6-ヒドロキシドパミン
- 関
- 6-hydroxydopamine、oxidopamine
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/11/19 10:49:06」(JST)
[Wiki en表示]
Oxidopamine |
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IUPAC name
5-(2-Aminoethyl)benzene-1,2,4-triol
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Identifiers |
CAS number |
1199-18-4 Y |
PubChem |
4624 |
ChemSpider |
4463 Y |
UNII |
8HW4YBZ748 N |
KEGG |
D05294 Y |
ChEMBL |
CHEMBL337702 Y |
Jmol-3D images |
Image 1 |
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-
InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2 Y
Key: DIVDFFZHCJEHGG-UHFFFAOYSA-N Y
InChI=1/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2
Key: DIVDFFZHCJEHGG-UHFFFAOYAG
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Properties |
Molecular formula |
C8H11NO3 |
Molar mass |
169.18 g/mol |
N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
Oxidopamine, also known as 6-hydroxydopamine (6-OHDA) or 2,4,5-trihydroxyphenethylamine, is a neurotoxic synthetic organic compound used by researchers to selectively destroy dopaminergic and noradrenergic neurons in the brain. 6-OHDA is thought to enter the neurons via the dopamine and noradrenaline (norepinephrine) reuptake transporters. Oxidopamine is often used in conjunction with a selective noradrenaline reuptake inhibitor (such as desipramine) to selectively destroy dopaminergic neurons only.
The main use for oxidopamine in scientific research is to induce Parkinsonism in laboratory animals such as mice, rats and monkeys, in order to develop and test new medicines and treatments for Parkinson's disease. In order to induce this condition in animals, around 70% of the dopaminergic neurons in the substantia nigra of the brain must be destroyed, and this is achieved either with oxidopamine or MPTP. Both these agents likely destroy neurons by generating reactive oxygen species such as superoxide radical. Oxidopamine toxicity in neonatal rodents is also used as an animal model for the Lesch-Nyhan syndrome.[1]
See also[edit]
- 5,7-Dihydroxytryptamine
- DSP-4
- MPTP
- Norsalsolinol
- Rotenone
References[edit]
- ^ Breese GR, Knapp DJ, Criswell HE, Moy SS, Papadeas ST, Blake BL (2005). "The neonate-6-hydroxydopamine-lesioned rat: a model for clinical neuroscience and neurobiological principles". Brain Res. Brain Res. Rev. 48 (1): 57–73. doi:10.1016/j.brainresrev.2004.08.004. PMID 15708628.
Neurotoxins
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Animal |
- Batrachotoxin
- Bestoxin
- Birtoxin
- Bungarotoxin
- Charybdotoxin
- Conotoxin
- Saxitoxin
- Tetrodotoxin
- Vanillotoxin
- Huwentoxin
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Bacterial |
- Botulinum toxin
- Tetanospasmin
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Plant |
- Penitrem A
- Picrotoxin
- Bicuculline
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Pesticides |
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Nerve agents |
- Cyclosarin
- EA-3148
- Novichok agent
- Sarin
- Soman
- Tabun
- VE
- VG
- VM
- VR
- VX
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Neurotransmitters
and precursors |
- Dopamine
- Glutamate
- L-Tyrosine
- L-Phenylalanine
- L-DOPA (Levodopa)
- L-Glutamine
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Neurotoxic drugs |
- 1,4-BD
- 5,7-DHT
- 6-OHDA
- αET
- αMT
- Dizocilpine (MK-801)
- DSP-4
- Ethanol
- GBL
- GHB
- Ibotenic acid
- Ketamine
- Methamphetamine
- MBDB
- MDA
- MDEA
- MDMA (Ecstasy)
- MPP+
- MPTP
- Norsalsolinol
- PBA
- PCA
- PIA
- Phencyclidine (PCP)
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Denaturants |
Methanol
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Adrenergics
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Receptor ligands
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α1
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- Agonists: 5-FNE
- 6-FNE
- Amidephrine
- Anisodamine
- Anisodine
- Cirazoline
- Dipivefrine
- Dopamine
- Ephedrine
- Epinephrine
- Etilefrine
- Ethylnorepinephrine
- Indanidine
- Levonordefrin
- Metaraminol
- Methoxamine
- Methyldopa
- Midodrine
- Naphazoline
- Norepinephrine
- Octopamine
- Oxymetazoline
- Phenylephrine
- Phenylpropanolamine
- Pseudoephedrine
- Synephrine
- Tetrahydrozoline
Antagonists: Abanoquil
- Adimolol
- Ajmalicine
- Alfuzosin
- Amosulalol
- Arotinolol
- Atiprosin
- Benoxathian
- Buflomedil
- Bunazosin
- Carvedilol
- CI-926
- Corynanthine
- Dapiprazole
- DL-017
- Domesticine
- Doxazosin
- Eugenodilol
- Fenspiride
- GYKI-12,743
- GYKI-16,084
- Hydroxyzine
- Indoramin
- Ketanserin
- L-765,314
- Labetalol
- Mephendioxan
- Metazosin
- Monatepil
- Moxisylyte
- Naftopidil
- Nantenine
- Neldazosin
- Nicergoline
- Niguldipine
- Pelanserin
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Piperoxan
- Prazosin
- Quinazosin
- Ritanserin
- RS-97,078
- SGB-1,534
- Silodosin
- SL-89.0591
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tibalosin
- Tiodazosin
- Tipentosin
- Tolazoline
- Trimazosin
- Upidosin
- Urapidil
- Zolertine
- Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone and trazodone all antagonize α1-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.
