4-Hydroxy-5-methoxytryptamine

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

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]

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)

References

1. Horn AS, Baumgarten HG, Schlosserberger HG (July 1973). "Inhibition of the uptake of 5-hydroxytryptamine, noradrenaline and dopamine into rat brain homogenates by various hydroxylated tryptamines". Journal of Neurochemistry. 21 (1): 233–236. doi:10.1111/j.1471-4159.1973.tb04242.x. PMID   4720899.
2. Schlossberger HG (1978). "Synthesis and Chemical Properties of Some Indole Derivatives". Annals of the New York Academy of Sciences. 305 (1): 25–35. Bibcode:1978NYASA.305...25S. doi:10.1111/j.1749-6632.1978.tb31508.x. ISSN   0077-8923.