ñ-Methyltryptamine (ñMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine and ñ-alkyltryptamine families. 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.
Side effects of ñMT include agitation, , confusion, lethargy, pupil dilation, jaw clenching, and rapid heart rate, among others. ñMT acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a serotonin receptor agonist, and as a weak monoamine oxidase inhibitor. ñMT is a substituted tryptamine and is closely related to ñ-ethyltryptamine (ñET) and other ñ-alkylated tryptamines.
ñMT appears to have first been described by at least 1929. It started being more studied in the late 1950s and was briefly used as an antidepressant in the Soviet Union in the 1960s. The drug started being used recreationally in the 1960s, with use increasing in the 1990s, and cases of death have been reported. ñMT is a controlled substance in various countries, including the United States.
Under the brand name Indopan or Indopane, ñMT at doses of was used for an antidepressant effect.
At a dose of , it produces euphoria, while doses above result in strong hallucinogenic effects. At doses over , the compound may cause several side effects, including anxiety, muscle tightness, vomiting, and hyperthermia. A dose exceeding is generally considered strong. In rare cases or extreme doses, the duration of effects might exceed . Users report that ñMT may be smoked, with doses between and .
A dose of of ñMT is said to be equivalent to of LSD. However, its onset of action is delayed, with effects appearing after only 3 to 4 hours, and it is longer-lasting. In addition, ñMT is described as unpleasant compared to LSD, with symptoms of nervousness, irritability, restlessness, and inability to relax.
Neurologic side effects of ñMT include agitation, , 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.
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.
ñMT is capable of causing life-threatening side effects including hyperthermia, hypertension, and tachycardia. Fatalities have been reported in association with high doses or concomitant use of other drugs.
Fatalities verified with toxicology and autopsy include those of a 22-year-old man in Miami-Dade County, Florida and a British teenager, both of whom died after consuming 1g of ñMT.
ñMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine, and as a non-selective serotonin receptor agonist. It has relatively weak psychedelic-like effects in animals compared to other psychedelic substituted tryptamines, for instance in terms of the head-twitch response in rodents.
ñMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in vitro and in vivo. In rats, the potency of ñMT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses. Dextroamphetamine did not enhance the 5-hydroxytryptophan-induced rise of serotonin at any level. The of ñMT for inhibition of MAO-A has been found to be 380nM. This is similar to that of agents like para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA).
A close analogue of ñMT, ñ-ethyltryptamine (ñET), is known to be a serotonergic neurotoxin similarly to MDMA and para-chloroamphetamine (PCA).
2-Oxo-ñMT, 6-hydroxy-ñMT, 7-hydroxy-ñMT, and 1â²-hydroxy-ñMT were detected as metabolites of ñMT in male Wistar rats.
ñMT is a synthetic substituted tryptamine with a methyl substituent at the alpha carbon. This alpha substitution makes it a relatively poor substrate for monoamine oxidase A, thereby prolonging ñMT'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 ñ-methylphenethylamine. ñMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action.
The chemical synthesis of ñMT has been described. Its synthesis can be accomplished through several different routes, there's two "common" routes mainly via the Henry reaction aka Nitroadol condensation between indole-3-carboxaldehyde and nitroethane under amine salt or ionic liquid catalysis which produces 1-(3-indolyl)-2-nitropropene-1, 1-(3-indolyl)-2-nitropropene-1 can subsequently be reduced via a reducing agent such as lithium aluminum hydride The alternative synthesis is the condensation between indole-3-acetone and hydroxylamine, followed by reduction of the obtained ketoxime with lithium aluminum hydride.
