JWH-019
Hexyl homologue of JWH-018, a high-affinity naphthoylindole, classified as a narcotic in France and Schedule I in the United States.
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.
C₂₅H₂₅NO
CAS 209414-08-4
- Family
- Synthetic CB receptor agonistNew psychoactive substance
- Molar mass
- 355.50 g/mol
Updated on
In plain terms
JWH-019 is a synthetic cannabinoid made in a laboratory. It does not exist in hemp and has nothing to do with cannabidiol: it has been detected in products sold as incense. It differs from JWH-018 only by one carbon atom on its side chain, acts on the same receptors as THC, and is classified as a narcotic in France.
Receptors and activity
Target network
- Activates
The lower the cited value, the closer the target sits to JWH-019: one ring per factor of 100. A target with no measured value stays on the edge.
Where these targets live
Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of JWH-019.
CB1CB1 found in 7 regions of the body
- Basal gangliadenseMost dense in basal ganglia outflow nuclei1
- CerebellumdenseVery dense in the cerebellum1
- HippocampusdenseVery high concentrations in the hippocampus2
- AmygdaladenseHigh concentrations in the amygdala2
- CortexpresentPresent throughout the neocortex2
- Adipose tissuepresentExpressed in adipose tissue3
- GutpresentColonic epithelium, smooth muscle and plexus4
Map sources
- Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
- Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
- Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
- Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)
Cited values
- CB1Agonistno measured value cited
High-affinity cannabimimetic agonist: chains of 3 to 6 carbons suffice for high affinity, optimum at 5 carbons (Aung et al., 2000); compound among the most potent of the series in vivo (Wiley et al., 2014); no Ki value of its own found in an open source
- CB2Agonistno measured value cited
High-affinity agonist according to the Aung et al. (2000) series; no Ki value of its own found in an open source
Pharmacology
JWH-019 is the hexyl homologue of JWH-018, and its story lies entirely in that extra carbon. The series of cannabimimetic indoles from the laboratory of John W. Huffman was meant to measure precisely what the length of the side chain changes in recognition by the cannabinoid receptors: the work published in 2000 by Aung, Griffin, Huffman and colleagues replaced the morpholinoethyl of WIN 55,212-2 with chains ranging from methyl to heptyl, and established that at least three carbons are needed for high affinity, that the optimum lies at five, and that a heptyl makes binding fall at CB1 as at CB2. With six carbons, this molecule remains in the high-affinity range, just beyond the optimum. No affinity value specific to it is reported here, since no open source consulted gives it; as a measured benchmark in the same family, JWH-018 lies around 9 nM at CB1 and 2.9 nM at CB2 (Wiley et al., 2012). Nothing is published on TRPV1, GPR55, PPARγ or 5-HT1A, and there is no controlled study in humans: neither dose, tolerance nor dependence is characterised.
Key sources.
- Aung MM, Griffin G, Huffman JW et al. Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug Alcohol Depend. 2000;60(2):133-140 (new tab)PMID 10940540
- Wiley JL, Compton DR, Dai D, Lainton JAH, Phillips M, Huffman JW, Martin BR. Structure-activity relationships of indole- and pyrrole-derived cannabinoids. J Pharmacol Exp Ther 1998;285:995-1004 (new tab)PMID 9618400
- Wiley JL, Marusich JA, Huffman JW. Moving around the molecule: relationship between chemical structure and in vivo activity of synthetic cannabinoids. Life Sci 2014 (JWH-019 among the most potent compounds in the series; detected in products from 2011) (new tab)PMID 24071522
- Wiley JL, Smith VJ, Chen J, Martin BR, Huffman JW. Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents. Bioorg Med Chem. 2012;20(6):2067-2081 (JWH-018 values in table 1) (new tab)PMID 22341572
- Hutter M, Kneisel S, Auwärter V, Neukamm MA. Determination of 22 synthetic cannabinoids in human hair by liquid chromatography-tandem mass spectrometry. J Chromatogr B. 2012;903:95-101 (new tab)PMID 22835826
- Howlett AC, et al. The Spicy Story of Cannabimimetic Indoles. Molecules 2021 (the 2012 US synthetic drug act naming JWH-019) (new tab)PMID 34684770
- Mercier G, Mohamed KA, Zagzoog A, et al. In vitro pharmacological activity of twenty-eight synthetic cannabinoid receptor agonists at the type 1 and 2 cannabinoid receptors. Neurochem Int. 2025 (abstract: class toxicities) (new tab)PMID 40876783
- Zangani C et al. The e-Psychonauts' 'Spiced' World: assessment of the synthetic cannabinoids' information available online. Curr Neuropharmacol 2020 (JWH-019 in the UNODC, EUDA and NPSFinder lists) (new tab)PMID 32116194
- ANSM, consolidated list of substances classified as narcotics, updated 16 February 2026 (annex IV, « indol-3-yl methanone » family, JWH-019 cited as an example) (new tab)
- Order of 31 March 2017 amending the order of 22 February 1990: « indol-3-yl methanone » family of annex IV (Légifrance, JORF of 6 April 2017) (new tab)
- PubChem, Compound Summary CID 52224389, JWH-019 (new tab)
History
- Source
- An entirely synthetic molecule, absent from hemp and from any living organism. Wiley et al. (2014) report that it figures, with JWH-073, JWH-018 and AM-2201, among the most potent compounds of their first studies and that it was detected in product samples bought in 2011 in North Carolina. It also appears in the lists of the EUDA and of UNODC recording the synthetic cannabinoids reported (Zangani et al., 2020). None of this relates to hemp or to cannabidiol products.
