592:
consequence of the general low yields and the relatively involved procedures, it is wished to report an alternate scheme for the synthesis of this pharmacon. In about 60% of the overall yield phenethylamine 3 is prepared via nitrostyrene by starting with isovanillin. The central step in synthesising oxidopamine is a Fremy's salt oxidation of 3-hydroxy-4-methoxyphenethylamine forming the corresponding p-quinone. The Teuber reaction only succeeds when the amino function is protected by acetylation, carbobenzoxylation or formylation. With the derivatives N-carbobenzoxy and N-acetyl almost quantitative yields of the p-quinone can be obtained.
304:
191:
529:, and is commonly used for making experimental animal models in Parkinson's disease. Parkinson disease leads to degeneration of dopaminergic midbrain neurons resulting in dopamine depletion. Therefore oxidopamine can induce Parkinson disease in animal models. These models can be used to do research for treatments for Parkinson's disease. The toxin is also used for experimental models of attention-deficit hyperactivity disorder and
44:
35:
728:, however it is often difficult what mechanism causes cell damage after exposure. It is also thought that toxic effects of 6-OHDA are caused by the uptake of the substance into the catecholaminergic nerve endings. This happens because the catecholaminergic transport system has a high affinity for 6-OHDA. Cell death by oxidopamine can be induced by three main mechanisms; ROS generation, H
420:
591:
Oxidopamine was long ago characterized and synthesized, starting from 2,4,5-trimethoxy and 2,4,5-tribenzyloxybenzaldehyde respectively, by Harley-Mason and Lee and
Dickson. The multistep synthesis of Senoh and Witkop involves the addition of Methanol to become an applicable o-quinone intermediate. In
582:
It has no rapid reactions with air or water. The reactive groups for oxidopamine are the phenol-, and amine-group. Oxidopamine primarily interacts with structures containing norepinephrine, but also with structures containing dopamine. However the interactions with dopamine-containing structures are
604:, targeting the dopamine transporters (DAT). This can be done through stereotaxic injections whereas bilateral as unilateral is experimentally permitted. It will cause loss of dopamine terminals in the striatum by affecting the nigrostriatal pathway and causes loss of dopamine neurons in the
550:
which is phenethylamine, where the hydrogens on the phenyl ring at positions 2, 4 and 5 are replaced by hydroxyl groups. Oxidopamine is a primary amino compound, a benzenetriol and a catecholamine. The molecular weight of this oxidopamine is 169.18 and has the following molecular formula;
739:
The reaction to oxidopamine is often very site specific, making it important to inject it at the location it has to function. In order to cause toxicity in the brain, the oxidopamine has to be injected directly into the brain, since it is not able to cross the
715:
There are several effects linked to the usage of 6-hydroxydopamine. The most common adverse effects caused by injections are hyperemia, subconjunctival hemorrhage, transient mydriasis, chemosis, lid edema, and ptosis (which may last for a few weeks).
1250:
513:
was developed by
Ungerstedt, obtaining an animal model of akinesia with a very high mortality rate. Ever since, oxidopamine has become an abundantly used neurotoxin for making animal models with
616:
Oxidopamine is taken up by and accumulates in catecholaminergic neurons. This uptake is facilitated by dopamine and noradrenaline membrane receptors due to the structural similarity with
3407:
982:
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".
3402:
433:
1292:
579:(ROS), mainly superoxide and hydrogen peroxide. ROS generation is also increased by oxidopamine via inhibition of complex I and IV of the electron transport chain.
1116:
Hernandez-Baltazar, Daniel; Nadella, Rasajna; Jesus
Rovirosa-Hernandez, Maria de; Zavala-Flores, Laura Mireya; Jarquin, Christian de Jesus Rosas (2017-12-20).
353:
3437:
3432:
662:
radicals. However, recent research suggests that 6-OHDA modifies proteins via cysteine modification, implying an additional cause of neuronal cell death.
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2435:
3452:
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3442:
3422:
3417:
1816:
1783:
1150:"Molecular mechanisms of 6-hydroxydopamine-induced cytotoxicity in PC12 cells: Involvement of hydrogen peroxide-dependent and -independent action"
855:
Höglinger, Günter U.; Rizk, Pamela; Muriel, Marie P.; Duyckaerts, Charles; Oertel, Wolfgang H.; Caille, Isabelle; Hirsch, Etienne C. (July 2004).
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1775:
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1779:
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Farzam, Ali; Chohan, Karan; Strmiskova, Miroslava; Hewitt, Sarah J.; Park, David S.; Pezacki, John P.; Özcelik, Dennis (January 2020).
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2352:
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318:
703:(IOP), lasting for a few days up to two weeks. The real purpose of 6-hydroxydopamine is to increase sensitivity to alpha- and beta-
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Saito, Yoshiro; Nishio, Keiko; Ogawa, Yoko; Kinumi, Tomoya; Yoshida, Yasukazu; Masuo, Yoshinori; Niki, Etsuo (2007-03-01).
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3382:
2970:
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1809:
1663:
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632:), catecholamine quinones and reactive oxygen species (ROS). These quinones can attack endocellular nucleophillic groups.
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261:
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571:
The toxin oxidopamine is a relatively unstable compound. In certain experimental conditions, oxidopamine will undergo
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1833:
1825:
1708:
624:. Within the neuron, oxidopamine is oxidized by monoamine oxidase producing the toxic products hydrogen peroxide (H
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1619:
514:
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oxidopamine has first been described in 1959. Years later, in 1968 the first model exploiting oxidopamine
494:
1584:
1119:
Animal Model of
Parkinson Disease: Neuroinflammation and Apoptosis in the 6-Hydroxydopamine-Induced Model
654:
of the brain must be destroyed, and this is often achieved either with oxidopamine or another neurotoxin
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917:
Pantic, Igor; Cumic, Jelena; Skodric, Sanja
Radojevic; Dugalic, Stefan; Brodski, Claude (2021-02-25).
