Talk:Phenethylamine

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Structural formula[edit]

Regarding the term "structural formula", although I am not a chemist it is my understanding that this is the correct term (I am still open to be corrected if you think I'm mistaken in what follows). "Chemical structure" is kind of synonymous but really refers to the structure itself rather than a 2D (or 3D) diagram of the structure. The distinction is important because a structural formula is an incomplete representation since it doesn't specify the full 3D geometry, of even which optical isomer is being referred to. I don't have any books handy but a quick web search find support for this:

http://www.cartage.org.lb/en/themes/Sciences/Chemistry/Organicchemistry/StructuralFormulas/StructuralFormulas.htm http://dl.clackamas.cc.or.us/ch106-01/strform.htm http://sci-toys.com/ingredients/how_to_read_structural_formulas.html

The entries for chemical structure and structural formula need to be clarified. --Rkundalini 07:08, 24 Apr 2004 (UTC)


Sorry, I must have been high on phenethylamine when I made this change. :)
Delta G 13:11, 24 Apr 2004 (UTC)

Chemistry[edit]

what about DOC? this list is incomplete. —Preceding unsigned comment added by 67.68.77.114 (talk) 04:41, 4 November 2008 (UTC)

"Phenethylamine (PEA) is an aromatic amine (...)": it is not, it is an aliphatic amine. —Preceding unsigned comment added by 87.5.169.213 (talk) 12:58, 2 May 2008 (UTC)

You are right, in aromatic amines the amino group is connected directly to the aromatic ring. --FK1954 (talk) 19:52, 25 September 2010 (UTC)

This is ture. DOC, or 2,5-dimethoxy-4-chloroamphetamine is missing from the table. 69.158.156.139 (talk) 15:45, 27 April 2009 (UTC)

Love drug[edit]

I have removed the claim that some "scientists" believe phenethylamine is implicated in feeling in love. As far as I know this is almost certainly false speculation that's only been promulgated because it makes for a cute story for journalists who like to pretend that scientists understand everything including the chemical formula for love ;). See e.g. the PiHKAL entry for phenethylamine [1]. If you can find some verifiable sources saying who originally made this claim and what others have said about it then put it back in the article, otherwise it should stay out IMO. --Russell E 22:10, 15 January 2006 (UTC)

Although a rocket scientist and not expert on polypeptides, I want to add to this discussion that PEA or the phenethylamines do appear to be involved in libido enhancement. So, although scientific proof may be lacking, I think it is fair to say that this is some of the most interesting scientific research going on today, and is likely to change the way we look at love and human emotional interactions. We dont have to wait for science to "prove" something to understand that these chemicals obviously are involved in our feelings, and may be the major determinator of our behavior. This is not dull and dry science indeed! 71.34.234.169 22:50, 3 February 2006 (UTC) Duane Barker
Although certain phenethylamines such as dopamine play a key role in increasing feelings of empathy and love, I don't think the "love molecule" sentence in the beginning of the article adds anything of importance to the issue (and as such, I have removed it.) Refault 08:32, 10 May 2006 (UTC)
Some mention should be added to the article, stating the claimed relationship and that it's not considered solid science, if only for the sake of the many who come to Wikipedia to look it up and don't know how Talk pages work. That way, they get *something*. 208.69.216.50 20:43, 20 March 2007 (UTC)
There is a large amount of scholarly literature pointing to phenylethylamine as one of the chemicals that are important in love. Are these all mis-citing a single source? I think someone knowledgeable should survey the literature and see if it's legit. If it's not, then we're doing a disservice to not include this material in this article. Either way, there is so much literature mentioning the relationship that even if it is false, it deserves mention in this article (along with whatever reasons why people reached false conclusions). Cazort (talk) 13:05, 24 January 2008 (UTC)

See: http://www.scq.ubc.ca/is-there-a-neurochemical-basis-for-falling-in-love/

However, no empirical data has been found to date that strongly supports the PEA theory of romantic love, and it has subsequently been suggested that different physiological mechanisms are involved in the early stages of falling in love (Marazziti and Canale, 2004).

