alpha-methylserotonin alpha-methylserotonin 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. α-methylserotoninclinical dataroutes ofadministrationoralatc codenonelegal statuslegal status uncontrolled (but may be covered under the federal analogue act in the united states and under similar bills in other countries) identifiers iupac name 3-(2-aminopropyl)-1h-indol-5-ol cas number304-52-9 ypubchem cid2107iuphar/bps152chemspider2023 yunii5y83tbc5nmchebichebi:48295 ychemblchembl275854 ycomptox dashboard (epa)dtxsid10657549 chemical and physical dataformulac11h14n2omolar mass190.246 g·mol−13d model (jsmol)interactive image smiles c2cc(o)cc1c2cc1cc(n)c inchi inchi=1s/c11h14n2o/c1-7(12)4-8-6-13-11-3-2-9(14)5-10(8)11/h2-3,5-7,13-14h,4,12h2,1h3 ykey:lypcgxkcqdytfv-uhfffaoysa-n y (verify) 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. 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. 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. 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. the o-methylated analogue of αms, 5-meo-αmt, also readily enters the brain and could be used for this purpose as well. legal status united states 5-hydroxy-alpha-methyltryptamine is not scheduled at the federal level in the united states, 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. florida 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.