A selective serotonergic neurotoxin used in scientific research
5,6-DihydroxytryptamineClinical data |
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Other names | 5,6-DHT |
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Chemical and physical data |
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Formula | C10H12N2O2 |
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Molar mass | 192.218 g·mol−1 |
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3D model (JSmol) | |
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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.
Dopaminergic | |
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Noradrenergic | |
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Serotonergic | - 2'-Amino-MPTP
- 2,4-DCA
- 2,4,5-THA
- 2,4,5-THMA
- 3-CA
- 3,4-DCA
- 4-CAB (α-ethyl-PCA)
- 5-IAI
- 5,6-DHT
- 5,7-DHT
- α-Me-DA (3,4-DHA)
- α,N-Dimethyldopamine
- αET
- DCA
- Fenfluramine
- Haloperidol
- HPP+
- HPTP
- MBDB
- MDA (tenamfetamine)
- MDAI
- MDEA
- MDMA (midomafetamine)
- Methamphetamine
- MMAI
- Norfenfluramine
- PBA
- PCA
- PCMA
- PIA
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Unsorted | |
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See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators |
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DATTooltip Dopamine transporter (DRIsTooltip Dopamine reuptake inhibitors) | |
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NETTooltip Norepinephrine transporter (NRIsTooltip Norepinephrine reuptake inhibitors) | | | | | | | - Others: Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine)
- Antipsychotics (e.g., loxapine, ziprasidone)
- Arylcyclohexylamines (e.g., ketamine, phencyclidine)
- Dopexamine
- Ephenidine
- Ginkgo biloba
- Indeloxazine
- Nefazodone
- Opioids (e.g., desmetramadol, methadone, pethidine (meperidine), tapentadol, tramadol, levorphanol)
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SERTTooltip Serotonin transporter (SRIsTooltip Serotonin reuptake inhibitors) | | | | | - Others: A-80426
- Amoxapine
- Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine)
- Antipsychotics (e.g., loxapine, ziprasidone)
- Arylcyclohexylamines (e.g., 3-MeO-PCP, esketamine, ketamine, methoxetamine, phencyclidine)
- Cyclobenzaprine
- Delucemine
- Dextromethorphan
- Dextrorphan
- Efavirenz
- Hypidone
- Medifoxamine
- Mesembrine
- Mifepristone
- MIN-117 (WF-516)
- N-Me-5-HT
- Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine), levorphanol, tapentadol, tramadol)
- Roxindole
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VMATsTooltip Vesicular monoamine transporters | |
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Others | |
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See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins |
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Tryptamines | - 1-Methylpsilocin
- 2-HO-NMT
- 2-Me-DET
- 2-Methyl-5-HT
- 2,N,N-TMT
