581:
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.
293:
180:
518:, 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
33:
24:
717:, 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
409:
580:
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
571:
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
593:, 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
539:
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;
728:
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
704:
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).
1239:
502:
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
605:
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
3396:
971:
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".
3391:
422:
1281:
568:(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.
1105:
Hernandez-Baltazar, Daniel; Nadella, Rasajna; Jesus
Rovirosa-Hernandez, Maria de; Zavala-Flores, Laura Mireya; Jarquin, Christian de Jesus Rosas (2017-12-20).
342:
3426:
3421:
651:
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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2424:
3441:
3416:
3436:
3431:
3411:
3406:
1805:
1772:
1139:"Molecular mechanisms of 6-hydroxydopamine-induced cytotoxicity in PC12 cells: Involvement of hydrogen peroxide-dependent and -independent action"
844:
Höglinger, Günter U.; Rizk, Pamela; Muriel, Marie P.; Duyckaerts, Charles; Oertel, Wolfgang H.; Caille, Isabelle; Hirsch, Etienne C. (July 2004).
2444:
1764:
3912:
2969:
1116:
3811:
1768:
1274:
1187:
Farzam, Ali; Chohan, Karan; Strmiskova, Miroslava; Hewitt, Sarah J.; Park, David S.; Pezacki, John P.; Özcelik, Dennis (January 2020).
3917:
2341:
2469:
2459:
2439:
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692:(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).
3376:
3371:
2959:
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2719:
1798:
1652:
1647:
1525:
621:), catecholamine quinones and reactive oxygen species (ROS). These quinones can attack endocellular nucleophillic groups.
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1744:
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3313:
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2353:
1718:
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1306:
560:
The toxin oxidopamine is a relatively unstable compound. In certain experimental conditions, oxidopamine will undergo
271:
2944:
1822:
1814:
1697:
613:. Within the neuron, oxidopamine is oxidized by monoamine oxidase producing the toxic products hydrogen peroxide (H
97:
3257:
3087:
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187:
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1608:
503:
498:
oxidopamine has first been described in 1959. Years later, in 1968 the first model exploiting oxidopamine
483:
1573:
1108:
Animal Model of
Parkinson Disease: Neuroinflammation and Apoptosis in the 6-Hydroxydopamine-Induced Model
643:
of the brain must be destroyed, and this is often achieved either with oxidopamine or another neurotoxin
137:
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3135:
3120:
3109:
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1687:
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908:
906:
Pantic, Igor; Cumic, Jelena; Skodric, Sanja
Radojevic; Dugalic, Stefan; Brodski, Claude (2021-02-25).
671:. Oxidopamine is often used in conjunction with a selective noradrenaline reuptake inhibitor (such as
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3150:
3140:
3130:
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2782:
2734:
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696:. The supersensitivity phase lasts for up to 6 months, and can be maintained by repeated injections.
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45:
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Oxidopamine is administered via an injection and causes an increase of outflow, and a decrease for
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63:
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3160:
3155:
2257:
996:
953:
881:
826:
457:
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2115:
909:"Oxidopamine and oxidative stress: Recent advances in experimental physiology and pharmacology"
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1682:
1672:
1642:
1424:
1409:
1189:"A functionalized hydroxydopamine quinone links thiol modification to neuronal cell death"
639:
In order to induce
Parkinsonism in animals, around 70% of the dopaminergic neurons in the
157:
73:
647:. Both these agents likely destroy neurons by generating reactive oxygen species such as
1154:
925:
535:
Oxidopamine is a neurotoxic, solid and organic compound, derived from dopamine. It is a
292:
179:
117:
3860:
3741:
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2268:
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2212:
1632:
1399:
1349:
1204:
672:
23:
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2414:
2348:
2331:
2242:
2237:
2207:
1467:
1339:
933:
846:"Dopamine depletion impairs precursor cell proliferation in Parkinson disease"
648:
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388:
148:
1162:
1091:
941:
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1848:
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3055:
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2197:
1535:
1462:
1457:
1414:
1384:
1364:
845:
762:
714:
660:
606:
515:
3881:
3846:
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2939:
2904:
2585:
2509:
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2140:
2105:
2095:
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2065:
1359:
1354:
806:
226:
188:
3796:
3716:
3581:
3572:
3513:
3016:
2934:
2924:
2914:
2899:
2889:
2884:
2489:
2389:
2192:
2170:
2165:
2045:
2040:
2035:
2020:
2015:
2010:
1985:
1950:
1945:
1940:
1935:
1930:
1925:
1920:
789:
767:
128:
1083:
399:
Except where otherwise noted, data are given for materials in their
1637:
1429:
1404:
861:
478:
in laboratory animals by lesioning the dopaminergic neurons of the
316:
InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2
214:
3831:
2989:
2909:
2879:
2429:
2379:
2374:
2247:
2175:
2000:
1965:
1905:
1890:
1783:
1520:
1419:
747:
326:
InChI=1/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2
108:
96:
86:
474:
The main use for oxidopamine in scientific research is to induce
3343:
2974:
2929:
2894:
2394:
2384:
2180:
2005:
1990:
1980:
1970:
1960:
1955:
1915:
1910:
1900:
1895:
1880:
1860:
1434:
752:
644:
482:, in order to develop and test new medicines and treatments for
205:
1787:
1263:
787:
Simola, Nicola; Morelli, Micaela; Carta, Anna R. (2007-09-01).
514:
The toxin oxidopamine is an antagonist of the neurotransmitter
3816:
276:
552:. The melting point of oxidopamine is 232 degrees celsius.
