View source for Alpha-Methyltryptamine

{{DISPLAYTITLE:''alpha''-Methyltryptamine}}
{{Drugbox
| drug_name = α-Methyltryptamine
| IUPAC_name = 2-(1''H''-indol-3-yl)-1-methyl-ethylamine
| image = AMT.svg
| image2 = Alpha-Methyltryptamine-3d-sticks.png
| width = 150px
| ChemSpiderID = 8930
| InChI = 1/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3
| InChIKey = QSQQQURBVYWZKJ-UHFFFAOYAU
| CAS_number = 299-26-3
| ATC_prefix = none
| ATC_suffix = 
| PubChem = 9287
| DrugBank = DB01446
| C = 11 | H = 14 | N = 2
| molecular_weight = 174.24 g/mol
| smiles = c1cccc2c1c(cn2)CC(N)C
| synonyms = Indopan; IT-290, IT-403, U-14,164E, 3-IT<ref name="urlErowid AMT Vault : FAQ by Dialtonez">{{cite web | url = http://www.erowid.org/chemicals/amt/amt_faq1.shtml | title = Erowid AMT Vault : FAQ by Dialtonez | format = | work = | accessdate = }}</ref>
| bioavailability = 
| metabolism = 
| elimination_half-life = 
| excretion = 
| pregnancy_category = 
| legal_AU = Schedule 8
| legal_CA = Uncontrolled
| legal_UK = Uncontrolled
| legal_US = Schedule I
| legal_status =
| routes_of_administration = [[Oral]], [[Insufflation]], [[Rectal]], [[Smoking|Smoked]], [[Intramuscular|IM]], [[Intravenous|IV]]<ref name="urlErowid AMT Vault : FAQ by Dialtonez"/>
}}

'''α-Methyltryptamine''' ('''αMT'''), also known as '''metryptamine''', is a [[psychedelic drug|psychedelic]], [[stimulant]], and [[entactogen]] [[drug]] of the [[tryptamine]] class.<ref name="urlErowid Online Books : TIHKAL - #48 a-MT">{{cite web | url = http://www.erowid.org/library/books_online/tihkal/tihkal48.shtml | title = Erowid Online Books : "TIHKAL" - #48 a-MT | format = | work = | accessdate = }}</ref><ref name="urlErowid AMT (alpha-methyltryptamine) Vault">{{cite web | url = http://www.erowid.org/chemicals/amt/amt.shtml | title = Erowid AMT (alpha-methyltryptamine) Vault | format = | work = | accessdate = }}</ref>

== History ==

Originally believed to act merely as [[monoamine oxidase inhibitor]]s, αMT and its close [[chemical structure|structural]] [[chemical analogue|analogue]] [[alpha-ethyltryptamine|α-ethyltryptamine]] (αET) were first used as [[antidepressant]]s in the 1960s under the trade names '''Indopan''' and '''Monase''', respectively.<ref name="urlErowid Online Books : TIHKAL - #48 a-MT"/> However, within a short amount of time both drugs fell out of clinical use due to [[toxicity]] and abuse concerns. αMT was also lightly used as a [[street drug]] for its psychedelic effects during this time period.

In the 1990s αMT resurfaced as a drug of recreational use via easy access through the internet, leading to its placement along with [[5-MeO-DiPT]] as [[List of Schedule I drugs (US)|schedule I]] [[controlled substance]]s in the [[Controlled Substances Act]] of the United States on April 4, 2003. αMT is still legal in most of the world and has continued to be encountered as a drug of [[drug abuse|abuse]].

== Chemistry ==

αMT is [[tryptamine]] with a [[methyl]] [[substituent]] at the [[alpha carbon]]. Its chemical relation to tryptamine is analogous to that of [[amphetamine]] to [[phenethylamine]], amphetamine being α-methylphenethylamine. αMT is closely related to the [[neurotransmitter]] [[serotonin]] (5-hydroxytryptamine) which partially explains its [[mechanism of action]].

== Pharmacology ==

αMT acts as relatively balanced [[releasing agent]] of [[serotonin]], [[norepinephrine]], and [[dopamine]],<ref name="pmid17223101">{{cite journal | author = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = European Journal of Pharmacology | volume = 559 | issue = 2-3 | pages = 132–7 | year = 2007 | month = March | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 | url = http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(06)01381-1}}</ref> and as a non-[[binding selectivity|selective]] [[serotonin receptor]] [[agonist]].<ref name="pmid18057721">{{cite journal | author = Nonaka R, Nagai F, Ogata A, Satoh K | title = In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes | journal = Biological & Pharmaceutical Bulletin | volume = 30 | issue = 12 | pages = 2328–33 | year = 2007 | month = December | pmid = 18057721 | doi = | url = http://joi.jlc.jst.go.jp/JST.JSTAGE/bpb/30.2328?from=PubMed}}</ref> It also acts as a very weak, non-selective and [[reversible reaction|reversible]] [[enzyme inhibitor|inhibitor]] of the [[enzyme]] [[monoamine oxidase]] (MAO), but this is unlikely to be very significant if at all with typical doses.{{Citation needed|date=April 2010}}

Like many other [[serotonin releasing agent]]s such [[MDMA]] ("Ecstasy"), αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity,<ref name="pmid1722753">{{cite journal | author = Huang XM, Johnson MP, Nichols DE | title = Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase) | journal = European Journal of Pharmacology | volume = 200 | issue = 1 | pages = 187–90 | year = 1991 | month = July | pmid = 1722753 | doi = | url = }}</ref> and the same likely holds true for αMT as well, though no studies have been performed to verify this as of yet. However, based on anecdotal reports, both αMT and αET appear to produce considerably less of a hangover in comparison to MDMA, although this is not necessarily an indication of long-term safety.<ref name="urlThe Big and Dandy AMT Thread (Archived)">{{cite web | url = http://www.bluelight.ru/vb/showthread.php?t=270474 | title = The Big and Dandy AMT Thread (Archived) | format = Web}}</ref><ref name="urlThe Big and Dandy AMT Thread - New incarnation">{{cite web | url = http://www.bluelight.ru/vb/showthread.php?t=344033 | title = The Big and Dandy AMT Thread - New incarnation | format = Web}}</ref>

