JWH-073

JWH-073
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I; Illegal in Latvia & Poland;
Identifiers
	IUPAC name Naphthalen-1-yl-(1-butylindol-3-yl)methanone;
CAS Number	208987-48-8 ;
PubChem CID	10471670;
ChemSpider	8647081 ;
UNII	BBX3BP2772;
KEGG	C22764;
CompTox Dashboard (EPA)	DTXSID20175042 ;
ECHA InfoCard	100.230.192
Chemical and physical data
Formula	C23H21NO
Molar mass	327.427 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43;
	InChI InChI=1S/C23H21NO/c1-2-3-15-24-16-21(19-12-6-7-14-22(19)24)23(25)20-13-8-10-17-9-4-5-11-18(17)20/h4-14,16H,2-3,15H2,1H3 ; Key:VCHHHSMPMLNVGS-UHFFFAOYSA-N ;
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JWH-073, a synthetic cannabinoid, is an analgesic chemical from the naphthoylindole family that acts as a full agonist^[3] at both the CB₁ and CB₂ cannabinoid receptors. It is somewhat selective for the CB₁ subtype, with affinity at this subtype approximately 5× the affinity at CB₂.^[4] The abbreviation JWH stands for John W. Huffman, one of the inventors of the compound.

On 20 April 2009, JWH-073 was claimed by researchers at the University of Freiburg to have been found in a "fertiliser" product called "Forest Humus", along with another synthetic cannabinoid (C8)-CP 47,497.^[5] These claims were confirmed in July 2009 when tests of Spice product, seized after the legal ban on JWH-018 had gone into effect in Germany, were shown to contain the unregulated compound JWH-073 instead.^[6]

Analgesic effects of cannabinoid ligands have been demonstrated in multiple animal pain models (neuropathic, nociceptive).^[7]

These compounds work by mimicking the body's naturally-produced endocannabinoid hormones such as 2-arachidonoylglycerol and anandamide, which are biologically active and can exacerbate or inhibit nerve signaling.^[7]

Pharmacology

JWH-073 has been shown to produce behavioral effects very similar to THC in animals.^[8]

Its effects are produced by binding and acting as an agonist to the CB₁ and CB₂ cannabinoid receptors. The CB₁ receptor is found in the brain. JWH-073 binds to CB₁ with a higher affinity than THC. CB₂ is found outside the brain, mostly in the immune system. The binding with CB₂ receptors has been shown to be similar between JWH-073 and THC.^[8]

A search in the literature yielded no published studies of the effects of JWH-073 in humans, but these studies in animals suggest with high probability that JWH-073 produces effects very similar to those of THC in humans.^[8]

Derivatives

The 4'-methyl derivative of JWH-073 has been encountered as an ingredient of synthetic cannabis blends in Germany and several other European countries since 2010.^[9] The 4'-methoxy derivative JWH-080 is also known to be a potent cannabinoid agonist and has been banned in some countries, though it is unclear if it has also been used in synthetic cannabis smoking blends.

Legal status

United States

The US DEA temporarily declared JWH-073 a schedule I controlled substance on 1 March 2011 through 76 FR 11075, and permanently instated the same schedule on 9 July 2012 in the Section 1152 of the Food and Drug Administration Safety and Innovation Act.^[10]

Australia

On 8 July 2011 the AUS government banned the sale of JWH-073.^[11] JWH-073 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).^[12] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.^[12]