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α2
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- Agonists: (R)-3-Nitrobiphenyline
- 4-NEMD
- 6-FNE
- Amitraz
- Apraclonidine
- Brimonidine
- Cannabivarin
- Clonidine
- Detomidine
- Dexmedetomidine
- Dihydroergotamine
- Dipivefrine
- Dopamine
- Ephedrine
- Ergotamine
- Epinephrine
- Esproquin
- Etilefrine
- Ethylnorepinephrine
- Guanabenz
- Guanfacine
- Guanoxabenz
- Levonordefrin
- Lofexidine
- Medetomidine
- Methyldopa
- Mivazerol
- Naphazoline
- Norepinephrine
- Oxymetazoline
- Phenylpropanolamine
- Piperoxan
- Pseudoephedrine
- Rilmenidine
- Romifidine
- Talipexole
- Tetrahydrozoline
- Tizanidine
- Tolonidine
- Urapidil
- Xylazine
- Xylometazoline
Antagonists: 1-PP
- Adimolol
- Aptazapine
- Atipamezole
- BRL-44408
- Buflomedil
- Cirazoline
- Efaroxan
- Esmirtazapine
- Fenmetozole
- Fluparoxan
- GYKI-12,743
- GYKI-16,084
- Idazoxan
- Mianserin
- Mirtazapine
- MK-912
- NAN-190
- Olanzapine
- Phentolamine
- Phenoxybenzamine
- Piperoxan
- Piribedil
- Rauwolscine
- Rotigotine
- SB-269,970
- Setiptiline
- Spiroxatrine
- Sunepitron
- Tolazoline
- Yohimbine
* Note that many atypical antipsychotics and azapirones like buspirone (via metabolite 1-PP) antagonize α2-adrenergic receptors as well.
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β
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Reuptake inhibitors
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NET
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- Selective norepinephrine reuptake inhibitors: Amedalin
- Atomoxetine (Tomoxetine)
- Ciclazindol
- Daledalin
- Edivoxetine
- Esreboxetine
- Lortalamine
- Mazindol
- Nisoxetine
- Reboxetine
- Talopram
- Talsupram
- Tandamine
- Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine
- Bupropion (Amfebutamone)
- Fencamine
- Fencamfamine
- Lefetamine
- Levophacetoperane
- LR-5182
- Manifaxine
- Methylphenidate
- Nomifensine
- O-2172
- Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine
- Desvenlafaxine
- Duloxetine
- Eclanamine
- Levomilnacipran
- Milnacipran
- Sibutramine
- Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: Brasofensine
- Diclofensine
- DOV-102,677
- DOV-21,947
- DOV-216,303
- JNJ-7925476
- JZ-IV-10
- Methylnaphthidate
- Naphyrone
- NS-2359
- PRC200-SS
- SEP-225,289
- SEP-227,162
- Tesofensine; Tricyclic antidepressants: Amitriptyline
- Butriptyline
- Cianopramine
- Clomipramine
- Desipramine
- Dosulepin
- Doxepin
- Imipramine
- Lofepramine
- melitracen
- Nortriptyline
- Protriptyline
- Trimipramine; Tetracyclic antidepressants: Amoxapine
- Maprotiline
- Mianserin
- Oxaprotiline
- Setiptiline; Others: Cocaine
- CP-39,332
- Ethanol
- EXP-561
- Fezolamine
- Ginkgo biloba
- Indeloxazine
- Nefazodone
- Nefopam
- Pridefrine
- Tapentadol
- Tedatioxetine
- Teniloxazine
- Tofenacin
- Tramadol
- Ziprasidone
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VMAT
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- Ibogaine
- Reserpine
- Tetrabenazine
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Enzyme inhibitors
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Anabolism
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PAH
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TH
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- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
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AAAD
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- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
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DBH
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- Bupicomide
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Phenopicolinic acid
- Tropolone
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PNMT
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- CGS-19281A
- SKF-64139
- SKF-7698
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Catabolism
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MAO
