Talk:Substituted amphetamine

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Improper consumption of amphetamine derivatives may result in addiction and aggressiveness, as well as in rapid deterioration of basic body functions and death.[edit]

That is somewhat ambiguous. Improper consumption of paracetamol, aspirin, ibuprofen and various other common off the shelf pharmaceuticals also cause a rapid deterioration in health and death when consumed inappropriately.

Consumption of alcohol is a prime cause of aggressiveness, rapid deterioration and death when consumed inappropriately. As well as some form of addiction; probably psychological. That is also available off the shelf.

The latter is allowed due to social norms. The former are allowed due their accepted medical worth versus harm potential. So it is not simply that amphetamines are controlled due to these risks, as many other uncontrolled examples exist.

With regards to addiction, that needs to be more clear. It is well accepted that people can become psychologically addicted, but a physical addiction is not as certain; as stated further down the page.

The sentence should simply read, "Amphetamines, and their derivatives, are controlled in many countries.". — Preceding unsigned comment added by (talk) 09:44, 20 November 2011 (UTC)

Amphetamine analogues.[edit]

  • This discussion forum thread has some very interesting information regarding selective monoamine affinity to various phenethylamine type stimulants of different kinds. Hopefully some of it could be of use to articles such as this one. Nagelfar (talk) 21:05, 13 February 2009 (UTC)

Requested move[edit]

The following discussion is an archived discussion of a requested move. Please do not modify it. Subsequent comments should be made in a new section on the talk page. No further edits should be made to this section.

The result of the move request was no consensus for move. Arbitrarily0 (talk) 14:29, 24 November 2009 (UTC)

Substituted amphetamineSubstituted amphetamines — In this context amphetamines is the name of a category of compounds, only used as plural. Single has another meaning here. --Wickey-nl (talk) 16:20, 17 November 2009 (UTC)

  • Each of the various substituted amphetamines is a substituted amphetamine. The singular seems valid to me. Anthony Appleyard (talk) 06:41, 18 November 2009 (UTC)
    • This argument would only be valid if the article was about one of the substituted amphetamines. This article is about the class and is a list of substituted amphetamines.--Wickey-nl (talk) 11:18, 18 November 2009 (UTC)
    • Likewise the page Frogman is not called Frogmen, although it is about all frogmen and not about a particular one. Anthony Appleyard (talk) 20:33, 18 November 2009 (UTC)
  • Oppose — This is standard English grammar. Most links to this article are likely to identify a member of the class, as in "X is a substituted amphetamine" rather than "X is a member of the class substituted amphetamines" and note that even in the plural use, the singular page name suffices. --Una Smith (talk) 22:58, 18 November 2009 (UTC)
  • The lede could be rewritten to discuss this topic in the singular. --Una Smith (talk) 23:04, 18 November 2009 (UTC)
  • Oppose Plural is unnecessary. This is consensus per WP:Manual of Style. Abductive (reasoning) 06:18, 22 November 2009 (UTC)
The above discussion is preserved as an archive of a requested move. Please do not modify it. Subsequent comments should be made in a new section on this talk page. No further edits should be made to this section.

Page history repair needed[edit]

Suggestion for reorganization and eliminating needless redundancy[edit]

This has come out of my proposal to eliminate "substituted phenethylamines" which has led me to think that merging and reorganization is a better idea.

As it stands, there is no verifiable definition of "substituted phenethylamine" or "substituted amphetamine" or "substituted methylenedioxyphenethylamine." They are potentially infinite classes of compounds. It seems very obvious to me that these lists are generated due to interest in Shulgin's book, but Shulgin's book is by no means the only book that lists phenethylamines.

We should keep "substituted phenethylamines" and merge "substituted amphetamines" and "substituted methylenedioxyphenehtylamines" into it, 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. Hell, LSD can be seen as a substituted amphetamine. Heroin can also be seen as a substituted amphetamine.

