Talk:MDMA/Archive 6

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Medical section

The Medical section currently reads as: MDMA currently has no accepted medical uses.[13][17] which is semi-correct but very sparse and misleading!

The last paragraph of the opening section relates to medical history and in my opinion should be moved to the Medical section.

Plus the DEA have recently approved trials into MDMA for seriously ill patients, so a note that the current status is always under review and flux would be a good idea.

So my proposed changes to the section would read as thus (or very similar):

---

Although at the current time MDMA is scheduled as Class I in the USA and the official state is it "has no accepted medical uses"[13][17] (with general worldwide agreement, see Legal Status section) there are DEA and other approved trials into its effectiveness in PTSD and other serious illnesses,[*1] which in the past have often had positive results.[*2] MAPS (the Multidisciplinary Association for Psychedelic Studies) hopes to make MDMA a FDA approved precription medicine by 2021.[*3]

In previous trials medical reviews have noted that MDMA has some limited therapeutic benefits in certain mental health disorders, but has potential adverse effects, such as neurotoxicity and cognitive impairment, associated with its use.[15][16] Further research will help determine if its potential usefulness in posttraumatic stress disorder (PTSD) treatment outweighs the risk of persistent neuropsychological harm to a patient.[15][16]

---

[*1] http://www.huffingtonpost.com/2015/03/18/dea-mdma-study_n_6888972.html [*2] http://www.usatoday.com/story/news/nation/2014/07/11/mdma-molly-therapy-ptsd-cure/10683963/ [*3] www.maps.org/research/mdma

---

Please review and edit if you agree these changes would make sense. Sorry I have never signed up and only ever done a small handful of minor edits in my life, with this being a Protected article here I can't so I hope you don't mind me going via this method instead. I know it's still a but messy but as I can't post directly hopefully somebody who agrees can tidy it up that last iota... — Preceding unsigned comment added by 101.99.4.59 (talk) 08:52, 9 April 2015 (UTC)

For content to be in the medical uses the general guideline is that it have at least reached clinical trials. The ongoing pilot studies by MAPS are noted in the research section at the end of the article. Sizeofint (talk) 16:49, 9 April 2015 (UTC)

Mistubishi

The previously good reputation of 'Mistubishi's' amongst ecstasy-users has been dealt a blow with the discovery of deadly batches PMA (aka White Mitsubishi in The Shulgin Index Vol 1, pp811), and PMMA (aka Red Mitsubishi).

Also, "According to the London Toxicology Group, ChEckiT in Austria analysed 48 tablets (September 2000) sold as Ecstasy and found that 4 contained about 40 mg PMA in combination with PMMA and amphetamine. They had the Mitsubishi logo, were red, 7 mm in diameter and 5 mm thick and weighed 230 mg. They were sold as 'red Mitsubishi' or 'killer'. PMA is thought to produce no colour change when tested with Marquis reagent." --94.245.53.33 (talk) 16:38, 29 April 2015 (UTC)

References

If this is notable enough we might be able to put this in the History or Society and Culture sections. Thanks for the info. Sizeofint (talk) 18:53, 29 April 2015 (UTC)

@Sizeofint PMA is listed as White Mistubishi in The Shulgin Index Vol 1, pp811. That should be notable enough. --94.245.53.33 (talk) 01:47, 1 May 2015 (UTC)

The Boston Group - Tenured professors from Harvard and MIT

I'd like to see a better source for this than Playboy Magazine. As a chemist, I can say that its very, very tough to get a position, let alone tenure at MIT or Harvard. And the people who succeed are generally not of the type who will put their careers at risk for social missions of the sort described in the article: they are more typically single minded careerists who would never take this kind of risk. The credibility of this story is not increased by the continuation of the story in the source, which states that "they were threatened by some very dangerous people and had two days to leave the country". A mass departure of tenured faculty from the two of the top five chemistry departments in the country would have made the newspapers, let alone the industry newsletters that I followed religiously during that period. This entire section of the article seems to be based on an urban myth, not scholarly research into the history of the drug. Formerly 98 ^{talk|contribs|COI statement} 17:19, 28 April 2015 (UTC)

None of the other sources I have read mention that the Boston Group was composed of tenured faculty. That statement and reference should probably be removed. The sources are fairly consistent about the rest of it though. I'm planning on improving the sourcing for this section in the coming weeks. Sizeofint (talk) 17:55, 28 April 2015 (UTC)

uh, Noam Chomsky MIT, Timothy Leary Harvard. So there's that.

Semi-protected edit request on 9 June 2015

The "Long term effects" under "Adverse effects" section of this page states that MDMA produces "brain lesions, a form of brain damage". Neither of the sources cited describe brain lesions. This initial statement is not adequately supported by the citations. It is important that the material presented in the article is accurate in terms of the source which it comes from.

Cv325 (talk) 15:29, 9 June 2015 (UTC)

Do you have access to the textbook cited? Cannolis (talk) 15:43, 9 June 2015 (UTC)

From Malenka, cited in the article: "MDMA has been proven to produce lesions of serotonin neurons in animals and humans." VQuakr (talk) 15:44, 9 June 2015 (UTC)

AlterNet article reliable source?

This AlterNet article http://www.alternet.org/story/16165/controlling_drugs has some details about the Boston Group I have not found anywhere else (namely that it was composed of medicinal chemistry graduate students). Is AlterNet considered a reliable source? I've searched the archives for old discussions (e.g. https://wiki.riteme.site/wiki/Wikipedia:Reliable_sources/Noticeboard/Archive_125) but I haven't found a straight-forward answer. Sizeofint (talk) 23:17, 7 August 2015 (UTC)

Depends on the claim you want to cite. In the past, I've cited somewhat crappy internet sources similar to that one to support statements on slang terms, certain historical/sociocultural claims, and the legality of compounds in small/relatively obscure nations in some articles (provided I can find this information repeated in other sources of similar quality), but I wouldn't use a website like that to cite anything outside of that context. Seppi333 (Insert 2¢) 02:26, 8 August 2015 (UTC)

Thanks, I'll leave it out. Sizeofint (talk) 20:30, 8 August 2015 (UTC)

I am glad, at this point, as I think it "crappy" also. From what I have seen it appears to be an extremely liberal media outlet. Nothing wrong with that, however, I looked at the article and the organization and a concern would be the stated goal of "strategic journalism". This would be "Communication management" or strategic communication. Strategic communication has been quoted as being "the synchronization of images, actions and words to achieve a desired effect.". The site does promote certain agendas and this brings thoughts of:

• 1)- subliminal messages,
• 2)- favorable advancement of a cause through directed writing,
• 3)- deliberate messages to gain a favorable or sought opinion.

