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α-Methyltryptamine

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α-Methyltryptamine
Clinical data
Trade namesIndopan; Indopane
Other namesalpha-Methyltryptamine; αMT; α-ET; AMT; IT-290; IT-403 ((+)-αMT); NSC-97069; PAL-17;[1] Ro 3-0926; U-14,164E; U-14,164-E; 3-(2-Aminopropyl)indole; 3-IT; α-Methyl-3-indoleethanamine; Metryptamine; Amtryptamine
Routes of
administration		Oral, insufflation, rectal, smoked, IM, IV[2]
Drug classEntactogen; Stimulant; Psychedelic; Hallucinogen; Monoamine releasing agent; Serotonin receptor agonist; Monoamine oxidase inhibitor
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of action3–4 hours[4]
Duration of action12–24 hours[4]
Identifiers
  • 1-(1H-Indol-3-yl)propan-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.522 Edit this at Wikidata
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
  • NC(CC1=CNC2=C1C=CC=C2)C
  • InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3 checkY
  • Key:QSQQQURBVYWZKJ-UHFFFAOYSA-N checkY
  (verify)

α-Methyltryptamine (αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine family.[5][6] It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.[4][7][8]

Side effects of αMT include agitation, restlessness, confusion, lethargy, pupil dilation, jaw clenching, and rapid heart rate, among others.[4][9] αMT acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a serotonin receptor agonist, and as a weak monoamine oxidase inhibitor.[1] αMT is a substituted tryptamine and is closely related to α-ethyltryptamine (αET) and other α-alkylated tryptamines.[1][5]

αMT appears to have first been described by at least 1929.[10][11] It started being more studied in the late 1950s and was briefly used as an antidepressant in the Soviet Union in the 1960s.[4][12][9][13][14] The drug started being used recreationally in the 1960s, with use increasing in the 1990s, and cases of death have been reported.[4][13][9][12] αMT is a controlled substance in various countries, including the United States.[13][4]

Medical uses

[edit]

Under the brand name Indopan or Indopane, αMT at doses of 5 to 10 mg was used for an antidepressant effect.[medical citation needed]

Effects

[edit]

With 20 to 30 mg, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours.[15] A dose exceeding 40 mg is generally considered strong. In rare cases or extreme doses, the duration of effects might exceed 24 hours. Users report that αMT in freebase form is smoked, with doses between and 2 and 5 mg.[2][unreliable source?][5]

Side effects

[edit]

Neurologic side effects of αMT include agitation, restlessness, confusion, and lethargy.[4][9] Physical manifestations including vomiting, mydriasis (pupillary dilation), jaw clenching, tachycardia, salivation, diaphoresis (sweating), and elevations in blood pressure, temperature, and respiratory rate.[4][9]

Side effects self-reported by recreational users include anxiety, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, as well as psychedelic effects including visual hallucinations and an altered state of mind.[5][16]

αMT is capable of causing life-threatening side effects including hyperthermia, hypertension, and tachycardia.[9][17] Fatalities have been reported in association with high doses or concomitant use of other drugs.[18] Fatalities verified with toxicology and autopsy include those of a 22-year-old man in Miami-Dade county and a British teenager, both of whom died after consuming 1 g of αMT.[19][9]

Pharmacology

[edit]

Pharmacodynamics

[edit]

αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine,[20] and as a non-selective serotonin receptor agonist.[21]

Activities of αMT and related compounds
Compound Monoamine release (EC50Tooltip half-maximal effective concentration, nM) 5-HT2A receptor agonism
Serotonin Dopamine Norepinephrine EC50Tooltip half-maximal effective concentration (nM) Emax (%)
Tryptamine 33 164 716 7.4 104
Serotonin 44 >10,000 >10,000 ND ND
N,N-DMT 114 >10,000 4,166 38 83
αMT 22–68 79–112 79–180 23 103
αET 23 232 640 (EmaxTooltip maximal efficacy = 78%) >10,000 21
5-MeO-αMT 460 8,900 1,500 2.0–8.4 ND
MDMA 57 376 77 ND ND
Notes: The smaller the value, the more strongly the compound produces the effect. Refs: [22][1][23][24][25]

Monoamine oxidase inhibition

[edit]

αMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro[26] and in-vivo.[27] In rats, the potency of αMT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses.[note 1] Dextroamphetamine did not enhance the 5-hydroxytryptophan-induced rise of serotonin at any level.[28] The IC50Tooltip half-maximal inhibitory concentration of αMT for inhibition of MAO-A has been found to be 380 nM.[29] This is similar to that of agents like para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA).[30]

Serotonergic neurotoxicity

[edit]

A close analogue of αMT, α-ethyltryptamine (αET), is known to be a serotonergic neurotoxin similarly to MDMA and para-chloroamphetamine (PCA).[31][22][32]

Pharmacokinetics

[edit]

2-Oxo-αMT, 6-hydroxy-αMT, 7-hydroxy-αMT, and 1′-hydroxy-αMT were detected as metabolites of αMT in male Wistar rats.[4][33][34]

Chemistry

[edit]

αMT is a synthetic substituted tryptamine with a methyl substituent at the alpha carbon.[1][9] This alpha substitution makes it a relatively poor substrate for monoamine oxidase A, thereby prolonging αMT's half-life, allowing it to reach the brain and enter the central nervous system. Its chemical relation to tryptamine is analogous to that of amphetamine to phenethylamine, amphetamine being α-methylphenethylamine.[9] αMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action.