682:. Oxidopamine is often used in conjunction with a selective noradrenaline reuptake inhibitor (such as
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707:. The supersensitivity phase lasts for up to 6 months, and can be maintained by repeated injections.
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56:
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Oxidopamine is administered via an injection and causes an increase of outflow, and a decrease for
299:
74:
1380:
3171:
3166:
2268:
1007:
964:
892:
837:
468:
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920:"Oxidopamine and oxidative stress: Recent advances in experimental physiology and pharmacology"
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2006:
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1435:
1420:
1200:"A functionalized hydroxydopamine quinone links thiol modification to neuronal cell death"
650:
In order to induce
Parkinsonism in animals, around 70% of the dopaminergic neurons in the
168:
84:
658:. Both these agents likely destroy neurons by generating reactive oxygen species such as
1165:
936:
546:
Oxidopamine is a neurotoxic, solid and organic compound, derived from dopamine. It is a
303:
190:
128:
3871:
3752:
3665:
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2616:
2279:
1224:
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17:
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34:
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1478:
1350:
944:
857:"Dopamine depletion impairs precursor cell proliferation in Parkinson disease"
659:
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399:
159:
1173:
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952:
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617:
526:
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1370:
1365:
817:
237:
199:
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3592:
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3027:
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2935:
2925:
2910:
2900:
2895:
2500:
2400:
2203:
2181:
2176:
2056:
2051:
2046:
2031:
2026:
2021:
1996:
1961:
1956:
1951:
1946:
1941:
1936:
1931:
800:
778:
139:
1094:
410:
Except where otherwise noted, data are given for materials in their
1648:
1440:
1415:
872:
489:
in laboratory animals by lesioning the dopaminergic neurons of the
327:
InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2
225:
3842:
3000:
2920:
2890:
2440:
2390:
2385:
2258:
2186:
2011:
1976:
1916:
1901:
1794:
1531:
1430:
758:
337:
InChI=1/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2
119:
107:
97:
485:
The main use for oxidopamine in scientific research is to induce
3354:
2985:
2940:
2905:
2405:
2395:
2191:
2016:
2001:
1991:
1981:
1971:
1966:
1926:
1921:
1911:
1906:
1891:
1871:
1445:
763:
655:
493:, in order to develop and test new medicines and treatments for
216:
1798:
1274:
798:
Simola, Nicola; Morelli, Micaela; Carta, Anna R. (2007-09-01).
525:
The toxin oxidopamine is an antagonist of the neurotransmitter
3827:
287:
563:. The melting point of oxidopamine is 232 degrees celsius.
428:
724:
There are several ways in which oxidopamine may cause
1245:
1243:
801:"The 6-Hydroxydopamine model of parkinson's disease"
3720:
3481:
3370:
3307:
3119:
3049:
2373:
1832:
1722:
1555:
1492:
1308:
1077:Wehrli, Pius A.; Pigott, F.; Chu, V. (1972-09-15).
1251:"Oxidopamine - an overview | ScienceDirect Topics"
1054:"Oxidopamine - an overview | ScienceDirect Topics"
918:
799:
736:generation, or direct inhibition of mitochondria.
249:
912:
910:
908:
906:
686:) to selectively destroy dopaminergic neurons.
670:6-OHDA is thought to enter the neurons via the
83:
1810:
1286:
8:
474:used by researchers to selectively destroy
1817:
1803:
1795:
1293:
1279:
1271:
600:Oxidopamine is directly injected into the
302:
189:
167:
26:
1223:
1023:
1021:
269:
790:
575:. This may result in the production of
358:
323:
298:
1079:"A New Synthesis of 6-Hydroxydopamine"
180:
1193:
1191:
330:Key: DIVDFFZHCJEHGG-UHFFFAOYSA-N
147:
127:
7:
1143:
1141:
1139:
3823:Lysergic acid 2,4-dimethylazetidide
1166:10.1016/j.freeradbiomed.2006.12.004
340:Key: DIVDFFZHCJEHGG-UHFFFAOYAG
240:
224:
61:5-(2-Aminoethyl)benzene-1,2,4-triol
25:
1154:Free Radical Biology and Medicine
996:10.1016/j.brainresrev.2004.08.004
418:
42:
33:
2754:N,alpha-Diethylphenylethylamine
1784:Monoamine metabolism modulators
925:Chemico-Biological Interactions
414:(at 25 °C , 100 kPa).
606:Substantia nigra pars compacta
491:substantia nigra pars compacta
465:2,4,5-trihydroxyphenethylamine
1:
1776:Monoamine reuptake inhibitors
1756:Receptor/signaling modulators
1083:Canadian Journal of Chemistry
3924:Peripherally selective drugs
3818:Lysergic acid 2-butyl amide
1216:10.1016/j.redox.2019.101377
3945:
3828:Lysergic acid diethylamide
1780:Monoamine releasing agents
404:169.18 g/mol
3929:Monoaminergic neurotoxins
1748:
1302:Monoaminergic neurotoxins
984:Brain Res. Brain Res. Rev
945:10.1016/j.cbi.2021.109380
690:Efficacy and side effects
408:
369:
349:
314:
67:
55:
50:
41:
32:
2718:(Dextromethamphetamine,
1034:pubchem.ncbi.nlm.nih.gov
567:Reactivity and reactions
537:Structure and reactivity
472:monoaminergic neurotoxin
3372:Phenylalkylpyrrolidines
3294:Methylenedioxycathinone
2971:3,4-MDA (tenamfetamine)
754:5,7-Dihydroxytryptamine
577:reactive oxygen species
2296:β-Methylphenethylamine
2290:α-Methylphenethylamine
806:Neurotoxicity Research
482:neurons in the brain.
