JWH-073 (original) (raw)

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Chemical compound

JWH-073
Legal status
Legal status BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I Illegal in Latvia[2] & Poland
Identifiers
IUPAC name Naphthalen-1-yl-(1-butylindol-3-yl)methanone
CAS Number 208987-48-8 checkY
PubChem CID 10471670
ChemSpider 8647081 ☒N
UNII BBX3BP2772
KEGG C22764
CompTox Dashboard (EPA) DTXSID20175042 Edit this at Wikidata
ECHA InfoCard 100.230.192 Edit this at Wikidata
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 ☒NKey: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]

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

1 g of JWH-073

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]

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]

On 8 May 2014 the New Zealand government banned the sale of JWH-073.[13]

On 7 January 2011 the Turkey government banned the sale of JWH-073.[14]

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ "Grozījumi Ministru kabineta 2005.gada 8.novembra noteikumos Nr.847 "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem"". Legal Acts of the Republic of Latvia (in Latvian).
  3. ^ Lisa K. Brents, Anna Gallus-Zawada, Anna Radominska-Pandya, Tamara Vasiljevik, Thomas E Prisinzano, William E Fantegrossi, Jeffery H Moran, Paul L Prather (2012). "Monohydroxylated metabolites of the K2 synthetic cannabinoid JWH-073 retain intermediate to high cannabinoid 1 receptor (CB1R) affinity and exhibit neutral antagonist to partial agonist activity". Biochemical Pharmacology. 83 (7): 952–961. doi:10.1016/j.bcp.2012.01.004. hdl:1808/22684. PMID 22266354. JWH-073 displays equivalent efficacy to that of the CB1R full agonist CP-55,940{{[cite journal](/wiki/Template:Cite%5Fjournal "Template:Cite journal")}}: CS1 maint: multiple names: authors list (link)
  4. ^ Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, et al. (August 2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding". Drug and Alcohol Dependence. 60 (2): 133–40. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.
  5. ^ Markuse P. "Forest Humus – Enthält synthetische Cannabinoide". Pierre Markuse Blog (in German). Archived from the original on 23 July 2012.
  6. ^ Lindigkeit R, Boehme A, Eiserloh I, Luebbecke M, Wiggermann M, Ernst L, Beuerle T (October 2009). "Spice: a never ending story?". Forensic Science International. 191 (1–3): 58–63. doi:10.1016/j.forsciint.2009.06.008. PMID 19589652.
  7. ^ a b Rani Sagar D, Burston JJ, Woodhams SG, Chapman V (December 2012). "Dynamic changes to the endocannabinoid system in models of chronic pain". Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences. 367 (1607): 3300–11. doi:10.1098/rstb.2011.0390. PMC 3481532. PMID 23108548.
  8. ^ a b c "DEA Diversion Control Division". Archived from the original on August 3, 2010. Retrieved August 5, 2010.
  9. ^ "EMCDDA Annual Report 2010" (PDF). Archived from the original (PDF) on 2012-03-14. Retrieved 2011-10-02.
  10. ^ "Schedules of Controlled Substances: Temporary Placement of Four Synthetic Cannabinoids Into Schedule I". DEA Office of Diversion Control. Archived from the original on 28 February 2014. Retrieved 11 March 2014.
  11. ^ "Final Decisions & Reasons for Decisions by Delegates of the Secretary to the Department of Health and Ageing" (PDF). Department of Health and Ageing. Australian Government. Archived from the original (PDF) on June 4, 2012. Retrieved August 2, 2011.
  12. ^ a b "Poisons Standard". Federal Register of Legislation. Government of Australia. October 2015.
  13. ^ "Synthetic cannabis › What they are". NZ Drug Foundation. Archived from the original on 2015-09-21. Retrieved 2014-05-11.
  14. ^ › Turkish Drug Law