Origin
Laboratory synthesis
No known biosynthetic pathway: the molecule is produced by no plant or living organism. It belongs solely to synthetic chemistry, described here by chemical class only.
Legal framework
- European Union
The substance is not listed in the Annex to Council Framework Decision 2004/757/JHA (consolidated version of 12 January 2026), which lists the new psychoactive substances controlled at European Union level; control is a matter for national law. It appears in the lists of the EUDA and of UNODC recording the synthetic cannabinoids reported (Zangani et al., 2020), which is monitoring and not control. It does not appear in the schedules of the 1971 Convention on Psychotropic Substances (green list of the INCB, 35th and 36th editions). France cites this molecule by name in annex IV of its list.
- France
JWH-019 is classified as a narcotic in France, and cited under its own name. The ANSM consolidated list (updated 16 February 2026) cites it in annex IV, under the entry « JWH-019 ou (1-hexyl-1H-indol-3-yl)-1-naphthalènylméthanone ou 1-hexyl-3-(1-naphthoyl) indole », as an example (« notamment ») of the generic family of the « indol-3-yl methanones » (a substituent on the indole nitrogen of the alkyl, haloalkyl, cycloalkylmethyl or related type, and a naphthyl, benzyl, phenyl, cyclopropyl or adamantyl group on the carbon of the methanone bridge), introduced into annex IV by the decree of 31 March 2017 (JORF of 6 April 2017). The clause on tetrahydrocannabinols (annex III since the decision of 6 February 2026) does not apply. Production, possession, transfer, transport and use fall under the criminal law on narcotics.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Classification
Family, origin and source verification
- Family
Synthetic CB receptor agonist › New psychoactive substance
- Class
naphthoylindole
- Verification
Classification, sources and binding values checked on 20 October 2026; text read against its sources and Wikipedia.
- Wikipedia (English)
Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.
References
- Aung MM, Griffin G, Huffman JW et al. Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug Alcohol Depend. 2000;60(2):133-140 (new tab)PMID 10940540
- Wiley JL, Compton DR, Dai D, Lainton JAH, Phillips M, Huffman JW, Martin BR. Structure-activity relationships of indole- and pyrrole-derived cannabinoids. J Pharmacol Exp Ther 1998;285:995-1004 (new tab)PMID 9618400
- Wiley JL, Marusich JA, Huffman JW. Moving around the molecule: relationship between chemical structure and in vivo activity of synthetic cannabinoids. Life Sci 2014 (JWH-019 among the most potent compounds in the series; detected in products from 2011) (new tab)PMID 24071522
- Wiley JL, Smith VJ, Chen J, Martin BR, Huffman JW. Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents. Bioorg Med Chem. 2012;20(6):2067-2081 (JWH-018 values in table 1) (new tab)PMID 22341572
- Hutter M, Kneisel S, Auwärter V, Neukamm MA. Determination of 22 synthetic cannabinoids in human hair by liquid chromatography-tandem mass spectrometry. J Chromatogr B. 2012;903:95-101 (new tab)PMID 22835826
- Howlett AC, et al. The Spicy Story of Cannabimimetic Indoles. Molecules 2021 (the 2012 US synthetic drug act naming JWH-019) (new tab)PMID 34684770
- Mercier G, Mohamed KA, Zagzoog A, et al. In vitro pharmacological activity of twenty-eight synthetic cannabinoid receptor agonists at the type 1 and 2 cannabinoid receptors. Neurochem Int. 2025 (abstract: class toxicities) (new tab)PMID 40876783
- Zangani C et al. The e-Psychonauts' 'Spiced' World: assessment of the synthetic cannabinoids' information available online. Curr Neuropharmacol 2020 (JWH-019 in the UNODC, EUDA and NPSFinder lists) (new tab)PMID 32116194
- ANSM, consolidated list of substances classified as narcotics, updated 16 February 2026 (annex IV, « indol-3-yl methanone » family, JWH-019 cited as an example) (new tab)
- Order of 31 March 2017 amending the order of 22 February 1990: « indol-3-yl methanone » family of annex IV (Légifrance, JORF of 6 April 2017) (new tab)
- PubChem, Compound Summary CID 52224389, JWH-019 (new tab)
Identifiers
Names
- IUPAC name
- (1-hexylindol-3-yl)-naphthalen-1-ylmethanone
- Other names
- 1-hexyl-3-(1-naphthoyl)indole
Identifiers
- Formula
- C₂₅H₂₅NO
- CAS
- 209414-08-4
- PubChem CID
- 52224389(new tab)
- InChIKey
- PALJPGHWDUHUPO-UHFFFAOYSA-N
- SMILES
- CCCCCCN1C=
C(C2= CC= CC= C21) C(= O) C3= CC= CC4= CC= CC= C43
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.