Alpha-Methylserotonin

α-Methylserotonin

α-Methyl-5-HT
Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal 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 Number	304-52-9 Y
PubChem CID	2107
IUPHAR/BPS	152
ChemSpider	2023 Y
ChEBI	CHEBI:48295 Y
ChEMBL	CHEMBL275854 Y
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.242 g/mol
3D model (Jmol)	Interactive image
SMILES c2cc(O)cc1c2ncc1CC(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 Y Key:LYPCGXKCQDYTFV-UHFFFAOYSA-N Y

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.

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.