5,7-Dihydroxytryptamine

5,7-Dihydroxytryptamine (5,7-DHT) is a purported neurotoxin[1][2] used in scientific research to decrease concentrations of serotonin in the brain. The mechanism behind this effect is not well understood, but it is speculated to selectively destroy serotonergic neurons, in a manner similar to the dopaminergic neurotoxicity of 6-hydroxydopamine (6-OHDA). What is known is that this compound is in fact not selective in depleting serotonin content, but also depletes norepinephrine. To selectively deplete serotonin stores, it is commonly administered in conjunction with desmethylimipramine (desipramine),[3] which inhibits the norepinephrine transporter.

5,7-Dihydroxytryptamine
Names
Preferred IUPAC name
3-(2-Aminoethyl)-1H-indole-5,7-diol
Other names
5,7-Dihydroxytryptamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.045.977
EC Number
  • 250-591-6
UNII
  • InChI=1S/C10H12N2O2/c11-2-1-6-5-12-10-8(6)3-7(13)4-9(10)14/h3-5,12-14H,1-2,11H2 checkY
    Key: LXWHQTNFZDTKBH-UHFFFAOYSA-N checkY
  • InChI=1/C10H12N2O2/c11-2-1-6-5-12-10-8(6)3-7(13)4-9(10)14/h3-5,12-14H,1-2,11H2
    Key: LXWHQTNFZDTKBH-UHFFFAOYAC
  • Oc1cc2c(c(O)c1)[nH]cc2CCN
Properties
C10H12N2O2
Molar mass 192.214 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

References
  1. Cairncross, KD; Cox, B; Forster, C; Wren, A (1977). "The ability of local injection of 6-OHDA, 5,6-DHT and 5,7-DHT into the olfactory bulbs to mimic the effects of bilateral bulbectomy in the rat proceedings". British Journal of Pharmacology. 61 (1): 145P–146P. doi:10.1111/j.1476-5381.1977.tb09748.x. PMC 1667625. PMID 912193.
  2. Liu, J; Chu, YX; Zhang, QJ; Wang, S; Feng, J; Li, Q (2007). "5,7-dihydroxytryptamine lesion of the dorsal raphe nucleus alters neuronal activity of the subthalamic nucleus in normal and 6-hydroxydopamine-lesioned rats". Brain Research. 1149: 216–22. doi:10.1016/j.brainres.2007.02.052. PMID 17376410. S2CID 46596561.
  3. Martin-Iverson, M.T., Leclere, J.F. and Fibiger, H.C., Cholinergic-dopaminergic interactions and the mechanisms of action of antidepressants, European Journal of Pharmacology, 94 (1983) 193–201.




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