Talk:Substituted phenethylamine

Considering requesting deletion of this article
Rationale:

There is no "proper" definition of what a "phenethylamine" or "substituted phenethylamine" is. Most references to "phenethylamines" derive from Shulgin's Phenethylamines I Have Known and Loved (PIHKAL) but the substances in that book are called "phenethylamines" for synthetic reasons: i.e. Shulgin was intentionally exploring the phenethylamine moiety and derivatives of it. Thus, his definition of "phenethylamine" was subjective and had to do with his intents and how much work he did. Had he continued his work in PIHKAL, he very easily could have ended up called dextrorphan a "phenethylamine" because it does have the phenethylamine moiety embedded in it (so does LSD). In patents, the term "substituted phenethylamines" is used very specifically and is defined in a specific manner in each patent so that there is no ambiguity.

If anyone can find a source that comes up with a standard definition for what a "substituted phenethylamine" is then I would like to see it. I think the category is largely arbitrary and in the eye of the beholder. —Preceding unsigned comment added by AlkaloidMan (talk • contribs) 04:25, 25 October 2010 (UTC)

What I really think would make most sense
Okay, some won't even bother reading my rationale for deletion, so I'll be concise.

As it stands, there is no verifiable definition of "substituted phenethylamine." It is a potentially infinite class of compounds. It seems very obvious to me that this list is generated due to interest in Shulgin's book, but Shulgin's book is by no means the only book that lists phenethylamines.

We should merge this group with the "substituted amphetamines" and "substituted methylenedioxyphenehtylamines" since the "susbtituted phenethylamines" includes both of those groups.

After merging those groups, we should break the categories apart into VERIFIABLE categories. "Substituted phenethylamines" can include thousands upon thousands of substances and has an absurd amount of overlap with the other two categories. After merging the two other groups, we should break the categories apart, or at least make sub-lists of "substituted phenethylamines with (some verifiable property)" such as "substituted PEAs with adrenergic activity" and "susbstituted PEAs with dopaminergic activity." We should also give the reader enough information to be able to discern which substituted PEAs are also susbtituted amphetamines and/or substituted methylenedioxyPEAs. I don't see why we should keep those lists that overlap so much.

I know that people like Shuglin's work, but limiting "substituted PEAs" to the compounds listed in Shulgin's book is arbitrary. The significance of the PEA moiety goes FAR beyond Shulgin's book and extends to more complex molecules like isoquinolines, benzomorphans, benzylisoquinolines, protoberberines, aporphines, protopines and narcotine.

I have a really hard time understanding why people want to maintain this list in its arbitrary form, especially when it overlaps so much with the susbtituted amphetamines and substituted methylenedioxyPEAs (and even the 2Cs and DOxes, because even most of those are substituted phenethylamines or substituted amphetamines, yet for some reason they have different lists, though some of the 2Cs and DOxes are listed here - and I think it's silly to give Shulgin's nomenclature such a special status, because his naming convention really doesn't change the fact that the 2Cs and DOxes are substituted phenethylamines and many are substituted amphetamines).

There's got to be a better way to organize these lists that isn't arbitrary.AlkaloidMan (talk) 12:51, 28 October 2010 (UTC) AlkaloidMechanic

just another example
Even in the scientific literature, not all sources agree on what a phenethylamine derivative is.

Rothman RB, Baumann MH. (2009) Appetite suppressants, cardiac valve disease and combination pharmacotherapy. Am J Ther. 16: 354 - 364. say, "With the exception of sibutramine, these medications are substituted phenylethylamine analogs."

On the other hand p.129 of Carel & Hochberg (and Bray et al., 1996) refers to sibutramine as a phenethylamine.

Why does one refer to it as such an one not? Neither source makes it explicitly clear? Maybe one has to do with conformational rigidity and the other doesn't. Maybe one source is considering phenethylamine and another closely related group and sibutramine fits better into the 2nd group (e.g. if talking about methamphetamine it would be more sensible to talk about it as a substituted amphetamine rather than a substituted phenethylamine if one were comparing the two). Maybe Rothman and Baumann (2009) just don't know what they're talking about, or they consider the cyclobutyl group to exclude sibutramine for some reason.

Bray GA, Ryan DH, Gordon D, Heidingsfelder S, Cerise F, Wilson K. (1996) A double-blind randomized placebo-controlled trial of sibutramine. Obes Res. 4: 263 - 270.