I have a really hard time understanding why people want to maintain these lists in their arbitrary form, especially when they overlaps so much with each other (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 list in substituted PEAs - 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) 13:00, 28 October 2010 (UTC)AlkaloidMan

Under "Synthesis"...[edit]

Under the section of synthesis, the first synthesis produces methamphetamine, but is labeled amphetamine. That's something that I think should be looked at. Unless catalytic hydrogenation demethylates the amine, and produces amphetamine, which to the best of my knowledge doesn't. Having said that under high enough pressures and temperatures palladium can reduce many organic moieties.

Structure-Activity - hTAAR1[edit] - compare to other methylPEAs as well in structure section. Seppi333 (Insert  | Maintained) 04:46, 12 November 2014 (UTC)

Issues & errors with term "substituted amphetamine"[edit]

I assert that amphetamine is not a substituted amphetamine. It would be appropriate to call amphetamine a substituted phenethylamine or an amphetamine but not a substituted amphetamine. (I concur with much of what AlkaloidMan said above.)

The cited claim "In 2013, it was estimated that between 13 and 54 million people used substituted amphetamines recreationally (0.3% to 1.1% of the global population between the ages of 15 and 65)" is simply wrong. The cited document gives those figures for "amphetamines" and other figures for "ecstasy" which truly is a substituted amphetamine. (The UN World Drug Report 2014 used the terms amphetamine-type stimulants and ecstasy.) Assuming the substituted amphetamine definition used, the actual figures would be a sum of both.

It is inappropriate for Wikipedia to redefine terms and substituted amphetamine(s) is being bandied about as including amphetamine itself repeatedly on Wikipedia and Wiktionary. An example is a table taken from the UN Drug Report 2014, used in the amphetamine article, where the term "ATS" ("amphetamine-type stimulants") was replaced with "substituted amphetamines" then also lists MDMA. I assert this is how the misapplication of the term is spreading.

I have found only one source using substituted amphetamines to include amphetamine itself[1] but many many others excluding amphetamine from this class: "Whilst MDMA and the substituted amphetamines have chemical structures similar to amphetamine, the psychoactive effects are markedly different."[2][3]

The solution to this might be to exclude amphetamine generally but if some essential fact combines amphetamine with substituted amphetamines, it should be clearly declared in the text of the fact (not in a footnote). Another option is to use the term amphetamines though some sources separate this from ecstasy type substituted amphetamines. This is a matter for discussion.

The distinction between the singular or plural isn't important to this issue and no significance should be given to the singular or plural (substituted amphetamine vs. substituted amphetamines) used in outside references.

Bottom line: substituted amphetamine does not include amphetamine itself.

Box73 (talk) 11:29, 18 August 2015 (UTC) / revised 23:14, 18 August 2015 (UTC)


