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 isn't well understood, but many believe (without clear substantiation) that it selectively kills serotonergic neurons, in a similar way that 6-hydroxydopamine (6-OHDA) is used to kill dopaminergic cells. 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
IUPAC name 3-(2-aminoethyl)-1H-indole-5,7-diol
Other names 5,7-Dihydroxytryptamine
Identifiers
CAS Number	31363-74-3
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL26726
ChemSpider	32913
ECHA InfoCard	100.045.977
PubChem CID	35781
UNII	Y4K1D1H82S
CompTox Dashboard (EPA)	DTXSID00185285
InChI 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 Key: LXWHQTNFZDTKBH-UHFFFAOYSA-N 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
SMILES Oc1cc2c(c(O)c1)[nH]cc2CCN
Properties
Chemical formula	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

• DSP-4
• 6-Hydroxydopamine (6-OHDA)
• para-Chlorophenylalanine (PCPA)

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.

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.