No different than government propaganda. The site states (in part http://www.alternet.org/about) "AlterNet has developed a unique model of journalism to confront the failures of corporate media, as well as the vitriol and disinformation of right wing media...", and "AlterNet believes that media must have a higher purpose beyond the essential goal of keeping people informed.". The site advocates that corporate and right wing media only provides disinformation "but" they ..."provide readers comprehensive information..." with ..."concrete action steps towards change.".

I am not saying this is bad or good, in all cases, but it is hard to be objective when an opinion is slanted to an agenda that might not be so obvious, or may be obvious propaganda, so I agree with Sizeofint essentially to use with caution. Otr500 (talk) 14:27, 23 August 2015 (UTC)

Research Section Needs Help

The research section cites Andrew Parrott's 2014 paper. Of particular concern is the line "A review of the safety and efficacy of MDMA as a treatment for various disorders, particularly PTSD, indicated that MDMA has therapeutic efficacy in some patients;[18] however, it emphasized that MDMA is not a safe medical treatment due to lasting neurotoxic and cognition impairing effects in humans.[18]" The lasting neurotoxic and cognition impairing effects in humans was specifically addressed in Danforth et al 2015. It was shown that the literature Parrott cites takes data from users of street Ecstasy (not pure MDMA and not taken in controlled environments) who have used hundreds of times and then wrongfully applies the harms from this literature base to MDMA assisted psychotherapy (which it's only taken 6 times at most per the current literature base). Additionally, the street populations that he cites often "stack" doses which greatly increases harm and all are polysubstance abusers which confounds the source of harm found in these studies. This polysubstance abuse statistic comes from his own data, see Wu et al 2009 which he's one of the authors (full ref in Danforth paper). He curiously leaves this confound out of his 2014 paper even though he's an author on the study which overtly shows that essentially all ecstasy users are polysubstance abusers. Here's a copy and paste of the section I'm referring to from Danforth.

"The Ecstasy user literature base also contains multiple factors that limit the generalizability of naturalistic studies of street Ecstasy to clinical settings in which pure MDMA is administered from one to several times within a psychotherapy paradigm. The most substantial of these limitations are the high quantities of doses taken in nearly all publications on recreational Ecstasy users, often on the order of several hundreds of doses. Critics of MDMA-assisted psychotherapy use this data to suggest a higher level of risk than logically can be inferred from no more than six exposures reported in MDMA-assisted psychotherapy clinical trials (e.g., Parrott, 2014). Additionally, “Ecstasy” refers to MDMA obtained from street sources which currently is almost always cut with other drugs as seized shipments from 2007 show only 3% of tablets destined for North American markets containing pure MDMA (Hudson et al., 2014) (https://www.ecstasydata.org/stats.php). Authors commonly cite Ecstasy user data and use it to draw conclusions about MDMA without citing the above purity limitation (Grob, 2000). Furthermore, Ecstasy users are also almost always polysubstance abusers as indicated in the 2007 National Epidemiologic Survey on Alcohol and Related Conditions (n = 43,093) ( Wu et al., 2009), and high polysubstance abuse rates confound nearly all of the Ecstasy correlations found in the medical literature to date. Other common notable hazards include adverse environmental conditions, polydrug use in dangerous combinations, and ingestion of high doses or stacking multiple doses to prolong drug effects. Therefore, research on recreational Ecstasy use has limited applicability to determining the safety of clinical investigations of MDMA-assisted therapy."

Please note that Meyer JS (2013) is a much better paper than Parrott (2014) but any data cited would still suffer from the same lack of generalizability to MDMA assisted psychotherapy research populations as nearly all of the research in humans we have showing cognitive or memory impairments is done with street users who've taken hundreds of doses and therefore suffers from the limitations above. Also, the term "neurotoxicity" is a vague term that seems to be used to hyperbolize risk. — Preceding unsigned comment added by 68.135.33.8 (talk) 16:40, 11 December 2015 (UTC)

Yes, I think this section needs to be updated. Personally, I think Parrot is rather biased, but then we all are and it is a reliable source. I'm working my way through the history section (albeit rather slowly) so I will eventually get to this. Feel free to take a stab at it yourself (unless you have a COI). Sizeofint (talk) 20:55, 11 December 2015 (UTC)

Link to Danforth et al 2015 Sizeofint (talk) 21:01, 11 December 2015 (UTC)

Parrot's paper is a review so technically it should be given higher weight than Danforth's. Are there any newer reviews? Sizeofint (talk) 21:07, 11 December 2015 (UTC)

External links modified

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Image neutrality

The images of the highlighted brain and the dilated pupil seem calibrated more for anti-MDMA propaganda than encyclopedic description of MDMA. To be clear, I'm not saying whoever put them there did so in bad faith. But I think there is an understandable tendency to take drugs of abuse and present them in light that is more cautionary than encyclopedic. Like, normally images from government publications or educational materials are great for Wikipedia. However, when the publishing body has an interest in effecting behavior change, the neutrality of its output becomes questionable. School health textbooks, I think it's fair to say, include anatomical pictures to convey a sense of bodily harm. That is understandable and perhaps appropriate if you want schools or the government to inculcate healthful behaviors. But Wikipedia is not a medium for inculcating sentiment or effecting public health or public morality outcomes.

Like, take the brain pic. It provides little information the text does not. If the article contained details about how MDMA acts on different regions of the brain, this might be a useful adjunct. But as it is, it is basically just This is your brain on drugs with rave-like coloring. Articles on other psychoactive drugs, even potentially harmful ones like haloperidol and methylphenidate do not include such imagery, and I think they'd be strictly worse if they did.

Or take the dilated pupil. Lots of things cause dilated pupils. There is nothing different about pupils dilated by MDMA, and certainly nothing that picture shows that tells you anything more than the text. Again, it has a "look at what drugs do to you" flavor that is decidedly un-encyclopedic.

I'm totally pro images that show the negative consequences of an action like the tooth decay in paan or meth mouth. But the images should be narrowly tailored to convey information, not a general "look at what drugs do to you." The overall presentation and aesthetic should have the same dispassionate, scientific flavor as articles on more respectable substances. I think this is a pervasive problem on article on illegal drugs, and one that maybe should be addressed more comprehensively. Acone (talk) 22:17, 3 February 2016 (UTC)

I put the dilated pupil image there following the lead of the Spanish Wikipedia (see es:MDMA). The image of brain I found while searching for some appropriately licensed content for the article. I thought it provided a convenient visual summary of the content. I personally don't perceive their presence as putting MDMA in a negative light, but then I have been working on this article for a while so I may be overexposed. I am neutral on the matter. If you see this as a POV issue feel free to remove them. Sizeofint (talk) 02:17, 4 February 2016 (UTC)

Unaccepted medical uses

I added a bit to the "Medical" section and an expand template in the medical section. Sizeofint (talk · contribs) and Seppi333 (talk · contribs) noted that current medical consensus does not indicate MDMA, and respectively removed the new text and the expand template.