  1. ^ Lees, Andrew. "The Story of "Speed" from "Cloud Nine" to Brain Gain.". PubMed. Retrieved August 18, 2015. 
  2. ^ Rattray, Marcus (2003). "12. Ecstasy". In Caan, Woody. Drink, Drugs and Dependence: From Science to Clinical Practice. Routledge. p. 133. 
  3. ^ O'Brien, BA (May 1982). "Differentiation of amphetamine and its major hallucinogenic derivatives using thin-layer chromatography." (PDF). Journal of Analytical Toxicology. 6 (3): 146. PMID 7109558. Retrieved August 18, 2015. Figure 1. Structures of amphetamine and the major substituted derivatives 
I would think it rather intuitive that a compound with no substitutions would be a parent compound for a chemical class defined by substitutions on that compound. Even so, we should probably cite a chemistry text that supports the definition of a chemical class based upon chemical substitutions. Seppi333 (Insert ) 05:10, 20 August 2015 (UTC)
It seems intuitive to me that a drug class defined by a distinction should only include substances with that distinction. The term "substituted amphetamines" is only used (outside Wikipedia) in texts, reference books and professional journals to deal with amphetamine derivatives distinguished by substitutions. The drug class you call "substituted amphetamines" is called "the amphetamines" and it includes amphetamine and substituted amphetamines. We should cite a few chemistry, pharmaceutical and medical texts specific to this term. The term substituted amphetamines invites confusion because of its association with MDMA and similar entactogen-hallucinogen type amphetamines. So why not just say the amphetamines.Box73 (talk) 08:04, 22 August 2015 (UTC)
I believe, as I read from the page notes at Amphetamine#Notes, that there is some ambiguity involved using it. "Amphetamines" and similarly "phenethylamines" can either refer to the chemical classes or be the plural forms of "amphetamine" and "phenethylamine" respectively. Sizeofint (talk) 18:16, 22 August 2015 (UTC)
Ambiguity may be somewhat of an issue. But as an encyclopedia, ours is to use the conventional terminology, and neither introduce new terms nor use marginal terms. We must use existing conventional terms and when ambiguity presents, clarify our intended meaning in the article copy. Indeed by using the term "substituted amphetamines" we may create reverse ambiguity: produce confusion and error in someone referencing other material which uses conventional terms or uses a more conventional definition for "substituted amphetamines". That is the danger involved.
When Wikipedia uses a term, generally a user should be able to search it on Google, or PubMed or similar and find that definition in wide use. Googling "substituted amphetamine" I find practically every result sourced from Wikipedia itself or referring to amphetamine derivatives. By Wikipedia's present definition, "substituted amphetamine" is not a common, conventional term.
I believe that it is the role of chemists, pharmacologists and related professions, their professional bodies, academia, publishers and expert consensus to provide terms and conventions, and revise these to resolve ambiguity. Presently the conventional term is "amphetamines" (or "amphetamine class") and not "substituted amphetamines". Box73 (talk) 07:43, 23 August 2015 (UTC)
I am not really familiar with the literature. If substituted amphetamine does not include amphetamine then the article should reflect this. We would likely need to revise Amphetamine as well. Sizeofint (talk) 18:04, 24 August 2015 (UTC)

──────────────────────────────────────────────────────────────────────────────────────────────────── Box, you don't seem to realize this, so I'll just state it outright. A "substituted chemical" is a chemistry concept, not a pharmacy concept, based upon substitution reactions. There isn't anything inherently unique about the term "substituted amphetamine" as compared to something like "substituted caffeine", as any compound can have a chemical class defined by various substitutions on that chemical. This is why I said we need a chemistry textbook that defines the general concept - potential sources would be the texts cited in the substitution reaction article. Seppi333 (Insert ) 00:24, 25 August 2015 (UTC)

