358:
209:
62:
519:
681:
53:
524:
570:
997:. The symptoms and brain structures of MPTP-induced Parkinson's disease are fairly indistinguishable to the point that MPTP may be used to simulate the disease in order to study Parkinson's disease physiology and possible treatments within the laboratory. Mouse studies have shown that susceptibility to MPTP increases with age.
887:
are much less susceptible. Rats are almost immune to the adverse effects of MPTP. Mice were thought to only suffer from cell death in the substantia nigra (to a differing degree according to the strain of mice used) but do not show
Parkinsonian symptoms; however, most of the recent studies indicate
860:
scavenges for excessive dopamine at the synaptic spaces and transports them back into the cell. Even though this property is exhibited by both VTA and SNc neurons, VTA neurons are protective against MPP insult due to the expression of calbindin. Calbindin regulates the availability of Ca within the
1902:
Manaye KF, Sonsalla PK, Barnett G, Heikkila RE, Woodward DJ, Smith WK, German DC (July 1989). "1-Methyl-4-(2'-methylphenyl)-1,2,3,6-tetrahydropyridine (2'CH3-MPTP)-induced degeneration of mesostriatal dopaminergic neurons in the mouse: biochemical and neuroanatomical studies".
522:
1938:
Andrews AM, Murphy DL (March 1993). "Sustained depletion of cortical and hippocampal serotonin and norepinephrine but not striatal dopamine by 1-methyl-4-(2'-aminophenyl)-1,2,3,6-tetrahydropyridine (2'-NH2-MPTP): a comparative study with 2'-CH3-MPTP and MPTP".
1015:
It has been postulated that
Parkinson's disease may be caused by minute amounts of MPP-like compounds from ingestion or exogenously through repeated exposure and that these substances are too minute to be detected significantly by epidemiological studies.
1000:
Knowledge of MPTP and its use in reliably recreating
Parkinson's disease symptoms in experimental models has inspired scientists to investigate the possibilities of surgically replacing neuron loss through fetal tissue implants,
1298:
Narmashiri, Abdolvahed; Abbaszadeh, Mojtaba; Ghazizadeh, Ali (2022). "The effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) on the cognitive and motor functions in rodents: A systematic review and meta-analysis".
1235:
888:
that MPTP can result in
Parkinsonism-like syndromes in mice (especially chronic syndromes). It is believed that the lower levels of MAO-B in the rodent brain's capillaries may be responsible for this.
1518:
Fahn, S. (1996). "Book Review -- The Case of the Frozen
Addicts: How the Solution of an Extraordinary Medical Mystery Spawned a Revolution in the Understanding and Treatment of Parkinson's Disease".
1062:. It was tested as a treatment for various conditions, but the tests were halted when Parkinson-like symptoms were noticed in monkeys. In one test of the substance, two of six human subjects died.
1974:
Castagnoli N, Castagnoli KP, Van der Schyf CJ, Usuki E, Igarashi K, Steyn SJ, Riker RR (1999). "Enzyme-catalyzed bioactivation of cyclic tertiary amines to form potential neurotoxins".
930:, US, were diagnosed with Parkinsonism after having used MPPP contaminated with MPTP, and as many as 120 were reported to have been diagnosed with Parkinson's symptoms. The neurologist
523:
876:, which then relay signals to the rest of the brain. This pathway is controlled via dopamine-using neurons, which MPTP selectively destroys, resulting, over time, in parkinsonism.
934:
in collaboration with NIH tracked down MPTP as the cause, and its effects on primates were researched. After performing neural grafts of fetal tissue on three of the patients at
1344:"Implanted fibroblasts genetically engineered to produce brain-derived neurotrophic factor prevent 1-methyl-4-phenylpyridinium toxicity to dopaminergic neurons in the rat"
583:
2005:
Langston, J. William; Ballard, Philip; Tetrud, James W.; Irwin, Ian (25 February 1983). "Chronic
Parkinsonism in Humans Due to a Product of Meperidine-Analog Synthesis".
