5,6-Dihydroxytryptamine

Last updated

5,6-Dihydroxytryptamine
5,6-Dihydroxytryptamine.svg
Clinical data
Other names5,6-DHT
Identifiers
  • 3-(2-aminoethyl)-1H-indole-5,6-diol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.023.464 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H12N2O2
Molar mass 192.218 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]

See also

References

  1. 1 2 3 4 5 6 7 8 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. 1 2 3 4 5 6 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. 1 2 3 4 5 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.