The Glennon chapter from Foye's Principles of Medicinal Chemistry does not use the term "substituted amphetamines". Rather it refers to amphetamine as unsubstituted. While amphetamine is rightly called the prototype member of this class, this reference text does not call the class "substituted amphetamines". A reference text such as this would explicitly use the term "substituted amphetamine"
One must be careful in reading this text, for example in the section "alpha-substituents" Glennon is talking about amphetamine in terms of phenethylamine. (The alpha methyl substitution of phenethylamine.)
"Substituted amphetamines" may not be technically incorrect but is too esoteric for the target audience of Wikipedia. Even when the term is used, the more general and frequent term "amphetamines" is principally used.
Some authors consider the term "amphetamines" synonymous with substituted amphetamines but they specifically refer to amphetamine derivatives. If the term substituted is necessary and amphetamine itself included, then "substituted phenethylamines" should be used. Otherwise amphetamines should be used. If ambiguity of the term "amphetamines" isn't an issue for the great majority of writings outside Wikipedia, it should not be so in Wikipedia.
While Wikipedia policy accepts use of a less common term when pronounced ambiguity presents, this term should not introduce reverse ambiguity. That is, the term in Wikipedia should not create confusion when readers expand beyond Wikipedia. If one first repeatedly reads about substituted amphetamines as hallucinogens, then in Wikipedia reads that amphetamine is a substituted amphetamine, he might well infer amphetamine is an hallucinogen. Nor should it be so esoteric.
I can think of no other drug class where such an esoteric term is used. Further amphetamines should be categorized as a drug rather than a chemical; it is not a controlled substance for chemical reasons and to my knowledge is only used as a drug. I wouldn't worry about substituted benzene as it is treated as a chemical and substituted benzene or benzene derivatives have many applications; the term does not cause confusion in outside use.
"Amphetamines" is preferable to "substituted amphetamines". The establishment of a term in Wikipedia is not sufficient reason for its existence. Are we writing for ourselves or to communicate to a wide audience? We are not our audience and forgive me but we should place apologetics above objective reason.
I am like an endless echo but bottom line: "Substituted amphetamines" may be technically acceptable but is too esoteric and misleading considering its common use. What are our options? Box73 (talk) 11:07, 27 September 2015 (UTC)
Phenylisopropylamine is amphetamine. With that in mind, reread the quote. Seppi333 (Insert ) 13:19, 27 September 2015 (UTC)
Which is the WP:COMMONNAME for the class? Wikipedia should reflect the use in literature? Sizeofint (talk) 17:41, 27 September 2015 (UTC)
Depends on the class in question, i.e. substituted derivatives or any derivatives/analogs. I've already pointed out that these are not the same sets of compounds on talk:amphetamine. Seppi333 (Insert ) 18:13, 27 September 2015 (UTC)
So are there really two parallel issues here? One being whether amphetamine is a member of the substituted amphetamines. The other being whether we should have an article for Amphetamines (which Amphetamine itself is definitely part of) for a more general group of amphetamine derivatives (those not necessarily formed by substitution reactions). Sizeofint (talk) 18:24, 27 September 2015 (UTC)
Most of the UNODC's "amphetamine-type stimulants" are functional analogs of amphetamine. These would be included in the "amphetamines" class by the MeSH categorization, which is what a few thousand papers on pubmed are indexed to. Most of those functional analogs aren't substituted amphetamines. Substituted compounds (in a medical/pharmacology context) are typically only discussed in textbooks and journal articles in the context of a structure activity relationship, hence the relative lack of coverage compared to the broader definition. Both cocaine and methylphenidate could be considered amphetamines, as they're both indirect agonists of monoamine receptors and therefore functional analogs in that sense.
In light of that, we could make a separate "amphetamines" page, but it would literally just be several lists of chemical subclasses of functionally and structurally related compounds. Seppi333 (Insert ) 19:00, 27 September 2015 (UTC)

SDRA ala Serotonin-dopamine reuptake inhibitor but a releaser[edit]

molecule structure of a substituted amphetamine with a cis (as opposed to trans) propenyl at the 4' or "para" position

RTI-83 & RTI-11w see the line along the top from the benzene forming the Phenethylamine skeleton, with a cis-propenyl at the para position make a greatly selective compound for DAT & SERT but not for NET (remember the larger the number the worse the ability to displace: for RTI-11w it is DAT = 15, SERT = 7, NET = 28,000; i.e. twenty-eight-thousand, not hundred). Does anyone know of any literature where this has been done with amphetamine? You'd think it would be intuitive to do so, since when they do it on MAT uptake pump ligands for radiolabeling, it is to great effect; namely cf. List of phenyltropanes#Radiolabeled (note however those are the "meta" or 3' position, not the para position; so the discrepancy is no where near as large). Nagelfar (talk) 17:45, 22 October 2015 (UTC)

Not familiar with any literature on that. Figured it might be worth noting that if the mechanism of release for those compounds is the same as amphetamine (i.e., TAAR1/VMAT2-mediated), such derivatives would also be very poor substrates of NET, but not DAT/SERT. Seppi333 (Insert ) 14:36, 23 October 2015 (UTC)

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Substituted amphetamine#Structure[edit]

  • [1] - citation; the carbons are labeled differently though. Seppi333 (Insert ) 01:15, 29 September 2016 (UTC)