3487:(and close relatives)
2986:MDMA (midomafetamine)
2328:-Methylphenethylamine
2320:-Methylphenethylamine
2312:-Methylphenethylamine
2304:-Methylphenethylamine
1679:MDMA (midomafetamine)
1255:www.sciencedirect.com
1058:www.sciencedirect.com
680:reuptake transporters
635:6-hydroxidopamine + O
602:nigrostriatal pathway
3651:N,N-Dimethyldopamine
3309:Phenylisobutylamines
3006:Naphthylaminopropane
2691:Isopropylamphetamine
2681:4-Hydroxyamphetamine
1542:Oxidopamine (6-OHDA)
1464:Oxidopamine (6-OHDA)
1454:-Methylnorsalsolinol
701:intraocular pressure
583:to a lesser extent.
531:Lesch-Nyhan syndrome
361:c1c(c(cc(c1O)O)O)CCN
57:Preferred IUPAC name
3813:Lysergic acid amide
3559:Ethylnorepinephrine
3362:Phenylisobutylamine
2814:Phenylpropanolamine
2749:-Norpseudoephedrine
2720:Levomethamphetamine
2607:Dimethylamphetamine
1664:MDA (tenamfetamine)
1595:4-CAB (α-ethyl-PCA)
1537:MDA (tenamfetamine)
937:2021CBI...33609380P
861:Nature Neuroscience
742:blood brain barrier
705:adrenergic agonists
674:and noradrenaline (
515:Parkinson's disease
495:Parkinson's disease
29:
2269:Phenylethanolamine
1332:-Cysteinyldopamine
818:10.1007/BF03033565
441:Infobox references
27:
3906:
3905:
3247:N-Ethylpentedrone
3207:Dimethylcathinone
2829:Propylamphetamine
2572:Dextroamphetamine
2244:Methallylescaline
1792:
1791:
1787:
1624:-Dimethyldopamine
1615:α-Me-DA (3,4-DHA)
1129:978-1-78923-165-6
1089:(18): 3075–3079.
457:6-hydroxydopamine
449:Chemical compound
447:
446:
283:CompTox Dashboard
109:Interactive image
18:6-Hydroxydopamine
16:(Redirected from
3936:
3612:
3604:
3595:
3586:
3527:
3488:
3242:N-Ethylhexedrone
3222:Hydroxybupropion
3062:Chlorphentermine
3039:
2748:
2726:Methoxyphenamine
2701:Lisdexamfetamine
2645:Levofenfluramine
2285:Phenpromethamine
1819:
1812:
1805:
1796:
1750:
1401:Dopamine quinone
1295:
1288:
1281:
1272:
1265:
1264:
1262:
1261:
1247:
1238:
1237:
1227:
1195:
1186:
1185:
1145:
1134:
1133:
1113:
1107:
1106:
1074:
1068:
1067:
1065:
1064:
1050:
1044:
1043:
1041:
1040:
1025:
1016:
1015:
979:
973:
972:
922:
914:
901:
900:
852:
846:
845:
803:
795:
652:substantia nigra
455:, also known as
431:
425:
422:
421:
377:Chemical formula
307:
306:
291:
289:
273:
253:
242:
228:
201:
193:
182:
171:
151:
131:
111:
87:
46:
37:
30:
21:
3944:
3943:
3939:
3938:
3937:
3935:
3934:
3933:
3909:
3908:
3907:
3902:
3838:Methoxphenidine
3716:
3681:Normetanephrine
3610:
3602:
3593:
3584:
3525:
3486:
3485:
3477:
3366:
3357:
3303:
3264:
3115:
3106:
3094:
3045:
3037:
3013:
2861:
2849:Tranylcypromine
2834:Pseudoephedrine
2746:
2741:Norfenfluramine
2716:Methamphetamine
2641:Dexfenfluramine
2576:Levoamphetamine
2523:
2421:Bromo-DragonFLY
2369:
2355:
2333:Methylphenidate
2264:
1834:Phenethylamines
1828:
1826:Phenethylamines
1823:
1793:
1788:
1744:
1718:
1694:Norfenfluramine
1684:Methamphetamine
1551:
1488:
1441:MPP (cyperquat)
1436:Methamphetamine
1347:ALDH inhibitors
1304:
1299:
1269:
1268:
1259:
1257:
1249:
1248:
1241:
1197:
1196:
1189:
1147:
1146:
1137:
1130:
1115:
1114:
1110:
1095:10.1139/v72-488
1076:
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1071:
1062:
1060:
1052:
1051:
1047:
1038:
1036:
1027:
1026:
1019:
981:
980:
976:
916:
915:
904:
854:
853:
849:
797:
796:
792:
787:
750:
735:
731:
722:
713:
711:Adverse effects
697:
692:
668:
646:
642:
638:
631:
627:
614:
598:
596:Available forms
589:
569:
562:
558:
554:
544:
539:
523:
503:
450:
443:
438:
437:
436: ?)
