5,6-Dihydroxytryptamine

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]

Other names5,6-DHT

CAS Number

• 5090-36-8

PubChem CID

• 21163

ChemSpider

• 19902

Quick facts Clinical data, Other names ...

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−1
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

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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]