Igottheconch (talk) 17:31, 14 May 2013 (UTC)

Etymology of the word 'Phenethylamine'[edit]

It is interesting to note that the word 'Phenethylamine' contains concatenations of the words (or rather chemicals) phenyl, ethyl and amine. I think this fact should be included into the article. Thank you. —Preceding unsigned comment added by 70.79.41.152 (talk) 23:48, 7 September 2007 (UTC)

I disagree... The etymology of a huge majority of organic compounds is made up of the different functional groups, but I don't believe it is worth mentioning for them either. In the chembox you will notice "Chemical name 2-Phenylethylamine", the wikilink describes how compounds are named, so that it need not be mentioned in every chemical article. --Mark PEA 15:15, 8 September 2007 (UTC)

Concur with the above, that's just pretty standard chemiclature. How amazing, benzoic acid contains benzene and acid! —Preceding unsigned comment added by 65.6.195.104 (talk) 16:04, 2 April 2010 (UTC)

More on Etymology[edit]

What about mentioning the fact that the word Amphetamine is composed of the following components:

[a]lpha[m]ethyl[ph]enyl[et]thyl[amine]

Following this model, Phenethylamine is a [ph][et][amine] as are all substituted Phenethylamines. As the word Amphetamine has such a stigma attached to it in our culture I'd like to see the point made that the Catecholamine neurotransmitters/hormones Adrenaline, Noradrenaline and Dopamine are also Phetamines and share many sympathomimetic attributes with Amphetamines. I just find this line of reasoning very interesting, but I don't feel qualified to edit the article text myself.

Special:Contributions/Sturu (talk) 21:51, 24 January 2008 (UTC)

Phenylethylamine used for psychoactive purposes[edit]

I have taken PEA in doses of 1 - 4 grams and it is definitely psychoactive. I can feel even 1g on an empty stomach, and cannabis and coffee seem to potentiate it strongly. It does not last long, around 20 minutes total depending on dose, but if enough is taken the effects are EXTREMELY intense and far more powerful than amphetamine. The effects are very unique, like a psycho-stimulant/enactogen but also different, and it feels extremely fast and speedy but there is almost no anxiety or jitteriness at all. There is not very much euphoria. It starts with a rush that lasts 5 minutes or so and comes on suddenly. PEA binds to sigma receptors so maybe that's what produces the unique effects. It does however feel somewhat toxic and hard on my body, like it's extremely acidic, for the duration. Also mixing MAOI-B's with PEA is very dangerous and addictive and people should not try it. 24.224.182.235 (talk) 23:18, 23 July 2011 (UTC)

PEA is metabolised before it can have a noticable effect on the CNS. Adding an Mao-b inhibitor will allow the PEA to stimulate the CNS. Personal experience indicates the effect is short lasting and noware near as stimulating as Amphetamine at normal doses, though in high doses it is much more stimulating and is comparable to cocaine/methamphetamine when high levels of Mao-b inhibiting drugs along with PEA are used. —Preceding unsigned comment added by 217.65.150.50 (talk) 12:54, 4 November 2008 (UTC)

hello, you mention that there are several reports of the use of high quantities of PEA (up to 4g) in th US. could you please give references for that? On e.g. Erowid no trip reports are listed. that would be very fine!! thank you. —Preceding unsigned comment added by 157.161.97.70 (talk) 17:04, 26 June 2008 (UTC)

Edit: I would also mention the discussion on the thread on the bluelight.ru forum: http://www.bluelight.ru/vb/showthread.php?t=383096 there it was assumed that this text (identical with the text herein) was posted probably to make propaganda only. it probably was posted there from the guy who wished to sell PEA over a web-shop. so could it be questionable to put this text here in wikipedia as it is?! better write a discussion, and that Sasha Shulgin showed no effects up to 1.6g, and about this mystery. —Preceding unsigned comment added by 157.161.97.70 (talk) 17:18, 26 June 2008 (UTC)

Occasionally people add things to this page such as that PEA is active, but as you say, it is probably people selling the product. When a reliable source is posted with a claim, then I will believe it. --Mark PEA (talk) 10:39, 27 June 2008 (UTC)