427:
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90:
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63:
62:
23:
22:
15:
12:
11:
5:
3942:
3940:
3932:
3931:
3926:
3921:
3919:Catecholamines
3911:
3910:
3904:
3903:
3901:
3900:
3895:
3890:
3885:
3880:
3875:
3872:Levosalbutamol
3865:
3860:
3855:
3850:
3845:
3840:
3835:
3830:
3825:
3820:
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3770:
3765:
3760:
3755:
3753:Desvenlafaxine
3750:
3745:
3740:
3735:
3730:
3724:
3722:
3718:
3717:
3715:
3714:
3709:
3704:
3696:
3688:
3683:
3678:
3668:
3666:Norepinephrine
3663:
3653:
3648:
3643:
3638:
3633:
3628:
3623:
3615:
3607:
3605:-Phenylalanine
3599:
3590:
3581:
3576:
3571:
3566:
3561:
3556:
3551:
3546:
3541:
3536:
3531:
3522:
3517:
3512:
3507:
3502:
3497:
3491:
3489:
3483:Catecholamines
3479:
3478:
3476:
3475:
3470:
3465:
3460:
3455:
3450:
3445:
3440:
3435:
3430:
3425:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3376:
3374:
3368:
3367:
3365:
3364:
3352:
3347:
3342:
3337:
3332:
3327:
3322:
3313:
3311:
3305:
3304:
3302:
3301:
3296:
3291:
3286:
3281:
3276:
3271:
3259:
3254:
3249:
3244:
3239:
3234:
3229:
3224:
3219:
3214:
3209:
3204:
3199:
3194:
3189:
3184:
3179:
3174:
3169:
3164:
3159:
3154:
3149:
3144:
3139:
3134:
3125:
3123:
3117:
3116:
3114:
3113:
3101:
3089:
3084:
3079:
3074:
3069:
3064:
3055:
3053:
3047:
3046:
3044:
3043:
3030:
3025:
3020:
3008:
3003:
2998:
2996:Methamnetamine
2993:
2988:
2983:
2978:
2973:
2968:
2963:
2958:
2953:
2948:
2943:
2938:
2933:
2928:
2923:
2918:
2913:
2908:
2903:
2898:
2893:
2888:
2883:
2878:
2873:
2868:
2856:
2851:
2846:
2841:
2836:
2831:
2826:
2821:
2816:
2811:
2806:
2801:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2761:
2756:
2751:
2743:
2738:
2733:
2728:
2723:
2713:
2708:
2703:
2698:
2693:
2688:
2683:
2678:
2673:
2668:
2663:
2658:
2653:
2648:
2634:
2629:
2624:
2619:
2617:Etilamfetamine
2614:
2609:
2604:
2599:
2594:
2589:
2584:
2579:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2518:
2513:
2508:
2503:
2498:
2493:
2488:
2483:
2478:
2473:
2468:
2463:
2458:
2453:
2448:
2443:
2438:
2433:
2428:
2423:
2418:
2413:
2408:
2403:
2398:
2393:
2388:
2379:
2377:
2371:
2370:
2368:
2367:
2362:
2350:
2345:
2336:
2335:
2330:
2322:
2314:
2306:
2298:
2293:
2287:
2282:
2280:Phenethylamine
2277:
2262:
2261:
2256:
2251:
2246:
2241:
2236:
2231:
2226:
2221:
2216:
2211:
2206:
2201:
2195:
2194:
2189:
2184:
2179:
2174:
2169:
2164:
2159:
2154:
2149:
2144:
2139:
2134:
2129:
2124:
2119:
2114:
2109:
2104:
2099:
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2034:
2029:
2024:
2019:
2014:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1974:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1934:
1929:
1924:
1919:
1914:
1909:
1904:
1899:
1894:
1889:
1884:
1879:
1874:
1868:
1867:
1862:
1857:
1852:
1847:
1838:
1836:
1830:
1829:
1824:
1822:
1821:
1814:
1807:
1799:
1790:
1789:
1749:
1746:
1745:
1743:
1742:
1737:
1732:
1726:
1724:
1720:
1719:
1717:
1716:
1711:
1706:
1701:
1696:
1691:
1686:
1681:
1676:
1671:
1666:
1661:
1656:
1651:
1646:
1641:
1636:
1631:
1626:
1617:
1612:
1607:
1602:
1597:
1592:
1587:
1582:
1577:
1572:
1567:
1561:
1559:
1553:
1552:
1550:
1549:
1544:
1539:
1534:
1529:
1524:
1519:
1514:
1509:
1504:
1498:
1496:
1490:
1489:
1487:
1486:
1481:
1476:
1471:
1466:
1461:
1456:
1448:
1443:
1438:
1433:
1428:
1423:
1418:
1413:
1408:
1403:
1398:
1393:
1388:
1383:
1378:
1373:
1368:
1363:
1358:
1344:
1342:6-OHDA quinone
1339:
1334:
1325:
1320:
1314:
1312:
1306:
1305:
1300:
1298:
1297:
1290:
1283:
1275:
1267:
1266:
1239:
1187:
1160:(5): 675–685.
1135:
1128:
1122:. IntechOpen.
1108:
1069:
1045:
1017:
974:
902:
873:10.1038/nn1265
867:(7): 726–735.
847:
812:(3): 151–167.