417:
713:
There are several ways in which oxidopamine may cause
1234:
1232:
790:"The 6-Hydroxydopamine model of parkinson's disease"
3709:
3470:
3359:
3296:
3108:
3038:
2362:
1821:
1711:
1544:
1481:
1297:
1066:Wehrli, Pius A.; Pigott, F.; Chu, V. (1972-09-15).
1240:"Oxidopamine - an overview | ScienceDirect Topics"
1043:"Oxidopamine - an overview | ScienceDirect Topics"
907:
788:
725:generation, or direct inhibition of mitochondria.
238:
901:
899:
897:
895:
675:) to selectively destroy dopaminergic neurons.
659:6-OHDA is thought to enter the neurons via the
72:
1799:
1275:
8:
463:used by researchers to selectively destroy
1806:
1792:
1784:
1282:
1268:
1260:
589:Oxidopamine is directly injected into the
291:
178:
156:
15:
1212:
1012:
1010:
258:
779:
564:. This may result in the production of
347:
312:
287:
1068:"A New Synthesis of 6-Hydroxydopamine"
169:
1182:
1180:
319:Key: DIVDFFZHCJEHGG-UHFFFAOYSA-N
136:
116:
7:
1132:
1130:
1128:
3812:Lysergic acid 2,4-dimethylazetidide
1155:10.1016/j.freeradbiomed.2006.12.004
329:Key: DIVDFFZHCJEHGG-UHFFFAOYAG
229:
213:
50:5-(2-Aminoethyl)benzene-1,2,4-triol
14:
1143:Free Radical Biology and Medicine
985:10.1016/j.brainresrev.2004.08.004
407:
31:
22:
2743:N,alpha-Diethylphenylethylamine
1773:Monoamine metabolism modulators
914:Chemico-Biological Interactions
403:(at 25 °C , 100 kPa).
595:Substantia nigra pars compacta
480:substantia nigra pars compacta
454:2,4,5-trihydroxyphenethylamine
1:
1765:Monoamine reuptake inhibitors
1745:Receptor/signaling modulators
1072:Canadian Journal of Chemistry
3913:Peripherally selective drugs
3807:Lysergic acid 2-butyl amide
1205:10.1016/j.redox.2019.101377
3934:
3817:Lysergic acid diethylamide
1769:Monoamine releasing agents
393:169.18 g/mol
3918:Monoaminergic neurotoxins
1737:
1291:Monoaminergic neurotoxins
973:Brain Res. Brain Res. Rev
934:10.1016/j.cbi.2021.109380
679:Efficacy and side effects
397:
358:
338:
303:
56:
44:
39:
30:
21:
2707:(Dextromethamphetamine,
1023:pubchem.ncbi.nlm.nih.gov
556:Reactivity and reactions
526:Structure and reactivity
461:monoaminergic neurotoxin
3361:Phenylalkylpyrrolidines
3283:Methylenedioxycathinone
2960:3,4-MDA (tenamfetamine)
743:5,7-Dihydroxytryptamine
566:reactive oxygen species
2285:β-Methylphenethylamine
2279:α-Methylphenethylamine
795:Neurotoxicity Research
471:neurons in the brain.
3476:(and close relatives)
2975:MDMA (midomafetamine)
2317:-Methylphenethylamine
2309:-Methylphenethylamine
2301:-Methylphenethylamine
2293:-Methylphenethylamine
1668:MDMA (midomafetamine)
1244:www.sciencedirect.com
1047:www.sciencedirect.com
669:reuptake transporters
624:6-hydroxidopamine + O
591:nigrostriatal pathway
3640:N,N-Dimethyldopamine
3298:Phenylisobutylamines
2995:Naphthylaminopropane
2680:Isopropylamphetamine
2670:4-Hydroxyamphetamine
1531:Oxidopamine (6-OHDA)
1453:Oxidopamine (6-OHDA)
1443:-Methylnorsalsolinol
690:intraocular pressure
572:to a lesser extent.
520:Lesch-Nyhan syndrome
350:c1c(c(cc(c1O)O)O)CCN
46:Preferred IUPAC name
3802:Lysergic acid amide
3548:Ethylnorepinephrine
3351:Phenylisobutylamine
2803:Phenylpropanolamine
2738:-Norpseudoephedrine
2709:Levomethamphetamine
2596:Dimethylamphetamine
1653:MDA (tenamfetamine)
1584:4-CAB (α-ethyl-PCA)
1526:MDA (tenamfetamine)
926:2021CBI...33609380P
850:Nature Neuroscience
731:blood brain barrier
694:adrenergic agonists
663:and noradrenaline (
504:Parkinson's disease
484:Parkinson's disease
18:
2258:Phenylethanolamine
1321:-Cysteinyldopamine
807:10.1007/BF03033565
430:Infobox references
16:
3895:
3894:
3236:N-Ethylpentedrone
3196:Dimethylcathinone
2818:Propylamphetamine
2561:Dextroamphetamine
2233:Methallylescaline
1781:
1780:
1776:
1613:-Dimethyldopamine
1604:α-Me-DA (3,4-DHA)
1118:978-1-78923-165-6
1078:(18): 3075–3079.
