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.[1]
Unlike serotonin, αMS is not metabolized by monoamine oxidase on account of the α-methyl substituent blocking the enzyme's access to the amine. As a result, it has a much longer half-life in comparison.[2] [3] Similarly to serotonin however, αMS poorly crosses the blood-brain-barrier due to its free hydroxyl group, and thus has only weak or no central effects when administered peripherally.[2]
α-Methyltryptophan (αMTP) is a prodrug to αMS which does cross the blood-brain-barrier and thus efficiently delivers αMS into the central nervous system.[4] [5] As a result, αMTP acts as an orally bioavailable false or substitute neurotransmitter for serotonin, and has been suggested as a possible therapeutic agent in the treatment of disorders where serotonin is deficient.[4] [5] The O-methylated analogue of αMS, 5-MeO-αMT, also readily enters the brain and could be used for this purpose as well.[2] [6]
5-Hydroxy-alpha-methyltryptamine is not scheduled at the federal level in the United States,[7] but it could be considered an analog of alpha-methyltryptamine (AMT), in which case, purchase, sales, or possession could be prosecuted under the Federal Analog Act.
5-Hydroxy-alpha-methyltryptamine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[8]