Last updated
AMT 3D BS.png
Clinical data
Other namesIndopan; IT-290, IT-403, U-14,164E, 3-IT [1]
Routes of
Oral, Insufflation, Rectal, Smoked, IM, IV [1]
ATC code
  • none
Legal status
Legal status
  • 1-(1H-Indol-3-yl)propan-2-amine
CAS Number
PubChem CID
ECHA InfoCard 100.005.522 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H14N2
Molar mass 174.247 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 Yes check.svgY

α-Methyltryptamine (abbreviated as αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine class. [2] [3] It was originally developed as an antidepressant by workers at Upjohn in the 1960s, [4] and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued. [5] [6] [7]



αMT is a tryptamine with a methyl substituent at the alpha carbon. 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. αMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action.


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 and the condensation between indole-3-acetone and hydroxylamine followed by reduction of the obtained ketoxime with lithium aluminum hydride. [8]


αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine, [9] and as a non-selective serotonin receptor agonist. [10]

MAOI activity

αMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro [11] and in-vivo . [12]

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. [13]


2-Oxo-αMT, 6-hydroxy-αMT, [14] 7-hydroxy-αMT and 1′-hydroxy-αMT were detected as metabolites of αMT in male Wistar rats . [15]

Dosage and effects

Under the trade name Indopan, 5-10 milligrams were used for an antidepressant effect.[ medical citation needed ]

With 20–30 milligrams, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours. [16] 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 milligrams. [1] [ unreliable source? ] [2]

Neurologic side effects of αMT include agitation, restlessness, confusion, and lethargy. Physical manifestations including vomiting, mydriasis (pupillary dilation), jaw clenching, tachycardia, salivation, diaphoresis (sweating), and elevations in blood pressure, temperature, and respiratory rate. [17]

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. [2] [18]



The 5-Methoxy analogue, 5-MeO-αMT is schedule 9 in Australia and αMT would be controlled as an analogue of this. [19]


As of October 2015 αMT is a controlled substance in China. [20]


In Denmark (2010), the Danish Minister for the Interior and Health placed αMT to their lists of controlled substances (List B). [21]


Canada has no mention of αMT in the Controlled Drugs and Substances Act. [22]


αMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany. [21]


αMT is placed under Austrian law (NPSG) Group 6. [21]


αMT was controlled on the Schedule C list in Hungary in 2013. [21]


αMT was placed in 2013 on the List of Hazardous Substances in Annex, § 2 in Slovakia. [21]


αMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013). [21]


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. [21]


αMT is legal in Spain. [23]


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. [24]

United Kingdom

αMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT. [25] 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. [26]

United States

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). [27]


AMT, alfa-methyltryptamine is a controlled drug in Finland [28]

Reported deaths

αMT is capable of causing life-threatening side-effects including hyperthermia, hypertension, and tachycardia. [17] [29] Fatalities have been reported in association with high doses or concomitant use of other drugs. [30] Fatalities verified with toxicology and autopsy include those of a 22 year old man in Miami-Dade county and a British teenager, both who died after consuming 1 g of αMT. [31] [17]

See also


  1. MAOI potency was comparable at 7 μM/kg, equivalent to 1.5mg/kg of Harmaline and 1.2mg/kg of αMT. At 70μM/kg αMT was a much less effective MAOI than harmaline. [13]

Related Research Articles

<span class="mw-page-title-main">2C-T-2</span> Chemical compound

2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug has structural and pharmacodynamic properties similar to those of 2C-T-7.

<span class="mw-page-title-main">5-MeO-DMT</span> Chemical compound

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, The power, and Toad venom.

5-Methoxy-<i>N</i>,<i>N</i>-diisopropyltryptamine Psychedelic tryptamine

5-Methoxy-N,N-diisopropyltryptamine is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).

<span class="mw-page-title-main">5-MeO-aMT</span> Chemical compound

5-MeO-aMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin (Alpha-O) is a potent psychedelic tryptamine. It is soluble in ethanol.

<i>alpha</i>-Ethyltryptamine Chemical compound

α-Ethyltryptamine, also known as etryptamine, is a psychedelic, stimulant, and entactogenic drug of the tryptamine class. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s.

<span class="mw-page-title-main">4-HO-DiPT</span> Chemical compound

4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.

