Talk:Α-Methyltryptamine

Some comments about effects

The following discussion is closed. Please do not modify it. Subsequent comments should be made on the appropriate discussion page. No further edits should be made to this discussion.

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I removed a purely speculative statement, which said that AMT acts as a stimulant because of "similarities in chemical structure to amphetamine". First of all, it is not that similar; amphetamine is a phenethylamine, and AMT is a tryptamine. Second of all, this drug is an MAOI, which means that it inhibits ALL monoamines to some extent. Third, levels of serotonin (which tryptamines primarily affect) have been shown to have some control over dopamine levels. Lastly, I would just like to say that the edits to this article have unfortunately been dominated by recreational drug users, rather than anyone who knows the first thing about what these drugs do in terms of biochemistry. I'll keep an eye on this article. Fuzzform 02:33, 9 February 2007 (UTC)

So you are implying that recreational drug users can't know the first thing about biochemistry? That's a faulty assumption. I *do* get what you are saying here to an extent... but I don't think it was phrased well, as it seems a bit derogatory. Granted you made these comment years ago so who knows if you will see this response. 74.80.58.186 (talk) 12:25, 19 October 2010 (UTC)

Hi Fuzzform, I for one welcome our biochemist overlords. 8-P No, but seriously, I added a quasi-minor edit which I would like checked by someone with deeper knowledge. It used to read Like many other tryptamines, at sufficient dosages α-MT a psychedelic hallucinogen. I turned it into "α-MT acts as a psychedelic hallucinogen". The most trivial edit would have been to add "is" rather than "acts a"; yet, naively, it seems to me that a substance belongs or not to a certain class regardless of the dosage at which it shows the relevant effects. What do you think? If it should read differently, please make it so. Apwith (talk) 14:47, 14 September 2009 (UTC)

I moved this section from the top of the page. Testem (talk) 13:39, 16 October 2013 (UTC)

MAOI

AMT and Amphetamine are boths MAOIs because the methyl screws up MAO by getting in the way and taking up its time. —Preceding unsigned comment added by The Right Honourable (talk • contribs) 08:03, August 28, 2007 (UTC)

The discussion above is closed. Please do not modify it. Subsequent comments should be made on the appropriate discussion page. No further edits should be made to this discussion.

Reported Deaths

'There have been at least two reported deaths due to αMT use.' I propose this be reworded, changing 'due to αMT use' => 'where αMT may have been a contributing factor' or something? — Preceding unsigned comment added by 81.105.214.67 (talk) 18:54, 13 December 2011 (UTC)

Seems that it has since been removed, but anyway...

There is no point in referring to purported fatalities unless there's irrefutable information available to support such claims. What dosage was involved and within what environment did the event occur? If these questions cannot be answered adequately then it's trivial.

Mere Mortal (talk)

unconfirmed??

αMT is reported to be a schedule 8 controlled drug in Australia, though this is unconfirmed. What the hell is this sentence supposed to mean? It can't be too difficult to find what the law says.--90.179.235.249 (talk) 21:12, 23 June 2012 (UTC)

Metabolism

It would be appreciated if somebody could offer some insight if they have knowledge of how this drug is metabolised and how it might interact with, not only other drugs, but also every day foodstuffs, particularly such that involves the P450 system.

The article currently states the following...

It acts as a very weak, non-selective and reversible inhibitor of the enzyme monoamine oxidase (MAO), but...

this is unlikely to be very significant if at all with typical doses.

A 'typical dose' is extremely subjective unless it has been tested in appropriate conditions. I'm not going to provide for a basis of my assumptions because any source would likely be of a commercial nature (as there is little proper research to source from), and this kind of subject would do well to avoid linking to potential vendors, but I have come to assume that a moderate oral dose is given as being between 24 and 32 milligrams. This, as a matter of opinion, is actually significant when it comes to drug metabolism, particularly when the P450 system is relevant.

Given that uninformed or ill-informed persons might encounter this drug on the street, I feel it prudent to provide factual information about the dangers one might face should they consume this compound. Suggesting that the MAO activity is not concerning requires reasoning. I am more inclined to suggest that the inhibition of MAO and other enzymes is indeed significant but I can't back that up, hence my bringing the matter to the table.

This paper appears relevant. Is there a german speaker with access who could give a translation?Szara, S. (1961). "6-Hydroxylation: An important metabolic route for α-methyltryptamine". Experientia. 17 (2): 76–76. doi:10.1007/BF02171429.Testem (talk) 08:23, 7 October 2013 (UTC)

Accordingly, I have marked this section for the attention of an expert. Mere Mortal (talk) 16:27, 21 August 2012 (UTC)

I have removed the "expert attention" tag for the time being. This section needs a lot of improvement but it needn't all be delivered by an "expert", if there really is such a thing for a drug with so little contemporary study. This article is top of my list for improvement - it is entirely likely that it will still need expert attention afterwards but we will cross that bridge when we come to it. Testem (talk) 15:33, 8 October 2013 (UTC)

In addition, I would also like to discuss the possibility of this compound exhibiting anti-inflammatory and anti-bacterial properties, to such an extent that may be extremely significant within pharmacology. See this paper here.

