JWH-073: Difference between revisions

{{short description|Chemical compound}}

| Verifiedfields = changed

| verifiedrevid =

| IUPAC_name = -1-yl-(1-butylindol-3-yl)methanone

| legal_BR = F2

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>

| = Schedule II

| legal_UK = Class B

| legal_US = Schedule I

| legal_DE = Anlage II

| legal_status = Illegal in Latvia<ref>{{cite web | title = Grozījumi Ministru kabineta 2005.gada 8.novembra noteikumos Nr.847 "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" | language = Latvian | work = Legal Acts of the Republic of Latvia | url = http://www.likumi.lv/doc.php?id=201101&from=off}}</ref> & Poland

| routes_of_administration =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = BBX3BP2772

| KEGG = C22764

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8647081

| smiles = CCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = VCHHHSMPMLNVGS-UHFFFAOYSA-N

'''JWH-073''' is an [[analgesic]] chemical from the [[naphthoylindole]] family acts as a partial agonist at both the CB₁ and CB₂ cannabinoid receptors. It is somewhat selective for the CB₁ subtype, with affinity at this subtype approximately the affinity at CB₂.<ref name="pmid10940540">{{cite journal |=Aung MM |title=Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding |journal=Drug Alcohol |volume=60 |issue=2 |pages=133–40 | =August |pmid=10940540 |doi=10.1016/S0376-8716(99)00152-0 }}</ref> 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]].<ref>http://www.pierre-markuse.de/2009/04/20/forest-humus-enthalt-synthetische-cannabinoide Forest Humus Enthält synthetische Cannabinoide German</ref> These claims were confirmed in July 2009 when tests of [[Spice (drug)|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.<ref name="pmid19589652">{{cite journal |=Lindigkeit R, Boehme A, Eiserloh I, Luebbecke M, Wiggermann M, Ernst L, Beuerle T |title=Spice: never ending story? |journal=Forensic Science International |volume= 191|issue= 1–3|pages= 58–63|=2009 | pmid=19589652 |doi=10.1016/j.forsciint.2009.06.008 |=}}</ref>

Analgesic effects of cannabinoid ligands have been demonstrated in multiple animal pain models (neuropathic, nociceptive).<ref name=":0">{{cite journal|vauthors=Rani Sagar D, Burston JJ, Woodhams SG, Chapman V|date=December 2012|title=Dynamic changes to the endocannabinoid system in models of chronic pain|journal=Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences|volume=367|issue=1607|pages=3300–11|doi=10.1098/rstb.2011.0390|pmc=3481532|pmid=23108548}}</ref>

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.<ref name=":0" />

JWH-073 has been shown to produce behavioral effects very similar to [[Tetrahydrocannabinol|THC]] in animals.<ref name="DEA">http://www.deadiversion.usdoj.gov/drugs_concern/spice/spice_jwh073.html</ref>

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 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.<ref name="DEA" />

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.<ref name="DEA" />

==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.<ref>{{cite web | url = http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf | title = EMCDDA Annual Report 2010 | access-date = 2011-10-02 | archive-date = 2012-03-14 | archive-url = https://web.archive.org/web/20120314043454/http://www.emcdda.europa.eu/attachements.cfm/att_132857_EN_EMCDDA-Europol%20Annual%20Report%202010A.pdf | url-status = dead }}</ref> 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. <!-- The code number for 4'-methyl-JWH-073 seems likely to be JWH-121, seeing as the ''N''-propyl homologue is listed as JWH-120 and the N-pentyl homologue is the widely known JWH-122. However I cannot find JWH-121 listed in any of Huffman's published reviews, despite this compound being listed under this code number by some websites -->

[[Image:4'-methyl-JWH-073 structure.png|180px|thumb|left|4'-Methyl-JWH-073]]{{clear-left}}

==Legal status==

=== United States ===

{{|JWH-018}}

The US [[Drug Enforcement Administration|DEA]] temporarily declared JWH-073 a [[Controlled Substances Act#Schedule I controlled substances|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]].<ref>{{cite web|title=Schedules of Controlled Substances: Temporary Placement of Four Synthetic Cannabinoids Into Schedule I|url=http://www.deadiversion.usdoj.gov/fed_regs/rules/2014/fr0110_10.htm|publisher=DEA Office of Diversion Control|access-date=11 March 2014|archive-date=28 February 2014|archive-url=https://web.archive.org/web/20140228122102/http://www.deadiversion.usdoj.gov/fed_regs/rules/2014/fr0110_10.htm|url-status=dead}}</ref>

{{|JWH-018}}

On 8 July 2011 the AUS government banned the sale of JWH-073.<ref>{{cite web | title = Final Decisions & Reasons for Decisions by Delegates of the Secretary to the Department of Health and Ageing | work = Department of Health and Ageing | publisher = Australian Government |url=http://www.tga.gov.au/pdf/scheduling/scheduling-decisions-1107-final.pdf |access-date=August 2, 2011 |url-status=dead |archive-url=https://web.archive.org/web/20120604101005/http://www.tga.gov.au/pdf/scheduling/scheduling-decisions-1107-final.pdf |archive-date=June 4, 2012 }}</ref> JWH-073 is considered a Schedule 9 prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">{{cite web | title = Poisons Standard | date = October 2015 | url = https://www.comlaw.gov.au/Details/F2015L01534 | work = Federal Register of Legislation | publisher = Government of Australia }}</ref> 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.<ref name="Poisons Standard" />

== ==

On 8 May 2014 the New Zealand government banned the sale of JWH-073.<ref>{{Cite web |url=https://www.drugfoundation.org.nz/synthetic-cannabinoids/what-they-are |title=Synthetic cannabis › What they are |access-date=2014-05-11 |archive-url=https://web.archive.org/web/20150921191334/http://www.drugfoundation.org.nz/synthetic-cannabinoids/what-they-are |archive-date=2015-09-21 |url-status=dead | work = NZ Drug Foundation }}</ref>

===Turkey===

On 2011 the government banned the sale of JWH-073.<ref>http://www..gov.///-.</ref>

== See also ==

*[[JWH-]]

*[[JWH-081]]

*[[MEPIRAPIM]]

==References==

{{reflist}}

{{Hallucinogens}}

{{Cannabinoidergics}}

[[Category:Designer drugs]]

[[Category:JWH cannabinoids]]

[[Category:Naphthoylindoles]]

[[Category:CB1 receptor agonists]]

[[Category:CB2 receptor agonists]]

[[Category:Butyl compounds]]