<span class="mw-page-title-main">Harmala alkaloid</span> Group of chemical compounds

Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of Peganum harmala, as well as tobacco leaves including harmine, harmaline, and harmalol, which are members of a group of substances with a similar chemical structure collectively known as harmala alkaloids. These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. The harmala alkaloid harmine, once known as telepathine and banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi and P. harmala. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are both a reversible inhibitor of monoamine oxidase A (RIMAs). They can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.

<span class="mw-page-title-main">4-HO-DET</span> Chemical compound

4-HO-DET, also known as 4-hydroxy-diethyl-tryptamine, CZ-74, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin, ethocybin, and 4-HO-DIPT.

<span class="mw-page-title-main">4-Acetoxy-DET</span> Chemical compound

4-Acetoxy-DET (4-Acetoxy-N,N-diethyltryptamine), also known as ethacetin, ethylacybin or 4-AcO-DET, is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.

<span class="mw-page-title-main">Harmaline</span> Chemical compound

Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partly hydrogenated form of harmine.

<span class="mw-page-title-main">4-HO-MiPT</span> Chemical compound

4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

<span class="mw-page-title-main">5-Fluoro-AMT</span> Chemical compound

5-Fluoro-α-methyltryptamine, also known as PAL-544, is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT). It has been found to act as a well-balanced serotonin-norepinephrine-dopamine releasing agent, a 5-HT2A receptor agonist, and a potent and specific MAO-A inhibitor. which suggests that 5-fluoro-αMT could be an active psychedelic in humans, although it is not known to have been tested in humans and could be dangerous due to its strong inhibition of MAO-A.

<i>alpha</i>-Methylserotonin Chemical compound

α-Methylserotonin (αMS), also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT) or 5-hydroxy-α-methyltryptamine (5-HO-αMT), is a tryptamine derivative closely related to the neurotransmitter serotonin (5-HT). It acts as a non-selective serotonin receptor agonist and has been used extensively in scientific research to study the function of the serotonin system.

A serotonin–norepinephrine–dopamine releasing agent (SNDRA), also known as a triple releasing agent (TRA), is a type of drug which induces the release of serotonin, norepinephrine/epinephrine, and dopamine in the brain and body. SNDRAs produce euphoriant, entactogen, and psychostimulant effects, and are almost exclusively encountered as recreational drugs.

<span class="mw-page-title-main">5-IT</span> Chemical compound

5-(2-Aminopropyl)indole is an indole and phenethylamine derivative with empathogenic effects. Its preparation was first reported by Albert Hofmann in 1962. It is a designer drug that has been openly sold as a recreational drug by online vendors since 2011.

<span class="mw-page-title-main">6-APB</span> Psychoactive drug

6-APB is an empathogenic psychoactive compound of the substituted benzofuran and substituted phenethylamine classes. 6-APB and other compounds are sometimes informally called "Benzofury" in newspaper reports. It is similar in structure to MDA, but differs in that the 3,4-methylenedioxyphenyl ring system has been replaced with a benzofuran ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB. It may appear as a tan grainy powder. While the drug never became particularly popular, it briefly entered the rave and underground clubbing scene in the UK before its sale and import were banned. It falls under the category of research chemicals, sometimes called "legal highs." Because 6-APB and other substituted benzofurans have not been explicitly outlawed in some countries, they are often technically legal, contributing to their popularity.

<span class="mw-page-title-main">Substituted tryptamine</span> Class of indoles

Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

<span class="mw-page-title-main">4-Acetoxy-MiPT</span> Chemical compound

4-AcO-MiPT is a psychedelic tryptamine. It is closely related to O-acetylpsilocin and MiPT.

<span class="mw-page-title-main">5-Chloro-αMT</span> Chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%, and almost assuredly acts as a potent agonist of other serotonin receptors as well.

<span class="mw-page-title-main">7-Chloro-AMT</span> Chemical compound

7-Chloro-α-methyltryptamine (7-Cl-AMT) is a tryptamine derivative with stimulant effects, invented in the 1960s. It is a weak monoamine oxidase inhibitor but its pharmacology has not otherwise been studied by modern techniques, though several closely related compounds are known to act as serotonin–dopamine releasing agents and agonists of the 5-HT2A receptor.


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