is introduced at the 4th carbon of the N-pentyl side chain Enzyme Involvement: Primarily metabolized by cytochrome P450 enzymes (CYPs) in the liver Hydroxylation increases polarity, aiding in renal excretion and forming the basis for urine drug testing.
Pharmacology

While the metabolite itself is less active than the parent compound (JWH-081), some hydroxylated metabolites of synthetic cannabinoids may retain partial agonist activity at cannabinoid receptors.
CB₁ Activity: Likely reduced compared to JWH-081 CB₂ Activity: Limited data available May contribute to overall pharmacodynamic profile in users
Detection in Biological Samples

Detection of this metabolite is critical for forensic and clinical toxicology, particularly where the parent drug has already been metabolized.
Common Analytical Methods: LC-MS/MS (Liquid Chromatography–Tandem Mass Spectrometry) GC-MS (Gas Chromatography–Mass Spectrometry) after derivatization High-resolution mass spectrometry (HRMS) for confirmation Biological Matrices: Urine: Primary matrix for metabolite detection Blood and plasma: Parent compound usually dominates Hair (occasionally): For retrospective analysis of chronic use
Forensic Significance

The presence of JWH-081 N-(4-hydroxypentyl) metabolite in a sample confirms recent exposure to JWH-081, even if the parent compound is no longer detectable.
Useful in postmortem toxicology Evidence of drug use in workplace, sports, or legal cases Helps distinguish specific synthetic cannabinoid intake, especially among similar compounds
Legal and Regulatory Implications

While metabolites themselves are not directly scheduled, detection of this metabolite often implies use of JWH-081, which is:
Controlled in many countries as part of synthetic cannabinoid legislation May fall under analogue drug laws where not explicitly listed Regulated in the U.S. under Schedule I (DEA)
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