I understand how it is important to separate established clinical practice from speculative research. But the term "medical" does not necessarily connote "scientific consensus among medical researchers and approved by regulators." For example, trazodone has many off-label uses, some with much evidence (like insomnia), some with very little (like OCD). The article clearly distinguishes the consensus uses from the investigational ones. This seems more natural and fairer than if they had banished the other uses to a "research" or "investigational use" section at the bottom of the article.

There is a such things as medical scientific consensus, and it does matter, but it does not monopolize the concept of "medical" to the point that anything less can't go in the same section. I would like to add a section for unsanctioned uses. Such a section would describe (and cite!) how MDMA is in fact used psychotherapeutically, even if not in an above-board clinical setting. It would not describe clinical research into that matter, which is, I agree, better reported in a separated section. Acone (talk) 22:54, 3 February 2016 (UTC)

For the material that is supposed to go in the medical uses section, see MOS:PHARM#Sections. MDMA has no current medical indications and no regulatory approval in any country, hence nothing else should go in that section.
There's no "off-label" for MDMA because MDMA doesn't have a "label" to begin with (again, because it lacks a medical indication). At the moment, MDMA is an experimental drug, which basically just means it's a compound that is/can be used in research. Seppi333 (Insert 2¢) 23:30, 3 February 2016 (UTC)

Seppi333 (talk · contribs) MOS:PHARM#Sections doesn't state that there needs to be a scientific consensus or regulatory approval for a drug to be described there. If someone uses the drug for something clinical, that is a clinical use, and from my reading of it, nothing in that guideline says it can't there. Whether MDMA is "indicated" is an interpretive judgment. There may not be a scientific consensus or regulatory approval stating that something is "indicated"—and that is important and should be noted—but if it is routinely used to treat a medical problem, well, then those people think it's "indicated." I don't think Wikipedia should be a platform for a given paradigm to assert its monopoly on the right to categorize something as medical. Acone (talk) 00:28, 4 February 2016 (UTC)

Anyway, Seppi333 (talk · contribs), my proposal was to add a new section. Unsanctioned medical uses are still uses, and even forgetting my view that "medical" is the right section, they are certainly not "research," "recreational," or "spiritual" uses. When vets or rape victims take MDMA to address their PTSD, this fits into none of those sections. If I can't put that information in the medical section, why not add another one? For example, Mitragyna speciosa simply has a "Uses" section, with subsections describing how it is in fact used (regardless of whether there is scientific consensus about the clinical validity). How would you feel about adding a comparable section here? Acone (talk) 00:28, 4 February 2016 (UTC)

Let me put it this way: "Medical uses" is basically just a more layman friendly section title for "Indications". When pharmaceuticals get approved, they've been evaluated for an indication as well as for contraindications: these terms basically just mean "a medical reason to use / not use the drug" respectively. Has any medical research been done in this area? Are we just going to ignore it if not, even though the list is probably extensive like it is for this drug? I have no idea how to go about writing those two sections in a manner that's not half-assed for drugs without a label. In any event, if a research section only covers clinical trials, then just rename it "Clinical research" like Lisdexamfetamine#Clinical research; otherwise, cover clinical and preclinical there in subsections. Seppi333 (Insert 2¢) 01:02, 4 February 2016 (UTC)

Perhaps add a section called "Underground psychiatric use" to "Society and culture". I think this use should be discussed somewhere in the article. I also think we need to be consistent in what we call "Medical uses". This might be a topic to raise at WP:Medicine. I don't think we have a guideline for handling unapproved medical uses of drugs that lack indications. Ibogaine suffers from the same problem and we lump everything under "Medical uses". Sizeofint (talk) 02:40, 4 February 2016 (UTC)

I will add there is a blurry line between "Research" and "Unapproved medical use". We'd have to discuss how to differentiate between the two. Sizeofint (talk) 02:48, 4 February 2016 (UTC)

Sizeofint (talk · contribs) I like the header underground therapeutic use because I think it correctly communicates what is going on. The user understands the use as therapeutic (some would say medical or psychiatric, others might reject that). And I prefer "underground" to "unapproved" because the matter is not just one of regulatory approval, but clinical and cultural acceptability. As for where it should go, I say under "uses" not "society and culture." If we want to talk about the societal or cultural contexts in which various use occurs, then sure, society and culture. But not the how and wherefore of the use itself. Personally, I do not find the line between "Research" and "Unapproved/Underground Medical/Therapeutic Use"' blurry. Research is about efforts to learn more, their methods, and their results. If a notable underground use is being researched, it may be a appropriate to discuss it in both sections. For example. people use MDMA to treat their PTSD. Sometimes they do this in the context of a research study. Use in the context of a study should go in "research," while use that is not in such context should be noted in "Uses," even if such use is itself the subject of research. I take your point about Ibogaine and general policy in re WP:Medicine. For now, I'd like to just settle on what makes maximal sense here. Acone (talk) 21:38, 9 February 2016 (UTC)

I think unless we get a general guideline at WP:PHARM or WP:MED this will wind up in an edit war. I wouldn't revert you if you add it, but after so many days or weeks a medical editor is going to come by and delete the content. I note this article is in the scope of WP:Alternative medicine. What about adding a subsection in "Uses" called "Alternative medicine" and placing it there? The content might find better reception in that setup. Sizeofint (talk) 22:39, 9 February 2016 (UTC)

IMO, "Alternative medicine" is the probably most appropriate heading for a section covering this content, so I'm happy with the current layout. Seppi333 (Insert 2¢) 18:29, 24 February 2016 (UTC)

Alternative medicine has a clear meaning that isn't really the same as implied by the section. I have changed it to something more neutral, although we can argue over whether "therapeutic" would be better than "medical." Nick Cooper (talk) 10:30, 18 March 2016 (UTC)

Alternative medicine states "It consists of a wide range of health care practices, products and therapies, ranging from being biologically plausible but not well tested, to being directly contradicted by evidence and science, or even harmful or toxic." To me, this seems to fit with our use of the term in this article. Yes, we have a handful of pilot studies and it seems probable that MDMA has medical applications, however currently MDMA is not well tested. Sizeofint (talk) 16:49, 18 March 2016 (UTC)

Naming discussion

Big blocks of content should not be hidden in "note" but placed in the body of the article IMO. Doc James (talk · contribs · email) 20:20, 30 March 2016 (UTC)

I'm of the opposite opinion in this case. Seppi333 (Insert 2¢) 00:06, 31 March 2016 (UTC)

I think the note allows us to include the relevant identifiers in the lead while not cluttering up the opening paragraphs explaining all the other names. We should probably have a general discussion about this since this is done at amphetamine, methamphetamine, and heroin. Sizeofint (talk) 01:04, 31 March 2016 (UTC)

I just noticed that this is also done at amfepramone. Seppi333 (Insert 2¢) 14:37, 4 April 2016 (UTC)

Psilocybin is the drug article where this convention (adding a synonyms note to the first word, the drug name, in the lead) was first used; it's one of Sasata's featured articles (see [1]). Seppi333 (Insert 2¢) 01:46, 31 March 2016 (UTC)

Okay adjusted to more closely match Psilocybin.

