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This is an old revision of this page, as edited by WikiLinuz (talk | contribs) at 17:50, 18 February 2024 (→Addressing the edit for lisdexamphetamine & CDS: edit reply to Димитрий Улянов Иванов). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

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view · edit Frequently asked questions Q1: Lisdexamfetamine is mentioned in the article along with levoamphetamine and dextroamphetamine. Is lisdexamfetamine (brand name: Vyvanse) a form of amphetamine? A1: No. At the molecular level, lisdexamfetamine has the molecular structure of amphetamine coupled with the amino acid lysine, making it chemically distinct from the amphetamine enantiomers (i.e., levoamphetamine and dextroamphetamine). Lisdexamfetamine has the chemical formula C15H25N3O; however, amphetamine, dextroamphetamine, and levoamphetamine have the formula C9H13N. Consequently, lisdexamfetamine is not an optical isomer of amphetamine like dextroamphetamine and levoamphetamine. As an inactive prodrug, it simply has no effect on the human body until enzymes metabolize it into dextroamphetamine. This is why it is covered in the article along with the enantiomers. References ^ "Identification". Lisdexamfetamine. University of Alberta. 16 September 2013. Retrieved 28 September 2014. {{cite encyclopedia}}: |work= ignored (help) "Identification". Amphetamine. University of Alberta. 8 February 2013. Retrieved 28 September 2014. {{cite encyclopedia}}: |work= ignored (help)

This article is written in American English, which has its own spelling conventions (color, defense, traveled) and some terms that are used in it may be different or absent from other varieties of English. According to the relevant style guide, this should not be changed without broad consensus.

	Amphetamine is a featured article; it (or a previous version of it) has been identified as one of the best articles produced by the Misplaced Pages community. Even so, if you can update or improve it, please do so.
	This article appeared on Misplaced Pages's Main Page as Today's featured article on April 3, 2015.
Article milestones Date Process Result October 19, 2013 Peer review Reviewed November 30, 2013 Good article nominee Listed January 22, 2014 Featured article candidate Not promoted April 21, 2014 Featured article candidate Not promoted August 1, 2014 Featured article candidate Not promoted October 8, 2014 Featured article candidate Not promoted January 14, 2015 Featured article candidate Promoted Current status: Featured article

Ideal sources for Misplaced Pages's health content are defined in the guideline Misplaced Pages:Identifying reliable sources (medicine) and are typically review articles. Here are links to possibly useful sources of information about Amphetamine. PubMed provides review articles from the past five years (limit to free review articles) The TRIP database provides clinical publications about evidence-based medicine. Other potential sources include: Centre for Reviews and Dissemination and CDC

Revisions succeeding this version of this article is substantially duplicated by a piece in an external publication. Since the external publication copied Misplaced Pages rather than the reverse, please do not flag this article as a copyright violation of the following source: Amphetamines: Potent Recreational Drug of Abuse (PDF), Journal of Addiction Research & Therapy, 21 July 2017 Additional comments At least half of this "review article" is composed of copy/pasted article text with superficial revision, tables (2 total), and diagrams (2 total) from Amphetamine and Adderall#Mechanism of action without attribution to these articles.

Section sizes Section size for Amphetamine (44 sections) Section name Byte count Section total (Top) 20,107 20,107 Uses 10 77,346 Medical 629 50,467 ADHD 19,441 19,441 Binge eating disorder 16,689 16,689 Narcolepsy 13,708 13,708 Enhancing performance 29 18,590 Cognitive performance 9,628 9,628 Physical performance 8,933 8,933 Recreational 8,279 8,279 Contraindications 4,747 4,747 Adverse effects 708 53,679 Physical 7,943 7,943 Psychological 5,237 5,237 Reinforcement disorders 31 39,791 Addiction 5,631 5,631 Biomolecular mechanisms 15,530 30,647 Pharmacological treatments 7,542 7,542 Behavioral treatments 7,575 7,575 Dependence and withdrawal 3,482 3,482 Overdose 5,375 11,376 Toxicity 4,838 4,838 Psychosis 1,163 1,163 Drug interactions 9,952 9,952 Pharmacology 18 59,617 Pharmacodynamics 18,435 35,272 Dopamine 6,279 6,279 Norepinephrine 806 806 Serotonin 1,213 1,213 Other neurotransmitters, peptides, hormones, and enzymes 8,539 8,539 Pharmacokinetics 12,392 12,392 Pharmacomicrobiomics 7,460 7,460 Related endogenous compounds 4,475 4,475 Chemistry 4,872 25,264 Substituted derivatives 2,641 2,641 Synthesis 9,875 9,875 Detection in body fluids 7,876 7,876 History, society, and culture 7,427 22,276 Legal status 6,269 6,269 Pharmaceutical products 8,580 8,580 Notes 98 98 Reference notes 49 49 References 28 28 External links 1,751 1,751 Total 286,290 286,290

