The Full Wiki

Alphamethyltryptamine: Wikis


Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

(Redirected to alpha-Methyltryptamine article)

From Wikipedia, the free encyclopedia

Alpha-Methyltryptamine
Systematic (IUPAC) name
2-(1H-indol-3-yl)-1-methyl-ethylamine
Identifiers
CAS number 299-26-3
ATC code none
PubChem 9287
ChemSpider 8930
Chemical data
Formula C 11H14N2  
Mol. mass 174.24 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (US)
Routes  ?

α-Methyltryptamine (αMT, AMT; IT-290; Indopan), also known as metryptamine, is a psychedelic, stimulant, and entactogen of the tryptamine chemical class.

Contents

History

Originally believed to act merely as monoamine oxidase inhibitors (MAOIs), αMT, along with its close structural analogue α-ethyltryptamine (αET), were first used as antidepressants in the 1960s under the trade names Indopan and Monase, respectively. However, within a short amount of time, both drugs fell out of clinical use due to toxicity concerns. αMT was also lightly abused as a street drug for its psychedelic effects during this time period. In the 1990s, αMT resurfaced as a drug of abuse via easy access through the internet, leading to its placement along with 5-MeO-DiPT as Schedule I controlled substances in the Controlled Substances Act of the United States on April 4, 2003.

Chemistry

αMT is tryptamine with a methyl substituent at the alpha carbon. Its chemistry is analogous to that of amphetamine to phenethylamine, amphetamine being α-methylphenethylamine. αMT is closely related to the neurotransmitter serotonin, which is 5-hydroxytryptamine, partially explaining its mechanism of action.

Pharmacology

αMT acts as relatively balanced releasing agent of serotonin, norepinephrine, and dopamine,[1] and as a non-selective serotonin receptor agonist.[2] It also acts as a very weak, non-selective and reversible inhibitor of the enzyme monoamine oxidase (MAO).

Like many other serotonin releasing agents such MDMA ("Ecstasy"), αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity,[3] and the same possibly holds true for αMT as well, though no studies have been performed on it as of yet. Though, based on anecdotal reports, both αMT and αET appear to produce considerably less of a hangover (and therefore likely less neurotoxicity) in comparison to MDMA. [4] [5]

Dose & Effects

αMT was used as an antidepressant at doses of 5-10 mg. At these levels it improves mood and produces stimulation. With 20-30 mg, psychedelic effects become apparent and can last as long as 12 hours. 60-80 mg is generally considered a strong dose, and may last for 24 hours or more. αMT in freebase form can be smoked, and 5-20 mg is typically used.

Legality

αMT is a 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.

Deaths

There have been at least two reported deaths due to αMT use. The first was a 21 year old in Alabama,[6] and the second a 22 year old FIU student in Miami.[7] There are reports of a third death, but there is currently no verifiable media information.[8]

See also

References

  1. ^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology 559 (2-3): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(06)01381-1.  
  2. ^ Nonaka R, Nagai F, Ogata A, Satoh K (December 2007). "In vitro screening of psychoactive drugs by [(35)SGTPgammaS binding in rat brain membranes"]. Biological & Pharmaceutical Bulletin 30 (12): 2328–33. PMID 18057721. http://joi.jlc.jst.go.jp/JST.JSTAGE/bpb/30.2328?from=PubMed.  
  3. ^ Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology 200 (1): 187–90. PMID 1722753.  
  4. ^ "The Big and Dandy AMT Thread (Archived)" (Web). http://www.bluelight.ru/vb/showthread.php?t=270474.  
  5. ^ "The Big and Dandy AMT Thread - New incarnation" (Web). http://www.bluelight.ru/vb/showthread.php?t=344033.  
  6. ^ Bay County Death
  7. ^ FIU Student's February Death Linked To AMT - Local News Story - WTVJ | Miami
  8. ^ Erowid AMT Vault : AMT Reported Deaths

External links








Got something to say? Make a comment.
Your name
Your email address
Message