W-18 (drug)

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477206908

| IUPAC_name = 4-chloro-N-[(2Z)-1-[2-(4-nitrophenyl)ethyl]piperidin-2-ylidene]benzene-1-sulfonamide

| image = Z-W-18.svg

| width =

| tradename =

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Illegal in Sweden and Canada

| routes_of_administration =

| bioavailability =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 93101-02-1

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

| UNII = 04WOYJF7QH

| ATC_prefix =

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| PubChem = 57501076

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 28537256

| C=19 | H=20 | Cl=1 | N=3 | O=4 | S=1

| smiles = C1CCN(/C(=N\S(=O)(=O)C2=CC=C(C=C2)Cl)/C1)CCC3=CC=C(C=C3)[N+](=O)[O-]

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H20ClN3O4S/c20-16-6-10-18(11-7-16)28(26,27)21-19-3-1-2-13-22(19)14-12-15-4-8-17(9-5-15)23(24)25/h4-11H,1-3,12-14H2/b21-19-

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BKRSVROQVRTSND-VZCXRCSSSA-N

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| melting_point = 157

| melting_high = 158

}}

W-18 is a compound in a series of 32 substances (named W-1 to W-32) that were first synthesized in academic research on analgesic drug discovery in the 1980s and appeared as a designer drug in the 2010s.

W-18 was invented at the University of Alberta by a lab working on analgesic drug discovery in the 1980s, and preliminary studies in animals showed it had pain-killing activity in mice.{{cite web|url=https://www.forbes.com/sites/davidkroll/2016/04/30/w-18-the-high-potency-research-chemical-making-news-what-it-is-and-what-it-isnt/#2b1ef5562354|title=W-18, The High-Potency Research Chemical Making News: What It Is And What It Isn't|date=30 April 2016| vauthors = Kroll D |work=Forbes}}{{cite web|url=http://www.cbc.ca/news/canada/edmonton/street-drug-w-18-is-highly-lethal-and-still-legal-1.3546094|title=Street drug W-18 is highly lethal, and still legal|publisher=CBC News|date=21 April 2016|access-date=20 April 2016| vauthors = Warnica M }}

The chemical was detected in connection with recreational drug use as substitute for other controlled substances in Europe in 2013,{{cite journal| vauthors = Gonçalves J |title=Notice to interested parties — Proposal regarding the scheduling of W-18 under the Controlled Drugs and Substances Act and its regulations|journal=Canada Gazette|date=13 February 2016|volume=150|issue=7|url=http://gazette.gc.ca/rp-pr/p1/2016/2016-02-13/html/notice-avis-eng.php#nl3|access-date=19 February 2016|publisher=Government of Canada}} and in the United States. In Canada, Alberta Law Enforcement Response Teams (ALERT) seized four kilograms of W-18 in a drug bust in Edmonton in December 2015{{cite news|url=http://www.cbc.ca/news/canada/edmonton/illicit-drug-w-18-is-100-times-stronger-than-fentanyl-police-warn-1.3544662|title=Illicit drug W-18 is 100 times stronger than fentanyl, police warn|work=CBC News|date=20 April 2016|access-date=20 April 2016}} and W-18 was also detected by Health Canada in at least three of 110 fentanyl tablets seized from a Calgary home in August 2015.{{cite web|url=https://www.vice.com/en_ca/read/everything-we-know-so-far-about-w-18-the-drug-thats-100-times-more-powerful-than-fentanyl|title=Everything We Know So Far About W-18, the Drug That's 100 Times More Powerful Than Fentanyl|publisher=Vice Media|work=Vice.com|date=1 February 2016|access-date=20 April 2016| vauthors = Elkin A }}{{cite web| vauthors = Markusoff J |title=A toxic drug, more powerful than fentanyl, hits the streets in Alberta|url=http://www.macleans.ca/?dpsfa_article=a-toxic-drug-more-powerful-than-fentanyl-hits-the-streets-in-alberta|website=macleans.ca|publisher=Maclean's|access-date=19 February 2016}}

W-18 was commonly reported to be an opioid in the popular press in the 2010s, which was later revealed not to be correct.{{cite web | url=https://calgaryherald.com/news/local-news/health-canada-statements-on-w-18-misleading-potentially-wrong-experts-warn | title=Health Canada statements on W-18 misleading, potentially wrong, experts warn | publisher=Postmedia Network Inc. | work=Calgary Herald | date=1 June 2016 | access-date=22 June 2016 | vauthors = Southwick R }}{{cite web | url=https://news.vice.com/article/canadas-ban-on-ultra-potent-drug-w-18-could-make-things-worse | title=Canada's Ban on Ultra-Potent Drug W-18 Could Make Things Worse | publisher=Vice | date=2 June 2016 | vauthors = Browne R }}{{cite journal | vauthors = Huang XP, Che T, Mangano TJ, Le Rouzic V, Pan YX, Majumdar S, Cameron MD, Baumann MH, Pasternak GW, Roth BL | display-authors = 6 | title = Fentanyl-related designer drugs W-18 and W-15 lack appreciable opioid activity in vitro and in vivo | journal = JCI Insight | volume = 2 | issue = 22 | date = November 2017 | pmid = 29202454 | pmc = 5752382 | doi = 10.1172/jci.insight.97222 | author10-link = Bryan Roth }} W-18 was found to obtain weak activity at both sigma receptors and the translocator protein (peripheral benzodiazepine receptor). It also inhibits the hERG potassium channel with micromolar affinity, which could potentially cause cardiac arrhythmia at high doses.{{Cite journal| vauthors = Huang XP, Che T, Mangano TJ, Le Rouzic V, Pan YX, Majumdar S, Cameron M, Bauman M, Pasternak GW, Roth BL | display-authors = 6 |date=2016-07-24|title=Pharmacology of W-18 and W-15 | journal = bioRxiv |language=en|pages=065623|doi=10.1101/065623|doi-access=free}}

• In Sweden, W-18 was made illegal in January 2016.{{cite web | url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/november/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/ | title=31 nya ämnen kan klassas som narkotika eller hälsofarlig vara | publisher=Folkhälsomyndigheten | language=Swedish | date=November 2015}}
• In Canada, W-18 and its analogues were made Schedule I controlled substances.{{cite journal | url=http://www.gazette.gc.ca/rp-pr/p2/2016/2016-06-01/html/sor-dors106-eng.php | title=Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18) | first = Denis | last = Arsenault | name-list-style = vanc | journal=Canada Gazette | date=1 June 2016 | volume=150 | issue=11 | publisher=Government of Canada}} Possession without legal authority can result in maximum 7 years imprisonment. Further, Health Canada amended the Food and Drug Regulations in May, 2016 to classify W-18 as a restricted drug. Only those with a law enforcement agency, person with an exemption permit or institutions with Minister's authorization may possess the drug.