alpha-Methyltryptamine

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α-Methyltryptamine
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150px
Systematic (IUPAC) name
2-(1H-indol-3-yl)-1-methyl-ethylamine
Clinical data
Routes of
administration		 Oral, Insufflation, Rectal, Smoked, IM, IV[1]
Legal status
Legal status
  • AU: S8 (Controlled)
  • CA: Uncontrolled
  • UK: Uncontrolled
  • US: Schedule I
Identifiers
CAS Number 299-26-3
ATC code none
PubChem CID 9287
DrugBank DB01446
ChemSpider 8930
Synonyms Indopan; IT-290, IT-403, U-14,164E, 3-IT[1]
Chemical data
Formula C11H14N2
Molar mass 174.24 g/mol[[Script error: No such module "String".]]
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α-Methyltryptamine (αMT), also known as metryptamine, is a psychedelic, stimulant, and entactogen drug of the tryptamine class.[2][3]

History

Originally believed to act merely as monoamine oxidase inhibitors, αMT and its close structural analogue α-ethyltryptamine (αET) were first used as antidepressants in the 1960s under the trade names Indopan and Monase, respectively.[2] 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 schedule I controlled substances 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 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,[4] and as a non-selective serotonin receptor agonist.[5] It also 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.[citation needed]

Like many other serotonin releasing agents such MDMA ("Ecstasy"), αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity,[6] 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.[7][8]

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, euphoria, empathy, and 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.[2][1]

Side effects

αMT can produce side effects including anxiety, restlessness, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, among others.[2][9]

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 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 schedule 8 controlled drug in Australia, though this is uncomfirmed.[3] It is known that 5-MeO-αMT is schedule 9 in Australia however.[10]

Deaths

There have been at least two reported deaths due to αMT use. The first was a 21 year old in Alabama,[11] and the second a 22 year old FIU student in Miami.[12] There are reports of a third death, but there is currently no verifiable media information.[13]

See also

References

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External links

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(and amphetamines,
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Piperazines: pFPP • TMFPP;
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine • 2,N,N-TMT • 4,N,N-TMT • 4-HO-5-MeO-DMT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-Acetoxy-DPT • 4-Acetoxy-MiPT • 4-HO-DPT • 4-HO-MET • 4-Propionyloxy-DMT • 4-Hydroxy-N-Methyl-(α,N-trimethylene)tryptamine • 5-Me-MIPT • 5-N,N-TMT • 5-AcO-DMT • 5-MeO-2,N,N-TMT • 5-MeO-4,N,N-TMT • 5-MeO-α,N,N-TMT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-EiPT • 5-MeO-MET • 5-MeO-MIPT • 5-Methoxy-N-methyl-(α,N-trimethylene)tryptamine • 7,N,N-TMT • α,N,N-TMT • α-ET • α-MT • AL-37350A • Baeocystin • Bufotenin • DALT • DBT • DET • DIPT • DMT • DPT • EiPT • Ethocin • Ethocybin • Iprocin • MET • Miprocin • MIPT • Norbaeocystin • PiPT • Psilocin • Psilocybin;
Others: AL-38022A • Ibogaine • Noribogaine • Voacangine
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Butane • Chloroform • Diethyl Ether (Ether) • Enflurane • Freon • Gasoline (Petrol) • Kerosene (Paraffin) • Propane
Others

2-Methyl-5-HT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-HO-αMT • 4-HO-DIPT • 4-HO-MET • 4-MeO-DMT • 4-Methyl-αET • 4-Methyl-αMT • 5-Benzyloxytryptamine • 5-Bromo-DMT • 5-Carboxamidotryptamine • 5-Fluoro-αMT • 5-HO-αMT • 5-HTP • 5-Fluoro-DMT • 5-Methyl-DMT • 5-Methoxytryptamine • 5-MeO-7,N,N-TMT • 5-MeO-αET  • 5-MeO-αMT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MIPT • 5,7-Dihydroxytryptamine • 7-Methyl-αET • 7-Methyl-DMT • αET • αMT • Aeruginascin • AL-37350A • BW-723C86 • Baeocystin • Bufotenidine • Bufotenin • DALT • Desformylflustrabromine • DET • DiPT • DMT • DPT • Ethocybin • EiPT • EMDT • Ethocin • FGIN-127 • FGIN-143 • Ibogaine • Iprocin • MET • MiPT • Miprocin • Melatonin • MS-245 • NAS • NMT • Norbaeocystin • Normelatonin • Oxypertine • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan • Yohimbine • Yuremamine • Zolmitriptan

de:Alpha-Methyltryptamin

ja:Α-メチルトリプタミン pl:Alfa-metylotryptamina ru:Альфа-метилтриптамин

fi:Alfametyylitryptamiini
  1. ↑ 1.0 1.1 1.2 "Erowid AMT Vault : FAQ by Dialtonez". 
  2. ↑ 2.0 2.1 2.2 2.3 "Erowid Online Books : "TIHKAL" - #48 a-MT". 
  3. ↑ 3.0 3.1 "Erowid AMT (alpha-methyltryptamine) Vault". 
  4. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  5. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  6. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  7. ↑ "The Big and Dandy AMT Thread (Archived)" (Web). 
  8. ↑ "The Big and Dandy AMT Thread - New incarnation" (Web). 
  9. ↑ "Erowid AMT Vault : Effects". 
  10. ↑ Bay County Death
  11. ↑ FIU Student's February Death Linked To AMT - Local News Story - WTVJ | Miami
  12. ↑ Erowid AMT Vault : AMT Reported Deaths
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