Α-Methylisotryptamine
Monoaminergic drug
From Wikipedia, the free encyclopedia
α-Methylisotryptamine (isoAMT or α-Me-isoT) is a synthetic compound belonging to the isotryptamine family, known for its psychoactive properties. As a structural analogue of α-methyltryptamine (αMT), isoAMT exhibits entactogenic and psychedelic effects.
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| Other names | isoAMT; iso-αMT; α-Me-isoT; PAL-569; 1-α-Methyltryptamine; 1-(2-Aminopropyl)indole; 1-API; 1-IT; α-Methyl-isotryptamine |
| Drug class | Serotonin–norepinephrine releasing agent; Serotonin receptor agonist |
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| Formula | C11H14N2 |
| Molar mass | 174.247 g·mol−1 |
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Pharmacology
α-Methylisotryptamine is a monoamine releasing agent and serotonin receptor agonist of the isotryptamine group.[1][2][3][4] It is the isotryptamine homologue of α-methyltryptamine (αMT), which is a more well-known serotonergic psychedelic, entactogen, and stimulant of the tryptamine family with similar pharmacological actions.[4][5][6]
Like αMT, α-methylisotryptamine is a monoamine releasing agent.[1][2] As the (–)-enantiomer, it specifically acts as a preferential serotonin and norepinephrine releasing agent (SNRA), with EC50 values of 177 nM for serotonin release, 81 nM for norepinephrine release, and 1,062 nM for dopamine release.[1][2] In contrast to amphetamine and similar agents acting as potent and selective dopamine and norepinephrine releasing agents, (–)-α-methylisotryptamine showed no misuse potential in animal studies, including no cocaine-like effects in drug discrimination tests and no facilitation of intracranial self-stimulation (ICSS).[1][2] In addition to its monoamine release, α-methylisotryptamine shows affinity for serotonin 5-HT2 receptors.[3]
Analogs
A derivative of α-methylisotryptamine, zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-N,N-dimethyl-isoAMT), is a non-hallucinogenic serotonin 5-HT2A receptor agonist and is being developed for potential medical use in the treatment depression and other neuropsychiatric disorders.[7][8][9][10][11] Other derivatives of α-methylisotryptamine have also been developed, such as the selective serotonin 5-HT2C receptor agonists (S)-5,6-difluoro-isoAMT and Ro60-0175 ((S)-5-fluoro-6-chloro-isoAMT), among others.[12][13][14][15][16]