Many analogues of αMT are known, including α-ethyltryptamine (αET), 4-methyl-αMT, 5-chloro-αMT (PAL-542), 5-fluoro-αMT (PAL-544), 5-fluoro-αET (PAL-545), 5-methoxy-αMT (5-MeO-αMT), α,N-dimethyltryptamine (α,N-DMT; N-methyl-αMT), α,N,N-trimethyltryptamine (α,N,N-TMT; N-dimethyl-αMT), α-methylserotonin (α-methyl-5-HT; 5-hydroxy-αMT), and indolylpropylaminopentane (IPAP; α,N-dipropyltryptamine or α,N-DPT), among others.[1][5]

α-Methyltryptophan, a prodrug of α-methylserotonin, also metabolizes into αMT, but only in small amounts.[35][36][37]

Synthesis

[edit]

The synthesis of αMT can be accomplished through several different routes, the two most widely known being the nitroaldol condensation between indole-3-carboxaldehyde and nitroethane under ammonium acetate catalysis which produces 1-(3-indolyl)-2-nitropropene-1, the product can subsequently be reduced using a reducing agent like lithium aluminum hydride[38] The alternative synthesis is the condensation between indole-3-acetone and hydroxylamine.[citation needed], followed by reduction of the obtained ketoxime with lithium aluminum hydride.[5]

History

[edit]

αMT has been said to have been first synthesized in 1947, alongside α-ethyltryptamine (αET).[12][22][39] However, other sources suggest that αMT was first described in the scientific literature by at least 1929.[10][11] It was specifically described as an antagonist of ergotamine at this time.[10][11]

αMT started to be more intensively studied, along with αET, in the late 1950s and early 1960s.[12][40][41][42][28][43][44][45][46][47] It was researched by Upjohn (code name U-14,164E) and Sandoz (code name IT-290) as a possible pharmaceutical drug and was simultaneously marketed in the Soviet Union as an antidepressant under the brand name Indopan or Indopane in the 1960s.[13][14][9][48] However, the drug was used clinically for only a short period of time before being withdrawn.[14]

αMT started being used as a recreational drug in the 1960s[9] and use as a designer drug increased in the 1990s.[13] It became a controlled substance in the United States in 2003.[13]

Society and culture

[edit]

Names

[edit]

αMT never received a formal generic name.[49] In the scientific literature, it has been referred to as α-methyltryptamine or alpha-methyltryptamine (abbreviated as α-MT, αMT, or AMT).[13][14] αMT has also been referred to by developmental code names including IT-290 (Sandoz),[50] NSC-97069,[12] PAL-17,[1] Ro 3-0926,[51][52] and U-14,164E (Upjohn).[53][54][12][9] In the Soviet Union, the drug was merely referred to by its brand name Indopan or Indopane.[55][9] Other synonyms of αMT include 3-(2-aminopropyl)indole and 3-IT.[12] (+)-αMT has been referred to by the code name IT-403.[12][9]

Legality

[edit]

Australia

[edit]

The 5-methoxy analogue, 5-MeO-αMT is schedule 9 in Australia and αMT would be controlled as an analogue of this.[56]

Austria

[edit]

αMT is placed under Austrian law (NPSG) Group 6.[57]

Canada

[edit]

Canada has no mention of αMT in the Controlled Drugs and Substances Act.[58]

China

[edit]

As of October 2015 αMT is a controlled substance in China.[59]

Denmark

[edit]

In Denmark (2010), the Danish Minister for the Interior and Health placed αMT to their lists of controlled substances (List B).[57]

Finland

[edit]

AMT, alfa-methyltryptamine, is a controlled drug in Finland.[60]

Germany

[edit]

αMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.[57]

Hungary

[edit]

αMT was controlled on the Schedule C list in Hungary in 2013.[57]

Lithuania

[edit]

In Lithuania (2012), αMT is controlled as a tryptamine derivative put under control in the 1st list of Narcotic Drugs and Psychotropic Substances which use is prohibited for medical purposes.[57]

Slovakia

[edit]

αMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia.[57]

Slovenia

[edit]

αMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).[57]

Spain

[edit]

αMT is legal in Spain.[61]

Sweden

[edit]

Sveriges riksdags health ministry Statens folkhälsoinstitut classified αMT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as alfa-metyltryptamin (AMT), making it illegal to sell or possess.[62]

United Kingdom

[edit]

αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT.[63] This was following the events of 10 June 2014 when the Advisory Council on the Misuse of Drugs recommended that αMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.[64]

United States

[edit]

The Drug Enforcement Administration (DEA) placed αMT temporarily in schedule I of the Controlled Substances Act (CSA) on April 4, 2003, pursuant to the temporary scheduling provisions of the CSA (68 FR16427). On September 29, 2004, αMT was permanently controlled as a schedule I substance under the CSA (69FR 58050).[65]

Research

[edit]

Besides depression, αMT has been studied in people with schizophrenia and other conditions.[1]

See also

[edit]

Notes

[edit]
  1. ^ MAOI potency was comparable at 7 μM/kg, equivalent to 1.5 mg/kg of Harmaline and 1.2 mg/kg of αMT. At 70 μM/kg αMT was a much less effective MAOI than harmaline.[28]

References

[edit]
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