5,6-Dihydroxytryptamine

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;
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;

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

^ ^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.
^ ^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.
^ ^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.
^ 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.

[PaterakStefański2022-1] ^ ^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.

[Kostrzewa2022-2] ^ ^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.

[BaumgartenLachenmayer2004-3] Baumgarten HG, Lachenmayer L (2004). "Serotonin neurotoxins--past and present". Neurotoxicity Research. 6 (7–8): 589–614. doi:10.1007/BF03033455. PMID 15639791.

[BaumgartenBjörklundLachenmayer1971-4] 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.

[1]

[2]

[3]

[4]