Most of these alternative names should go in the infobox which they currently do under "Synonyms"

Will start a general discussion at WT:PHARM Doc James (talk · contribs · email) 10:44, 31 March 2016 (UTC)

The current setup is really weird. There's a hatnote pointing to ecstasy (disambiguation) at the top of the article. With a hatnote to a dab page, I'd expect to see the undabbed term in bold somewhere in the lead. "Ecstasy" is first bolded (in a table) the 15th time it's mentioned in the article, and first explained and bolded as a common/slang term the 19th time it appears (as a "Note" at the very bottom of the article). The lead probably shouldn't include a comprehensive list of common terms, but explaning the term "ecstasy" in a note at the very bottom of the article is ultimately confusing and unhelpful. Creating a section for "Etymology" or "Nomenclature" or something else along those lines and putting it immediately after the lead seems like the best way to deal with common/slang terms for recreational drugs. Plantdrew (talk) 05:01, 2 April 2016 (UTC)

That hatnote template shouldn't have been used since the term isn't the page title and doesn't redirect here, hence it didn't need to be disambiguated in this article. Seppi333 (Insert 2¢) 05:54, 2 April 2016 (UTC)

Text should not be in the lead only. Thus we need a section on names in th body. Doc James (talk · contribs · email) 13:17, 2 April 2016 (UTC)

Pronunciation in infobox

The infobox gives the IPA pronunciation for "methylenedioxymethamphetamine", a name which appears nowhere in the infobox, nor even in the lead or body of the article, though it is common in the titles of the sources cited. This can't be right. Maproom (talk) 07:31, 7 April 2016 (UTC)

@ Maproom - That's because "methylenedioxymethamphetamine" is currently buried in a "note". (Am referring to this version. Confusingly it keeps changing because editors are revert-warring even while in the middle of an RfC.) --Middle 8 (t • c | privacy • COI) 15:04, 7 April 2016 (UTC)

P.S. @ Maproom - actually this is easily solved... cf. above --Middle 8 (t • c | privacy • COI) 00:45, 8 April 2016 (UTC)

Technically, it is in the infobox, although you'd need to put your cursor over the abbreviated text (3,4-MDMA) to see it. Seppi333 (Insert 2¢) 03:06, 8 April 2016 (UTC)

Maproom, sure a bad situation. For now, I'll add the name right with the pronunciation key (which might introduce a repetition). MAybe the lead-RfC discussion might end up somewhere else.

Still, in general the pronunciation placement has a problem in itself. First: of course it should pertain to the title (there can be exceptional cases; such as when infobox title differs from article title). This established, the question is where exactly to position the pronunciation data in the infobox. Ideally, the pronunciation is directly with the word itself (like in the in opening sentence). As it is now, it is disconnected from the word it describes!

This issue has not been solved in the infobox. The problem is discussed here, buried in multiple discussions aboutnames. For example, see the image in there about the various name types the infobox has to cover.

-DePiep (talk) 08:11, 9 April 2016 (UTC)

Treatment of medical uses of MDMA in lead

I've updated the last paragraph of the lead to (A) more accurately reflect the sources that were already cited and (B) comply with WP:FRINGE. It was in two separate edits, so here's what it said earlier before I made any changes: MDMA may have benefits in certain mental disorders such as posttraumatic stress disorder (PTSD), depression, and substance abuse. More research is needed to determine if its usefulness outweighs the risk of harm.[11][18] Both sources are very clear that recent research using MDMA has been on its use as a therapeutic aid in the treatment of a single disorder (PTSD) in a specific population (patients with chronic, severe, treatment-resistant PTSD). The references to other disorders are in the context of, "If we could do more research, we could find out if it would help for other things too, like depression, etc." It's also important to be clear that individuals are being treated with MDMA in a clinical setting on a limited number of occasions. The purpose is believed to be that it helps the person tolerate more in-depth discussion of past traumatic events DURING THERAPY and therefore allows the therapeutic techniques to be more effective. They are very clear that they're talking about a limited number of MDMA treatments at very low doses. I'd be fine with taking it out of the lead completely, but if it's going to be there, the wording must make all of the above clear and also that this is not a mainstream belief or it violates WP:FRINGE and WP:DUE. PermStrump(talk) 16:41, 5 April 2016 (UTC)

Also, given the lack of support from the broader community about its effectiveness, it's irresponsible to name any specific disorders in the lead (including PTSD). PermStrump(talk) 16:44, 5 April 2016 (UTC)

I'm not sure about mainstream here. For example, if we take this review paper, it has a full section about this discussion:

• Parrott A. C. Human psychobiology of MDMA or 'Ecstasy': an overview of 25 years of empirical research // Human psychopharmacology. — 2013. — Vol. 28, no. 4. — P. 289—307. — ISSN 1099-1077. — DOI:10.1002/hup.2318. — PMID 23881877.

Another recent review of MDMA by Meyer, used in the text, again discusses this problem in a separate section. There is a specialized review of the points raised and some discussion papers:

• Patel R., Titheradge D. MDMA for the treatment of mood disorder: all talk no substance? // Therapeutic advances in psychopharmacology. — 2015. — Vol. 5, no. 3. — P. 179—88. — DOI:10.1177/2045125315583786. — PMID 26199721.
• Sessa B., Nutt D. Making a medicine out of MDMA // The British journal of psychiatry : the journal of mental science. — 2015. — Vol. 206, no. 1. — P. 4—6. — ISSN 1472-1465. — DOI:10.1192/bjp.bp.114.152751. — PMID 25561485.
• Rick Doblin, George Greer, Julie Holland, Lisa Jerome, Michael C. Mithoefer A reconsideration and response to Parrott AC (2013) “Human psychobiology of MDMA or ‘Ecstasy’: an overview of 25 years of empirical research” // Human Psychopharmacology: Clinical and Experimental. — 2014-03-01. — Vol. 29, no. 2. — P. 105-108. — ISSN 1099-1077. — DOI:10.1002/hup.2389.