Many analogues of ñMT are known, including ñ-ethyltryptamine (ñET), ñ-propyltryptamine (ñPT), 4-methyl-ñMT, 5-chloro-ñMT (PAL-542), 5-fluoro-ñMT (PAL-544), 5-fluoro-ñET (PAL-545), 5-methoxy-ñMT (5-MeO-ñMT), ñ,N-dimethyltryptamine (ñ,N-DMT; N-methyl-ñMT), ñ,N,N-trimethyltryptamine (ñ,N,N-TMT; N-dimethyl-ñMT), ñ-methylserotonin (ñ-methyl-5-HT; 5-hydroxy-ñMT), and indolylpropylaminopentane (IPAP; ñ,N-dipropyltryptamine or ñ,N-DPT), among others. Another analogue of ñMT is the ò-keto and N-methylated derivative BK-NM-AMT.
ñ-Methyltryptophan, a prodrug of ñ-methylserotonin, also metabolizes into ñMT, but only in small amounts.
There are seven possible positional isomers of aminopropylindole (API; IT), wherein the side chain is located at different positions of the indole ring system. These positional isomers include 1-API (ñ-methylisotryptamine; isoAMT; PAL-569), 2-API, 3-API (3-IT; ñ-methyltryptamine; AMT; PAL-17), 4-API, 5-API (5-IT; 3,4-pyrrolo[b]amphetamine; PAL-571), 6-API, and 7-API. 3-API or AMT is an ñ-alkyltryptamine, 1-API or isoAMT is an isotryptamine, and 4-API, 5-API, 6-API, and 7-API are all phenethylamines and amphetamines.
The analogue of AMT without the benzene part of the indole ring is 3-pyrrolylpropylamine.
ñMT has been said to have been first synthesized in 1947, alongside ñ-ethyltryptamine (ñET). However, other sources suggest that ñMT was first described in the scientific literature by at least 1929. It was specifically described as an antagonist of ergotamine at this time.
ñMT started to be more intensively studied, along with ñET, in the late 1950s and early 1960s. 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. However, the drug was used clinically for only a short period of time before being withdrawn.
ñMT started being used as a recreational drug in the 1960s and use as a designer drug increased in the 1990s. It became a controlled substance in the United States in 2003.
ñMT never received a formal generic name. In the scientific literature, it has been referred to as ñ-methyltryptamine or alpha-methyltryptamine (abbreviated as ñ-MT, ñMT, or AMT). ñMT has also been referred to by developmental code names including IT-290 (Sandoz), NSC-97069, PAL-17, Ro 3-0926, and U-14,164E (Upjohn). In the Soviet Union, the drug was merely referred to by its brand name Indopan or Indopane. Other synonyms of ñMT include 3-(2-aminopropyl)indole and 3-IT. (+)-ñMT has been referred to by the code name IT-403.
The 5-methoxy analogue, 5-MeO-ñMT is schedule 9 in Australia and ñMT would be controlled as an analogue of this.
ñMT is placed under Austrian law (NPSG) Group 6.
AMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.
As of October 2015 ñMT is a controlled substance in China.
In Denmark (2010), the Danish Minister for the Interior and Health placed ñMT to their lists of controlled substances (List B).
AMT, alfa-methyltryptamine, is a controlled drug in Finland.
ñMT is listed under the Narcotics Act in schedule 1 (narcotics not eligible for trade and medical prescriptions) in Germany.
ñMT was controlled on the Schedule C list in Hungary in 2013.
In Lithuania (2012), ñMT 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.
ñMT was placed in 2013 on the List of Hazardous Substances in Annex, ç 2 in Slovakia.
ñMT appeared on the Decree on Classification of Illicit Drugs in Slovenia (2013).
ñMT is legal in Spain.
Sveriges riksdags health ministry classified ñMT as "health hazard" under the act (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.
ñMT was made illegal in the United Kingdom as of 7 January 2015, along with 5-MeO-DALT. This was following the events of 10 June 2014 when the Advisory Council on the Misuse of Drugs recommended that ñMT be scheduled as a class A drug by updating the blanket ban clause on tryptamines.
The Drug Enforcement Administration (DEA) placed ñMT 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, ñMT was permanently controlled as a schedule I substance under the CSA (69FR 58050).
Besides depression, ñMT has been studied in people with schizophrenia and other conditions.