446:6-hydroxydopamine
438:Chemical compound
436:
435:
272:CompTox Dashboard
98:Interactive image
3925:
3601:
3593:
3584:
3575:
3516:
3477:
3231:N-Ethylhexedrone
3211:Hydroxybupropion
3051:Chlorphentermine
3028:
2737:
2715:Methoxyphenamine
2690:Lisdexamfetamine
2634:Levofenfluramine
2274:Phenpromethamine
1808:
1801:
1794:
1785:
1739:
1390:Dopamine quinone
1284:
1277:
1270:
1261:
1254:
1253:
1251:
1250:
1236:
1227:
1226:
1216:
1184:
1175:
1174:
1134:
1123:
1122:
1102:
1096:
1095:
1063:
1057:
1056:
1054:
1053:
1039:
1033:
1032:
1030:
1029:
1014:
1005:
1004:
968:
962:
961:
911:
903:
890:
889:
841:
835:
834:
792:
784:
641:substantia nigra
444:, also known as
420:
414:
411:
410:
366:Chemical formula
296:
295:
280:
278:
262:
242:
231:
217:
190:
182:
171:
160:
140:
120:
100:
76:
35:
26:
19:
3933:
3932:
3928:
3927:
3926:
3924:
3923:
3922:
3898:
3897:
3896:
3891:
3827:Methoxphenidine
3705:
3670:Normetanephrine
3599:
3591:
3582:
3573:
3514:
3475:
3474:
3466:
3355:
3346:
3292:
3253:
3104:
3095:
3083:
3034:
3026:
3002:
2850:
2838:Tranylcypromine
2823:Pseudoephedrine
2735:
2730:Norfenfluramine
2705:Methamphetamine
2630:Dexfenfluramine
2565:Levoamphetamine
2512:
2410:Bromo-DragonFLY
2358:
2344:
2322:Methylphenidate
2253:
1823:Phenethylamines
1817:
1815:Phenethylamines
1812:
1782:
1777:
1733:
1707:
1683:Norfenfluramine
1673:Methamphetamine
1540:
1477:
1430:MPP (cyperquat)
1425:Methamphetamine
1336:ALDH inhibitors
1293:
1288:
1258:
1257:
1248:
1246:
1238:
1237:
1230:
1186:
1185:
1178:
1136:
1135:
1126:
1119:
1104:
1103:
1099:
1084:10.1139/v72-488
1065:
1064:
1060:
1051:
1049:
1041:
1040:
1036:
1027:
1025:
1016:
1015:
1008:
970:
969:
965:
905:
904:
893:
843:
842:
838:
786:
785:
781:
776:
739:
724:
720:
711:
702:
700:Adverse effects
686:
681:
657:
635:
631:
627:
620:
616:
603:
587:
585:Available forms
578:
558:
551:
547:
543:
533:
528:
512:
492:
439:
432:
427:
426:
425: ?)
416:
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103:
90:
79:
66:
52:
51:
12:
11:
5:
3931:
3929:
3921:
3920:
3915:
3910:
3908:Catecholamines
3900:
3899:
3893:
3892:
3890:
3889:
3884:
3879:
3874:
3869:
3864:
3861:Levosalbutamol
3854:
3849:
3844:
3839:
3834:
3829:
3824:
3819:
3814:
3809:
3804:
3799:
3794:
3789:
3784:
3779:
3774:
3769:
3764:
3759:
3754:
3749:
3744:
3742:Desvenlafaxine
3739:
3734:
3729:
3724:
3719:
3713:
3711:
3707:
3706:
3704:
3703:
3698:
3693:
3685:
3677:
3672:
3667:
3657:
3655:Norepinephrine
3652:
3642:
3637:
3632:
3627:
3622:
3617:
3612:
3604:
3596:
3594:-Phenylalanine
3588:
3579:
3570:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3511:
3506:
3501:
3496:
3491:
3486:
3480:
3478:
3472:Catecholamines
3468:
3467:
3465:
3464:
3459:
3454:
3449:
3444:
3439:
3434:
3429:
3424:
3419:
3414:
3409:
3404:
3399:
3394:
3389:
3384:
3379:
3374:
3365:
3363:
3357:
3356:
3354:
3353:
3341:
3336:
3331:
3326:
3321:
3316:
3311:
3302:
3300:
3294:
3293:
3291:
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3248:
3243:
3238:
3233:
3228:
3223:
3218:
3213:
3208:
3203:
3198:
3193:
3188:
3183:
3178:
3173:
3168:
3163:
3158:
3153:
3148:
3143:
3138:
3133:
3128:
3123:
3114:
3112:
3106:
3105:
3103:
3102:
3090:
3078:
3073:
3068:
3063:
3058:
3053:
3044:
3042:
3036:
3035:
3033:
3032:
3019:
3014:
3009:
2997:
2992:
2987:
2985:Methamnetamine
2982:
2977:
2972:
2967:
2962:
2957:
2952:
2947:
2942:
2937:
2932:
2927:
2922:
2917:
2912:
2907:
2902:
2897:
2892:
2887:
2882:
2877:
2872:
2867:
2862:
2857:
2845:
2840:
2835:
2830:
2825:
2820:
2815:
2810:
2805:
2800:
2795:
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2745:
2740:
2732:
2727:
2722:
2717:
2712:
2702:
2697:
2692:
2687:
2682:
2677:
2672:
2667:
2662:
2657:
2652:
2647:
2642:
2637:
2623:
2618:
2613:
2608:
2606:Etilamfetamine
2603:
2598:
2593:
2588:
2583:
