4-Hydroxy-5-methoxytryptamine

4-Hydroxy-5-methoxytryptamine (4-HO-5-MeO-T) is a serotonergic neurotoxin of the tryptamine family.^[1][2] It is structurally related to the monoamine neurotransmitter serotonin (5-hydroxytryptamine; 5-HT).^[2][1] The drug is also a monoamine reuptake inhibitor.^[2][1] Its analogue 4,5-dihydroxytryptamine (4,5-DHT) is also a serotonergic neurotoxin.^[2][1] Rapid auto-oxidation of 4-HO-5-MeO-T and 4,5-DHT prevents them from being used as serotonergic neurotoxins in scientific research.^[2]

4-Hydroxy-5-methoxytryptamine

Clinical data
Other names	4-HO-5-MeO-T; 5-MeO-4-HT
Drug class	Serotonergic neurotoxin
Identifiers
IUPAC name 3-(2-aminoethyl)-5-methoxy-1H-indol-4-ol
PubChem CID	84076774
ChemSpider	45633071
Chemical and physical data
Formula	C11H14N2O2
Molar mass	206.245 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=C(C2=C(C=C1)NC=C2CCN)O
InChI InChI=1S/C11H14N2O2/c1-15-9-3-2-8-10(11(9)14)7(4-5-12)6-13-8/h2-3,6,13-14H,4-5,12H2,1H3 Key:OPLJHPODCQWRFI-UHFFFAOYSA-N

See also

• 5,6-Dihydroxytryptamine (5,6-DHT)
• 5,7-Dihydroxytryptamine (5,7-DHT)
• Psilomethoxin (4-HO-5-MeO-N,N-DMT)
• 6,7-Dihydroxytryptamine (6,7-DHT)