- 4,5-DHP-DMT
- 4-AcO-DALT
- 4-AcO-DET
- 4-AcO-DiPT
- 4-AcO-EPT
- 4-AcO-NMT
- 4-AcO-MALT
- 4-AcO-MET
- 4-AcO-DPT
- 4-AcO-MiPT
- 4-F-5-MeO-DMT
- 4-HO-5-MeO-DMT
- 4-HO-DALT
- 4-HO-DBT
- 4-HO-DET
- 4-HO-DiPT
- 4-HO-DPT
- 4-HO-DSBT
- 4-HO-EPT
- 4-HO-MALT
- 4-HO-MET
- 4-HO-McPT
- 4-HO-McPeT
- 4-HO-MiPT
- 4-HO-MPT
- 4-HO-MsBT
- 4-HO-NALT
- 4-HO-NMT
- 4-HO-PiPT
- 4-HO-pyr-T
- 4-MeO-DiPT
- 4-MeO-DMT
- 4-MeO-MiPT
- 4-PrO-DMT
- 4,5-MDO-DMT
- 4,5-MDO-DiPT
- 5-BT
- 5-Bromo-DMT
- 5-CT
- 5-Chloro-DMT
- 5-Ethoxy-DMT
- 5-Ethyl-DMT
- 5-Fluoro-DET
- 5-Fluoro-DMT
- 5-Fluoro-EPT
- 5-Fluoro-MET
- 5-HO-DiPT
- 5-HTP (oxitriptan)
- 5-MeO-2-TMT
- 5-MeO-34MPEMT
- 5-MeO-7,N,N-TMT
- 5-MeO-DALT
- 5-MeO-DBT
- 5-MeO-DET
- 5-MeO-DiPT
- 5-MeO-DMT
- 5-MeO-DPT
- 5-MeO-EiPT
- 5-MeO-EPT
- 5-MeO-MALT
- 5-MeO-MET
- 5-MeO-MiPT
- 5-MeO-NMT
- 5-MeO-pyr-T
- 5-MeO-NBpBrT
- 5-MeO-T-NBOMe
- 5-MeS-DMT
- 5-Methoxytryptamine (5-MT; mexamine)
- 5-Methyl-DMT
- 5-Methyltryptamine
- 5-MT-NB3OMe
- 5-(Nonyloxy)tryptamine
- 5,6-MeO-MiPT
- 5,6-MDO-DiPT
- 5,6-MDO-DMT
- 5,6-MDO-MiPT
- 5,6-DHT
- 5,7-DHT
- 6-Fluoro-DMT
- 7-Methyl-DMT
- Acetryptine (5-AT)
- Aeruginascin (4-PO-TMT)
- AGH-107
- AGH-192
- AH-494
- ALiPT
- Baeocystin (4-PO-NMT)
- Benzotript (4-chlorobenzoyl-L-tryptophan)
- Bufotenidine (5-HTQ)
- Bufotenin (5-HO-DMT)
- Convolutindole A
- CP-132,484
- DALT
- DBT
- Desformylflustrabromine
- DET
- DiPT
- DMT
- DPT
- E-6801
- E-6837
- EiPT
- EMDT
- EPT
- Ethocybin (4-PO-DET)
- FGIN-127
- FGIN-143
- FT-104
- HIOC
- Idalopirdine
- Indolylethylfentanyl
- Indorenate
- Iprocin (4-HO-DiPT)
- Lespedamine
- MET
- Methylbutyltryptamine
- Miprocin (4-HO-MiPT)
- MiPT
- MPT
- Milipertine
- MS-245
- MSBT
- N-Feruloylserotonin (moschamine)
- NET
- NMT
- Norbaeocystin (4-PO-T)
- NTBT
- O-4310
- Oxypertine
- PiPT
- Psilacetin (O-acetylpsilocin; 4-AcO-DMT)
- Psilocin (4-HO-DMT)
- Psilocybin (4-PO-DMT)
- Pyr-T
- RS134-49
- Serotonin (5-HT)
- Solypertine
- ST-1936
- Tryptamine
- Tryptophan
- Yuremamine
- Z2876442907
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N-Acetyltryptamines | |
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α-Alkyltryptamines | |
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Triptans | |
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Cyclized tryptamines | - Bay R 1531
- Ciclindole
- Cyclic 3-OHM
- Ergolines and lysergamides (e.g., LSD)
- Flucindole
- Harmala alkaloids and β-carbolines (e.g., 6-MeO-THH, 9-Me-BC, β-carboline (norharman), harmaline, harmalol, harmane, harmine, pinoline, tetrahydroharmine, tryptoline)
- Iboga alkaloids and related (e.g., DM-506 (ibogaminalog), ibogaine, ibogamine, noribogaine, tabernanthalog, tabernanthine)
- Metralindole
- NDTDI
- PHA-57378
- PNU-22394
- PNU-181731
- RU-28306
- Yohimbans (e.g., yohimbine, rauwolscine, spegatrine, corynanthine, ajmalicine, reserpine, deserpidine, rescinnamine)
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Related compounds | |
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