2578:
2573:
2568:
2554:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2507:
2502:
2497:
2492:
2487:
2482:
2477:
2472:
2467:
2462:
2457:
2452:
2447:
2442:
2437:
2432:
2427:
2422:
2417:
2412:
2407:
2402:
2397:
2392:
2387:
2382:
2377:
2368:
2366:
2360:
2359:
2357:
2356:
2351:
2339:
2334:
2325:
2324:
2319:
2311:
2303:
2295:
2287:
2282:
2276:
2271:
2269:Phenethylamine
2266:
2251:
2250:
2245:
2240:
2235:
2230:
2225:
2220:
2215:
2210:
2205:
2200:
2195:
2190:
2184:
2183:
2178:
2173:
2168:
2163:
2158:
2153:
2148:
2143:
2138:
2133:
2128:
2123:
2118:
2113:
2108:
2103:
2098:
2093:
2088:
2083:
2078:
2073:
2068:
2063:
2058:
2053:
2048:
2043:
2038:
2033:
2028:
2023:
2018:
2013:
2008:
2003:
1998:
1993:
1988:
1983:
1978:
1973:
1968:
1963:
1958:
1953:
1948:
1943:
1938:
1933:
1928:
1923:
1918:
1913:
1908:
1903:
1898:
1893:
1888:
1883:
1878:
1873:
1868:
1863:
1857:
1856:
1851:
1846:
1841:
1836:
1827:
1825:
1819:
1818:
1813:
1811:
1810:
1803:
1796:
1788:
1779:
1778:
1738:
1735:
1734:
1732:
1731:
1726:
1721:
1715:
1713:
1709:
1708:
1706:
1705:
1700:
1695:
1690:
1685:
1680:
1675:
1670:
1665:
1660:
1655:
1650:
1645:
1640:
1635:
1630:
1625:
1620:
1615:
1606:
1601:
1596:
1591:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1550:
1548:
1542:
1541:
1539:
1538:
1533:
1528:
1523:
1518:
1513:
1508:
1503:
1498:
1493:
1487:
1485:
1479:
1478:
1476:
1475:
1470:
1465:
1460:
1455:
1450:
1445:
1437:
1432:
1427:
1422:
1417:
1412:
1407:
1402:
1397:
1392:
1387:
1382:
1377:
1372:
1367:
1362:
1357:
1352:
1347:
1333:
1331:6-OHDA quinone
1328:
1323:
1314:
1309:
1303:
1301:
1295:
1294:
1289:
1287:
1286:
1279:
1272:
1264:
1256:
1255:
1228:
1176:
1149:(5): 675–685.
1124:
1117:
1111:. IntechOpen.
1097:
1058:
1034:
1006:
963:
891:
862:10.1038/nn1265
856:(7): 726–735.
836:
801:(3): 151–167.
778:
777:
775:
772:
771:
770:
765:
760:
755:
750:
745:
738:
735:
722:
718:
710:
707:
701:
698:
685:
682:
680:
677:
665:norepinephrine
656:
653:
633:
629:
628:→ quinones + H
625:
618:
614:
602:
599:
586:
583:
577:
574:
557:
554:
549:
545:
541:
532:
529:
527:
524:
511:
508:
491:
488:
437:
434:
433:
428:
406:
405:
401:standard state
398:
395:
394:
391:
385:
384:
380:
376:
372:
369:
364:
361:
360:
356:
355:
353:
352:
349:
341:
340:
339:
336:
335:
333:
332:
328:
325:
324:
322:
318:
315:
314:
306:
305:
304:
301:
300:
298:
297:
284:
282:
270:
267:
266:
264:
263:
255:
253:
247:
246:
244:
243:
235:
233:
225:
222:
221:
219:
218:
210:
208:
202:
201:
199:
198:
194:
192:
184:
183:
173:
165:
164:
162:
161:
153:
151:
145:
144:
142:
141:
133:
131:
125:
124:
122:
121:
113:
111:
105:
104:
102:
101:
93:
91:
84:
81:
80:
78:
77:
69:
67:
62:
59:
58:
54:
53:
49:
48:
42:
41:
37:
36:
28:
27:
13:
10:
9:
6:
4:
3:
2:
3930:
3919:
3916:
3914:
3911:
3909:
3906:
3905:
3903:
3888:
3885:
3883:
3880:
3878:
3877:Thiamphenicol
3875:
3873:
3872:Theodrenaline
3870:
3868:
3865:
3862:
3858:
3855:
3853:
3850:
3848:
3845:
3843:
3840:
3838:
3835:
3833:
3830:
3828:
3825:
3823:
3820:
3818:
3815:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3788:
3787:Fluorolintane
3785:
3783:
3780:
3778:
3775:
3773:
3770:
3768:
3765:
3763:
3760:
3758:
3755:
3753:
3750:
3748:
3745:
3743:
3740:
3738:
3735:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3715:
3714:
3712:
3710:Miscellaneous
3708:
3702:
3699:
3697:
3696:Phenylephrine
3694:
3692:
3690:
3686:
3684:
3682:
3678:
3676:
3675:Orciprenaline
3673:
3671:
3668:
3665:
3661:
3658:
3656:
3653:
3650:
3649:Levonordefrin
3646:
3643:
3641:
3638:
3636:
3633:
3631:
3628:
3626:
3623:
3621:
3618:
3616:
3613:
3611:
3609:
3605:
3603:
3597:
3595:
3589:
3586:
3580:
3577:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3526:
3524:
3521:
3518:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3481:
3479:
3473:
3469:
3463:
3460:
3458:
3455:
3453:
3450:
3448:
3445:
3443:
3440:
3438:
3435:
3433:
3430:
3428:
3425:
3423:
3420:
3418:
3415:
3413:
3410:
3408:
3405:
3403:
3400:
3398:
3395:
3393:
3390:
3388:
3385:
3383:
3380:
3378:
3375:
3373:
3370:
3367:
3366:
3364:
3362:
3358:
3352:
3349:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3307:
3304:
3303:
3301:
3299:
3295:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3252:
3249:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3224:
3222:
3219:
3217:
3216:Methcathinone
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3197:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3116:
3115:
3113:
3111:
3107:
3101:
3098:
3094:
3091:
3089:
3086:
3082:
3079:
3077:
3074:
3072:
3071:Mephentermine
3069:
3067:
3064:
3062:
3059:
3057:
3054:
3052:
3049:
3046:
3045:
3043:
3041:
3037:
3030:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3005:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2946:
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2920:6-Chloro-MDMA
2918:
2916:
2913:
2911:
2908:
2906:
2903:
2901:
2898:
2896:
2893:
2891:
2888:
2886:
2883:
2881:
2878:
2876:
2873:
2871:
2868:
2866:
2863:
2861:
2858:
2856:
2853:
2849:
2846:
2844:
2843:Xylopropamine
2841:
2839:
2836:
2834:
2831:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2804:
2801:
2799:
2796:
2794:
2791:
2789:
2786:
2784:
2781:
2779:
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
2746:
2744:
2741:
2739:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2710:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2681:
2678:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2653:
2651:
2648:
2646:
2643:
2641:
2638:
2635:
2631:
2627:
2624:
2622:
2619:
2617:
2614:
2612:
2609:
2607:
2604:
2602:
2599:
2597:
2594:
2592:
2589:
2587:
2584:
2582:
2581:Benzphetamine
2579:
2577:
2574:
2572:
2569:
2566:
2562:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2511:
2508:
2506:
2503:
2501:
2498:
2496:
2493:
2491:
2488:
2486:
2483:
2481:
2478:
2476:
2473:
2471:
2468:
2466:
2463:
2461:
2458:
2456:
2453:
2451:
2448:
2446:
2443:
2441:
2438:
2436:
2433:
2431:
2428:
2426:
2423:
2421:
2418:
2416:
2413:
2411:
2408:
2406:
2403:
2401:
2398:
2396:
2393:
2391:
2388:
2386:
2383:
2381:
2378:
2376:
2373:
2372:Psychedelics:
2370:
2369:
2367:
2365:
2361:
2355:
2352:
2350:
2347:
2343:
2340:
2338:
2335:
2333:
2330:
2327:
2326:
2323:
2320:
2318:
2316:
2312:
2310:
2308:
2304:
2302:
2300:
2296:
2294:
2292:
2288:
2286:
2283:
2281:(amphetamine)
2280:
2277:
2275:
2272:
2270:
2267:
2265:
2262:
2261:
2260:
2259:
2256:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2221:
2219:
2216:
2214:
2211:
2209:
2206:
2204:
2203:Isoproscaline
2201:
2199:
2196:
2194:
2191:
2189:
2188:Allylescaline
2186:
2185:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2149:
2147:
2144:
2142:
2139:
2137:
2134:
2132:
2129:
2127:
2124:
2122:
2119:
2117:
2114:
2112:
2109:
2107:
2104:
2102:
2099:
2097:
2094:
2092:
2089:
2087:
2084:
2082:
2079:
2077:
2074:
2072:
2069:
2067:
2064:
2062:
2059:
2057:
2054:
2052:
2049:
2047:
2044:
2042:
2039:
2037:
2034:
2032:
2029:
2027:
2024:
2022:
2019:
2017:
2014:
2012:
2009:
2007:
2004:
2002:
1999:
1997:
1994:
1992:
1989:
1987:
1984:
1982:
1979:
1977:
1974:
1972:
1969:
1967:
1964:
1962:
1959:
1957:
1954:
1952:
1949:
1947:
1944:
1942:
1939:
1937:
1934:
1932:
1929:
1927:
1924:
1922:
1919:
1917:
1914:
1912:
1909:
1907:
1904:
1902:
1899:
1897:
1894:
1892:
1889:
1887:
1884:
1882:
1879:
1877:
1874:
1872:
1869:
1867:
1864:
1862:
1859:
1858:
1855:
1852:
1850:
1847:
1845:
1842:
1840:
1837:
1835:
1832:
1831:Psychedelics:
1829:
1828:
1826:
1824:
1820:
1816:
1809:
1804:
1802:
1797:
1795:
1790:
1789:
1786:
1775:
1774:
1770:
1766:
1762:
1761:Serotonergics
1758:
1757:Melatonergics