99.177.132.142 (talk) 09:12, 6 August 2008 (UTC)If you do a search on Bodybuilding.com forum there's over 30 logs on PEA reporting effects. While they could all be lying it seems abit weird. I think everyones PEA experience probably varies due to different levels of MAO-B in the brain and it seems to not work when food is taken. I'll probably try this at some point since there's no reason not to try it. M&M has some logs maybe you guys can ask them some questions?

doom3q's Log http://www.mindandmuscle.net/forum/index.php?showtopic=34528

djremix's Log http://www.mindandmuscle.net/forum/index.php?showtopic=34541

gotDOMS's Log http://www.mindandmuscle.net/forum/index.php?showtopic=34484

Sup3rman's Report http://www.mindandmuscle.net/forum/index.p...st&p=489168

BlackFlag's Log http://www.mindandmuscle.net/forum/index.php?showtopic=34431

Raymond333's Log http://www.mindandmuscle.net/forum/index.php?showtopic=34461

Necrosis's Log http://www.mindandmuscle.net/forum/index.php?showtopic=34513 99.177.132.142 (talk) 09:12, 6 August 2008 (UTC)

Wikipedia does not accept original research as reliable. The reason for this is that it can be anecdotal, and anecdotal evidence can be unreliable due to cognitive biases, especially the placebo effect --Mark PEA (talk) 14:19, 28 August 2008 (UTC)
Shulgin found no effects up to 1600 mg and 50 mg i.v.

http://www.erowid.org/library/books_online/pihkal/pihkal142.shtmlAlkaloidMan (talk) 19:27, 28 October 2010 (UTC)AlkaloidMan

Dubious[edit]

Added a dubious section as the statements made go against scientific conventional wisdom that PEA has no psychoactive effect, and this is an issue for Wikipedia as it may be targeted by those trying to improve the sales of their product, for example. --Mark PEA (talk) 18:49, 2 August 2008 (UTC)

I think it's interesting that the original post has a footnote for its claims, whereas your objections are based on "scientific conventional wisdom." At the very least if you think the claim is dubious then you should cite something saying so and not rely on "conventional wisdom" to overcome something documented. I personally think your dubious section should be removed unless you provide some documentaion of your claim.71.15.92.103 (talk) 16:10, 23 August 2008 (UTC)

