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5,6-Dihydroxytryptamine

5,6-Dihydroxytryptamine
Clinical data
Other names5,6-DHT
Identifiers
  • 3-(2-aminoethyl)-1H-indole-5,6-diol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC10H12N2O2
Molar mass192.218 g·mol−1
3D model (JSmol)
  • C1=C2C(=CC(=C1O)O)NC=C2CCN
  • 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).[1][2][3] It is a relatively selective serotonergic neurotoxin, but also acts as a dopaminergic and noradrenergic neurotoxin at higher doses.[1][2][3] In addition, it produces widespread generalized toxicity at higher doses.[1] Its selective serotonergic neurotoxicity is due to its high affinity for the serotonin transporter (SERT).[2] Because of its SERT affinity, 5,6-DHT has activity as a serotonin reuptake inhibitor.[1]

The compound can be used in scientific research to lesion the brain serotonergic system in animals.[1][2][3] 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.[3][1][2] Administration of 5,6-DHT (and 5,7-DHT) to animals causes dramatic behavioral changes.[1]

5,6-DHT was first described in the scientific literature by 1971.[1][2][3][4]

References

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  1. ^ a b c d e f g h 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. ^ a b c d e f 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. ^ a b c d e 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.