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Transclusion

This article is a source for transcluded sections in Adderrall. Its a real house of cards -- reference definitions must be in certain spots, different sections are tagged with <noinclude and one article or another is often broken because of problems. Is transclusion really the best way to build these articles? -- Mikeblas (talk) 16:48, 31 May 2020 (UTC)

Selective transclusion prevents information/content on multiple pages that cover the exact same topic from diverging over time. Yes, it does make it harder for unfamiliar editors to edit the source, at least initially when they're unfamiliar with the markup (see WP:SELTRANS for a primer). In this particular case, selective transclusions from amphetamine are used to ensure that this article, dextroamphetamine, lisdexamfetamine, and Adderall uniformly cover the same information in relevant sections. Seppi333 (Insert 2¢) 04:22, 17 November 2022 (UTC)

Reference to fraction bound by plasma proteins

1. I just corrected the value for the fraction bound to 20%, according to the already linked source. Maybe they changed the value at some point. At the moment the source is DrugBank; section Protein binding: https://go.drugbank.com/drugs/DB00182#pharmacology. For said parameter the reference on DrugBank is solely this article: https://link.springer.com/article/10.2165/00003088-200443030-00002. Would it not be better if this source was mentioned in the article instead of Drugbank?

2. I also cross-checked said 20% with other publications and it's about right. So I guess there is no point in adding additional sources to prove the same number?

PENDRAGON (talk) 11:23, 13 October 2020 (UTC)

Dopamine neuron should be changed to dopaminergic neuron

On of the image titles says "Pharmacodynamics of amphetamine in a dopamine neuron" there is no such thing as a dopamine neuron, it should be changed to dopaminergic neuron. — Preceding unsigned comment added by Ihazevich (talk • contribs) 16:22, 17 February 2021 (UTC)

Semi-protected edit request on 24 December 2021

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The Safety of Stimulant Medication Use in Cardiovascular and Arrhythmia Patients - American College of Cardiology

yo, stimulants are in fact cardio protective. has anyone given careful thought to this? The heart is a muscle. Muscles become stronger the more they work, The faster the heart beats the more oxygen is delivered. Blood circulates faster. these are good things. w/out preexisting heart conditions theres no issue… do marathon runners die prematurely? … i’ve taken these medications for decades - its only Vyvanese that has brought premature aging up - the 80 years before Vyvanese no one conclusively proved stimulants shorten people’s life spans. The truth is probnly that the way Vyvanese is metabolizedin the live by whatever enzynmee is it is in the liver that activates it causes long-term live damage and when your liver is gone - its over. Lastly speaking from personal experience Real Dexedrine or Adderall make my heart beat WAY faste than Vyvanese so that simple fact tells me this is to put it politely, highly questionable and to put it bluntly, bullshit . and if you drive a car on on overdrive but give extra attention to maintainihg it it will last long - its only if you aren’t healthy or dont maintauin your car in the first place that a issuew MAY come up. and people if you don’t know for god’s sake, if your skin doesn’t look good drink more water until you’re drinking 6liters a day. I bet crackheads who drink 6 liters of water a day have great skin! 72.143.21.46 (talk) 07:39, 24 December 2021 (UTC)

 Not done: it's not clear what changes you want to be made. Please mention the specific changes in a "change X to Y" format and provide a reliable source if appropriate. Cannolis (talk) 07:43, 24 December 2021 (UTC)

Policy on chemical data

I am curious about what the policy is for including physicochemical data for pharmaceutical drugs. The box in this page gives the data for amphetamine base racemate, yet this is not a form that is available on the market, legal or illegal. There are of course many different salts and derivatives of the compound with different chemical structures and physical properties. Is it standard to give the base form of amines? How about tertiary amines, which have no stable base form and potentially different counterions? Would it make more sense to include all the common salts? Or perhaps have another page dedicated to it? Kilgore T (talk) 13:31, 26 October 2022 (UTC)

In the US, there are at least two brand names of amphetamine, EVEKEO ODT is the racemic sulfate salt, while DYANAVELXR is a 3.2 to 1 mixture of d- to l-amphetamine and is a mixed salt. I don't think it is practical to list all the avaiable salts, nor enantiomeric mixtures in the physicochemical properties section of the infobox, so I think it is appropiate to limit this section to the parent racemic free base. Tertiary amines are stable compounds that can be isolated. It is the quaternary amine which when isolated, must be complexed with a counter ion. Amphetamine is a primary amine. I would not object if someone wanted to create a seperate data sheet for the racemic sulfate, etc. Boghog (talk) 07:41, 27 October 2022 (UTC)