Just another example of why I find this list hard to swallow. It sems very obviously derived from Shulgin fanboism.AlkaloidMan (talk) 03:21, 29 October 2010 (UTC)AlkaloidMan


 * Not a pharmacologist or chemist; noticed that Phenylpiracetam is a stimulant and take a good, hard look at that molecule. The NH2 is an N bonded to 3 carbons instead, essentially substituting Piracetam for the carbon R[beta] is bound to.  If R[beta] is CH2-CO, NH is just N bound to that CO's C, and R[N] is CH2-CO-NH2, you've got Phenylpiracetam.  That looks a *lot* like a substituted phenethylamine to me, but isn't.  Isn't it interesting, though, that it's a pretty potent stimulant?  --John Moser (talk) 23:44, 29 June 2016 (UTC)

Opinion
'Disagree': page is well interconnected (hub-like), the erroneousness of the title can be stated in the text and I do not really follow what is the actual reason for deletion. Additionally:
 * From what I know the term "substituted" itself is vague without a IUPAC-agreed mathematical threshold-kind of metric and that many chemical categories are infinitely big, but few have common names, e.g. only 20 alpha amino acids are worth mentioning.
 * Regarding lists that can be infinetely long (most of them actually), a notoriety threshold generally suffices, without the need of a hatnote warning.
 * Regarding hub-like statement: It is a page visited by 100 people a day (moderately low) but many page link to this page, there is a whole table template to link to the various pages and regarding the list, there is the category Category:Phenethylamines, which contains a few more, but not that many more are present in wikipedia, furthermore this table is informative. It seems to me that this article acts as a hub so it would be a sin to break up the flow.
 * The book "Shulgin's Phenethylamines I Have Known and Loved" is not a reference on the page, if this chap is indeed the source of this vague term, it should be added clearly that due to Shulgin Substituted phenethylamines=hallucinogens.
 * PS. A friendly hint, do not insult possible readers — albeit true that few read discussion pages—, it comes across badly. --Squidonius (talk) 05:57, 29 October 2010 (UTC)

Deletion? No. Merger with "Phenylethylamine" & editing
How this can possibly be considered deserving of its own article is beyond me. There is simply no reason why it should not be included in the main phenylethylamine article. EVEN IF phenylethylamines as psychoactive (typically scheduled/controlled/prohibited) drugs are the most widely notable aspect of this chemical motif... it STILL means that it should be included as a prominent and detailed subsection in the main article.184.189.220.114 (talk) 20:25, 31 December 2012 (UTC)

Full (chemical) names
Hi, currently the chemical names are expressed in a way that I think is less than helpful. By this I mean as this page is about substituted phenethylamines the chemical names should be expressed solely in terms of phenethylamine, instead of phenethylamine and amphetamine, depending on the compound mentioned. For example bupropion would become: 5-chloro-N-tert-butyl-α-methyl-β-ketophenethylamine instead of 5-chloro-N-tert-butyl-β-ketoamphetamine. Brenton (contribs · email · talk · uploads) 01:54, 14 September 2014 (UTC)

Confusion over hormones, monoamines and trace amines; epinephrine/adrenaline naming
In the introduction there is currently this sentence: "Numerous endogenous compounds – including hormones, monoamine neurotransmitters, and many trace amines (e.g., dopamine, norepinephrine, adrenaline, phenethylamine itself, tyramine, thyronamine, and iodothyronamine) – are substituted phenethylamines."

I believe that in its current form it could lead people to believe that all of the compounds in the parentheses are trace amines. It should read something like this: "...including hormones (e.g. adrenaline...), monoamine neurotransmitters (e.g. dopamine, noradrenaline...), and many trace amines (e.g....) - are..." I also think that either the pair "norepinephrine"/"epinephrine" or "noradrenaline"/"adrenaline" should be used in this sort of context. I am British and so opt for adrenaline and noradrenaline, but wouldn't know if one term is "better" than the other in an unbiased way. I am not changing the sentence myself as I would easily end up sticking a hormone in as a trace amine or something, so if someone else could sort these compounds out, that would be fab. Anditres (talk) 09:50, 29 December 2020 (UTC)

Diagram of Phenylethylamine vs Phenethylamine
I'm no chemist, but why is the image "Phenylethyl Amine General Formula" marked as "The structural formula of phenethylamine"? The image directly under it says there's an "NH2" on the right whereas this image says there's a "HN". Sorry if I'm just uneducated on chemistry, but aren't Phenylethylamine and Phenethylamine different, and if so shouldn't the difference be signposted?

Sorry if I'm doing something wrong, I'm not used to talk pages. 222.154.151.244 (talk) 04:05, 21 June 2021 (UTC)

Psilocybin magic mushrooms
Albino penis envies 208.123.177.207 (talk) 05:16, 19 December 2022 (UTC)

Mescaline
I thought it was entirely appropriate/NECESSARY to add MESCALINE near the top of all this since it is so well-known (relatively speaking - i.e., MOST people have heard of it, or at least many people can make some kind of vague connection between it and peyote, etc...) I know DOM is a related compound, but really, unless you're an über-nerd what comes to this sort of stuff (like me), who in the hell has heard of DOM, much less knows what it is? (I had to look it up to be sure, but yeah...) I left it in there, but MESCALINE is the KING in this case and it feels like a glaring omission!

P.S. I've only edited a handful of articles in my entire life and realize I've likely created some formatting inconsistencies / messed something up / don't entirely know what I'm doing... So if anything needs cleaning up, formatting-wise please do it. And if my edit is somehow "out of line" or "wrong"(?), please do let me know and perhaps explain why if you can (please) At the same time, SEE ABOVE... :-) Echo1434 (talk) 12:53, 11 March 2023 (UTC)