789:
788:
786:
783:
782:
781:
776:
771:
766:
761:
756:
749:
746:
733:
729:
721:
718:
712:
709:
696:
693:
691:
688:
676:norepinephrine
667:
664:
644:
640:
639:→ quinones + H
636:
629:
625:
613:
610:
597:
594:
588:
585:
568:
565:
560:
556:
552:
543:
540:
538:
535:
522:
519:
502:
499:
448:
445:
444:
439:
417:
416:
412:standard state
409:
406:
405:
402:
396:
395:
391:
387:
383:
380:
375:
372:
371:
367:
366:
364:
363:
360:
352:
351:
350:
347:
346:
344:
343:
339:
336:
335:
333:
329:
326:
325:
317:
316:
315:
312:
311:
309:
308:
295:
293:
281:
278:
277:
275:
274:
266:
264:
258:
257:
255:
254:
246:
244:
236:
233:
232:
230:
229:
221:
219:
213:
212:
210:
209:
205:
203:
195:
194:
184:
176:
175:
173:
172:
164:
162:
156:
155:
153:
152:
144:
142:
136:
135:
133:
132:
124:
122:
116:
115:
113:
112:
104:
102:
95:
92:
91:
89:
88:
80:
78:
73:
70:
69:
65:
64:
60:
59:
53:
52:
48:
47:
39:
38:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3941:
3930:
3927:
3925:
3922:
3920:
3917:
3916:
3914:
3899:
3896:
3894:
3891:
3889:
3888:Thiamphenicol
3886:
3884:
3883:Theodrenaline
3881:
3879:
3876:
3873:
3869:
3866:
3864:
3861:
3859:
3856:
3854:
3851:
3849:
3846:
3844:
3841:
3839:
3836:
3834:
3831:
3829:
3826:
3824:
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3798:Fluorolintane
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3739:
3736:
3734:
3731:
3729:
3726:
3725:
3723:
3721:Miscellaneous
3719:
3713:
3710:
3708:
3707:Phenylephrine
3705:
3703:
3701:
3697:
3695:
3693:
3689:
3687:
3686:Orciprenaline
3684:
3682:
3679:
3676:
3672:
3669:
3667:
3664:
3661:
3660:Levonordefrin
3657:
3654:
3652:
3649:
3647:
3644:
3642:
3639:
3637:
3634:
3632:
3629:
3627:
3624:
3622:
3620:
3616:
3614:
3608:
3606:
3600:
3597:
3591:
3588:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3540:
3537:
3535:
3532:
3529:
3523:
3521:
3518:
3516:
3513:
3511:
3508:
3506:
3503:
3501:
3498:
3496:
3493:
3492:
3490:
3484:
3480:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3378:
3377:
3375:
3373:
3369:
3363:
3360:
3356:
3353:
3351:
3348:
3346:
3343:
3341:
3338:
3336:
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3315:
3314:
3312:
3310:
3306:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3277:
3275:
3272:
3270:
3267:
3263:
3260:
3258:
3255:
3253:
3250:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3230:
3228:
3227:Methcathinone
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3208:
3205:
3203:
3200:
3198:
3195:
3193:
3190:
3188:
3185:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3127:
3126:
3124:
3122:
3118:
3112:
3109:
3105:
3102:
3100:
3097:
3093:
3090:
3088:
3085:
3083:
3082:Mephentermine
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3057:
3056:
3054:
3052:
3048:
3041:
3034:
3031:
3029:
3026:
3024:
3021:
3019:
3016:
3012:
3009:
3007:
3004:
3002:
2999:
2997:
2994:
2992:
2989:
2987:
2984:
2982:
2979:
2977:
2974:
2972:
2969:
2967:
2964:
2962:
2959:
2957:
2954:
2952:
2949:
2947:
2944:
2942:
2939:
2937:
2934:
2932:
2931:6-Chloro-MDMA
2929:
2927:
2924:
2922:
2919:
2917:
2914:
2912:
2909:
2907:
2904:
2902:
2899:
2897:
2894:
2892:
2889:
2887:
2884:
2882:
2879:
2877:
2874:
2872:
2869:
2867:
2864:
2860:
2857:
2855:
2854:Xylopropamine
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2810:
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2760:
2757:
2755:
2752:
2750:
2744:
2742:
2739:
2737:
2734:
2732:
2729:
2727:
2724:
2721:
2717:
2714:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2687:
2684:
2682:
2679:
2677:
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2646:
2642:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2592:Benzphetamine
2590:
2588:
2585:
2583:
2580:
2577:
2573:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2522:
2519:
2517:
2514:
2512:
2509:
2507:
2504:
2502:
2499:
2497:
2494:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2474:
2472:
2469:
2467:
2464:
2462:
2459:
2457:
2454:
2452:
2449:
2447:
2444:
2442:
2439:
2437:
2434:
2432:
2429:
2427:
2424:
2422:
2419:
2417:
2414:
2412:
2409:
2407:
2404:
2402:
2399:
2397:
2394:
2392:
2389:
2387:
2384:
2383:Psychedelics:
2381:
2380:
2378:
2376:
2372:
2366:
2363:
2361:
2358:
2354:
2351:
2349:
2346:
2344:
2341:
2338:
2337:
2334:
2331:
2329:
2327:
2323:
2321:
2319:
2315:
2313:
2311:
2307:
2305:
2303:
2299:
2297:
2294:
2292:(amphetamine)
2291:
2288:
2286:
2283:
2281:
2278:
2276:
2273:
2272:
2271:
2270:
2267:
2260:
2257:
2255:
2252:
2250:
2247:
2245:
2242:
2240:
2237:
2235:
2232:
2230:
2227:
2225:
2222:
2220:
2217:
2215:
2214:Isoproscaline
2212:
2210:
2207:
2205:
2202:
2200:
2199:Allylescaline
2197:
2196:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2163:
2160:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2115:
2113:
2110:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2043:
2040:
2038:
2035:
2033:
2030:
2028:
2025:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2005:
2003:
2000:
1998:
1995:
1993:
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1973:
1970:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1935:
1933:
1930:
1928:
1925:
1923:
1920:
1918:
1915:
1913:
1910:
1908:
1905:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1885:
1883:
1880:
1878:
1875:
1873:
1870:
1869:
1866:
1863:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1842:Psychedelics:
1840:
1839:
1837:
1835:
1831:
1827:
1820:
1815:
1813:
1808:
1806:
1801:
1800:
1797:
1786:
1785:
1781:
1777:
1773:
1772:Serotonergics
1769:
1768:Melatonergics
1765:
1764:Dopaminergics
1761:
1757:
1754:
1747:
1741:
1738:
1736:
1733:
1731:
1728:
1727:
1725:
1721:
1715:
1712:
1710:
1707:
1705:
1702:
1700:
1697:
1695:
1692:
1690:
1687:
1685:
1682:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1662:
1660:
1657:
1655:
1652:
1650:
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1630:
1627:
1625:
1623:
1618:
1616:
1613:
1611:
1608:
1606:
1603:
1601:
1598:
1596:
1593:
1591:
1588:
1586:
1583:
1581:
1578:
1576:
1573:
1571:
1568:
1566:
1565:2'-Amino-MPTP
1563:
1562:
1560:
1558:
1554:
1548:
1545:
1543:
1540:
1538:
1535:
1533:
1530:
1528:
1525:
1523:
1522:6-Hydroxydopa
1520:
1518:
1515:
1513:
1510:
1508:
1505:
1503:
1502:2'-Amino-MPTP
1500:
1499:
1497:
1495:
1494:Noradrenergic
1491:
1485:
1482:
1480:
1477:
1475:
1472:
1470:
1467:
1465:
1462:
1460:
1459:Norsalsolinol
1457:
1455:
1453:
1449:
1447:
1444:
1442:
1439:
1437:
1434:
1432:
1429:
1427:
1424:
1422:
1419:
1417:
1414:
1412:
1409:
1407:
1406:Fenpropathrin
1404:
1402:
1399:
1397:
1394:
1392:
1391:DOPAL quinone
1389:
1387:
1384:
1382:
1379:
1377:
1374:
1372:
1369:
1367:
1364:
1362:
1359:
1356:
1355:methylmercury
1352:
1348:
1345:
1343:
1340:
1338:
1335:
1333:
1331:
1326:
1324:
1321:
1319:
1316:
1315:
1313:
1311:
1307:
1303:
1296:
1291:
1289:
1284:
1282:
1277:
1276:
1273:
1256:
1252:
1246:
1244:
1240:
1235:
1231:
1226:
1221:
1217:
1213:
1209:
1205:
1204:Redox Biology
1201:
1194:
1192:
1188:
1183:
1179:
1175:
1171:
1167:
1163:
1159:
1155:
1151:
1144:
1142:
1140:
1136:
1131:
1125:
1121:
1120:
1112:
1109:
1104:
1100:
1096:
1092:
1088:
1084:
1080:
1073:
1070:
1059:
1055:
1049:
1046:
1035:
1031:
1030:"Oxidopamine"
1024:
1022:
1018:
1013:
1009:
1005:
1001:
997:
993:
989:
985:
978:
975:
970:
966:
962:
958:
954:
950:
946:
942:
938:
934:
930:
926:
921:
913:
911:
909:
907:
903:
898:
894:
890:
886:
882:
878:
874:
870:
866:
862:
858:
851:
848:
843:
839:
835:
831:
827:
823:
819:
815:
811:
807:
802:
794:
791:
784:
780:
777:
775:
772:
770:
769:Norsalsolinol
767:
765:
762:
760:
757:
755:
752:
751:
747:
745:
743:
737:
727:
719:
717:
710:
708:
706:
702:
694:
689:
687:
685:
681:
677:
673:
665:
663:
661:
657:
653:
648:
633:
623:
622:noradrenaline
619:
611:
609:
607:
603:
595:
593:
586:
584:
580:
578:
574:
566:
564:
549:
541:
536:
534:
532:
528:
520:
518:
516:
512:
511:neurotoxicity
508:
500:
498:
496:
492:
488:
483:
481:
480:noradrenergic
477:
473:
470:
466:
462:
458:
454:
442:
435:
430:
413:
407:
403:
401:
398:
397:
381:
378:
374:
373:
368:
359:
355:
348:
334:
324:
320:
313:
305:
301:
300:DTXSID0036768
297:
296:
294:
284:
280:
279:
272:
268:
267:
265:
263:
260:
259:
252:
248:
247:
245:
239:
235:
234:
227:
223:
222:
220:
218:
215:
214:
207:
206:
204:
202:
197:
196:
192:
188:
185:
183:
181:ECHA InfoCard
178:
177:
170:
166:
165:
163:
161:
158:
157:
150:
146:
145:
143:
141:
138:
137:
130:
126:
125:
123:
121:
118:
117:
110:
106:
105:
103:
99:
94:
93:
86:
82:
81:
79:
76:
72:
71:
66:
58:
54:
49:
45:
40:
36:
31:
19:
3878:Solriamfetol
3793:Famprofazone
3699:
3691:
3677:-Octopamine)
3674:
3671:Norfenefrine
3626:Metanephrine
3618:
3574:Isoprenaline
3530:(Dextrodopa)
3515:Adrenochrome
3473:Pyrovalerone
3379:
3358:
3317:Entactogens:
3316:
3266:Entactogens:
3265:
3212:Ethcathinone
3128:
3107:
3096:Entactogens:
3095:
3058:
3051:Phentermines
3014:
2863:Entactogens:
2862:
2859:Zylofuramine
2637:Fenfluramine
2632:Fenethylline
2582:Amphetaminil
2563:Amfepentorex
2524:
2382:
2375:Amphetamines
2356:
2340:Entactogens:
2339:
2325:
2317:
2309:
2301:
2265:
2263:
2239:Metaescaline
1841:
1752:
1751:
1639:Fenfluramine
1621:
1557:Serotonergic
1541:
1463:
1451:
1381:DOPA quinone
1329:
1310:Dopaminergic
1258:. Retrieved
1254:
1207:
1203:
1157:
1153:
1118:
1111:
1086:
1082:
1072:
1061:. Retrieved
1057:
1048:
1037:. Retrieved
1033:
990:(1): 57–73.