1754:
1753:Dopaminergics
1750:
1746:
1743:
1736:
1730:
1727:
1725:
1722:
1720:
1717:
1716:
1714:
1710:
1704:
1701:
1699:
1696:
1694:
1691:
1689:
1686:
1684:
1681:
1679:
1676:
1674:
1671:
1669:
1666:
1664:
1661:
1659:
1656:
1654:
1651:
1649:
1646:
1644:
1641:
1639:
1636:
1634:
1631:
1629:
1626:
1624:
1621:
1619:
1616:
1614:
1612:
1607:
1605:
1602:
1600:
1597:
1595:
1592:
1590:
1587:
1585:
1582:
1580:
1577:
1575:
1572:
1570:
1567:
1565:
1562:
1560:
1557:
1555:
1554:2'-Amino-MPTP
1552:
1551:
1549:
1547:
1543:
1537:
1534:
1532:
1529:
1527:
1524:
1522:
1519:
1517:
1514:
1512:
1511:6-Hydroxydopa
1509:
1507:
1504:
1502:
1499:
1497:
1494:
1492:
1491:2'-Amino-MPTP
1489:
1488:
1486:
1484:
1483:Noradrenergic
1480:
1474:
1471:
1469:
1466:
1464:
1461:
1459:
1456:
1454:
1451:
1449:
1448:Norsalsolinol
1446:
1444:
1442:
1438:
1436:
1433:
1431:
1428:
1426:
1423:
1421:
1418:
1416:
1413:
1411:
1408:
1406:
1403:
1401:
1398:
1396:
1395:Fenpropathrin
1393:
1391:
1388:
1386:
1383:
1381:
1380:DOPAL quinone
1378:
1376:
1373:
1371:
1368:
1366:
1363:
1361:
1358:
1356:
1353:
1351:
1348:
1345:
1344:methylmercury
1341:
1337:
1334:
1332:
1329:
1327:
1324:
1322:
1320:
1315:
1313:
1310:
1308:
1305:
1304:
1302:
1300:
1296:
1292:
1285:
1280:
1278:
1273:
1271:
1266:
1265:
1262:
1245:
1241:
1235:
1233:
1229:
1224:
1220:
1215:
1210:
1206:
1202:
1198:
1194:
1193:Redox Biology
1190:
1183:
1181:
1177:
1172:
1168:
1164:
1160:
1156:
1152:
1148:
1144:
1140:
1133:
1131:
1129:
1125:
1120:
1114:
1110:
1109:
1101:
1098:
1093:
1089:
1085:
1081:
1077:
1073:
1069:
1062:
1059:
1048:
1044:
1038:
1035:
1024:
1020:
1019:"Oxidopamine"
1013:
1011:
1007:
1002:
998:
994:
990:
986:
982:
978:
974:
967:
964:
959:
955:
951:
947:
943:
939:
935:
931:
927:
923:
919:
915:
910:
902:
900:
898:
896:
892:
887:
883:
879:
875:
871:
867:
863:
859:
855:
851:
847:
840:
837:
832:
828:
824:
820:
816:
812:
808:
804:
800:
796:
791:
783:
780:
773:
769:
766:
764:
761:
759:
758:Norsalsolinol
756:
754:
751:
749:
746:
744:
741:
740:
736:
734:
732:
726:
716:
708:
706:
699:
697:
695:
691:
683:
678:
676:
674:
670:
666:
662:
654:
652:
650:
646:
642:
637:
622:
612:
611:noradrenaline
608:
600:
598:
596:
592:
584:
582:
575:
573:
569:
567:
563:
555:
553:
538:
530:
525:
523:
521:
517:
509:
507:
505:
501:
500:neurotoxicity
497:
489:
487:
485:
481:
477:
472:
470:
469:noradrenergic
466:
462:
459:
455:
451:
447:
443:
431:
424:
419:
402:
396:
392:
390:
387:
386:
370:
367:
363:
362:
357:
348:
344:
337:
323:
313:
309:
302:
294:
290:
289:DTXSID0036768
286:
285:
283:
273:
269:
268:
261:
257:
256:
254:
252:
249:
248:
241:
237:
236:
234:
228:
224:
223:
216:
212:
211:
209:
207:
204:
203:
196:
195:
193:
191:
186:
185:
181:
177:
174:
172:
170:ECHA InfoCard
167:
166:
159:
155:
154:
152:
150:
147:
146:
139:
135:
134:
132:
130:
127:
126:
119:
115:
114:
112:
110:
107:
106:
99:
95:
94:
92:
88:
83:
82:
75:
71:
70:
68:
65:
61:
60:
55:
47:
43:
38:
34:
29:
25:
20:
3867:Solriamfetol
3782:Famprofazone
3688:
3680:
3666:-Octopamine)
3663:
3660:Norfenefrine
3615:Metanephrine
3607:
3563:Isoprenaline
3519:(Dextrodopa)
3504:Adrenochrome
3462:Pyrovalerone
3368:
3347:
3306:Entactogens:
3305:
3255:Entactogens:
3254:
3201:Ethcathinone
3117:
3096:
3085:Entactogens:
3084:
3047:
3040:Phentermines
3003:
2852:Entactogens:
2851:
2848:Zylofuramine
2626:Fenfluramine
2621:Fenethylline
2571:Amphetaminil
2552:Amfepentorex
2513:
2371:
2364:Amphetamines
2345:
2329:Entactogens:
2328:
2314:
2306:
2298:
2290:
2254:
2252:
2228:Metaescaline
1830:
1741:
1740:
1628:Fenfluramine
1610:
1546:Serotonergic
1530:
1452:
1440:
1370:DOPA quinone
1318:
1299:Dopaminergic
1247:. Retrieved
1243:
1196:
1192:
1146:
1142:
1107:
1100:
1075:
1071:
1061:
1050:. Retrieved
1046:
1037:
1026:. Retrieved
1022:
979:(1): 57–73.
