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W-18 (drug)

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
W-18 (drug)
Legal status
Legal status
  • Illegal in Sweden and Canada
Identifiers
  • 4-Chloro-N-[(2Z)-1-[2-(4-nitrophenyl)ethyl]piperidin-2-ylidene]benzene-1-sulfonamide
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H20ClN3O4S
Molar mass421.90 g·mol−1
3D model (JSmol)
Melting point157 to 158 °C (315 to 316 °F)
  • C1CCN(/C(=N\S(=O)(=O)C2=CC=C(C=C2)Cl)/C1)CCC3=CC=C(C=C3)[N+](=O)[O-]
  • 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- checkY
  • Key:BKRSVROQVRTSND-VZCXRCSSSA-N checkY
 ☒NcheckY (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 onanalgesicdrug discovery in the 1980s and appeared as adesigner drug in the 2010s.

History

[edit]

W-18 was invented at theUniversity of Alberta by a lab working onanalgesicdrug 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 othercontrolled 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 inEdmonton in December 2015[5] and W-18 was also detected byHealth Canada in at least three of 110fentanyl tablets seized from aCalgary home in August 2015.[6][4]

Pharmacology

[edit]

W-18 was commonly reported to be anopioid 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 bothsigma receptors and thetranslocator protein (peripheral benzodiazepine receptor).[9] It also inhibits thehERG potassium channel with micromolar affinity, which could potentially cause cardiac arrhythmia at high doses.[10]

Legality

[edit]
  • 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 theFood 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

[edit]

References

[edit]
  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. Retrieved20 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. Retrieved19 February 2016.
  4. ^abMarkusoff J."A toxic drug, more powerful than fentanyl, hits the streets in Alberta".macleans.ca. Maclean's. Retrieved19 February 2016.
  5. ^"Illicit drug W-18 is 100 times stronger than fentanyl, police warn".CBC News. 20 April 2016. Retrieved20 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. Retrieved20 April 2016.
  7. ^Southwick R (1 June 2016)."Health Canada statements on W-18 misleading, potentially wrong, experts warn".Calgary Herald. Postmedia Network Inc. Retrieved22 June 2016.
  8. ^Browne R (2 June 2016)."Canada's Ban on Ultra-Potent Drug W-18 Could Make Things Worse". Vice.
  9. ^abHuang 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.
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
σ1
σ2
Unsorted
Agonists
Antagonists
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