987:
983:
977:
928:
924:
864:
860:
850:
809:
805:
793:
738:
723:
714:
698:
669:
649:
634:
615:
599:
590:
581:
573:autoxidation
570:
548:benzenetriol
545:
524:
504:
487:Parkinsonism
484:
476:dopaminergic
464:
460:
456:
452:
451:
149:ChEMBL337702
68:Identifiers
28:Oxidopamine
3898:Venlafaxine
3863:Pronethalol
3833:Methoxamine
3763:Dizocilpine
3758:Diphenidine
3733:Amidephrine
3694:-Octopamine
3631:Metaraminol
3598:(Droxidopa)
3544:Epinephrine
3534:Dimetofrine
3380:Stimulants:
3359:Stimulants:
3187:Brephedrone
3177:Amfepramone
3129:Stimulants:
3111:Cericlamine
3092:Phentermine
3072:Clortermine
3059:Stimulants:
2839:Sibutramine
2824:Prenylamine
2759:Oxifentorex
2711:Metaraminol
2651:Fenproporex
2622:Fencamfamin
2602:Clobenzorex
2568:Amphetamine
2525:Stimulants:
2266:Stimulants:
2224:Macromerine
1760:Adrenergics
1644:Haloperidol
1411:Haloperidol
1361:Amphetamine
684:desipramine
453:Oxidopamine
370:Properties
187:100.013.493
129:CHEBI:78741
3913:Categories
3868:Salbutamol
3803:Hexapradol
3783:Etafedrine
3778:Ephenidine
3773:Dopexamine
3768:Dobutamine
3748:Denopamine
3738:Arbutamine
3712:Synephrine
3646:Methyldopa
3641:Metirosine
3589:(Levodopa)
3579:Isoetarine
3564:Fenclonine
3554:Etilefrine
3468:Prolintane
3299:Mephedrone
3262:Radafaxine
3252:Pentedrone
3232:Methedrone
3192:Buphedrone
3182:Benzedrone
3121:Cathinones
3033:Selegiline
3023:Amiflamine
2819:Pholedrine
2769:Ortetamine
2764:Oxilofrine
2696:Lefetamine
2686:Iofetamine
2671:Furfenorex
2666:Formetorex
2656:Flucetorex
2587:Benfluorex
2558:Amfecloral
2553:Alfetamine
2426:D-Deprenyl
2343:Lophophine
2254:Psi-2C-T-4
2249:Proscaline
2219:Jimscaline
1580:2,4,5-THMA
1479:Salsolinol
1351:disulfiram
1323:2,4,5-THMA
1260:2022-03-04
1210:: 101377.
1063:2022-03-04
1039:2022-03-04
931:: 109380.
785:References
666:Metabolism
660:superoxide
612:Mechanisms
507:neurotoxin
400:Molar mass
271:8HW4YBZ748
160:ChemSpider
96:3D model (
75:CAS Number
3848:PARGY-LAD
3743:Cafedrine
3702:-Tyramine
3656:Nordefrin
3636:Metaterol
3621:-Tyramine
3613:-Tyrosine
3569:Ibopamine
3458:Naphyrone
3289:Methylone
3257:Pentylone
3202:Cathinone
3197:Bupropion
3040:-Deprenyl
2706:Mefenorex
2676:Gepefrine
2627:Fencamine
2612:Ephedrine
2548:Acridorex
2275:Hordenine
2234:Mescaline
2127:2C-T-22.5
1865:25N-NBOMe
1860:25I-NBOMe
1855:25D-NBOMe
1850:25C-NBOMe
1845:25B-NBOMe
1753:See also:
1575:2,4,5-THA
1507:2,4,5-THA
1318:2,4,5-THA
1174:0891-5849
1103:0008-4042
1028:PubChem.
969:231622597
953:0009-2797
881:1546-1726
826:1476-3524
587:Synthesis
542:Structure
469:synthetic
208:214-842-3
200:EC Number
85:1199-18-4
3853:Phenibut
3539:Dopamine
3520:Ciladopa
3510:a-Me-TRA
3350:Eutylone
3340:Butylone
3284:Ethylone
3279:Butylone
3269:3,4-DMMC
3217:Eutylone
3167:4-MeMABP
3087:Pentorex
3077:Etolorex
3067:Cloforex
2844:Tiflorex
2736:Morforex
2661:Fludorex
2416:Beatrice
2209:Escaline
1723:Unsorted
1547:Xylamine
1474:Rotenone
1469:Paraquat
1426:Mancozeb
1396:Dopamine
1376:Dieldrin
1234:31760358
1182:17291991
1012:22599841
1004:15708628
961:33450287
889:15195095
842:25556004
834:17449457
774:Rotenone
748:See also
726:toxicity
720:Toxicity
695:Efficacy
672:dopamine
618:dopamine
608:(SNpc).
527:dopamine
3893:UWA-101
3858:PRO-LAD
3788:ETH-LAD
3549:Epinine
3505:a-Me-DA
3428:4-MePPP
3423:4-MePHP
3418:4-MePBP
3330:Ariadne
3108:Others:
3018:3,4-DCA
3015:Others:
2966:2,3-MDA
2951:6-MAPDB
2916:5-MAPDB
2597:Cathine
2521:ZDCM-04
2506:Psi-DOM
2491:Ganesha
2357:Others:
2172:2C-T-33
2167:2C-T-32
2162:2C-T-31
2157:2C-T-30
2152:2C-T-28
2147:2C-T-27
2142:2C-T-25
2137:2C-T-24
2132:2C-T-23
2122:2C-T-22
2117:2C-T-21
2112:2C-T-20
2107:2C-T-19
2102:2C-T-18
2097:2C-T-17
2092:2C-T-16
2087:2C-T-15
2082:2C-T-14
2077:2C-T-13
