5,6-Dihydroxytryptamine Explained

Cas Number:	5090-36-8
Pubchem:	21163
Chemspiderid:	19902
Unii:	W2QY253O8S
Chembl:	303916
Synonyms:	5,6-DHT
Iupac Name:	3-(2-aminoethyl)-1H-indole-5,6-diol
C:	10
H:	12
N:	2
O:	2
Smiles:	C1=C2C(=CC(=C1O)O)NC=C2CCN
Stdinchi:	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
Stdinchikey:	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. 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.^[4]

Notes and References

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