Semi-protected edit request on 8 April 2023

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Má huáng 1015 (talk) 22:25, 8 April 2023 (UTC)

i think it would be better if the image that shows the structure of amphetamine in 2D would be replaced with the image that Wiktionary uses the reason why i think this change should be made is the image from wiktionary shows that there are two enantiomers i do want to make it clear that i don't know a lot about chemistry unfortunately https://en.wiktionary.org/amphetamine#/media/File:Amphetamine-2D-skeletal.svg

 Not done for now: the image doesn't look line an improvement, though you're welcome to seek consensus for the alteration. M.Bitton (talk) 19:33, 9 April 2023 (UTC)

Removal of lack of neurotoxicity in humans statement due to serious misinterpretation of the sources

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Please either remove "There is no evidence that amphetamine is directly neurotoxic in humans" or change to "The neurotoxicity in humans under therapeutic doses is currently not understood" as there is no basis to sustain the current sentence using current citations.

"Amphetamine". United States National Library of Medicine – Toxicology Data Network. Hazardous Substances Data Bank. Archived from the original on 2 October 2017. Retrieved 2 October 2017. Direct toxic damage to vessels seems unlikely because of the dilution that occurs before the drug reaches the cerebral circulation.

This citation is talking about vascular toxicity in the brain, rather than neurotransmitter toxicity (neurotoxicity), thus can't sustain the above statement.

Malenka RC, Nestler EJ, Hyman SE (2009). "Chapter 15: Reinforcement and addictive disorders". In Sydor A, Brown RY (eds.). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2nd ed.). New York, USA: McGraw-Hill Medical. p. 370. ISBN 9780071481274. Unlike cocaine and amphetamine, methamphetamine is directly toxic to midbrain dopamine neurons.

This citation is a secondary source with no basis on research.

Throughout my search for alternative sources, I have not found any concrete research into neurotoxic effects in humans rather than lab animals at all. Review of the existing literature links to effects in humans being not understood

Thus I believe that the sentence as it is currently written in the article leads readers to false conclusions that it's safe to take amphetamines in therapeutic doses as there is research with no evidence, rather than that there is no research at all. Ritave (talk) 16:30, 24 April 2023 (UTC)

@Ritave: The Toxnet source does indeed talk about neurovascular damage. It's still a form neurotoxicity. The molecular neuropharmacology textbook is a graduate-level text written by three researchers who read, perform, write, and synthesize research in this field. In fact, one of them is heavily cited throughout this article. In any event, it is a WP:MEDRS-compliant source.

That being said, Amphetamine has been a pharmaceutical drug with an ongoing medical use for 80 years; in spite of the large population size of active medical amphetamine users, researchers have not identified neurotoxicity in the brains of individuals who take amphetamine pharmaceuticals at therapeutic doses and published a paper about it. You can't "prove" a negative finding with the vast majority of statistical hypothesis tests employed in statistical models; that's just not how statistical inference works. Hence, why nobody publishes papers saying "hey, we did all these brain scans and found that amphetamine is not neurotoxic". What you can say is, "we failed to detect evidence of neurotoxicity", but literally no one publishes research papers with a negative result like that because it's not a research finding (seriously, I challenge you to find one); rather, it's a lack of one. If you expect a stronger statement to be made based on more research, you'll be waiting a while because that will never happen. Seppi333 (Insert 2¢) 04:50, 7 May 2023 (UTC)

Thank you for the explanation, it helped me understand a different view.

Regarding the first citation, I'd say using data showing no dangers in a subset of a category by extending it to a whole category is misleading. Especially when the main mechanism of action of the drug is based on a nervous system rather than the vascular system.

I understand that Amphetamine was not found to be neurotoxic and I don't expect research stating negative result to exist. I tried to find one before asking for a change.

The sentence I'm asking to change is making deductions rather than inductions from the data to a general audience, creating a sense of security about a topic. That sense of security might be well based from unwritten experience of doctors over the world, but as a layman, I could not find more data outside of this single book that would either confirm or deny such statement.

