Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and W-18 (drug): Difference between pages

{{Short description|Chemical compound}}

| 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_category =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Illegal in Sweden and Canada

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

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

| CAS_number = 93101-02-1

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

| UNII = 04WOYJF7QH

| ATC_prefix =

| ATC_suffix =

| PubChem = 57501076

| DrugBank =

| 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 = 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 = BKRSVROQVRTSND-VZCXRCSSSA-N

| synonyms =

'''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.<ref name=forbes>{{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}}</ref><ref>{{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 }}</ref>

The chemical was detected in connection with recreational drug use as substitute for other [[controlled substance]]s in Europe in 2013,<ref name=Gazette>{{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}}</ref> and in the United States.<ref name=macleans/> In Canada, [[Alberta Law Enforcement Response Teams]] (ALERT) seized four kilograms of W-18 in a drug bust in [[Edmonton]] in December 2015<ref name="cbc-news">{{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}}</ref> 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.<ref>{{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 }}</ref><ref name=macleans>{{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}}</ref>

W-18 was commonly reported to be an [[opioid]] in the popular press in the 2010s, which was later revealed not to be correct.<ref name="calgaryherald">{{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 }}</ref><ref>{{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 }}</ref><ref name="Roth">{{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 }}</ref> W-18 was found to obtain weak activity at both [[sigma receptor]]s and the [[translocator protein]] (peripheral benzodiazepine receptor).<ref name="Roth"/> It also inhibits the [[hERG]] potassium channel with micromolar affinity, which could potentially cause cardiac arrhythmia at high doses.<ref>{{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}}</ref>

* In Sweden, W-18 was made illegal in January 2016.<ref>{{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}}</ref>

* In Canada, W-18 and its analogues were made Schedule I controlled substances.<ref>{{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}}</ref> 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.

== See also ==

* [[Ro5-4864]]

== References ==

{{Reflist}}

{{Ion channel modulators}}

{{Sigma receptor modulators}}

{{Translocator protein modulators}}

{{DEFAULTSORT:W-18}}

[[Category:Chlorobenzene derivatives]]

[[Category:Nitrobenzene derivatives]]

[[Category:Piperidines]]

[[Category:Sigma receptor ligands]]

[[Category:Sulfonamides]]

[[Category:TSPO ligands]]