So I'm not sure that WP:FRINGE is applicable here. In my PoV it is a discussion with more or less equal sides. But current formulation is OK. --Melirius (talk) 00:27, 21 April 2016 (UTC)

Alternative psychology needs sources

I deleted the section on alternative uses in psychology/counseling because the sources were very low quality. I'd like a decent source to state they are alternative medicine — otherwise its simply like listing malpractice use. CFCF 💌 📧 20:50, 10 April 2016 (UTC)

On a similar note, I noticed that someone moved this sentence, "As of 2016, MDMA has no accepted medical uses," to the first paragraph of the lead. It used to be at the very end in the paragraph that talks about ongoing research. I'm torn about the better placement because on the one hand, it's important enough that it belongs in the first paragraph. On the other hand, I feel like the last paragraph needs more balance with the predominant perspective. Maybe there's an alternate solution I haven't though of. Any ideas? (This is to anyone, not just CFCF.) PermStrump(talk) 21:08, 10 April 2016 (UTC)

Hmm, what about page 152 of

• Freye E., Levy J.V. Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs: A comprehensive review on their mode of action, treatment of abuse and intoxication. — Springer Netherlands, 2009. — (Biomedical and Life Sciences). — ISBN 9789048124480.

as a source? --Melirius (talk) 00:29, 21 April 2016 (UTC)

That should work. Sizeofint (talk) 02:29, 21 April 2016 (UTC)

Chirality and drug classes

@CFCF: Where in MOS:MED does it say that we don't cover chirality or drug classes in the lead? I might be missing something, but MOS:MED says

The lead should highlight the name of the treatment product as per normal guidelines.
In the case of drugs, this would include the International Nonproprietary Name, while the BAN or USAN variant may also be mentioned with title words in bold. The initial brand name(s) and manufacturer follows, in parentheses. Indicate the drug class and family and the main indications.

while MOS:PHARM states

The article title and the first name to mention in the lead should be the International Nonproprietary Name (INN) of the drug; see below. The British Approved Name (BAN) or United States Adopted Name (USAN) variant may also be mentioned. The initial brand name(s) and manufacturer follows, in parentheses. All drug names should be in boldface per WP:BOLDTITLE. Indicate the drug class and family and the main therapeutic uses.

I can't find anything about chemical properties in these guidelines. This article is also subject to MOS:CHEM/Chemicals since it's tagged as part of WP:CHEMS. Seppi333 (Insert 2¢) 12:57, 26 April 2016 (UTC)

Per MOS:CHEM/Chemicals

Introductory paragraph should classify the compound either generally (organic compound vs inorganic compound) or more specifically (e.g., organometallic compound or organoarsenic compound). A few properties should be described, assuming STP, and noteworthy features should be mentioned (e.g. extreme toxicity, odor, hygroscopicity). For simpler organic compounds, the main functional group is mentioned, whereas for complex molecules, a parent molecule should be mentioned.

This seems to explicitly ask for the content. Sizeofint (talk) 17:35, 26 April 2016 (UTC)

IMO chirality is not sufficiently important to be in the lead. Belongs in the body. Doc James (talk · contribs · email)

@Doc James: I think the thing that annoys me most about editing Wikipedia is what's happening here. If someone were to push this article through FA, it would never pass without it conforming to every project MOS and comprehensively covering every major aspect of the compound in every significant topical area, both in the lead as a summary and in the article body in detail. That includes content that some editors don't care about having in an article, like in this case. You are a doctor, not a chemist, so naturally you care much more about the clinical aspects as opposed to the structural properties of drugs. The current lead covers pretty much every major area covered in the article - clinical, recreational, pharmacodynamic, pharmacokinetic, historical, and cultural - except chemical.

The only slightly relevant chemistry statement is saying "It is structurally similar to methamphetamine"; however, that's a rather vague statement because it doesn't specify how it's related (meth is a parent compound of MDMA). It's also not anywhere near as notable as the fact that the term "MDMA" refers to 1:1 mixture of (S)-MDMA and (R)-MDMA. It blows my mind that I have to actually argue about including a statement about how MDMA refers to 2 different molecules in the lead; if an article topic refers to 2 different things instead of just 1 thing, you'd think that's something worth stating in like the first or second sentence of the first paragraph. Unfortunately, that's a chemistry statement in this case, and not a medical statement, so medical editors won't really give a shit unless it has significant medical relevance. For example, I'm sure medical editors would care if 1 enantioner was largely responsible for the toxicity of MDMA while the other enantiomer was FDA-approved for something or available OTC (e.g., methamphetamine). But, in cases where enantiomers are more or less the same pharmacological entities or where there's a lack of research on pharmacological differences between enantiomers, medical editors don't really seem to give a shit. WP:CHEMS does though, which is why they've explicitly stated that notable features of a compound be mentioned in the lead in their MOS. I've asked for their input though - WT:CHEMS#Question. Seppi333 (Insert 2¢) 21:07, 26 April 2016 (UTC)

• I think my position ought to be pretty clear, but to elaborate — our primary concern must be the reader — and the reader interested in chemical properties of MDMA is vastly outnumbered by those to whom it does not matte the leastest. There are examples where chirality of drugs is important enough to merit mention in the lede — such as Thalidomide and Escitalopram, but it is not important enough here as it bears little importance beyond synthesis of the drug, and hardly even there. Carl Fredik 💌 📧 21:21, 26 April 2016 (UTC)

It has bearing on the pharmacology as well. The two forms are metabolized at different rates and have different effects. Sizeofint (talk) 21:41, 26 April 2016 (UTC)

So, you're essentially saying that we should systematically ignore MOS:CHEM for all WP:MED-tagged articles because we suppose that most people don't go to a drug article to read anything about its chemical properties, classification, or synthesis. Did I misinterpret? We basically have 3 options here: mention chirality in the lead, mention a different chemical property of MDMA in the lead (I might be okay with that), or completely ignore a project MOS. Right now, we seem to be going with the last option based upon this discussion; that seems like a decent precedent to ignore MOS:MED as well. Seppi333 (Insert 2¢) 05:37, 27 April 2016 (UTC)

This is a medication first and foremost. So yes we should not necessarily follow MOS:CHEM. Doc James (talk · contribs · email) 15:53, 27 April 2016 (UTC)

No, first and foremost this is a recreational drug. No government or major NGO has recommended MDMA for medical use yet. Sizeofint (talk) 18:40, 27 April 2016 (UTC)

Drugs and medicines fall under the pharmaceutical project not the chemistry one IMO. But regardless we go by consensus here. Doc James (talk · contribs · email) 20:43, 27 April 2016 (UTC)