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- Nonselective: Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivalylbenzhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine; MAO-A selective: Amiflamine
- Bazinaprine
- Befloxatone
- Befol
- Brofaromine
- Cimoxatone
- Clorgiline
- Esuprone
- Harmala alkaloids (Harmine,
- Harmaline
- Tetrahydroharmine
- Harman
- Norharman, etc)
- Methylene blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
- Tyrima; MAO-B selective:
- Ladostigil
- Lazabemide
- Milacemide
- Mofegiline
- Pargyline
- Rasagiline
- Safinamide
- Selegiline (also D-Deprenyl)
* Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.
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COMT
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- Entacapone
- Nitecapone
- Tolcapone
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Others
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Precursors
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- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine
- L-DOPS (Droxidopa)
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Cofactors
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- Ferrous Iron (Fe2+)
- S-Adenosyl-L-Methionine
- Vitamin B3 (Niacin
- Nicotinamide → NADPH)
- Vitamin B6 (Pyridoxine
- Pyridoxamine
- Pyridoxal → Pyridoxal Phosphate)
- Vitamin B9 (Folic acid → Tetrahydrofolic acid)
- Vitamin C (Ascorbic acid)
- Zinc (Zn2+)
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Others
|
- Activity enhancers: BPAP
- PPAP; Release blockers: Bethanidine
- Bretylium
- Guanadrel
- Guanazodine
- Guanclofine
- Guanethidine
- Guanoxan; Toxins: 6-OHDA
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List of adrenergic drugs
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Dopaminergics
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Receptor ligands
|
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Agonists
|
- Adamantanes: Amantadine
- Memantine
- Rimantadine; Aminotetralins: 7-OH-DPAT
- 8-OH-PBZI
- Rotigotine
- UH-232; Benzazepines: 6-Br-APB
- Fenoldopam
- SKF-38,393
- SKF-77,434
- SKF-81,297
- SKF-82,958
- SKF-83,959; Ergolines: Bromocriptine
- Cabergoline
- Dihydroergocryptine
- Epicriptine
- Lisuride
- LSD
- Pergolide; Dihydrexidine derivatives: 2-OH-NPA
- A-86,929
- Ciladopa
- Dihydrexidine
- Dinapsoline
- Dinoxyline
- Doxanthrine; Others: A-68,930
- A-77636
- A-412,997
- ABT-670
- ABT-724
- Aplindore
- Apomorphine
- Aripiprazole
- Bifeprunox
- BP-897
- CY-208,243
- Dizocilpine
- Etilevodopa
- Flibanserin
- Ketamine
- Melevodopa
- Modafinil
- Pardoprunox
- Phencyclidine
- PD-128,907
- PD-168,077
- PF-219,061
- Piribedil
- Pramipexole
- Propylnorapomorphine
- Pukateine
- Quinagolide
- Quinelorane
- Quinpirole
- RDS-127
- Ro10-5824
- Ropinirole
- Rotigotine
- Roxindole
- Salvinorin A
- SKF-89,145
- Sumanirole
- Terguride
- Umespirone
- WAY-100,635
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Antagonists
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- Typical antipsychotics: Acepromazine
- Azaperone
- Benperidol
- Bromperidol
- Clopenthixol
- Chlorpromazine
- Chlorprothixene
- Droperidol
- Flupentixol
- Fluphenazine
- Fluspirilene
- Haloperidol
- Levosulpiride
- Loxapine
- Mesoridazine
- Methotrimeprazine
- Nemonapride
- Penfluridol
- Perazine
- Periciazine
- Perphenazine
- Pimozide
- Prochlorperazine
- Promazine
- Sulforidazine
- Sulpiride
- Sultopride
- Thioridazine
- Thiothixene
- Trifluoperazine
- Triflupromazine
- Trifluperidol
- Zuclopenthixol; Atypical antipsychotics: Amisulpride
- Asenapine
- Blonanserin
- Cariprazine
- Carpipramine
- Clocapramine
- Clorotepine
- Clozapine
- Gevotroline
- Iloperidone
- Lurasidone
- Melperone
- Molindone
- Mosapramine
- Olanzapine
- Paliperidone
- Perospirone
- Piquindone
- Quetiapine
- Remoxipride
- Risperidone
- Sertindole
- Tiospirone
- Zicronapine
- Ziprasidone
- Zotepine; Antiemetics: AS-8112
- Alizapride
- Bromopride
- Clebopride
- Domperidone
- Metoclopramide
- Thiethylperazine; Others: Amoxapine
- Buspirone