2072:2C-T-12
2067:2C-T-11
2062:2C-T-10
1877:2C-B-AN
1610:5,7-DHT
1605:5,6-DHT
1590:3,4-DCA
1570:2,4-DCA
1527:DOPEGAL
1517:5,7-DHT
1512:5,6-DHT
1371:Daidzin
1366:Benomyl
1349:(e.g.,
1337:5,6-DHT
1225:6880099
933:Bibcode
501:History
467:, is a
434:what is
432: (
394:
238:PubChem
3808:IP-LAD
3728:AL-LAD
3500:6-OHDA
3035:(also
3028:DiFMDA
2946:6-MAPB
2936:6-EAPB
2926:6-APDB
2911:5-MAPB
2901:5-EAPB
2896:5-APDB
2501:MMDA-2
2401:3C-MAL
2353:MDMPEA
2204:DESOXY
2182:2C-TFM
2177:2C-TFE
2057:2C-T-9
2052:2C-T-8
2047:2C-T-7
2042:2C-T-6
2037:2C-T-5
2032:2C-T-4
2027:2C-T-3
2022:2C-T-2
1997:2C-O-4
1987:2C-NH2
1962:2C-G-N
1957:2C-G-6
1952:2C-G-5
1947:2C-G-4
1942:2C-G-3
1937:2C-G-2
1932:2C-G-1
1730:5-HIAL
1232:
1222:
1180:
1172:
1126:
1101:
1010:
1002:
967:
959:
951:
897:952173
895:
887:
879:
840:
832:
824:
779:FAUC50
461:6-OHDA
429:verify
426:
354:SMILES
226:D05294
140:ChEMBL
51:Names
3843:MT-45
3596:-DOPS
3587:-DOPA
3528:-DOPA
3495:6-FNE
3438:MOPVP
3433:MOPPP
3408:MDPPP
3403:MDPBP
3398:α-PVP
3393:α-PPP
3388:α-PHP
3383:α-PBP
3325:4-MAB
3320:4-CAB
3274:3-MMC
3172:4-MPD
3162:4-MEC
3157:4-FMC
3152:4-EMC
3147:4-CMC
3142:4-BMC
3132:3-FMC
3104:MDMPH
3001:MMDMA
2981:MDHMA
2921:6-APB
2891:5-APB
2886:4-MTA
2881:4-MMA
2871:4-FMA
2543:3-FMA
2533:2-FMA
2486:DOTFM
2441:DMMDA
2436:DMCPA
2411:Aleph
2391:3C-BZ
2386:3C-AL
2365:DMPEA
2348:MDPEA
2259:TCB-2
2229:MEPEA
2187:2C-YN
2012:2C-SE
2007:2C-Ph
1977:2C-iP
1917:2C-EF
1902:2C-CP
1897:2C-CN
1887:2C-Bu
1882:2C-Bn
1740:RHPTP
1600:5-IAI
1532:DSP-4
1484:Ziram
1431:Maneb
1386:DOPAL
1008:S2CID
965:S2CID
893:S2CID
838:S2CID
759:DSP-4
521:Usage
463:) or
319:InChI
120:ChEBI
98:JSmol
3453:MPPP
3448:MPHP
3443:MPBP
3413:MDPV
3355:MBDB
3345:EBDB
3137:4-MC
3099:MDPH
2991:MDOH
2976:MDEA
2941:6-IT
2906:5-IT
2876:4-MA
2866:4-FA
2809:PMMA
2804:PMEA
2789:PFMA
2538:3-FA
2528:2-FA
2516:TeMA
2496:MMDA
2481:DOPR
2461:DOET
2456:DOEF
2406:3C-P
2396:3C-E
2192:2C-V
2017:2C-T
2002:2C-P
1992:2C-O
1982:2C-N
1972:2C-I
1967:2C-H
1927:2C-G
1922:2C-F
1912:2C-E
1907:2C-D
1892:2C-C
1872:2C-B
1735:RHPP
1709:PCMA
1689:MMAI
1674:MDEA
1669:MDAI
1659:MBDB
1654:HPTP
1585:3-CA
1446:MPTP
1421:HPTP
1230:PMID
1178:PMID
1170:ISSN
1124:ISBN
1099:ISSN
1000:PMID
957:PMID
949:ISSN
885:PMID
877:ISSN
830:PMID
822:ISSN
764:MPTP
656:MPTP
620:and
505:The
478:and
262:UNII
251:4624
217:KEGG
169:4463
3463:PEP
3335:BDB
3237:NEB
3011:TAP
2961:IAP
2956:EDA
2799:PMA
2794:PIA
2784:PFA
2779:PCA
2774:PBA
2731:MMA
2511:TMA
2476:DON
2471:DOM
2466:DOI
2451:DOC
2446:DOB
2431:DMA
2360:BOH
1714:PIA
1704:PCA
1699:PBA
1649:HPP
1634:DCA
1629:αET
1416:HPP
1220:PMC
1212:doi
1162:doi
1091:doi
992:doi
941:doi
929:336
869:doi
814:doi
288:EPA
241:CID
3915::
2643:,
2574:,
1782:•
1778:•
1774:•
1770:•
1766:•
1762:•
1758:•
1620:α,
1353:,
1328:5-
1253:.
1242:^
1228:.
1218:.
1208:28
1206:.
1202:.
1190:^
1176:.
1168:.
1158:42
1156:.
1152:.
1138:^
1097:.
1087:50
1085:.
1081:.
1056:.
1032:.
1020:^
1006:.
998:.
988:48
986:.
963:.
955:.
947:.
939:.
927:.
923:.
905:^
891:.
883:.
875:.
863:.
859:.
836:.
828:.
820:.
810:11
808:.
804:.
744:.
678:)
647:.
559:NO
557:11
533:.
517:.
497:.
390:NO
388:11
3874:)
3870:(
3700:p
3692:p
3675:m
3673:(
3662:)
3658:(
3619:m
3611:L
3603:L
3594:L
3585:L
3526:D
3042:)
3038:D
2747:L
2722:)
2647:)
2639:(
2578:)
2570:(
2326:p
2318:o
2310:N
2302:m
1818:e
1811:t
1804:v
1622:N
1452:N
1357:)
1330:S
1294:e
1287:t
1280:v
1263:.
1236:.
1214::
1184:.
1164::
1132:.
1105:.
1093::
1066:.
1042:.
1014:.
994::
971:.
943::
935::
899:.
871::
865:7
844:.
816::
734:2
732:O
730:2
645:2
643:O
641:2
637:2
630:2
628:O
626:2
561:3
555:H
553:8
551:C
459:(
424:N
392:3
386:H
384:8
382:C
290:)
286:(
100:)
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