In that case per MOS:PHARM we should include information about the drug class in the lede. Sizeofint (talk) 22:10, 27 April 2016 (UTC)

Doesn't seem to be a consensus because no one seems interested in compromise. Seppi333 (Insert 2¢) 21:26, 27 April 2016 (UTC)

Do we need another RFC? Sizeofint (talk) 22:01, 27 April 2016 (UTC)

That's really up to CFCF and Doc James. Adding the drug class and chirality statements to the lead really just boil down to MOS compliance, although I personally think these are important statements to mention regardless. Even so, I'm willing to explore another option for a chemistry-related statement and drug class. Seppi333 (Insert 2¢) 00:21, 28 April 2016 (UTC)

Sure lets have another RfC. Most biologically active molecules exist in at least two forms. It has little specific importance and therefore is undue weight in the lead. Doc James (talk · contribs · email) 17:50, 28 April 2016 (UTC)

Ecstacy or MDMA

These terms mean more or less the same thing? Not sure why both are listed more than half a dozen times [2]? Doc James (talk · contribs · email) 22:24, 2 May 2016 (UTC)

#Section "Long-term" Seppi333 (Insert 2¢) 22:25, 2 May 2016 (UTC)

Thanks replied in that section. Doc James (talk · contribs · email) 22:31, 2 May 2016 (UTC)

Section "Long-term"

The section MDMA#Long-term is written very badly. It consistently uses term "MDMA" instead of right term "ecstasy" for most human studies of damage. Problem of attribution of damage discovered on ecstasy users to MDMA is widely recognized in the literature on the subject. It should be checked against the sources and corrected. --Melirius (talk) 16:18, 21 April 2016 (UTC)

I found one that warranted change. Any others? The ones with reference quotes seem fine. Sizeofint (talk) 02:43, 22 April 2016 (UTC)

If you take Carvalho paper, it appears that he uses much more careful language for MDMA, see p. 1193. Further, «MDMA also produces persistent cognitive impairments in human users.» — Parrot uses Ecstasy/MDMA, Meyer uses MDMA/ecstasy. Another problem is «In addition, long-term exposure to MDMA in humans has been shown to produce marked neurotoxicity in serotonergic axon terminals.» — if you take review of Meyer, or even better specialized reviews [3], [4], you will find much more careful statements. --Melirius (talk) 15:45, 22 April 2016 (UTC)

And I think it should be mentioned that these proven impairments in cognitive functions are small enough to be clinically insignificant and—possibly—that they are not specific to ecstasy, but other recreational drugs also produce similar results, including alcohol. Refs:

• Rogers G., Elston J., Garside R., Roome C., Taylor R., Younger P., Zawada A., Somerville M. The harmful health effects of recreational ecstasy: a systematic review of observational evidence // Health technology assessment (Winchester, England). — 2009. — Vol. 13, no. 6. — P. iii—iv, ix-xii, 1-315. — ISSN 2046-4924. — DOI:10.3310/hta13050. — PMID 19195429.
• Advisory Council on the Misuse of Drugs. MDMA (‘ecstasy’): A review of its harms and classification under the Misuse of Drugs Act 1971. — Home Office of UK, 2009.
• Cole J. C. MDMA and the "ecstasy paradigm" // Journal of psychoactive drugs. — 2014. — Vol. 46, no. 1. — P. 44—56. — DOI:10.1080/02791072.2014.878148. — PMID 24830185.

Something like this. --Melirius (talk) 16:00, 22 April 2016 (UTC)

Another problem here: «Evidence in animals and humans has shown that, at high doses, MDMA induces a neuroimmune response which, through several mechanisms, increases the permeability of the blood-brain barrier, thereby making the brain more susceptible to environmental toxins and pathogens.» In the first source there is no human studies at all. Second source need clarification. --Melirius (talk) 16:18, 22 April 2016 (UTC)

• Changing "MDMA" to "MDMA or ecstasy" when refs use the term "Ecstasy/MDMA" seems fine, although it's fairly redundant since ecstasy exposure is correlated with MDMA exposure. Ecstasy adulterants and polydrug use with MDMA are not necessarily neurotoxic or neuroprotective. Feel free to make this change where appropriate though.
• MDMA also produces persistent cognitive impairments in human users. is just a generalized topic sentence for the paragraph on cognitive deficits; the subsequent sentences in that paragraph are more specific.
• In addition, long-term exposure to MDMA in humans has been shown to produce marked neurotoxicity in serotonergic axon terminals. I've added the regions where this phenomenon has been observed in humans and included the review () you listed that wasn't cited in the article.
• Evidence in animals and humans has shown that, at high doses, MDMA induces a neuroimmune response which, through several mechanisms, increases the permeability of the blood-brain barrier, thereby making the brain more susceptible to environmental toxins and pathogens. The human BBB and BCSF barrier both exhibit increased permeability as a result of protracted (e.g., 1+ hours) and excessive core/brain hyperthermia, which is a symptom of MDMA overdose; hyperthermia-induced BBB permeability is not unique to MDMA ([5]). It might be worth mentioning this at some point, but for now I've simply cut the struckout text in this quote.
• I've also cut some outdated/primary-sourced content from the section. Seppi333 (Insert 2¢) 21:36, 23 April 2016 (UTC)

Using both is unnecessary IMO as we say they more or less mean the same in the first sentence. I have no strong feeling on which is used. Doc James (talk · contribs · email) 22:30, 2 May 2016 (UTC)

I think we should normally use MDMA and explicitly mention adulteration is the author intends to discuss only adulterated MDMA. Sizeofint (talk) 22:42, 2 May 2016 (UTC)

Agree with User:Sizeofint. We should use the term that is the name of this article. If people wish to use ecstasy instead we should move the article first. Doc James (talk · contribs · email) 15:44, 3 May 2016 (UTC)

References

Lead desired effects, MDMA and meth but..., and, Did Parrott warn of neurotoxicity in psychotherapy use?

• Aren't happiness and pleasure the same? OED defines happy: feeling or showing pleasure; and, pleasure: a feeling of happy satisfaction. Isn't listing either one or the other appropriate in the lead?

• Re McElrath and sex, scratch her own research but simply look at her review of the literature. She says, "Most of this research suggests that feelings of sensuality, openness, and collective empathy take precedence over sexual pursuits." This part qualifies as a secondary source. I will find others. But that statement grasps the sex effect better than papers that just provide a list. There's a phenomenological aspect to this drug that gets lost in reducing effects to symptoms, so to speak.