Rather than strengthening the statement on more data, I'm asking to relax the statement to a more ambiguous one, more in line of the intent of "it should be safe to administer based on previous experience" rather than "it's safe to administer and here's proof of such". Ritave (talk) 20:39, 21 May 2023 (UTC)

@Seppi333: I've dug into this subject a bit (131 MEDRS refs in the last decade) and found a few interesting ones which I suggest you check out. A 2020 review states that the neurotoxicity of amphetamine increases the risk of Parkinon's severalfold after exposure, but is silent about dose. Some of the cited sources in the review apply this to therapeutic doses as well. Anything of substance in your opinion? Wretchskull (talk) 17:18, 16 July 2023 (UTC)

@Wretchskull: Really busy off-wiki right now, so I'll follow up on this by Friday. There's a lot to unpack on this topic, so I'll probably give you a more comprehensive/detailed response on the concordant and inconsistent evidence of direct neurotoxicity by amphetamine vs certain substituted amphetamines (meth & MDMA) in humans of which I am aware; I wrote/cited virtually all the pharmacology and neurotoxicity-related content in these articles, so I'm familiar with the similarities and differences between them. FWIW, that review makes a fairly weak assertion about the strength of the association with PD relative to the relationship mentioned in methamphetamine#Neurotoxic_and_neuroimmunological. Seppi333 (Insert 2¢) 06:26, 19 July 2023 (UTC)

@Wretchskull: Just read through the review you linked. I think the only thing really worth adding to an article from that paper is the involvement of α-synuclein as a mechanism of methamphetamine-induced direct neurotoxicity within the nigrostriatal pathway.

This statement - The molecular studies show that amphetamine upregulates α-syn in substantia nigra which accumulates leading to aggregation, which in turn damages neurons contributing to the Parkinson’s-like behavior . - seemed like a bombshell until I looked at the citations and realized the authors are discussing evidence involving methamphetamine; I'm not sure how the authors and peer reviewers missed this. The only evidence they actually provided about amphetamine from a research paper is that amphetamine and methamphetamine both bind to N-terminus of intrinsically unstructured α-synuclein, which induces a folded conformation; in turn, this increases the likelihood of protein misfolding and aggregation. The fact that amphetamine and methamphetamine have similar effects on body temperature and similar mechanisms for causing it would seem to suggest that amphetamine would also increase α-synuclein expression through cerebral hyperpyrexia. Taken together, it seems plausible that amphetamine neurotoxicity could increase PD risk. The relationship between methamphetamine and PD is well-established in humans, but, the evidence supporting this relationship for amphetamine is entirely based on in vitro evidence of α-synuclein protein binding and its shared mechanisms of neurotoxicity with methamphetamine. So, there's basically no evidence in humans from a retrospective study to support that claim; it's just a well-founded suspicion at this point. Seppi333 (Insert 2¢) 15:12, 20 July 2023 (UTC)

I appreciate the thorough reply! Makes a lot of sense now. By the way, I've also discovered a review stating that ADHD may be neuroprotective later in life due to the effects of stimulation-seeking behavior, and that amphetamine may strip that. Would you consider this notable in any way? Wretchskull (talk) 22:55, 20 July 2023 (UTC)

Interesting hypothesis. I don't think it's worth covering research topics that are under investigation on Misplaced Pages, though. Better to wait until there are published research findings, as it avoids misleading readers whenever results differ from expectations and precludes the need to update the information later on when findings are published. Seppi333 (Insert 2¢) 00:33, 22 July 2023 (UTC)

Seppi I have been waiting for another amphetamine infodump from you for literal YEARS. Like, holy shit. Reading the archives of this talk page and the FA reviews back in the day taught me a ridiculous amount and happened to benefit my own Dexedrine treatment plan overall. Why don't you start a blog or something? It'd be great to read your insight on a number of things in greater detail regarding this compound without it being necessarily an exercise in improving the composition of this article. I know I don't just speak for myself on this. Like, you're the man, man! 103.51.113.44 (talk) 16:09, 22 July 2023 (UTC)

Hahaha, I appreciate the sentiment. I've been a bit preoccupied with work at my company since mid-2020, so I've been much less active on Misplaced Pages for the past 3 years compared to the preceding 7-ish. For the same reason, I haven't really have much time available for other activities like blogging either. That being said, my workload recently decreased, and I'll likely be reasonably active on Misplaced Pages at least until the end of the year. Seppi333 (Insert 2¢) 06:49, 23 July 2023 (UTC)

Amine

Shouldn’t “amine”, located in the very first paragraph, be transformed into a link?

Is there a reason it hasn’t? HockeyCowboy (talk) 09:31, 28 April 2023 (UTC)

I did. Hope that’s ok. HockeyCowboy (talk) 05:54, 30 April 2023 (UTC)

Lead content

@Dexedream: I apologize for undoing what you wrote, but a lot of the content you introduced to the lead section is way too technical per MOS:INTRO. Also, the article originally had a 4-paragraph, 20-sentence lead section, which was already above average for a featured article, per MOS:LEADLENGTH. The lead looks to be about ~50% longer (24 vs 16 line breaks) on my screen with your changes relative to the original version, which pushes it well outside the guidelines.

