JWH-073

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Legal status
JWH-073
Legal status
Legal status
Identifiers
  • Naphthalen-1-yl-(1-butylindol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.230.192 Edit this at Wikidata
Chemical and physical data
FormulaC23H21NO
Molar mass327.427 g·mol−1
3D model (JSmol)
  • CCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43
  • 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 ☒N
  • Key:VCHHHSMPMLNVGS-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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]

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.

4'-Methyl-JWH-073

See also

References

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