I'll find secondary sources. "Empathy" is a compressed word for the effects. The empathy isn't just outward but inward. That's the intimacy, introspection and insight; the utility in psychotherapy. This evades reductionist thinking and isn't important in material written for ER doctors. I will find secondary sources to better describe the 'flavor' of this drug.

Lookit, when MDMA was made a C-I drug, it halted research of medical (psych) use and benefits. Meanwhile NIDA funded and facilitated research toward toxicity and against use; rewarded those who presented what was desired. There were/are no govt funds going to current psychotherapy research. A bias already exists. The desired effects described come from recreational use. Imagine if this were the case with other drugs with medical utility.

• "It is structurally similar to methamphetamine, but it has more in common with the pharmacological effects of amphetamine and hallucinogens." What is the significance of this statement? It isn't explained in the article. It isn't supported in the cited refs. Generally, the effects of methamphetamine and amphetamine are the same. MDMA is a milder stimulant than either. And a number of amphetamines have hallucinogenic effects. Wouldn't it be more apt to say "MDMA is structurally similar to methamphetamine, but has milder psychostimulant effects" and possibly add, "and produces mild psychedelic effects as well." or similar?

• Lastly, in research: "A review ... emphasized that MDMA is not a safe medical treatment due to lasting neurotoxic and cognition impairing effects in humans." That not what Parrott said. Unless I missed something, he attributed lasting neurotoxic/cognitive effects to regular use. Rather he warned of possible adverse psychological effects or a desire to use the drug again, in limited administration in psychotherapy. — Box73 (talk) 11:13, 4 May 2016 (UTC) (emphasis + added) — Box73 (talk) 19:49, 4 May 2016 (UTC)

Per the first one agree and trimmed one. Doc James (talk · contribs · email) 14:56, 4 May 2016 (UTC)

I agree that McElrath's paper is a secondary source for the statement it was supporting. It's somewhat on the old side, although I doubt reasons for use would have changed substantially in ten years. I deleted the sentence on similarity since it misstates the source and what the source does actually say about similarity is extremely vague. I've altered the statement in the research section to more accurately reflect the conclusions of the source. Sizeofint (talk) 22:32, 4 May 2016 (UTC)

Sense of time

Ref says "producing an energizing effect, as well as distortions in time and perception and enhanced enjoyment from tactile experiences"

This was summarized as "altered sense of time". Not sure the issue? Doc James (talk · contribs · email) 16:10, 4 May 2016 (UTC)

Do people use MDMA because they want to achieve an "altered sense of time"? "Desired effects", in the lead, alludes to common reasons people do this drug. Why isn't temporal distortions mentioned routinely in other secondary sources? (It exists the NIDA presentation, last.) The energizing effect and tactile delight are much more important, much more central to users. List those in the lead and move temporal distortions into the body. — Box73 (talk) 19:17, 4 May 2016 (UTC) (added NIDA comment) — Box73 (talk) 19:26, 4 May 2016 (UTC)

Yes, per this doesn't seem to have enough weight in the literature to justify inclusion in the lead. Most reviews I have read don't list this as a significant reason for MDMA use. Sizeofint (talk) 23:13, 4 May 2016 (UTC)

I guess the question is how does one break down effects versus desired effects. Might be simpler to concentrate on effects. Doc James (talk · contribs · email) 07:17, 5 May 2016 (UTC)

limited use in therapy

In §Uses, Medical: "Previously, it saw limited use in therapy." This is a well written, concise sentence, if you know what it means, possibly misleading if you don't.

1. Does therapy mean massage therapy, hydrotherapy, chemotherapy? (MDMA apoptosis may provide a new chemotherapy.) Also medical therapy is sometimes distinguished from psychotherapy. It needs to say psychotherapy.
2. Does limited use mean limited indications or limited number of practitioners? It needs to say that it was used by a limited number of psychotherapists (~4000, i.e., several thousand, see below).
3. "Previously" and "limited use" tend to be misleading because it can infer that MDMA was tried, found generally ineffective ("limited use") and rejected ("previously"). Rather MDMA wasn't Rx, wasn't FDA approved or Pharma promoted; it was used/spread informally by psych practitioners, and use ended not by lack of utility but by the DEA reacting to tragic recreational use.

The following sentence is less eloquent but also less vague and misleading: Before it became illegal, several thousand practitioners employed it in psychotherapy. Or similar.

Mithoefer et.al. say, "...in the late 1970s and early 1980s, before MDMA became an illegal Schedule 1 compound, it was used in conjunction with psychotherapy by an estimated 4000 psychiatrists and psychologists." in "Novel psychopharmacological therapies for psychiatric disorders: psilocybin and MDMA." (secondary source, full text available free with registration at The Lancet.) — Box73 (talk) 00:27, 6 May 2016 (UTC)

I have no problem with this proposed wording. Sizeofint (talk) 02:15, 6 May 2016 (UTC)

We should say massage therapy. lol. Seppi333 (Insert 2¢) 05:01, 7 May 2016 (UTC)

RFC: Chirality and drug class in lead

There has been an unresolved discussion about what content to include in the second paragraph of the lead (see above). The content of discussion is highlighted below:

Adverse effects of MDMA use include addiction, memory problems, paranoia, difficulty sleeping, teeth grinding, blurred vision, sweating, and a rapid heartbeat. Use may also lead to depression and fatigue. Deaths have been reported due to increased body temperature and dehydration. MDMA increases the release and slows the reuptake of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain — and has stimulant and psychedelic effects. The initial increase is followed by a short-term decrease in the neurotransmitters. MDMA belongs to the substituted methylenedioxyphenethylamine and substituted amphetamine drug classes. It is structurally similar to methamphetamine, but it has more in common with the pharmacological effects of amphetamine and hallucinogens. MDMA has two forms that are mirror images of each other which have different effects and metabolisms.

Seppi333 and I support the inclusion of this content. As Seppi333 argues above, WP:MEDMOS and WP:PHARMMOS both ask for information about the drug class in the lead. We believe the information about chirality is a noteworthy feature that should be included in the lead per MOS:CHEM/Chemicals and that it is important to tell the reader that MDMA refers to two different molecules, (R)-MDMA and (S)-MDMA. Seppi333 also argues that without conforming to these style manuals this article fail any FA-nomination (progress toward which should ideally be the goal of editors of this article).

Doc James and CFCF believe this content is not important enough to the general reader to warrant inclusion in the lead (WP:UNDUE for the lead). You can read their arguments in the section above.

