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5,6-Dihydroxytryptamine

Clinical data
Other names	5,6-DHT
Identifiers
IUPAC name 3-(2-aminoethyl)-1H-indole-5,6-diol
CAS Number	5090-36-8
PubChem CID	21163
ChemSpider	19902
UNII	W2QY253O8S
ChEMBL	ChEMBL303916
CompTox Dashboard (EPA)	DTXSID40198930
ECHA InfoCard	100.023.464
Chemical and physical data
Formula	C10H12N2O2
Molar mass	192.218 g·mol
3D model (JSmol)	Interactive image
SMILES C1=C2C(=CC(=C1O)O)NC=C2CCN
InChI InChI=1S/C10H12N2O2/c11-2-1-6-5-12-8-4-10(14)9(13)3-7(6)8/h3-5,12-14H,1-2,11H2 Key:SKOKLDQYOKPCPU-UHFFFAOYSA-N

5,6-Dihydroxytryptamine (5,6-DHT) is a monoaminergic neurotoxin and tryptamine derivative related to serotonin (5-hydroxytryptamine) and 5,7-dihydroxytryptamine (5,7-DHT). It is a relatively selective serotonergic neurotoxin, but also acts as a dopaminergic and noradrenergic neurotoxin at higher doses. In addition, it produces widespread generalized toxicity at higher doses. Its selective serotonergic neurotoxicity is due to its high affinity for the serotonin transporter (SERT). Because of its SERT affinity, 5,6-DHT has activity as a serotonin reuptake inhibitor.

The compound can be used in scientific research to lesion the brain serotonergic system in animals. It has a number of limitations and disadvantages relative to 5,7-DHT however, which have made 5,7-DHT a more preferred serotonergic neurotoxin in scientific research. Administration of 5,6-DHT (and 5,7-DHT) to animals causes dramatic behavioral changes.

5,6-DHT was first described in the scientific literature by 1971.

References

1. ^ Paterak J, Stefański R (2022). "5,6- and 5,7-Dihydroxytryptamines as Serotoninergic Neurotoxins". Handbook of Neurotoxicity. Cham: Springer International Publishing. pp. 691–717. doi:10.1007/978-3-031-15080-7_76. ISBN 978-3-031-15079-1.
2. ^ Kostrzewa RM (2022). "Survey of Selective Monoaminergic Neurotoxins Targeting Dopaminergic, Noradrenergic, and Serotoninergic Neurons". Handbook of Neurotoxicity. Cham: Springer International Publishing. pp. 159–198. doi:10.1007/978-3-031-15080-7_53. ISBN 978-3-031-15079-1.
3. ^ Baumgarten HG, Lachenmayer L (2004). "Serotonin neurotoxins--past and present". Neurotoxicity Research. 6 (7–8): 589–614. doi:10.1007/BF03033455. PMID 15639791.
4. Baumgarten HG, Björklund A, Lachenmayer L, Nobin A, Stenevi U (1971). "Long-lasting selective depletion of brain serotonin by 5,6-dihydroxytryptamine". Acta Physiologica Scandinavica. Supplementum. 373: 1–15. PMID 5291907.

• Hydroxyarenes
• Monoaminergic neurotoxins
• Serotonin reuptake inhibitors
• Tryptamines
• Diols