Template talk:Psychedelics

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Re: the 25-NB subgroup

Hello. I recently split this navbox from Template:Hallucinogens (original) and greatly overhauled and improved it.

Previously, there was a very large 25-NB subgroup in this table (see this revision). This subgroup was much larger than any other subgroup. I decided to slim this subgroup down, for a number of reasons. One was that the navbox was very large and unwieldy (and, to a lesser extent, still is). Another was that the 25-NB subgroup was highly and arbitrarily disproportionate in size relative to the other subgroups and structural classes. And the third was that, to my knowledge, most of the 25-NB compounds in the subgroup had never actually been shown to be psychedelic in humans or to produce psychedelic-like behavioral effects in animals. I ended up deciding to consider that a requirement for inclusion of compounds in this table (rightfully so, I would add). So I slimmed the subgroup down and moved the original subgroup to be a table here in the 25-NB article instead so that the information wasn't lost.

Today, CrispyCupcake added the large 25-NB subgroup back into the navbox (revision link) with the following edit note: "merged the [25-NB] group, which, contrary to previous statements, had actually never been merged (https://en.wikipedia.org/w/index.php?title=Template:Hallucinogens&diff=prev&oldid=1284882187)". I don't quite understand the reason for this or what they meant in the edit note. In any case, considering my reasoning above, I've reverted the edits and restored the navbox to the original version. I put a lot of thought into the new reworked navbox and I don't think that re-including that large subgroup of 25-NB compounds would be beneficial. Happy to discuss further if needed.

Thank you. – AlyInWikiWonderland (talk, contribs) 05:40, 22 May 2025 (UTC)[reply]

I’ve updated the template once more—please take a look. --CrispyCupcake (talk) 06:59, 22 May 2025 (UTC)[reply]

@AlyInWikiWonderland: Was it necessary to revert every revision? What issues are there with this version? --CrispyCupcake (talk) 07:05, 22 May 2025 (UTC)[reply]

@AlyInWikiWonderland: Are you objecting to the fact that "25x-NB (NBOMes) are considered a sub-family derived from the 2C-x series, modified by the addition of an N-benzyl group" --CrispyCupcake (talk) 07:13, 22 May 2025 (UTC)[reply]

Hi CrispyCupcake. I've rolled the navbox back again. Please discuss here and reach consensus before making changes re: this matter.

I think the new groupings are still overkill in terms of the subgroup categorization and unnecessarily add to the navbox length. It's also not clear to me that many or most of those added have actually been shown to be psychedelic in humans or psychedelic-like in animals. Readers can consult the 25-NB page for more in-depth information re: the categorization. Remember that this is a navbox and is intended for helping with navigation—it doesn't need to be exhaustive or comprehensive.

Re: the placement under 2Cs, I designed the current navbox with aesthetic considerations to have similar/consistent indentation levels and to look nice and clean. While it is true that 25-NB may be technically considered a subgroup of the 2Cs, the DOx family and other groups could also just as validly be considered subgroups of the 2Cs (e.g., DOx are α-methyl-2Cs). But putting all of those in a branched tree under 2Cs, even if technically correct, would look really awkward and would likely be confusing to viewers. Also not all members of the "25-NB" family are 2C derivatives, for instance NBOMe-mescaline (though it's not technically even "25-NB" as it's not 2,5-dimethoxylated, but still generally lumped in with them as an N-benzylphenethylamine). So I prefer having 25-NB in their own same-level subgroup.

I'm off to sleep for now. – AlyInWikiWonderland (talk, contribs) 07:18, 22 May 2025 (UTC)[reply]

I have great respect for the decisions you make and trust your judgment. By the way, I didn't realize that you had already merged the list into the 25-NB article when I restored it to this template—thank you very much for taking care of that! --CrispyCupcake (talk) 12:23, 22 May 2025 (UTC)[reply]

Thanks CrispyCupcake, I appreciate that. And my pleasure. – AlyInWikiWonderland (talk, contribs) 05:32, 23 May 2025 (UTC)[reply]

Rollback of sorting changes

Hi again CrispyCupcake. I rolled back the sorting changes you made to the navbox and I'll explain why here. As part of the new navbox and design, I had carefully and meticulously considered all aspects of it, including the sorting. The navbox was basically "perfect" in my view as it was once I was finished with the work. After thinking about it a lot, I had opted against alphabetical sorting during the work on it. There is a logic to the current sorting that involves a combination of considerations of chemistry, history, and pharmacology and that I feel makes a lot of sense and is a better approach.

As an example, in the case of the phenethylamines, the scalines (namely mescaline) were the first and most well-known psychedelic phenethylamines to be discovered as well as among the simplest structurally, the 2Cs are positional isomers of the scalines with a single substituent moved, the 3C-X, DOx, and 4C-X compounds are "higher" or more complex α-alkyl analogues of those groups with an additional substitution, the MDxx compounds are generally only mild psychedelics with an unusual structural feature (a bridged benzodioxole ring), and the FLY and 25-NB compounds are the most structurally distinct as well as most recently discovered compounds and "build on" the preceding groups. Moreover, the side chain-cyclized compounds and the bioisosteres make the most sense at the bottoms of the groups as they are no longer simple phenethylamines or tryptamines but are more of "related" forms. There were similar considerations for all other relevant subgroup sortings (tryptamines, lysergamides, natural sources, etc.).

I hope that that makes sense. Thanks. – AlyInWikiWonderland (talk, contribs) 05:55, 23 May 2025 (UTC)[reply]

@AlyInWikiWonderland: Please include an explanation of the structural policy in markup comments within this template (and in any other templates or related pages you have worked on). Without this clarification, others may inadvertently spend time re-sorting the entries alphabetically in the future. --CrispyCupcake (talk) 07:36, 23 May 2025 (UTC)[reply]