== Dose & Effects ==

αMT was used as an antidepressant at doses of 5–10&nbsp;mg. At these levels it improves [[Mood (psychology)|mood]] and produces [[stimulant|stimulation]]. With 20–30&nbsp;mg, [[euphoria]], [[empathy]], and [[psychedelic]] effects become apparent and can last as long as 12 hours. 60–80&nbsp;mg is generally considered a strong dose, and may last for 24 hours or more. αMT in [[freebase (chemistry)|freebase]] [[drug form|form]] can be [[smoked]], and 5–20&nbsp;mg is typically used.<ref name="urlErowid Online Books : TIHKAL - #48 a-MT"/><ref name="urlErowid AMT Vault : FAQ by Dialtonez"/>

== Side effects ==

αMT can produce [[side effect]]s including [[anxiety]], [[restlessness]], [[muscle tension]], [[trisma|jaw tightness]], [[pupil dilation]], [[tachycardia]], [[headache]]s, [[nausea]], and [[vomiting]], among others.<ref name="urlErowid Online Books : TIHKAL - #48 a-MT"/><ref name="urlErowid AMT Vault : Effects">{{cite web | url = http://www.erowid.org/chemicals/amt/amt_effects.shtml | title = Erowid AMT Vault : Effects | format = | work = | accessdate = }}</ref>

== Overdose ==

In [[overdose]], αMT may cause [[serotonin syndrome]], [[hypertensive crisis]], and/or acute [[psychosis]], of which can potentially result in death.

== Legality ==

αMT is a [[List of Schedule I drugs (US)|schedule I]] [[controlled substance]] in the United States. It is legal in the United Kingdom, however, and does not fall under the tryptamine clause as its [[substituent]] is not on the [[nitrogen]] position. See "2001 Misuse of Drugs Act: Schedule 1, Regulation 3" for more information. αMT is reported to be a [[Standard_for_the_Uniform_Scheduling_of_Drugs_and_Poisons#Schedule_8_Controlled_Drug_.28Possession_without_authority_illegal.29|schedule 8]] controlled drug in [[Australia]], though this is uncomfirmed.<ref name="urlErowid AMT (alpha-methyltryptamine) Vault">{{cite web | url = http://www.erowid.org/chemicals/amt/amt.shtml | title = Erowid AMT (alpha-methyltryptamine) Vault | format = | work = | accessdate = }}</ref> It is known that [[5-MeO-αMT]] is [[Standard_for_the_Uniform_Scheduling_of_Drugs_and_Poisons#Schedule_9_Prohibited_Substance|schedule 9]] in Australia however.<ref name="urlErowid 5-MeO-AMT Vault : Legal Status">{{cite web | url = http://www.erowid.org/chemicals/5meo_amt/5meo_amt_law.shtml | title = Erowid 5-MeO-AMT Vault : Legal Status | format = | work = | accessdate = }}</ref>

== Deaths ==

There have been at least two reported deaths due to αMT use. The first was a 21 year old in [[Alabama]],<ref>[http://www.wtvynews4.com/news/headlines/208701.html Bay County Death]</ref> and the second a 22 year old [[FIU]] student in [[Miami]].<ref>[http://www.nbc6.net/news/2112709/detail.html FIU Student's February Death Linked To AMT - Local News Story - WTVJ | Miami]</ref> There are reports of a third death, but there is currently no verifiable media information.<ref>[http://www.erowid.org/chemicals/amt/amt_death1.shtml Erowid AMT Vault : AMT Reported Deaths]</ref>

== See also ==
<div style="-moz-column-count:2; column-count:2; -webkit-column-count:2;">
* [[4-Methyl-AMT|4-Methyl-αMT]]
* [[5-Fluoro-AMT|5-Fluoro-αMT]]
* [[5-MeO-AET|5-MeO-αET]]
* [[5-MeO-AMT|5-MeO-αMT]]
* [[Alpha-ethyltryptamine|α-Ethyltryptamine]]
* [[Alpha,N-DMT|α,N-DMT]]
* [[alpha-N,N-Trimethyltryptamine|α,N,N-TMT]]
* [[alpha-Methyl-5-hydroxytryptamine|α-Methyl-5-HT]]
</div>

== References ==
{{Reflist}}

== External links ==
* [[TiHKAL]] [http://www.erowid.org/library/books_online/tihkal/tihkal48.shtml entry]
* [http://tihkal.info/read.php?domain=tk&id=48 αMT Entry in TiHKAL • info]
* [http://www.erowid.org/chemicals/amt/ Erowid page on αMT]
* [http://leda.lycaeum.org/Chemicals/AMT.168.shtml Lycaeum page on αMT]

{{Entactogens}}
{{Hallucinogens}}
{{Stimulants}}
{{Adrenergics}}
{{Dopaminergics}}
{{Serotonergics}}
{{Tryptamines}}

{{DEFAULTSORT:Methyltryptamine, alpha-}}
[[Category:Entactogens and Empathogens]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Psychedelic tryptamines]]
[[Category:Stimulants]]

[[de:Alpha-Methyltryptamin]]
[[ja:Α-メチルトリプタミン]]
[[pl:Alfa-metylotryptamina]]
[[ru:Альфа-метилтриптамин]]
[[fi:Alfametyylitryptamiini]]
[[Category:2Fix]]