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Kembali ke Ensiklopedia Arsip Wikipedia Indonesia 6-Hydroxydopa 6-HydroxydopaCatecholaminergic neurotoxin Pharmaceutical compound6-HydroxydopaClinical dataOther names6-OH-DOPA; 6-OHDOPADrug classCatecholaminergic neurotoxinIdentifiers IUPAC name (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid CAS Number27244-64-0PubChem CID33755ChemSpider31117UNII580PK2O48OChEBICHEBI:72753ChEMBLChEMBL1256516Chemical and physical dataFormulaC9H11NO5Molar mass213.189 g·mol−13D model (JSmol)Interactive image SMILES C1=C(C(=CC(=C1O)O)O)C[C@@H](C(=O)O)N InChI InChI=1S/C9H11NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11-13H,1,10H2,(H,14,15)/t5-/m0/s1Key:YLKRUSPZOTYMAT-YFKPBYRVSA-N 6-Hydroxydopa (6-OH-DOPA; 6-OHDOPA) is a catecholaminergic neurotoxin that damages noradrenergic and dopaminergic neurons and is used in scientific research.[1][2][3] It is a precursor and prodrug of 6-hydroxydopamine (6-OHDA).[1][2][3] The drug is a derivative of levodopa (L-DOPA).[1][2][3] It has certain advantages over 6-OHDA, such as the ability to cross the blood–brain barrier into the central nervous system and hence the ability to be administered systemically rather than directly into the brain.[1][2][3] 6-OH-DOPA was first described in the scientific literature by 1969.[4] References 1 2 3 4 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. 1 2 3 4 Kostrzewa RM (2016). "Perinatal Lesioning and Lifelong Effects of the Noradrenergic Neurotoxin 6-Hydroxydopa". Current Topics in Behavioral Neurosciences. Vol. 29. pp. 43–50. doi:10.1007/7854_2015_414. ISBN 978-3-319-34134-7. PMID 26660536. 1 2 3 4 Kostrzewa RM, Brus R (1998). "Destruction of catecholamine-containing neurons by 6-hydroxydopa, an endogenous amine oxidase cofactor". Amino Acids. 14 (1–3): 175–179. doi:10.1007/BF01345259. PMID 9871458. ↑ Ong HH, Creveling CR, Daly JW (May 1969). "The synthesis of 2,4,5-trihydroxyphenylalanine (6-hydroxydopa). A centrally active norepinephrine-depleting agent". Journal of Medicinal Chemistry. 12 (3): 458–462. doi:10.1021/jm00303a028. PMID 5788162. vteMonoaminergic neurotoxinsDopaminergic 2′-CH3-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 4-MMA 5-S-Cysteinyldopamine 5,6-DHT 6-Hydroxydopa 6-OHDA quinone 6,7-DHT ALDH inhibitors (e.g., disulfiram, methylmercury) Amphetamine Benomyl Daidzin Dieldrin DOPA quinone DOPAL DOPAL quinone Dopamine Dopamine quinone Fenpropathrin Haloperidol HPP+ HPTP Imidazole propionate (ImP) Mancozeb Maneb Mephedrone Methamphetamine Methcathinone Methylone MPP+ (cyperquat) MPTP N-Methylnorsalsolinol Norsalsolinol Oxidopamine (6-OHDA) Paraquat Rotenone Salsolinol Ziram Noradrenergic 2′-NH2-MPTP (2′-amino-MPTP) 2,4,5-THA 4,5-DHT 5,6-DHT 5,7-DHT 6-Hydroxydopa DOPEGAL DSP-4 MDA (tenamfetamine) Oxidopamine (6-OHDA) Xylamine Serotonergic 2′-NH2-MPTP (2′-amino-MPTP) 2,4-DCA 2,4,5-THA 2,4,5-THMA pCPE 3-CA 3,4-DCA 4-CAB (α-ethyl-PCA) 4-CMA 4-HO-5-MeO-T 4,5-DHT 5-IAI 5-MAPB 5-MeO-DiPT 5,6-DHT 5,7-DHT 6,7-DHT αET ETAI Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP+ HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PBMA PCA PCMA PIA TAI Unsorted 2,5-DDM-DOM 5-HIAL RHPP+ RHPTP See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators vtePhenethylaminesPhenethylamines Psychedelics: 3,4-DMPEA-NDEPA 24H-NBOMe 25B-NBOMe 25C-NBOMe 25D-NBOMe 25D-NM-NDEAOP 25H-NBOMe 25I-NBOMe 25N-NBOMe 25O-NBOMe 2C-B 2C-B-AN 2C-B-OH 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-DB 2C-E 2C-EF 2C-F 2C-G 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-O 2C-O-2 2C-O-4 2C-P 2C-Ph 2C-Se 2C-Se-TFM 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-21.5 2C-T-22 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-tBu 2C-Te 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline BOH-2C-B CT-5172 DESOXY N,N-Diformylmescaline Escaline N-Formylmescaline Isoproscaline 3-Methoxy-4,5-dihydroxyphenethylamine M-NDEPA Macromerine MEPEA Mescaline Metaescaline Methallylescaline N-DEAOP-NMPEA N-Methylmescaline Proscaline Psi-2C-T-4 Trichocereine (N,N-dimethylmescaline) Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Phenacylamine (β-ketophenethylamine) Solriamfetol Entactogens: Lophophine MDPEA MDMPEA Others: N-Acetylmescaline Amidephrine ASR-2001 Biscaline BOH Buscaline Denopamine Desvenlafaxine DMPEA F-17475 Phenibut 4-PhPr-PEA pCPE Pronethalol Salbutamol Levosalbutamol Venlafaxine Amphetamines Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY DMA DMMDA DOB DOB-NDEPA DOC DODB DOEF DOET DOI DOI-NDEPA DOM DOM-NDEPA DON DOPR DOTFM DOTFM-NDEPA DOTMA Ganesha MMDA MMDA-2 MMDA-3a MMDA-3b N-Hydroxy-DOM Psi-DOM TMA TMA-2 TMA-2-NDEPA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA β-Phenylmethamphetamine Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Deprenyl D-Deprenyl Dimethylamphetamine Ephedrine FDE Ephenidine Etafedrine Etilamfetamine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine Dexfenfluramine Levofenfluramine Fenproporex Flucetorex Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine 4-ME Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Lomardexamfetamine Mefenorex Metaraminol Methamphetamine Dextromethamphetamine Levomethamphetamine Methoxamine Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine α,N-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PBMA PCA PCMA PFA PFMA PIA PIMA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APBT 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-APBT 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane ODMA SDA (3T-MDA) SDMA (3T-MDMA) SeDMA TAP TDMA Others: 3,4-DCA DOOH Amiflamine Cafedrine Deprenyl D-Deprenyl Selegiline (L-deprenyl) DiFMDA 4-Fluorodeprenyl 4-Fluoroselegiline Thiamphenicol UWA-101 (α-cPr-MDMA) Phentermines Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine Cathinones Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone Propylone Phenylisobutylamines(and further-extended) Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: α-Propylphenethylamine Hexapradol Phenylisobutylamine (α-ethylphenethylamine) Catecholamines(and close relatives) 6-FNE 6-OHDA α-Me-DA α-Me-TRA Adrenochrome Arbutamine Ciladopa D-DOPA (dextrodopa) Dimetofrine Dipropyldopamine (DPDA) Dobutamine Dopamine Dopexamine Epinephrine (adrenaline) Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (levodopa) L-DOPS (droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin Levonordefrin Norepinephrine (noradrenaline) Norfenefrine (m-octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine Theodrenaline CyclizedphenethylaminesPhenylalkylpyrrolidines α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP Fluorolintane MOPPP MOPVP MPBP MPEP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone 2-Benzylpiperidines(phenidates) 2-Benzylpiperidine 3-Bromomethylphenidate 3-Chloromethylphenidate 3-Methylmethylphenidate 3,4-Dichloro-2-benzylpiperidine 3,4-Dichloroethylphenidate 3,4-Dichloromethylphenidate 4-Bromoethylphenidate 4-Bromomethylphenidate 4-Chloromethylphenidate 4-Fluoroethylphenidate 4-Fluoroisopropylphenidate 4-Fluoromethylphenidate 4-Methyl-2-benzylpiperidine 4-Methylisopropylphenidate 4-Methylmethylphenidate 4-Nitromethylphenidate α-Acetyl-2-benzylpiperidine α-Keto-2-benzylpiperidine CPMBP DMBMPP Desoxypipradrol (2-DPMP) Difemetorex Ethylnaphthidate (HDEP-28) Ethylphenidate Isopropylnaphthidate Isopropylphenidate MDMPH Methylnaphthidate (HDMP-28) Methylphenidate Phacetoperane Pipradrol Propylphenidate Rimiterol Ritalinamide Ritalinic acid SCH-5472 Serdexmethylphenidate Phenylmorpholines(phenmetrazines) (2R,3R)-Hydroxybupropion 2-(2,5-Dimethoxy-4-bromophenyl)morpholine 2-Fluorophenmetrazine 2-Methylphenmetrazine 2-Phenylmorpholine 2-Phenyl-3,6-dimethylmorpholine 3-Chlorophenmetrazine (PAL-594) 3-Fluorophenetrazine 3-Fluorophenmetrazine (PAL-593) 3-Methoxyphenmetrazine 3-Methylphenmetrazine (PAL-773) 4-Fluorophenmetrazine (PAL-748) 4-Methylphendimetrazine 4-Methylphenmetrazine (PAL-747) 2C-B-morpholine Fenbutrazate Fenmetramide Flumexadol G-130 Isophenmetrazine Manifaxine Methylenedioxyphenmetrazine Morazone N-Ethylphenmetrazol Naphthylmetrazine (PAL-704) Naphthylmorpholine (PAL-678) Oxaflozane PDM-35 PF-219,061) Phendimetrazine Phenetrazine Phenmetetrazine Phenmetrazine Phenmetrazol Pseudophenmetrazine Radafaxine ((2S,3S)-hydroxybupropion) Phenyloxazolamines(aminorexes) 3-Methylaminorex 4-Ethylaminorex (4-EAR) 4'-Fluoroaminorex 4-Methylaminorex (4-MAR) 4,4'-Dimethylaminorex (4,4'-DMAR) 2C-B-aminorex 2F-MAR 4B-MAR 4C-MAR 4F-MAR Aminorex Clominorex Cyclazodone Ephedroxane Fenozolone Fluminorex MDMAR Methylenedioxyaminorex (MDAR) N-Methylcyclazodone N,N-Dimethylaminorex Pemoline Thozalinone Isoquinolines andtetrahydroisoquinolines Anhalamine Anhalidine Anhalinine Anhalonidine Anhalonine Anhalotine Arizonine Calycotomine Carnegine (pectenine) Corypalline Debrisoquine Deglucopterocereine Deutetrabenazine Diclofensine DOB-CR DOM-CR Esproquin Gigantine Hedycarine Heliamine Hydrastinine Hydrocotarnine Hydrohydrastinine (MDMTHIQ; MDMA-CR) Isoanhalamine Isoanhalidine Isoanhalonidine Isocorypalline Isopellotine Isosalsoline Lemaireocereine Longimammamine Longimammatine Longimammidine Longimammosine Lophocerine Lophophorine Lophotine MDMA-CR Mescalotam N-Methylanhalinine N-Methylheliamine N-Methylisosalsoline N-Methyl-DOM-CR (Beatrice-CR) N-Methyl-THIQ (METH-CR) Nomifensine Norsalsolinol Nortehaunine Norweberine O-Methylanhalonidine O-Methylpellotine Pachycereine Pellotine Perafensine Peyoglutam Peyophorine Peyotine PMMA-CR Quinisocaine Reticuline Salsolidine Salsoline