976:
972:
966:
917:
913:
853:
849:
839:
798:
794:
782:
727:
712:
703:
687:
658:
638:
623:
604:
588:
579:
570:
562:autoxidation
559:
537:benzenetriol
534:
513:
493:
476:Parkinsonism
473:
465:dopaminergic
453:
449:
445:
441:
440:
138:ChEMBL337702
57:Identifiers
17:Oxidopamine
3887:Venlafaxine
3852:Pronethalol
3822:Methoxamine
3752:Dizocilpine
3747:Diphenidine
3722:Amidephrine
3683:-Octopamine
3620:Metaraminol
3587:(Droxidopa)
3533:Epinephrine
3523:Dimetofrine
3369:Stimulants:
3348:Stimulants:
3176:Brephedrone
3166:Amfepramone
3118:Stimulants:
3100:Cericlamine
3081:Phentermine
3061:Clortermine
3048:Stimulants:
2828:Sibutramine
2813:Prenylamine
2748:Oxifentorex
2700:Metaraminol
2640:Fenproporex
2611:Fencamfamin
2591:Clobenzorex
2557:Amphetamine
2514:Stimulants:
2255:Stimulants:
2213:Macromerine
1749:Adrenergics
1633:Haloperidol
1400:Haloperidol
1350:Amphetamine
673:desipramine
442:Oxidopamine
359:Properties
176:100.013.493
118:CHEBI:78741
3902:Categories
3857:Salbutamol
3792:Hexapradol
3772:Etafedrine
3767:Ephenidine
3762:Dopexamine
3757:Dobutamine
3737:Denopamine
3727:Arbutamine
3701:Synephrine
3635:Methyldopa
3630:Metirosine
3578:(Levodopa)
3568:Isoetarine
3553:Fenclonine
3543:Etilefrine
3457:Prolintane
3288:Mephedrone
3251:Radafaxine
3241:Pentedrone
3221:Methedrone
3181:Buphedrone
3171:Benzedrone
3110:Cathinones
3022:Selegiline
3012:Amiflamine
2808:Pholedrine
2758:Ortetamine
2753:Oxilofrine
2685:Lefetamine
2675:Iofetamine
2660:Furfenorex
2655:Formetorex
2645:Flucetorex
2576:Benfluorex
2547:Amfecloral
2542:Alfetamine
2415:D-Deprenyl
2332:Lophophine
2243:Psi-2C-T-4
2238:Proscaline
2208:Jimscaline
1569:2,4,5-THMA
1468:Salsolinol
1340:disulfiram
1312:2,4,5-THMA
1249:2022-03-04
1199:: 101377.
1052:2022-03-04
1028:2022-03-04
920:: 109380.
774:References
655:Metabolism
649:superoxide
601:Mechanisms
496:neurotoxin
389:Molar mass
260:8HW4YBZ748
149:ChemSpider
85:3D model (
64:CAS Number
3837:PARGY-LAD
3732:Cafedrine
3691:-Tyramine
3645:Nordefrin
3625:Metaterol
3610:-Tyramine
3602:-Tyrosine
3558:Ibopamine
3447:Naphyrone
3278:Methylone
3246:Pentylone
3191:Cathinone
3186:Bupropion
3029:-Deprenyl
2695:Mefenorex
2665:Gepefrine
2616:Fencamine
2601:Ephedrine
2537:Acridorex
2264:Hordenine
2223:Mescaline
2116:2C-T-22.5
1854:25N-NBOMe
1849:25I-NBOMe
1844:25D-NBOMe
1839:25C-NBOMe
1834:25B-NBOMe
1742:See also:
1564:2,4,5-THA
1496:2,4,5-THA
1307:2,4,5-THA
1163:0891-5849
1092:0008-4042
1017:PubChem.
958:231622597
942:0009-2797
870:1546-1726
815:1476-3524
576:Synthesis
531:Structure
458:synthetic
197:214-842-3
189:EC Number
74:1199-18-4
3842:Phenibut
3528:Dopamine
3509:Ciladopa
3499:a-Me-TRA
3339:Eutylone
3329:Butylone
3273:Ethylone
3268:Butylone
3258:3,4-DMMC
3206:Eutylone
3156:4-MeMABP
3076:Pentorex
3066:Etolorex
3056:Cloforex
2833:Tiflorex
2725:Morforex
2650:Fludorex
2405:Beatrice
2198:Escaline
1712:Unsorted
1536:Xylamine
1463:Rotenone
1458:Paraquat
1415:Mancozeb
1385:Dopamine
1365:Dieldrin
1223:31760358
1171:17291991
1001:22599841
993:15708628
950:33450287
878:15195095
831:25556004
823:17449457
763:Rotenone
737:See also
715:toxicity
709:Toxicity
684:Efficacy
661:dopamine
607:dopamine
597:(SNpc).
516:dopamine
3882:UWA-101
3847:PRO-LAD
3777:ETH-LAD
3538:Epinine
3494:a-Me-DA
3417:4-MePPP
3412:4-MePHP
3407:4-MePBP
3319:Ariadne
3097:Others:
3007:3,4-DCA
3004:Others:
2955:2,3-MDA
2940:6-MAPDB
2905:5-MAPDB
2586:Cathine
2510:ZDCM-04
2495:Psi-DOM
2480:Ganesha
2346:Others:
2161:2C-T-33
2156:2C-T-32
2151:2C-T-31
2146:2C-T-30
2141:2C-T-28
2136:2C-T-27
2131:2C-T-25
2126:2C-T-24
2121:2C-T-23
2111:2C-T-22
2106:2C-T-21
2101:2C-T-20
2096:2C-T-19
2091:2C-T-18
2086:2C-T-17
2081:2C-T-16
2076:2C-T-15
2071:2C-T-14
2066:2C-T-13
2061:2C-T-12
2056:2C-T-11
2051:2C-T-10