Should the proposed content, part of the proposed content, a modified form of the proposed content, or none of the proposed content be included in the lead? Sizeofint (talk) 23:15, 29 April 2016 (UTC)

Support

• Support per above Sizeofint (talk) 23:15, 29 April 2016 (UTC)
• Support per above. Seppi333 (Insert 2¢) 23:11, 29 April 2016 (UTC)
• Support per above and this is not Simple English Wikipedia. --I am One of Many (talk) 23:36, 29 April 2016 (UTC)

Simple English Wikipedia should be treated as if it did not exist, it has no readership. Carl Fredik 💌 📧 11:57, 30 April 2016 (UTC)

• Support per the above. The article on methamphetamine mentions the enantiomers and chemical classes of the subject in a similar fashion. ~ Erick Shepherd • (Talk) • 01:53, 30 April 2016 (UTC)
• Support including drug class. The 4 paragraph lead has extensive detail on what it does (effects) and social aspects (history, legality), but next to nothing on what it is. Drug class provides context on what it is. Not sure about including enantiomers; most biologically active compounds have enantiomers that differ in activity. Plantdrew (talk) 15:36, 30 April 2016 (UTC)
• Support including drug class, per Wikipedia:Manual of Style/Chemistry/Chemicals #Introductory paragraph. --RexxS (talk) 13:38, 2 May 2016 (UTC)
• Support per above Sizeofint, and at least the image could show it. -Christian75 (talk) 15:38, 12 May 2016 (UTC)
• Support including drug classes, but I don't see the relevance of the chirality note in lede. -DePiep (talk) 18:17, 30 May 2016 (UTC)

Oppose

• oppose while i can see why one would support (chemically),... in this case it is not due...IMO--Ozzie10aaaa (talk) 00:04, 30 April 2016 (UTC)
• Oppose Many medications exist in two forms / enantiomer. It is not really special. Belongs best in the body of the text and not the lead. Doc James (talk · contribs · email) 07:26, 30 April 2016 (UTC)
• Oppose agree that it is not due. There's a lot of great info in this article. If you were to summarize it all in a few paragraphs at the top, I don't think the enantiomers would merit mention.Ajpolino (talk) 07:33, 30 April 2016 (UTC)
• Oppose Pigeonholing statements into the lede with realistically very little bearing on anything whatsoever is pointless. It is not due, nor is it relevant for pretty much any purpose beyond synthesis - which should not belong in the lede. There are cases where enantionmers are important enough to merit lede-placement, such as; thalidomide or escitalopram - but for the most part it is unnecessary bloat. As for the drug class, the wording above is unnecessarily detailed. Carl Fredik 💌 📧 11:05, 30 April 2016 (UTC)
• Oppose inclusion of enantiomers in lead of this article. Per Wikipedia:Manual of Style/Chemistry/Chemicals #Introductory paragraph, I don't see anything that makes chirality a "noteworthy feature" in this case. Are there other chemical properties or features that might be worthy of mention? --RexxS (talk) 13:44, 2 May 2016 (UTC)
• Oppose I'm not sure this is even really a question of style - it is just one of relavance: unless there is some point related to stereochemistry to be made subsequently, the statement is true but does not actually provide a reader with any more useful information than can be gleaned from the structure - I'd argue that the image showing both enantiomers is also unnecessary really. --The chemistds (talk)

Discussion

For those opposed to the inclusion of drug class information, why should we ignore MEDMOS and PHARMMOS in this case? Do we need to modify the manuals of style? Sizeofint (talk) 01:52, 30 April 2016 (UTC)

Which wording supports the inclusion of the enantiomer? I am fine with the drug class but were is it mentioned the other stuff needs to be included in the lead? Doc James (talk · contribs · email) 07:28, 30 April 2016 (UTC)

That portion is not required by a MOS. CHEMMOS can be read to support including the enantiomer information as a "noteworthy feature", though it does not require it. I'm more of the view that the enantiomer information should be included because the reader needs to should be aware MDMA is two different molecules with different effects. Also, our GA and FA articles on amphetamines (Methamphetamine and Amphetamine) all do this in the lead. Sizeofint (talk) 07:50, 30 April 2016 (UTC)

Many meds and drugs are two different molecules. If they were both notable individually, like omeprazole and esoomeprazole, than yes maybe. Doc James (talk · contribs · email) 15:17, 30 April 2016 (UTC)

Sizeofint, why does the reader "need" to be aware that MDMA is chiral? It has seemingly no bearing on anything an average reader would do, or that there ever are any standard methods to separate out the enantiomers? Do you have any source showing any non-trivial differences (as in beyond a t½ which is slightly different, minor differences in receptor-affinity etc.)? Carl Fredik 💌 📧 15:24, 30 April 2016 (UTC)

Non-cathinone substituted amphetamines are stereoselective agonists at hTAAR1, which reflects their enantiomeric potency in vivo - PMID 22037049. Seppi333 (Insert 2¢) 15:34, 30 April 2016 (UTC)

My view is less about the chances of encountering non-racemic MDMA and more about an understanding of what MDMA is. At the fundamental molecular level, MDMA is two structurally different molecules. Does it make a practical difference to the average person? No. Is it essential to scientifically understanding MDMA? I believe so. It's difference between pure science and applied science. I think our differences on this matter come from fundamental differences in what information we value and we believe readers value. Sizeofint (talk) 22:58, 30 April 2016 (UTC)

PMID 22037049 is a primary study in primates and is not cited in this article. The article doesn't discuss the stereochemistry of MDMA, because it's no different from the chemistry of most enantiomers as far as I can see. Without substance in the body, it doesn't belong in the lead. The pharmaceutical properties of MDMA's enantiomers are indeed discussed, but that is an argument for compliance with Wikipedia:WikiProject Pharmacology/Style guide (a project-specific guideline) and Wikipedia:Manual of Style/Medicine-related articles (the project-wide guideline). I'm a long way from being convinced that even Wikipedia:Manual of Style/Chemistry/Chemicals #Introductory paragraph supports the inclusion of a discussion of chirality, because I can see no evidence that it is a "noteworthy feature" of MDMA. It makes sense to summarise the key points of MDMA #Physical and chemical properties in the lead, of course, but what's in that section that's worth calling a "key point". The insolubility of the free base? the solubility of the hydrochloride salt? the principal means of synthesis? - those are what the article covers. In short, without something substantial in the body of the article describing a feature, it is very difficult to make a case for including it in the lead. --RexxS (talk) 14:22, 2 May 2016 (UTC)

PMID 22037049 repeatedly mentions hTAAR1, hence why I said hTAAR1. hTAAR1 is the human TAAR1 receptor, not the rhesus monkey TAAR1 receptor nor the TAAR1 receptor for any other mammal. The fact that this is a primary source doesn't really matter because the statement I made isn't a medical claim, it's a molecular neurobiology statement. It also covers both (S)- and (R)-MDMA. Seppi333 (Insert 2¢) 10:53, 7 May 2016 (UTC)

References