Mere Mortal (talk) 02:17, 30 October 2012 (UTC)

Links to Forums

I appreciate that drug-related community forums can provide for some rather interesting information and vantage points, but is it really appropriate to link to them on an article such as this? When it comes to pharmacology, should relevant information be valid then it would serve best within the article itself than to be externally linked. Mere Mortal (talk) 16:57, 21 August 2012 (UTC)

Sometimes such sources are the only sources of information, especially when it comes to novel drugs. Where little is known or where forum discussion is inherently important as a source I think it does have value. Outside of these cases WP:MEDRS should be used. Testem (talk) 15:37, 8 October 2013 (UTC)

Unbalanced Article

I have marked this article as unbalanced because it is focusing too much on psychological side-effects rather than those relating to standard pharmacology. Mere Mortal (talk) 18:16, 21 August 2012 (UTC)

Note to General Practitioners

Please stop using this article as a reference point when discussing with patients their use of this substance. This article is not a valid source for NHS purposes, using it in an official capacity would be extremely unprofessional and potentially dangerous. I personally do not feel that it is appropriate for a patient's medical record to point out that "Wikipedia states aMT is a very weak MAOI", whereas it is actually quite effective at inhibiting this enzyme, and possibly others. If I could cite my own claims then I'd amend the article without hesitation, but I'm afraid that I don't have any such sources to use. Make no mistake, though, that aMT can cause severe problems with regards to metabolism, blood pressure, insulin levels and who knows what else, if mixed with the wrong drugs or foodstuffs. A hypertensive crisis is a very real possibility where aMT is used incorrectly so please maintain extreme caution, particularly if there are intentions to prescribe an SSRI, which would require a cool-off period of at least two weeks, possibly longer. Thank you.

Mere Mortal (talk) 12:29, 25 July 2013 (UTC)

Duration

The duration of freebase alphamethyltryptamine is 10-12 hours when ingested orally (even when substantial quantities are consumed). I doubt that the salt would last signifigantly longer. I strongly suspect that the 18-24 hour duration listed is actually refering to 5-meo-amt, a drug that is subjectively substantially different.

I moved this section from the top of the page. It's not clear who created it or when. Testem (talk) 13:39, 16 October 2013 (UTC)

The dosage for the hydrochloric form may be higher, but given a comparable dose the duration would likely not differ much. In any case, the duration might differ greatly between individuals.

Mere Mortal (talk) 04:50, 7 December 2013 (UTC)

Orthostatic hypotension

This condition becomes apparent as the primary effects wear off after around 36 hours, which can continue for as long as a week after cessation of long-term usage. In severe cases, this can result in fainting. Not recommended whilst using heavy machinery, driving vehicles or indeed any other activity which requires a constant safety check. Any reputable links to this subject would be greatly appreciated.

Mere Mortal (talk) 04:50, 7 December 2013 (UTC)

MAOI activity

I have marked the final paragraph of this section for clarification. I'm concerned that the wording could imply, at least to the lesser-educated, that a slightly lower dose might be perfectly fine. I agree that the danger rises exponentially at around 150mg but consuming even half of that would be a very stupid thing to do. This needs to be made clear and with appropriate citation, or the paragraph removed.

Mere Mortal (talk) 23:52, 23 October 2014 (UTC)

I'm not sure I agree. 75mg is not an uncommon or entirely unreasonable dose. I also do not think it is particularly unclear, but if you think it needs a disclaimer then perhaps "it may still be dangerous at doses below 150mg" could be added, or the dosage be genericised to "at higher doses".

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Enantiomers

I haven't found an appropriate reference but self-experiment has shown that (R)AMT is hallucinogenic while (S)AMT is purely an entactogen. If the isomers are overlayed with the ring-substituted phenethlamines & LSD itself (the 8-nitrogen overlaying the basic amine of the PEAs and indolamines you will see it is true for all). The subjective effects are further quantified in the action of 𝛂,7-dimethyl tryptamine. The (R) isomer is equipotent to (R)AMT (as 5HT2a ligand) while the (S)isomer is equipotent with (S)MDA as VMAT-2- ligand producing and SRI/DRI action. As with MDMA, the mixture has a 'magic' that is better than that of either isomer alone.

