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]

As the cause is poorly understood in chronic pain states, more research and development must be done before we can realize the therapeutic potential of this class of biologic compounds.^[7]

^ 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.
^ "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).
^ 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}}: CS1 maint: multiple names: authors list (link)
^ 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.
^ Markuse P. "Forest Humus – Enthält synthetische Cannabinoide". Pierre Markuse Blog (in German). Archived from the original on 23 July 2012.
^ 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.
^ ^a ^b ^c 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.

[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).

[pmid22266354-3] 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}}: CS1 maint: multiple names: authors list (link)

[pmid10940540-4] 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.

[pmid19589652-6] 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.

[:0-7] 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.

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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^Y
PubChem CID	10471670
ChemSpider	8647081^N
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^N Key:VCHHHSMPMLNVGS-UHFFFAOYSA-N^N
^NY (what is this?) (verify)