1866:2C-B-AN
1599:5,7-DHT
1594:5,6-DHT
1579:3,4-DCA
1559:2,4-DCA
1516:DOPEGAL
1506:5,7-DHT
1501:5,6-DHT
1360:Daidzin
1355:Benomyl
1338:(e.g.,
1326:5,6-DHT
1214:6880099
922:Bibcode
490:History
456:, is a
423:what is
421: (
383:
227:PubChem
3797:IP-LAD
3717:AL-LAD
3489:6-OHDA
3024:(also
3017:DiFMDA
2935:6-MAPB
2925:6-EAPB
2915:6-APDB
2900:5-MAPB
2890:5-EAPB
2885:5-APDB
2490:MMDA-2
2390:3C-MAL
2342:MDMPEA
2193:DESOXY
2171:2C-TFM
2166:2C-TFE
2046:2C-T-9
2041:2C-T-8
2036:2C-T-7
2031:2C-T-6
2026:2C-T-5
2021:2C-T-4
2016:2C-T-3
2011:2C-T-2
1986:2C-O-4
1976:2C-NH2
1951:2C-G-N
1946:2C-G-6
1941:2C-G-5
1936:2C-G-4
1931:2C-G-3
1926:2C-G-2
1921:2C-G-1
1719:5-HIAL
1221:
1211:
1169:
1161:
1115:
1090:
999:
991:
956:
948:
940:
886:952173
884:
876:
868:
829:
821:
813:
768:FAUC50
450:6-OHDA
418:verify
415:
343:SMILES
215:D05294
129:ChEMBL
40:Names
3832:MT-45
3585:-DOPS
3576:-DOPA
3517:-DOPA
3484:6-FNE
3427:MOPVP
3422:MOPPP
3397:MDPPP
3392:MDPBP
3387:α-PVP
3382:α-PPP
3377:α-PHP
3372:α-PBP
3314:4-MAB
3309:4-CAB
3263:3-MMC
3161:4-MPD
3151:4-MEC
3146:4-FMC
3141:4-EMC
3136:4-CMC
3131:4-BMC
3121:3-FMC
3093:MDMPH
2990:MMDMA
2970:MDHMA
2910:6-APB
2880:5-APB
2875:4-MTA
2870:4-MMA
2860:4-FMA
2532:3-FMA
2522:2-FMA
2475:DOTFM
2430:DMMDA
2425:DMCPA
2400:Aleph
2380:3C-BZ
2375:3C-AL
2354:DMPEA
2337:MDPEA
2248:TCB-2
2218:MEPEA
2176:2C-YN
2001:2C-SE
1996:2C-Ph
1966:2C-iP
1906:2C-EF
1891:2C-CP
1886:2C-CN
1876:2C-Bu
1871:2C-Bn
1729:RHPTP
1589:5-IAI
1521:DSP-4
1473:Ziram
1420:Maneb
1375:DOPAL
997:S2CID
954:S2CID
882:S2CID
827:S2CID
748:DSP-4
510:Usage
452:) or
308:InChI
109:ChEBI
87:JSmol
3442:MPPP
3437:MPHP
3432:MPBP
3402:MDPV
3344:MBDB
3334:EBDB
3126:4-MC
3088:MDPH
2980:MDOH
2965:MDEA
2930:6-IT
2895:5-IT
2865:4-MA
2855:4-FA
2798:PMMA
2793:PMEA
2778:PFMA
2527:3-FA
2517:2-FA
2505:TeMA
2485:MMDA
2470:DOPR
2450:DOET
2445:DOEF
2395:3C-P
2385:3C-E
2181:2C-V
2006:2C-T
1991:2C-P
1981:2C-O
1971:2C-N
1961:2C-I
1956:2C-H
1916:2C-G
1911:2C-F
1901:2C-E
1896:2C-D
1881:2C-C
1861:2C-B
1724:RHPP
1698:PCMA
1678:MMAI
1663:MDEA
1658:MDAI
1648:MBDB
1643:HPTP
1574:3-CA
1435:MPTP
1410:HPTP
1219:PMID
1167:PMID
1159:ISSN
1113:ISBN
1088:ISSN
989:PMID
946:PMID
938:ISSN
874:PMID
866:ISSN
819:PMID
811:ISSN
753:MPTP
645:MPTP
609:and
494:The
467:and
251:UNII
240:4624
206:KEGG
158:4463
3452:PEP
3324:BDB
3226:NEB
3000:TAP
2950:IAP
2945:EDA
2788:PMA
2783:PIA
2773:PFA
2768:PCA
2763:PBA
2720:MMA
2500:TMA
2465:DON
2460:DOM
2455:DOI
2440:DOC
2435:DOB
2420:DMA
2349:BOH
1703:PIA
1693:PCA
1688:PBA
1638:HPP
1623:DCA
1618:αET
1405:HPP
1209:PMC
1201:doi
1151:doi
1080:doi
981:doi
930:doi
918:336
858:doi
803:doi
277:EPA
230:CID
3904::
2632:,
2563:,
1771:•
1767:•
1763:•
1759:•
1755:•
1751:•
1747:•
1609:α,
1342:,
1317:5-
1242:.
1231:^
1217:.
1207:.
1197:28
1195:.
1191:.
1179:^
1165:.
1157:.
1147:42
1145:.
1141:.
1127:^
1086:.
1076:50
1074:.
1070:.
1045:.
1021:.
1009:^
995:.
987:.
977:48
975:.
952:.
944:.
936:.
928:.
916:.
912:.
894:^
880:.
872:.
864:.
852:.
848:.
825:.
817:.
809:.
799:11
797:.
793:.
733:.
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636:.
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546:11
522:.
506:.
486:.
379:NO
377:11
3863:)
3859:(
3689:p
3681:p
3664:m
3662:(
3651:)
3647:(
3608:m
3600:L
3592:L
3583:L
3574:L
3515:D
3031:)
3027:D
2736:L
2711:)
2636:)
2628:(
2567:)
2559:(
2315:p
2307:o
2299:N
2291:m
1807:e
1800:t
1793:v
1611:N
1441:N
1346:)
1319:S
1283:e
1276:t
1269:v
1252:.
1225:.
1203::
1173:.
1153::
1121:.
1094:.
1082::
1055:.
1031:.
1003:.
983::
960:.
932::
924::
888:.
860::
854:7
833:.
805::
723:2
721:O
719:2
634:2
632:O
630:2
626:2
619:2
617:O
615:2
550:3
544:H
542:8
540:C
448:(
413:N
381:3
375:H
373:8
371:C
279:)
275:(
89:)
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