Salsolinol TDIQ (MDTHIQ, MDA-CR) Tehaunine Tehaunine N-oxide Tepenine Tetrabenazine Tetrahydroisoquinoline (THIQ; AMPH-CR) Tetrahydropapaveroline Tilisolol Tretoquinol Uberine Valbenazine Weberidine Weberine Zelandopam 2-Aminoindanes 2-Aminoindane (2-AI) 5-IAI Aprindine BFAI BFMAI DHAI DOM-AI ETAI Indantadol MDAI MDMAI MEAI (5-MeO-AI) MMAI NM-2-AI PNU-99,194 Pyr-AI TAI 2-Aminotetralins 2-Aminotetralin (2-AT) 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 CHF-1024 DOM-AT MDAT MDMAT Nolomirole UH-232 Others / unsorted 1-Aminomethylindanes (e.g., 2CB-Ind, AMMI, bromojimscaline, jimscaline) 2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Aminochromans (e.g., CT-5126, 5-MeO-DPAC, robalzotan, ebalzotan) 3-Benzazepines (e.g., fenoldopam, lorcaserin, 7-chlorolorcaserin, SCHEMBL5334361) 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine, 3-PPP, OSU-6162 (PNU-96391), LPH-5, LPH-48, 2C-B-3PIP, 2C-B-3PIP-NBOMe, 2C-B-3PIP-POMe, Z3517967757 (Z7757)) 6-AB AL-1095 Aminochromes (e.g., adrenochrome, adrenolutin) Benzocyclobutenes (e.g., 2CBCB-NBOMe, bromotomscaline, S33005, TCB-2, tomscaline) Benzoxepins (e.g., BBOX, IBOX, TFMBOX) Butyltolylquinuclidine Camfetamine Clausenamide Cypenamine (trans-2-phenylcyclopentylamine) Diphenidine Diphenylprolinol Ergolines (e.g., LSD) Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g., NDTDI, RU-27849, DEIMDHPCA, DEMPDHPCA, DEMPDHPCA-2C-D, RU-27251) PF-592,379 Phenanthrenes (e.g., atherosperminine (atherospermine)) Phenylcyclopropylamines (e.g., DMCPA, TMT, tranylcypromine) Phenylmethylpyrrolidines (e.g., APA-01) Phenylpiracetams (e.g., phenylpiracetam, MRZ-9547, RGPU-95) Pyridopyrroloquinoxalines (e.g., lumateperone, deulumateperone, IHCH-7079, IHCH-7086, IHCH-7113, ITI-1549) Thienopyridines (e.g., SKF-89145, SKF-89615, SKF-89626) Tolazoline Tricyclics (e.g., AMDA, AMDH, benzoctamine, dizocilpine, SpAMDA) ZC-B Related compounds 2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBATooltip 1,3-dimethylbutylamine, 1,4-DMAATooltip 1,4-dimethylamylamine, heptaminol, iproheptine, isometheptene, methylhexanamine/1,3-DMAA, octodrine, oenethyl, tuaminoheptane) Benzylamines (e.g., benzylamine, α-methylbenzylamine, MDM1EA, ALPHA, M-ALPHA, pargyline) Benzylpiperazines (e.g., benzylpiperazine, MDBZP, fipexide) Cyclohexylaminopropanes (e.g., propylhexedrine, norpropylhexedrine) Cyclopentylaminopropanes (e.g., isocyclamine, cyclopentamine) Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine, CT-4719, ORG-37684) Phenylalkenylamines (e.g., phenylbutenamine) Phenylalkynylamines (e.g., phenylbutynamine) Phenylpiperazines (e.g., 1-phenylpiperazine, mCPPTooltip meta-chlorophenylpiperazine, TFMPPTooltip trifluoromethylphenylpiperazine, oMPPTooltip ortho-methylphenylpiperazine, pFPPTooltip para-fluorophenylpiperazine, pMeOPPTooltip para-methoxyphenylpiperazine) Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA) Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone) Phenylbutylamines (e.g., 4-Phenylbutylamine, 4-Phenylpentan-1-amine) See also: Tryptamines Ergolines and lysergamides Stimulants Entactogens Psychedelics This neurotoxin article is a stub. 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