4,5-Dihydroxytryptamine

4,5-Dihydroxytryptamine

Clinical data
Other names	4,5-DHT
Drug class	Serotonergic neurotoxin
Identifiers
IUPAC name 3-(2-aminoethyl)-1H-indole-4,5-diol
CAS Number	42241-03-2
PubChem CID	179537
ChemSpider	156274
CompTox Dashboard (EPA)	DTXSID30195079
Chemical and physical data
Formula	C10H12N2O2
Molar mass	192.218 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC(=C(C2=C1NC=C2CCN)O)O
InChI InChI=1S/C10H12N2O2/c11-4-3-6-5-12-7-1-2-8(13)10(14)9(6)7/h1-2,5,12-14H,3-4,11H2 Key:HKPREGWFNPFQEA-UHFFFAOYSA-N

4,5-Dihydroxytryptamine (4,5-DHT) is a serotonergic neurotoxin of the tryptamine family. ^{[1] [2]} It is structurally related to the monoamine neurotransmitter serotonin (5-hydroxytryptamine; 5-HT). ^{[1] [2]} The drug is also a monoamine reuptake inhibitor. ^[3] Its analogue 4-hydroxy-5-methoxytryptamine (4-HO-5-MeO-T) is also a serotonergic neurotoxin. ^[3] Rapid auto-oxidation of 4,5-DHT and 4-HO-5-MeO-T prevents them from being used as serotonergic neurotoxins in scientific research. ^[4]

See also

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

References

1. Nobin A, Björklund A (June 1978). "Degenerative effects of various neurotoxic indoleamines on central monoamine neurons". Annals of the New York Academy of Sciences. 305 (1): 305–327. Bibcode:1978NYASA.305..305N. doi:10.1111/j.1749-6632.1978.tb31531.x. PMID   360938.
2. Björklund A, Nobin A, Stenevi U (December 1973). "The use of neurotoxic dihydroxytryptamines as tools for morphological studies and localized lesioning of central indolamine neurons". Zeitschrift Fur Zellforschung und Mikroskopische Anatomie. 145 (4): 479–501. doi:10.1007/BF00306720. PMID   4774982.
3. 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.
4. 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.