I don't see a problem with introducing this content with citations in the body of the article, though. Seppi333 (Insert 2¢) 00:27, 22 July 2023 (UTC)

Semi-protected edit request on 11 September 2023

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Change dependance/abuse liability from "moderate" to "high" as per the cited reference (Stahl) P3nt0th41 (talk) 04:59, 11 September 2023 (UTC)

@P3nt0th41: I am able to access a copy of the source - it doesn't seem to state that the dependence liability is high. The source states:

•High abuse potential, Schedule II drug
•Patients may develop tolerance, psychological dependence

While I agree it clearly states that abuse potential is high, dependence liability is not listed in the same way. Is there some reason to interpret "may" as a high rather than moderate risk? I've closed the edit request to get it out of the queue but am completely open to discussion. Tollens (talk) 02:12, 14 September 2023 (UTC)

The text does not indicate the abuse liability is "moderate" either? That is your interpretation.

The prescribing information for amphetamine explicitly states the same fact.

The dependence liability of amphetamine is widely known with a plethora of literature supporting the fact - including any prescribing information published after 1980.

T

The fact that it's listed as moderate on the page is discrediting the veracity of the article.

Furthermore, it is baffling as to why methylphenidate is listed as "high", and yet amphetamine is listed as "moderate". Anyone with a basic understanding of psychostimulant pharmacology would be dismayed by how ridiculous this is.

I assumed this would have been obvious edit and not something that required discussion. P3nt0th41 (talk) 05:01, 14 September 2023 (UTC)

Multiple Effect Citations Needed

Why does this page list increased cognitive performance and increased muscle strength as effects? There have been no specifically conclusive, academically acceptable or even scientifically reasonable studies done to show that either of these effects occur in a significant enough portion of the general population to include them as "effects". There have, however, been studies to the contrary. 74.140.151.89 (talk) 20:43, 16 January 2024 (UTC)

Addressing the edit for lisdexamphetamine & CDS

In this edit, I included cognitive disengagement syndrome as a condition treatable by amphetamine. It was redacted here on the basis of an absent secondary source and it being lisdexamphetamine.

First, contrary to the statement, I believe I have cited a secondary source: the International Consensus Statement on CDS. It is a scientific consensus, analysis and evaluation/review of the scientific literature including the primary evidence of lisdexamphetamine as a treatment. As the WP:Secondary states: "A secondary source provides thought and reflection based on primary sources, generally at least one step removed from an event. It contains analysis, evaluation, interpretation, or synthesis of the facts, evidence, concepts, and ideas taken from primary sources".

Second, lisdexamphetamine is a valid derivative of amphetamine. As stated in the article: "currently, pharmaceutical amphetamine is prescribed as racemic amphetamine, Adderall, dextroamphetamine, or the inactive prodrug lisdexamfetamine".

Thus I fail to see the issue here. Please discuss. Thanks. Димитрий Улянов Иванов (talk) 01:25, 18 February 2024 (UTC)

WP:LEAD summarizes the body. There is no mention of cognitive disengagement syndrome in the body and it isn't prominent enough (see WP:UNDUE) to be added to the lead.I know lisdexamphetamine formulation will be converted to dexamphetamine but the sources should mention amphetamine. Besides, the very source you cited is a proposal/study asking to recognize CDS as a distinct syndrome (which means it still hasn't been recognized). This is primary source, a clinical trial. And this doesn't even mention amphetamine and still is WP:UNDUE. --WikiLinuz (talk) 04:36, 18 February 2024 (UTC)

No, it is not a proposal for it to be recognised. It’s a consensus in changing terms. They concluded: “it is evident that CDS has reached the threshold of recognition as a distinct syndrome”. While the clinical trial itself does not mention the term CDS, it is cited as part of the international consensus and refers to the same syndrome as they make plain. Димитрий Улянов Иванов (talk) 10:55, 18 February 2024 (UTC)

CDS is not recognized yet. You can come back once standardized diagnostic manuals recognize it. Your source is a study and not a prominent one either. See what WP:WEIGHT says. --WikiLinuz (talk) 17:41, 18 February 2024 (UTC)

You also didn't address the fact the neither of your sources mention "amphetamine" at all, besides them being poor sources to be used here. You cannot add UNDUE material into lead when there is no mention of it in the body. --WikiLinuz (talk) 17:49, 18 February 2024 (UTC)

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