The problem for me was that one of the citations doesn't even have an abstract, so is kind of useless to me as I can't read what the study says. The other problem is that though the 2 studies discuss the effects of endogenous phenethylamine, it is implied in the article that exogenous phenethylamine can have these same effects, when "conventional scientific wisdom" (which has derived from countless studies) says that PEA is rapidly metabolized by MAO present in the gut and CNS. A big problem with Phenethylamine is that many online vendors are making it out to be psychoactive to make a profit from it. I honestly cannot be bothered to keep editing out these claims. --Mark PEA (talk) 14:14, 28 August 2008 (UTC)
I tend to agree with this. If you look at the claims made at http://neuro.psychiatryonline.org/cgi/content/abstract/8/2/168 - another article with Sabelli's name on it, you'll see some rather far-reaching claims made for PEA/MAOI therapy, such as "PEA improves mood as rapidly as amphetamine but does not produce tolerance." In the absence of a much more massive study or a very involved explanation as to why PEA is so much like amphetamine, but yet magically, is not in like it at all in it's negative effects, its a whole lot more logical to conclude that the study participants must have been influenced, at least indirectly, by Sabelli's obvious enthusiasm for this compound. Even a double-blind study wouldn't do much to prevent this, as if the substance has any effect, chances are the patients involved would be able to figure out if they were in a placebo group or not. Even incorporating an active placebo would be difficult here.
Still, it is a compound worth researching, both because its endogenous and because it is totally possible that some alternative drug-delivery method (besides outright MAO suppression) could make this into a subpart of a viable therapeutic psychoactive compound someday.129.219.65.102 (talk) 19:16, 12 September 2008 (UTC)
Is this not already the case? Amphetamine is PEA with a methyl group attached to it. It seems to me that the methyl group performs the same function as the MAO-B inhibitor in MAOI/PEA therapy: it slows down the elimination of the substance. (Methamphetamine takes this one step further, by adding another methyl group, and has a correspondingly longer half-life.) René van Buuren (talk) 14:38, 10 December 2008 (UTC)
Not agreeing or disagreeing - interested only in accuracy. But in this regard, read more carefully what the intro to the article says about MAO acting on PEA (emphasis added): "However trace amounts from food are quickly metabolized by the enzyme MAO-B, preventing significant concentrations from reaching the brain." Maybe the therapeutic effects can be produced by ingesting large amounts of PEA, overwhelming MAO? Just asking. Wlegro (talk) 14:53, 2 December 2008 (UTC)
It certainly seems that way to me. I've taken up to 2.5 g of pure phenylethylamine hydrochloride powder before (dissolved in drinks); there is a strong stimulant effect from 1.5 g or so, and it gets very euphoric above 2 g, though it only lasts for about 45 minutes. I've never taken illegal stimulants, but it does feel the way I imagined amphetamines would. (Obviously this is anecdotal evidence, but I think it does answer your question.) René van Buuren (talk) 14:38, 10 December 2008 (UTC)
I can confirm this from first hand experience. The body only has a finite number of MAO-B enzymes. Flooding them with too much PEA allows considerable portions to reach the brain. 1.6 grams if you're 130 pounds to 2 grams if you're 150 pounds to 2.5 grams if you're 180 pounds seem to be the ideal levels based on numerous experiments on myself and my friends. Not sure if the relationship is linear. The effect is markedly different if taken with alcohol though. This is odd, because alcohol also increases PEA levels, but it doesn't feel anything like a PEA overdose. It actually feels quite good. In any case, the initial effects produced are nothing like amphetamine. There is a somewhat amphetamine like euphoria for about an hour afterwards, but this is only experienced if you've taken caffeine beforehand to mitigate the ridiculous wish for a nap on the comedown. —Preceding unsigned comment added by 98.118.69.202 (talk) 03:38, 15 April 2010 (UTC)
Regardless of whether or not this method would actually work (I have no idea), overwhelming your body's supply of MAO enzymes to the point of exhaustion would be extremely dangerous. This article reads way too much like an advertisement than is appropriate for Wikipedia's NPV requirement among others.71.10.74.4 (talk) 01:06, 9 January 2011 (UTC)

The need for substituents on the phenyl group seem to be a necessity for CNS activity especially at the 4-position or at minimum a tri-substitution usually involving the 2 and 4 position. Work done by Nichols et al. have provided insight with their homology model of 5-HT2A as well as biochemical assays that show a hydrogen at the 4-position greatly diminishes binding at the 5-HT2A receptor. I would then make the extrapolation that having no substitutions on the phenyl ring would pretty much reducing any binding to above micromolar concentrations which is essentially no substantial binding. Please read J. Med. Chem. 1996, 39, 2953-2961 as well as J. Comput.-Aided Mol. Des. 2002, 16, 511-520. Trimethoxy (talk) 20:39, 26 August 2008 (UTC)

I put a dubious tag on "Antidepressant drug therapy is an indirect (pharmacological) "replacement" of brain phenylethylamine." mostly because it's quite an inflammatory statement, and the study is unavailable for access.69.205.97.220 (talk) 03:50, 20 June 2009 (UTC)

http://neuro.psychiatryonline.org/cgi/content/abstract/8/2/168 I would hardly consider a trial on 14 people, with no controls or blinds, and when subjects were already taking a known antidepressant worthy enough evidence to suggest that PEA has notable psychoactive effects —Preceding unsigned comment added by 65.92.197.38 (talk) 04:24, 14 December 2010 (UTC)

I read the Sabelli/Borison/Diamond/etc. article and fixed an incorrectly quoted line about "increasing brain levels 1000-fold when taken with a MAOI and 3-4 times when taken by itself." That is simply not what the author stated. I fixed the line to what it should be (a MAOI increases concentration a 1000-fold if brain concentration were low initially and by 3-4 times if concentration was already high). —Preceding unsigned comment added by 169.229.72.74 (talk) 01:13, 8 April 2011 (UTC)