- Butaclamol
- Ecopipam
- EEDQ
- Eticlopride
- Fananserin
- Hydroxyzine
- L-745,870
- Nafadotride
- Nuciferine
- PNU-99,194
- Raclopride
- Sarizotan
- SB-277,011-A
- SCH-23,390
- SKF-83,959
- Sonepiprazole
- Spiperone
- Spiroxatrine
- Stepholidine
- Tetrahydropalmatine
- Tiapride
- UH-232
- Yohimbine
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Reuptake inhibitors
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Plasmalemmal
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DAT inhibitors
|
- Piperazines: DBL-583
- GBR-12,935
- Nefazodone
- Vanoxerine; Piperidines: BTCP
- Desoxypipradrol
- Dextromethylphenidate
- Difemetorex
- Ethylphenidate
- Methylnaphthidate
- Methylphenidate
- Phencyclidine
- Pipradrol; Pyrrolidines: Diphenylprolinol
- MDPV
- Naphyrone
- Prolintane
- Pyrovalerone; Tropanes: Altropane
- Brasofensine
- CFT
- Cocaine
- Dichloropane
- Difluoropine
- FE-β-CPPIT
- FP-β-CPPIT
- Ioflupane (123I)
- Iometopane
- RTI-112
- RTI-113
- RTI-121
- RTI-126
- RTI-150
- RTI-177
- RTI-229
- RTI-336
- Tenocyclidine
- Tesofensine
- Troparil
- Tropoxane
- WF-11
- WF-23
- WF-31
- WF-33; Others: Adrafinil
- Armodafinil
- Amfonelic acid
- Amphetamine
- Amineptine
- Benzatropine
- Bromantane
- BTQ
- BTS-74,398
- Bupropion
- Ciclazindol
- Diclofensine
- Dimethocaine
- Diphenylpyraline
- Dizocilpine
- DOV-102,677
- DOV-21,947
- DOV-216,303
- Etybenzatropine
- EXP-561
- Fencamine
- Fencamfamine
- Fezolamine
- GYKI-52,895
- Indatraline
- Ketamine
- Lefetamine
- Levophacetoperane
- LR-5182
- Manifaxine
- Mazindol
- Medifoxamine
- Mesocarb
- Modafinil
- Nefopam
- Nomifensine
- NS-2359
- O-2172
- Pridefrine
- Propylamphetamine
- Radafaxine
- SEP-225,289
- SEP-227,162
- Sertraline
- Sibutramine
- Tametraline
- Tedatioxetine
- Tripelennamine
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Vesicular
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VMAT inhibitors
|
- Deserpidine
- Ibogaine
- Reserpine
- Tetrabenazine
|
|
|
|
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Allosteric modulators
|
|
- Quinazolinamines: SoRI-9804
- SoRI-20040
- SoRI-20041
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|
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Enzyme inhibitors
|
|
Anabolism
|
PAH inhibitors
|
|
|
TH inhibitors
|
- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
|
|
AAAD/DDC inhibitors
|
- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
|
|
|
Catabolism
|
MAO inhibitors
|
- Nonselective: Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivalylbenzhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine; MAO-A selective: Amiflamine
- Bazinaprine
- Befloxatone
- Befol
- Brofaromine
- Cimoxatone
- Clorgiline
- Esuprone
- Harmala alkaloids
- Methylene Blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
- Tyrima; MAO-B selective: D-Deprenyl
- Ethanol
- L-Deprenyl (Selegiline)
- Ladostigil
- Lazabemide
- Milacemide
- Nicotine
- Pargyline
- Rasagiline
- Safinamide
|
|
COMT inhibitors
|
- Entacapone
- Nitecapone
- Tolcapone
|
|
DBH inhibitors
|
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Tropolone
|
|
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|
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Others
|
|
Precursors
|
- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa)
|
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Cofactors
|
- Ferrous iron (Fe2+)
- Tetrahydrobiopterin
- Vitamin B3 (Niacin
- Nicotinamide → NADPH)
- Vitamin B6 (Pyridoxine
- Pyridoxamine
- Pyridoxal → Pyridoxal phosphate)
- Vitamin B9 (Folic acid → Tetrahydrofolic acid)
- Vitamin C (Ascorbic acid)
- Zinc (Zn2+)
|
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Others
|
- Activity enhancers: BPAP
- PPAP; Toxins: 6-OHDA
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List of dopaminergic drugs
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English Journal
- High frequency electro-acupuncture enhances striatum DAT and D1 receptor expression, but decreases D2 receptor level in 6-OHDA lesioned rats.
