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5,6-Dihydroxytryptamine

From Wikipedia, the free encyclopedia
Serotonergic neurotoxin

Pharmaceutical compound
5,6-Dihydroxytryptamine
Clinical data
Other names5,6-DHT
Identifiers
  • 3-(2-aminoethyl)-1H-indole-5,6-diol
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.023.464Edit this at Wikidata
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 amonoaminergic neurotoxin andtryptaminederivative related toserotonin (5-hydroxytryptamine) and5,7-dihydroxytryptamine (5,7-DHT).[1][2][3] It is a relatively selectiveserotonergic neurotoxin, but also acts as adopaminergic andnoradrenergic neurotoxin at higher doses.[1][2][3] In addition, it produces widespread generalizedtoxicity at higher doses.[1] Its selective serotonergic neurotoxicity is due to its highaffinity for theserotonin transporter (SERT).[2] Because of its SERT affinity, 5,6-DHT has activity as aserotonin reuptake inhibitor.[1]

The compound can be used inscientific research tolesion thebrainserotonergic 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 thescientific literature by 1971.[1][2][3][4]

See also

[edit]

References

[edit]
  1. ^abcdefghPaterak 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. ^abcdefKostrzewa 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. ^abcdeBaumgarten 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.
Dopaminergic
Noradrenergic
Serotonergic
Unsorted
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
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