Dear Mark PEA and others: Due to my involvement in academia, I have unlimited pubmed (and others) access. I already have the two documents sitting on my hard drive. I really don't have time to look at them just now and then speculate on here about their contents. Whats the appropriate way of getting them to you? I'm rather certain it would be a violation of copyright law to upload them on my server and post a link here? How about this, you drop an email address in my talk page or wiki-mail with a little note like 'PEA Docs' so I know what its regarding, and Ill email them on over or provide an http link if you prefer? Certainly, given the limited distribution and context in which they are being used would be acceptable. Especially when one considers that most publishers will likely give limited free access to students for, or document for research if you simply ask. Furthermore, are none of you enrolled at a university? If so, chances are high that your student enrollment can benefit you free access to most pubmed documents, just ask at the library, might allow access through their website, you can even log in from home and download till your hard drive chokes. Let me know.
DrBurningBunny (talk) 13:24, 22 April 2011 (UTC)
Dear DrBurningBunny: I applaud your respect of the copyright of the documents in question, and your efforts to assist others in accessing them without violating any laws. I do find it interesting that you have the time to post on this talk page and offer to share them upon request but not to look at the documents, but without the ability to view them myself I can't know how time consuming that might be. Regardless, the statement tagged as dubious by user 69.205.97.220 ("Antidepressant drug therapy is an indirect (pharmacological) "replacement" of brain phenylethylamine.") no longer appears in the article; the dubious tags are currently only applied to the statements about the half-life of phenylethylamine and the potential increases of its brain levels by MAOIs and alcohol or THC. Are these statements not verifiable? They don't seem particularly controversial and I don't see a mention of them on this discussion page, can those dubious tags be removed? 74.72.193.118 (talk) 08:18, 9 October 2011 (UTC)

Graphical overview[edit]

Is it just me or is this all wrong? Compare, for example, methamphetamine's picture to http://en.wikipedia.org/wiki/Image:Methamphetamine-2D-skeletal-.svg --212.159.16.241 (talk) 20:11, 10 September 2008 (UTC)

No, it isn't just you... this graphic has several errors in it. You cited methamphetamine as a wrong example; amphetamine itself isn't correct!!! The amine and the terminal methyl need to be switched in many of the compounds shown. I would condone removing this graphic unless someone could point out how those structures are correct. --128.230.201.69 (talk) 03:20, 10 October 2008 (UTC)
The structures aren't wrong. They are just different ways of representing the same molecule. The connectivity remains the same in each case. In a way, they depict different conformations of the same chemical structure. -- Ed (Edgar181) 12:51, 10 October 2008 (UTC)
They are not different conformations, per se, they are just rotations around the alpha-carbon.Trimethoxy (talk) 20:31, 16 December 2008 (UTC)


Relationship to Dopamine[edit]

The introduction refers to dopamine as "this phenethylamine" (PEA), suggesting that "phenethylamines" are a class of related chemicals. However, the article on PEA seems to describe PEA as a specific chemical. I think this needs to be clarified. Attys (talk) 06:14, 7 December 2010 (UTC)

PEA refers both to the chemical in this article and a group of structurally related chemicals. This is covered in the lead of this article. Every link referring to the group should go to substituted phenethylamines, but that article may be doomed.

ButOnMethItIs (talk) 12:16, 7 December 2010 (UTC)

Phenethylamine is both an active psychotropic compound (though not potent without some sort of MAOI co-administered. As well as a class of chemicals (Phenethylamines). This should already be made clear in the early parts of the wiki. ***slow pony*** ~_~ 71.10.74.4 (talk) 14:34, 27 January 2011 (UTC)71.10.74.4 (talk) 14:37, 27 January 2011 (UTC)

Page title change request[edit]

Correct (full) substance chemical name is "phenylethylamine". Only abbreviated [or sometimes referred to] as "phenethylamine".
That's why I am requesting [editors with admin privileges] to change the page title to reflect full chemical name: "Phenylethylamine".
Thanks for listening. ;-)
MDGx 19:37, 19 April 2011 (UTC)

