4,5-Dihydroxytryptamine

4,5-Dihydroxytryptamine
Clinical data
Other names4,5-DHT
Drug classSerotonergic neurotoxin
Identifiers
  • 3-(2-aminoethyl)-1H-indole-4,5-diol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H12N2O2
Molar mass192.218 g·mol−1
3D model (JSmol)
  • C1=CC(=C(C2=C1NC=C2CCN)O)O
  • 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

References

  1. ^ a b 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. ^ a b 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 für Zellforschung und Mikroskopische Anatomie. 145 (4): 479–501. doi:10.1007/BF00306720. PMID 4774982.
  3. ^ a b 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.
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