Page last updated: 2024-12-06

5,6-dihydroxytryptamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

5,6-dihydroxytryptamine (5,6-DHT) is a neurotoxin that selectively destroys serotonergic neurons. It is synthesized by reacting tryptamine with 5-hydroxytryptamine (serotonin) in the presence of a strong oxidizing agent. 5,6-DHT is a widely used research tool to investigate the role of serotonin in various physiological and pathological processes, including mood, sleep, appetite, and pain. 5,6-DHT is administered to animal models to study the effects of serotonin depletion on behavior, cognition, and neurodevelopment. 5,6-DHT can cause significant damage to serotonergic neurons, leading to a range of behavioral and physiological changes. Its use is ethically debated, with potential for neurotoxicity. The compound's importance lies in its ability to selectively deplete serotonin, enabling researchers to study the role of this neurotransmitter in various biological processes. 5,6-DHT is studied to understand the mechanisms of serotonin action, explore treatments for serotonin-related disorders, and investigate the effects of serotonin depletion on various aspects of brain function.'

5,6-Dihydroxytryptamine: Tryptamine substituted with two hydroxyl groups in positions 5 and 6. It is a neurotoxic serotonin analog that destroys serotonergic neurons preferentially and is used in neuropharmacologic research. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID21163
CHEMBL ID303916
SCHEMBL ID3807782
MeSH IDM0023255

Synonyms (24)

Synonym
einecs 225-810-3
3-(2-aminoethyl)indole-5,6-diol
3-(2-aminoethyl)-1h-indole-5,6-diol
1h-indole-5,6-diol, 3-(2-aminoethyl)-
brn 0475698
indole-5,6-diol, 3-(2-aminoethyl)-
5,6-dihydroxytryptamine
PDSP1_000539
PDSP2_000537
CHEMBL303916 ,
L000696
2-(5,6-dihydroxy-1h-indol-3-yl)-ethyl-ammonium
bdbm50012672
3-(2-amino-ethyl)-1h-indole-5,6-diol
2-(5,6-dihydroxy-1h-indol-3-yl)-ethyl-ammonium(5,6-dht)
5090-36-8
AKOS006279613
unii-w2qy253o8s
5-22-12-00350 (beilstein handbook reference)
w2qy253o8s ,
SCHEMBL3807782
DTXSID40198930
Q27292226
PD094267

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"A comparison of the acute toxicity and a histological examination of the toxic effects in mouse of 4,7-; 5,6-; 5,7- and 6,7-dihydroxytryptamines and related compounds are present."( Cardiovascular toxicity of dihydroxytryptamines.
Creveling, CR; Highman, B; Lundstrom, J, 1976
)
0.26
" The neurochemical and histological effects of PCA are very similar to those produced by a large dose of methylamphetamine (MA) in that both drugs are toxic to serotonergic nerve terminals and neuronal perikarya in the somatosensory cortex."( Endogenously produced 5,6-dihydroxytryptamine may mediate the neurotoxic effects of para-chloroamphetamine.
Axt, KJ; Commins, DL; Seiden, LS; Vosmer, G, 1987
)
0.59

Dosage Studied

ExcerptRelevanceReference
" Evidence of tolerance was indicated by the fact that when the antinociceptive response to morphine was assessed by the hot-plate and the tail-flick procedures, a shift in the dose-response curve of morphine to the right occurred after an adequate single priming dose of morphine."( Studies on tolerance development to single doses of morphine in mice.
Huidobro, F; Huidobro-Toro, JP; Leong Way, E, 1976
)
0.26
" Dose-response curves for both NE or 5-HT, determined 7 days after pretreatment with their respective neurotoxins, were shifted significantly to the left as compared to controls."( Changes in sensitivity to intrathecal norepinephrine and serotonin after 6-hydroxydopamine (6-OHDA), 5,6-dihydroxytryptamine (5,6-DHT) or repeated monoamine administration.
Howe, JR; Yaksh, TL, 1982
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Catechol O-methyltransferaseRattus norvegicus (Norway rat)Ki328.00000.00150.00660.0159AID49933
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)IC50 (µMol)6.00000.00030.81978.4900AID204380
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID147663Inhibition of [3H]- Thymidine incorporation into the DNA of differentiated neuroblastoma clone N-2a cells1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and biological evaluation of 4-fluoro-, 7-fluoro-, and 4,7-difluoro-5,6-dihydroxytryptamines.
AID147662Effect on the uptake of [3H]5-HT into differentiated N-2a cells.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and biological evaluation of 4-fluoro-, 7-fluoro-, and 4,7-difluoro-5,6-dihydroxytryptamines.
AID49933Kinetic constants for the inactivation of Catechol O-methyltransferase by the compound1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Catechol O-methyltransferase. 12. Affinity labeling the active site with the oxidation products of 5,6-dihydroxyindole.
AID49945Compound was evaluated for its ability to inactivate Catechol O-methyltransferase before dialysis1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Catechol O-methyltransferase. 12. Affinity labeling the active site with the oxidation products of 5,6-dihydroxyindole.
AID50075Evaluated for its ability to inactivate Catechol O-methyltransferase under anaerobic conditions, after 60 min at 37 degree. C1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Catechol O-methyltransferase. 12. Affinity labeling the active site with the oxidation products of 5,6-dihydroxyindole.
AID49931Kinetic constants for the inactivation of Catechol O-methyltransferase by the compound1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Catechol O-methyltransferase. 12. Affinity labeling the active site with the oxidation products of 5,6-dihydroxyindole.
AID49944Compound was evaluated for its ability to inactivate Catechol O-methyltransferase after dialysis1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Catechol O-methyltransferase. 12. Affinity labeling the active site with the oxidation products of 5,6-dihydroxyindole.
AID49946Evaluated for its ability to inactivate Catechol O-methyltransferase under aerobic conditions, after 60 min at 37 degree. C1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Catechol O-methyltransferase. 12. Affinity labeling the active site with the oxidation products of 5,6-dihydroxyindole.
AID204380Inhibitory activity against incorporation of Serotonin transporter uptake into the differentiated N-2a cells.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Molecular mechanism of action of 5,6-dihydroxytryptamine. Synthesis and biological evaluation of 4-methyl-, 7-methyl-, and 4,7-dimethyl-5,6-dihydroxytryptamines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (351)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990278 (79.20)18.7374
1990's47 (13.39)18.2507
2000's17 (4.84)29.6817
2010's8 (2.28)24.3611
2020's1 (0.28)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.15

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index8.15 (24.57)
Research Supply Index5.92 (2.92)
Research Growth Index4.07 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.15)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews12 (3.23%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other360 (96.77%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]