I concur. Just wanted to raise my hand in support of this suggestion.Kailey elise (talk) 18:14, 26 April 2011 (UTC)

solubility[edit]

Predicted Water Solubility 2.19 mg/mL [Predicted by ALOGPS] http://www.hmdb.ca/metabolites/HMDB12275 --Ryan W (talk) 07:41, 20 February 2012 (UTC)

Pronounciation[edit]

how is it pronounced? would be good to have that here. A few people i know are calling it crazy things such as "pen-ate-mine" and "pee-nth-lime"

would "fen-eth-el-ah-meen" be correct? im not sure on wikipedia's standards for pronouncing it — Preceding unsigned comment added by 46.7.101.47 (talk) 06:37, 10 April 2012 (UTC)

Suggestion for sub-topic, how phenethylamine is commercially produced[edit]

An addition to this article that I would find interesting is the process by which PEA is manufactured for commercial use.67.167.106.3 (talk) 03:10, 5 May 2012 (UTC)

Inconsistency[edit]

This article is inconsistent with intimate relationship. If this is correct, that one should be edited. 217.114.191.154 (talk) 18:36, 17 June 2012 (UTC)

Chocolate theory of love[edit]

While skeptical myself, the sources indicate phenethylamine does not reach the brain in *significant* concentrations. There is no citation indicating that phenethylamine never reaches the brain in any concentration. The phrase, "[metabolized,] preventing significant concentrations from reaching the brain, thus contributing no perceptible psychoactive effect without the use of an MAOI" is therefore contradictory. If some amount of phenethylamine present in chocolate is digested and able to reach the brain, even if not psychoactive, it is at least a plausible hypothesis for the so called "chocolate theory of love". 75.108.157.56 (talk) 14:29, 28 July 2013 (UTC)

Evidence that phenethylamine is in fact pharmacologically active[edit]

Animal studies indicate phenethylamine is pharmacologically active despite its short half life. This includes routes of administration through the stomach (intragastric, intraduodenal) as well as intravenous routes of administration. These studies indicate PEA levels increase throughout the body -- including the brain -- but with the exception of the liver. They also indicate habituation / self-administration in dogs and rats. Other pharmacological features of PEA include increased blood pressure.

See:

http://www.ncbi.nlm.nih.gov/pubmed/4075021

http://www.ncbi.nlm.nih.gov/pubmed/263551

http://www.ncbi.nlm.nih.gov/pubmed/2392508

75.108.157.56 (talk) 20:26, 28 July 2013 (UTC)

abuse and addiction[edit]

I added this section a few days ago. I see that someone has added a tag suggesting that original research was used in it. That's false, and as such I'm going to remove that tag. None of the research is original, based entirely on what I've read.

I do get the unreliable source thing. However, when it comes to abuse and addiction to obscure compounds, unfortunately there's almost nothing in the official literature. Occasionally there are case studies published on these things, but they've become less common. Since this sort of recreational drug abuse won't ever occur on any sort of widespread basis. Additionally, because this abuse and addiction is purely the result of speculation on the sorts of forums I've cited. If it weren't for these forums, information of the abuse potential of the combination wouldn't have spread of it weren't for these forums. As a result, these are the most reliable source of information on the topic. These forums are used by the government in monitoring drug trends and identifying new drugs abuse, it's logical and reasonable to reference them. The statements in these posts aren't used to draw conclusions, but only to make statements about individual expesriences- exactly what they'd be useful for were they used in a case study. — Preceding unsigned comment added by 216.105.211.130 (talk) 09:19, 21 November 2013 (UTC)

I didn't tag that section, but I agree that a forum of personal experiences is original research - it's also not a reliable source per the stricter MEDRS criteria which applies to all medicine-related articles. The types of sources which you could use to cite that paragraph would be reviews like PMID 7906896. I've read newer reviews which state the same thing you wrote, but what's currently cited isn't suitable as a source for this article. Seppi333 (talk) 19:20, 21 November 2013 (UTC)

Review content to add[edit]

PMID 24482732

Seppi333 (Insert  | Maintained) 07:19, 24 June 2014 (UTC)