W-18

W-18
Systematic (IUPAC) name
(NE)-4-chloro-N-[1-[2-(4-nitrophenyl)ethyl]piperidin-2-ylidene]benzenesulfonamide
Legal status
Legal status
  • Illegal in Sweden
Identifiers
CAS Number 93101-02-1 N
PubChem CID 13373555
ChemSpider 10544260 YesY
Synonyms W-18
Chemical data
Formula C19H20ClN3O4S
Molar mass 421.91 g/mol
Physical data
Melting point 157 to 158 °C (315 to 316 °F)
 NYesY (what is this?)  (verify)

1-(4-Nitrophenylethyl)piperidylidene-2-(4-chlorophenyl)sulfonamide (W-18) is an analgesic thought to be highly potent but with no history of human use. Though commonly reported as an opioid in the popular press, it is not known how the drug works, whose distinctive structure differs somewhat to known opioid drugs.[1] It was invented at the University of Alberta[2] by the chemists Edward Knaus, Brent Warren and Theodore Ondrus in 1981.[3][4] The compound, whose toxicity is not fully characterized, but whose potency and poor characterization give it potential for fatal abuse, is an emerging concern as an unregulated alternative in the economy of recreational drug production and use (including as an undeclared additive in other illicit drug preparations).

Toxicity

The Canadian government, which is taking a lead regarding the risks and regulation of W-18, notes in its Department of Health's announcement to proposed changes to the Controlled Drugs and Substances Act, that:

there are no published studies regarding the toxicity of W-18… [but] the high analgesic potency of W-18… suggests a potential severe risk for overdose. In addition… risks associated with W-18 can be elevated because of lack of data about toxicity, bioavailability, tolerance, half-life and onset of effects, which can lead users to experiment blindly with this substance.[5]

As of February 2016, it was not yet known if naloxone, the standard emergency antidote for opioids, is effective against W-18.[6]

Recreational use

This chemical compound has been detected at least on two continents, in connection with recreational drug use as substitute for other controlled substances that has not been made illegal:[7] in Europe in 2013, and in Canada in 2015 (with the U.S. DEA confirming seizures of W-18, but declining to state where and when[8]).

Alberta Law Enforcement Response Teams (ALERT) seized four kilograms of an unrecognized powder in a drug bust in Edmonton in December 2015.[9] Investigators sent it to be tested, and received confirmation in April 2016 that it was W-18.

W-18 was also detected by Health Canada in at least three of 110 fentanyl tablets seized from a Calgary home in August 2015.[10] Authorities warn that the dose of fentanyl alone could be lethal to inexperienced users, and combined with W-18 a fraction of a tablet could be lethal within minutes.[8]

Chemistry

The invention described in the patent concerns the reaction of a substituted azide with a 1-substituted 1,2,3,4-tetrahydropyridine, with various classes of substituents claimed for each, "allowing the reaction to occur (normally at room temperature) with evolution of nitrogen gas to convert to 1-alkyl(arylalkyl,cycloalkylalkyl,alkenyl)piperidylidene-2-sulfon (cyan)amides" in inert organic solvents.[3]

The final step in synthesis is the nitration of W-15:[3]

A mixture of 1-phenylethylpiperdylidene-2-(4-chlorophenyl)sulfonamide (1.17 g, 3.11 mmol) W-15, 90% fuming nitric acid (3.0 ml) and concentrated nitric acid (2.0 ml) were stirred vigorously for 4 hours at 25° C. This mixture was poured onto 50 ml water and the pH adjusted to 10 using 1 N sodium hydroxide. Extraction with methylene chloride (4×50 ml), drying (Na2 SO4) and removal of the solvent in vacuo gave a yellow gum which was purified by preparative tlc using 0.75 mm silica gel G plates with acetone: ether (1:1 v/v) as development solvent. Extraction of the band having Rf 0.88 gave 1-(4-nitrophenylethyl)piperidylidene-2-(4-chlorophenyl)sulfonamide as a pale yellow solid (0.734 g, 61%) having mp 157°-158°; IR (KBr) 1350 and 1540 cm-1 (NO2).

Legal status

References

  1. ↑ Kroll,David (30 April 2016). "W-18, The High-Potency Research Chemical Making News: What It Is And What It Isn't". Retrieved 5 May 2016.W-18, The High-Potency Research Chemical Making News: What It Is And What It Isn't
  2. ↑ Warnica,Marion (21 April 2016). "Street drug W-18 is highly lethal, and still legal". CBC News. Retrieved 20 April 2016.
  3. 1 2 3 Edward E. Knaus, Brent K. Warren, Theodore A. Ondrus (28 August 1984). "Patent US 4468403 - Analgesic substituted piperidylidene-2-sulfon(cyan)amide derivatives" (PDF). USPTO. (see index information on Lens.org. Also available from Google.)
  4. ↑ Edward F. Knaus Brent K. Warren Theodore A. Ondrus (1989-06-13). "Analgesic substituted piperidylidene-2-sulfon (cyan) amide derivatives CA 1255680 A1". [Canadian patent]. In this patent it is compound 19.
  5. 1 2 Gonçalves, Jacqueline (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 (Government of Canada) 150 (7). Retrieved 19 February 2016.
  6. ↑ Russell, Andrew (3 February 2016). "What we know about W-18, a drug ‘100 times more powerful than fentanyl’". Global News BC. Global News. Retrieved 19 February 2016.
  7. 1 2 "Consultation - Proposal regarding the scheduling of W-18 under the Controlled Drugs and Substances Act and its Regulations". Health Canada. Canadian Government. Retrieved 19 February 2016.
  8. 1 2 Markusoff, Jason. "A toxic drug, more powerful than fentanyl, hits the streets in Alberta". macleans.ca. Maclean's. Retrieved 19 February 2016.
  9. ↑ "Illicit drug W-18 is 100 times stronger than fentanyl, police warn". CBC News. 20 April 2016. Retrieved 20 April 2016.
  10. ↑ Elkin, Allison (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.
  11. ↑ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
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