Talk:W-18 (drug)

Comment

The IUPAC used in the image is incorrect. I placed the correct IUPAC into the drugbox, but the incorrect is still shown (and more prominently).

Hammilton —Preceding unsigned comment added by 68.117.96.159 (talk) 13:30, 14 January 2009 (UTC)

According to [research.omicsgroup.org/index.php/1-%284-Nitrophenylethyl%29piperidylidene-2-%284-chlorophenyl%29sulfonamide Omics International] the Systematic/IUPAC name is (E)-4-chloro-N-(1-(4-nitrophenethyl)piperidin-2-ylidene)benzenesulfonamide, slightly different from the name in the drugbox. AromSyn gives both "Z" (cis) & "NE" (trans) prefixes and slightly different punctuation as synonyms. The IUPAC reference book Principles of Nomenclature (1998, possibly out-of-date) gives only E, Z, R & S as enantiomer prefixes so I presume the "N" in "(NE)" indicates the chirality at the nitrogen atom (but which N?). I guess even IUPAC has its ambiguities and evolution! D A Patriarche, BSc (talk) (talk) 06:04, 19 February 2016 (UTC)

The double bond between the sulfonamide nitrogen and the piperidine ring makes necessary the inclusion of the (E) stereochemical descriptor. Almost all readers will be unfamiliar with combining of the atom identity tag and the stereochemical descriptor in the same parens, as (NE)-, as appears now in the chembox. I would recommend using the ACD-generated IUPAC name as first appearing in the chembox (shown here, with ChemSpider link, where it has been validated by experts):

• 4-Chloro-N-{(2E)-1-[2-(4-nitrophenyl)ethyl]-2-piperidinylidene}benzenesulfonamide

which can be read and sorted by most chemists and students of chemistry, without assistance. This can be followed, then, by the PubChem reported (NE)-containing variant that currently appears alone.

Also, as happens often at Wikipedia articles about chemical compounds for which one stereoisomer is of greatest interest, this article is unnecessarily confusing in presenting a structure of one stereoisomer in the chembox (the E-, as discussed), but then opening the body of the main article referring to a chemical compound that is (by virtue of the name given) stereochemically inexplicit.

This matter is for the committed, regular editors to address, and here is the question:

Is the drug that is circulating, and of interest, one stereoisomer, or a mix? That is, does W-18 refer to the E- stereoisomer, or does it refer to any mix of E- and Z- isomers of the compound named in the opening of the lede? Once this matter is sorted, then the naming can be made consistent, explicit, and clear. (Either the article is about the E-stereoisomer, in which case the lede needs to be edited to match the chembox, or it is about the mix, in which case a structure with a "squiggly" line between the sulfonamide nitrogen and the piperidine carbon should appear in the chembox, and the data in the chembox should be clarified as to what it describes, e.g., asterisked to say it refers just to one of two, the E-stereoisomer.)

Also of some concern is the fact that the style of the name provided in the lede differs from that provided in the chembox—the lede naming it as a piperidylidene- derivative of (4-chlorophenyl)sulfonamide, and the chembox with the yet simpler benzenesulfonamide as the core structure. While there are likely sources and reasons for each, does it make sense that the opening names in the lede and chembox are different, for an article aimed at general audiences? For instance, can the lede and chembox not open with 4-Chloro-N-{(2E)-1-[2-(4-nitrophenyl)ethyl]-2-piperidinylidene}benzenesulfonamide (if, it proves to be the case, that W-18 refers to one stereoisomer)? Or another name identical between the two places, chembox and lede, that is otherwise chosen?

In case it helps, here is another sourced synonym that omits the "N" in the (NE)-prefix that currently appears in the chembox:

• (E)-4-Chloro-N-(1-(4-nitrophenethyl)piperidin-2-ylidene)benzenesulfonamide

Cheers, and good luck. I will look in again. Le Prof Leprof 7272 (talk) 16:40, 27 April 2016 (UTC)

Likely legallity

The article read "This makes it likely that it would be legal throughout the world.". The 'legallity' of unscheduled drugs is a gray area in many scenarios and the previous wording (I believe) gives the wrong impression. I rewrote the sentence as "This makes it likely that it would not be illegalized under drug analog laws." The substance could still be illegalized under other laws, and a lack of specific illegalization is not always equivalent to explicit legality. 173.209.172.90 (talk) 02:04, 24 March 2013 (UTC)

Now that W-18 is a hot topic in the news (especially here in Canada) I expect the legal issues will be resolved quickly in most countries. I added rather a lot of detail on the current status in Canada because it is currently in flux, and interested parties may submit opinions (follow ref link 6, "Consultation....", to the Health Canada site for instructions) only until 14 March 2016: once a decision comes down, the section can be pruned. D A Patriarche, BSc (talk) (talk) 04:58, 19 February 2016 (UTC)

Well done

I rarely have a chance to say this, so I will, emphatically. Well done on creating an informative, well-sourced, and timely stub. Cheers, and thanks to all involved. Le Prof Leprof 7272 (talk) 15:51, 27 April 2016 (UTC)

Maybe add a "Mechanism and discovery" (or just "Discovery") section? That way, the lede content can appear and be sourced in the article, and so the lede can reflect the article (better). Cheers. Le Prof Leprof 7272 (talk) 17:20, 27 April 2016 (UTC)

update

just did a search of pubmed, FDA, DEA, CDC, NHS... nothing more on this from MEDRS sources at this time. Jytdog (talk) 08:07, 11 October 2016 (UTC)

What does W stand for?

Equinox ◑ 17:57, 3 September 2017 (UTC)

hERG channel binding claim - failed verification

I used "find in page" on the citation for the claim of w-18 binding to the hERG channel, however I was unable to find the claim in either that article or this one, which was cited by the first article. The same error appeared on the page for Brorphine. I hate to assume bad faith, but I will investigate this issue to see if that could be the case.
Update: I found the original edit that mentioned hERG. Somehow, the citation was switched. I've fixed this and clarified the claim
(I absolutely butchered the signatures on this)

Towelbin (talk) 00:29, 13 May 2021 (UTC)