W-18 (drug)

W-18 (drug)

Legal status
Legal status	Illegal in Sweden and Canada
Identifiers
IUPAC name 4-Chloro-N-[(2Z)-1-[2-(4-nitrophenyl)ethyl]piperidin-2-ylidene]benzene-1-sulfonamide
CAS Number	93101-02-1  N
PubChem CID	57501076
ChemSpider	28537256  Y
UNII	04WOYJF7QH
CompTox Dashboard (EPA)	DTXSID90726944
Chemical and physical data
Formula	C19H20ClN3O4S
Molar mass	421.90 g·mol−1
3D model (JSmol)	Interactive image
Melting point	157 to 158 °C (315 to 316 °F)
SMILES C1CCN(/C(=N\S(=O)(=O)C2=CC=C(C=C2)Cl)/C1)CCC3=CC=C(C=C3)[N+](=O)[O-]
InChI InChI=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- Y Key:BKRSVROQVRTSND-VZCXRCSSSA-N Y
NY  (what is this?)    (verify)

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.

History

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. ^{[1] [2]}

The chemical was detected in connection with recreational drug use as substitute for other controlled substances in Europe in 2013, ^[3] and in the United States. ^[4] In Canada, Alberta Law Enforcement Response Teams (ALERT) seized four kilograms of W-18 in a drug bust in Edmonton in December 2015 ^[5] 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. ^{[6] [4]}

Pharmacology

W-18 was commonly reported to be an opioid in the popular press in the 2010s, which was later revealed not to be correct. ^{[7] [8] [9]} W-18 was found to obtain weak activity at both sigma receptors and the translocator protein (peripheral benzodiazepine receptor). ^[9] It also inhibits the hERG potassium channel with micromolar affinity, which could potentially cause cardiac arrhythmia at high doses. ^[10]

Legality

• In Sweden, W-18 was made illegal in January 2016. ^[11]
• In Canada, W-18 and its analogues were made Schedule I controlled substances. ^[12] 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

1. Kroll D (30 April 2016). "W-18, The High-Potency Research Chemical Making News: What It Is And What It Isn't". Forbes.
2. Warnica M (21 April 2016). "Street drug W-18 is highly lethal, and still legal". CBC News. Retrieved 20 April 2016.
3. Gonçalves J (13 February 2016). "Notice to interested parties — Proposal regarding the scheduling of W-18 under the Controlled Drugs and Substances Act and its regulations". Canada Gazette. 150 (7). Government of Canada. Retrieved 19 February 2016.
4. Markusoff J. "A toxic drug, more powerful than fentanyl, hits the streets in Alberta". macleans.ca. Maclean's. Retrieved 19 February 2016.
5. "Illicit drug W-18 is 100 times stronger than fentanyl, police warn". CBC News. 20 April 2016. Retrieved 20 April 2016.
6. Elkin A (1 February 2016). "Everything We Know So Far About W-18, the Drug That's 100 Times More Powerful Than Fentanyl". Vice.com. Vice Media. Retrieved 20 April 2016.
7. Southwick R (1 June 2016). "Health Canada statements on W-18 misleading, potentially wrong, experts warn". Calgary Herald. Postmedia Network Inc. Retrieved 22 June 2016.
8. Browne R (2 June 2016). "Canada's Ban on Ultra-Potent Drug W-18 Could Make Things Worse". Vice.
9. Huang XP, Che T, Mangano TJ, Le Rouzic V, Pan YX, Majumdar S, et al. (November 2017). "Fentanyl-related designer drugs W-18 and W-15 lack appreciable opioid activity in vitro and in vivo". JCI Insight. 2 (22) e97222. doi:10.1172/jci.insight.97222. PMC   5752382 . PMID   29202454.
10. Huang XP, Che T, Mangano TJ, Le Rouzic V, Pan YX, Majumdar S, et al. (2016-07-24). "Pharmacology of W-18 and W-15". bioRxiv 065623. doi: 10.1101/065623 .
11. "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
12. Arsenault D (1 June 2016). "Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18)". Canada Gazette. 150 (11). Government of Canada.