- Rui G, Guangjian Z, Yong W, Jie F, Yanchao C, Xi J, Fen L.SourceNuclear Medicine Department of The 1st Affiliated Hospital of Xi'an Jiao Tong University, China.
- Behavioural brain research.Behav Brain Res.2013 Jan 15;237:263-9. doi: 10.1016/j.bbr.2012.09.047. Epub 2012 Oct 2.
- The direct effects of electro-acupuncture (EA) on the dopaminergic neurotransmitter system in Parkinson's disease (PD) patients remain elusive. In the present study, 0, 2 or 100Hz EA was applied to acupoints Sanyinjiao (SP6), Yanglingquan (GB34) and Zusanli (ST36) in a rat model unilaterally lesione
- PMID 23036843
- Characterisation of spatial neglect induced by unilateral 6-OHDA lesions on a choice reaction time task in rats.
- Heuer A, Dunnett SB.SourceBrain Repair Group, School of Bioscience, Cardiff University, Cardiff, Wales, UK. Electronic address: HeuerA@cf.ac.uk.
- Behavioural brain research.Behav Brain Res.2013 Jan 15;237:215-22. doi: 10.1016/j.bbr.2012.09.038. Epub 2012 Sep 27.
- Unilateral dopamine depletion and excitotoxic lesions of the striatum have been shown to induce a contralateral neglect when rats have to respond in a choice reaction time setting. Whereas, in a lateralised setting when response options are to either side of the animal's head all contralateral respo
- PMID 23022749
Japanese Journal
- Brain Science(103)パーキンソン病モデルにおける線条体遺伝子ネットワーク解析と治療薬による遺伝子発現修飾
- 成体期黒質損傷ラットにおける時間知覚の行動科学的検討 <論文>
- 氏田 麻美,坂田 省吾,ウジタ アサミ,サカタ ショウゴ,Ujita Asami,Sakata Shogo
- 広島大学大学院総合科学研究科紀要. I, 人間科学研究 6, 1-11, 2011-12-31
- … We studied the effects of an injection of 6-hydroxydopamine (6-OHDA) into the substantianigra of rats on the performance of timing behavior by using a peak interval (PI) procedure. … Then, subjects were divided into three groups: lesion (n=6), operational sham lesion (n=3) and intact (n=3). …
- NAID 80022327864
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- 結 果 6-OHDAの脳内投与手術は36匹行った。2匹が手術後死亡し、4匹がアポモルフィン投与において全く 回転しなかったため30匹を成功とした。手術後、動物は破壊した右脳側に湾曲した姿勢をとり、尾を刺激
- hon p.4 [100%] 1202 Fig. 3. Preconditioning EŠect of Apo on 6-OHDA-induced Cell Death A: SH-SY5Y cells were pretreated with various concentrations of Apo. After the medium containing Apo was completely removed, the ...
Related Pictures
★リンクテーブル★
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- 英
- 6-hydroxydopamine、6-OHDA
- 関
- 6-ハイドロキシドパミン、オキシドパミン
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6-ヒドロキシドパミン、6-ハイドロキシドパミン
- 関
- 6-OHDA、oxidopamine
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オキシドパミン
- 関
- 6-hydroxydopamine、6-OHDA
[★]
- 関
- hydroxydopamine
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眼圧亢進、ocular hypertension