I do not know if the above information is of any scientific or legal import. The latter because the US CsA act would fail since the effect of (S)𝛂,7-dimethyl tryptamine is unlike it's 'parent' i.e. AMT so it would fail to be 'substantially similar to or more potent than <the parent controlled substance>'. — Preceding unsigned comment added by 81.99.74.135 (talk) 09:41, 31 May 2018 (UTC)

Moved from article

I have moved the following content here because it lacks context/explanation. If anyone wants to use it to improve the article, here it is. -- Ed (Edgar181) 13:07, 8 January 2019 (UTC)

Prepn:<ref>{{cite journal|last1=Snyder|first1=H. R.|last2=Katz|first2=Leon|title=The Alkylation of Aliphatic Nitro Compounds with Gramine. A New Synthesis of Derivatives of Tryptamine1,2|journal=Journal of the American Chemical Society |volume=69 |issue=12 |year=1947 |pages=3140–3142 |issn=0002-7863 |doi=10.1021/ja01204a061 }}</ref><ref>{{cite journal |last1=Ash |first1 =A. S. F.| last2=Wragg| first2=W. R.| title=790. Synthesis of the 3-2?-aminopropyl- and 3-2?-aminobutyl-derivatives of 5-hydroxyindole, and an alternative synthesis of 5-hydroxytryptamine |journal=Journal of the Chemical Society (Resumed) |year=1958 |pages=3887–3892 |issn=0368-1769 |doi=10.1039/jr9580003887 }}</ref><ref>{{cite journal|last1=Terzian |first1=A. G. |last2=Safrasbekian |first2=R. R. |last3=Sukasian |first3=R. S. |last4=Tatevosian |first4=G. T. |title=Synthesis and some pharmacological properties of alpha-methyltryptamine and its 5-methoxy derivative |journal=Experientia |date=15 November 1961 |volume=17 |issue=11 |pages=493–4 |pmid=13920395 |doi=10.1007/bf02158615 }}</ref><ref>{{cite journal|last1=Lloyd|first1=David H.|last2=Nichols|first2=David E.|title=Nickel boride/hydrazine hydrate reduction of aromatic and aliphatic nitro compounds. Synthesis of 4-(benzyloxy)indole and .alpha.-alkyltryptamines |journal=The Journal of Organic Chemistry |volume=51 |issue=22 |year=1986 |pages=4294–4295 |issn=0022-3263 |doi=10.1021/jo00372a037 }}</ref>

Cited overdoses and reasons for bans

"A British teenager died after consuming 1 g of αMT in August 2013."

So, depending on what you call an average dose, ~30-50x overdosage? At least 10x if you're aiming high on what anyone reasonably would take? So it's still safer than Tylenol... I really think these articles should quote the reasons used to ban various drugs, rather than just blank statement of laws. For example, from the US ban paper:

Emergency designation of AMT as a Schedule I controlled substance by the Drug Enforcement Administration occurred shortly after the Miami-Dade Medical Examiner reported the death of a 22-year old college student who ingested a large amount of AMT (4). Prior to death, the deceased advised his roommate that he was "taking hallucinating drugs" and as a result had "discovered the secret of the universe". The roommate reported that the deceased was shaking and sweating profusely, waving a knife, and threatening to commit suicide. The roommate tied the deceased to the bed for his own protection and left him to "sleep it off". Approximately 12 h later, the roommate discovered the deceased lying in bed unresponsive.

The moral of this story is drugs don't kill people, drugs get banned for killing people after psychopathic roommates tie people to beds and kill people. At least the roommate faced charges for all this, amirite? *crickets* --A Shortfall Of Gravitas (talk) 19:41, 2 February 2021 (UTC)

"Trymene" listed at Redirects for discussion

The redirect Trymene has been listed at redirects for discussion to determine whether its use and function meets the redirect guidelines. Readers of this page are welcome to comment on this redirect at Wikipedia:Redirects for discussion/Log/2023 September 18 § Trymene until a consensus is reached. Mdewman6 (talk) 22:25, 18 September 2023 (UTC)

Indopan/Indopane are medicines containing (S) α-methyl tryptamine.

https://pubchem.ncbi.nlm.nih.gov/#query=N%5BC%40%40H%5D(C)Cc1c%5BNH%5Dc2ccccc12

According to PubChem (a resource generally considered to be reliable), it was the (S) enantiomer of α-methyl tryptamine that was used medically. I believe that the (S) enantiomer has much higher affinity for the 5HT2a receptors but as far as I am aware, both isomers are equally active as MAOIs. So it would be logical to use the more potent isomer to reduce the chances of side-effects. 2A0A:EF40:E1C:DF01:C9E8:AC60:B426:7B34 (talk) 12:26, 12 November 2024 (UTC)