911:
in his lab. They tested the substances on rats, but due to rodents' tolerance for this type of neurotoxin, nothing was observed. Kidston's
Parkinsonism was treated with
525:
1545:
Davis GC, Williams AC, Markey SP, Ebert MH, Caine ED, Reichert CM, Kopin IJ (1979). "Chronic parkinsonism secondary to intravenous injection of meperidine analogs".
2131:
1634:
1168:
the protagonist administers MPTP to the anti-heroine’s former nurse, who had stolen her painkillers in life, doing so as a means of neurodegenerative torture.
900:, US, synthesized MPPP with MPTP as a major impurity and self-injected the result. Within three days he began exhibiting symptoms of Parkinson's disease. The
407:
1786:
1867:
Maret G, Testa B, Jenner P, el Tayar N, Carrupt PA (1990). "The MPTP story: MAO activates tetrahydropyridine derivatives to toxins causing parkinsonism".
2058:
1489:
2644:
547:
2636:
1851:
1685:
28:
667:(meperidine). The Parkinson-inducing effects of MPTP were first discovered following accidental injection as a result of contaminated MPPP.
1164:
282:
2640:
2124:
901:
2680:
1804:
Lee, J.; Ziering, A.; Heineman, S. D.; Berger, L. (1947). "Piperidine
Derivatives. Part II. 2-Phenyl- and 2-Phenylalkyl-Piperidines".
1700:"The Case of the Frozen Addicts" first broadcast 7 April 1986 and "Awakening the Frozen Addicts" first broadcast 4 January 1993. See
2539:
2383:
2336:
764:
372:
849:. MAOIs prevent the metabolism of MPTP to MPP by inhibiting the action of MAO-B, minimizing toxicity, and preventing neural death.
2549:
2529:
2199:
1588:
2440:
2238:
2170:
1758:
1208:
Buchi, I. J. (1952). "Synthese und analgetische
Wirkung einiger 1-Methyl-4-phenyl-piperidin-(4)-alkylsulfone. 1. Mitteilung".
2534:
2117:
1030:
causes
Parkinsonism in rats by killing dopaminergic neurons in the substantia nigra. Like MPP, rotenone also interferes with
927:
841:
Because MPTP itself is not directly harmful, toxic effects of acute MPTP poisoning can be mitigated by the administration of
702:
245:
2524:
2519:
2393:
2670:
2616:
2500:
315:
2590:
2455:
2435:
2363:
2165:
956:
842:
796:
336:
1614:
942:, the motor symptoms of two of the three patients were successfully treated, and the third showed partial recovery.
2569:
1154:
745:
590:
126:
2675:
1790:
950:
896:
The neurotoxicity of MPTP was hinted at in 1976 after Barry Kidston, a 23-year-old chemistry graduate student in
717:
216:
2495:
2194:
2140:
1701:
1035:
827:
622:
276:
861:
cell, which is not the case in SNc neurons due to their high-calcium-dependent autonomous pacemaker activity.
789:
2066:
1059:
533:
2480:
2470:
2465:
2450:
2430:
2373:
2368:
2184:
1055:
724:
691:
17:
2303:
2175:
204:
2632:
2628:
2624:
2564:
1251:"Animal models of Parkinson's disease: A source of novel treatments and clues to the cause of the disease"
1005:
964:
868:
control of complex movements. The direction of complex movement is based from the substantia nigra to the
629:
2445:
2559:
2475:
2098:
2074:
698:
656:
618:
166:
1713:
Jackson-Lewis, V.; Przedborski, S. (2007). "Protocol for the MPTP Mouse Model of Parkinson's Disease".
2253:
1464:
731:
2620:
2574:
2460:
2014:
1765:
1355:
857:
74:
1402:
2243:
800:
353:
92:
2233:
2046:
2030:
1740:
1619:
1570:
1403:"Richardson, Jason R., et al. "Paraquat neurotoxicity is distinct from that of MPTP and rotenone"
1324:
713:
614:
1342:
Frim, D. M.; Uhler, T. A.; Galpern, W. R.; Beal, M. F.; Breakefield, X. O.; Isacson, O. (1994).
2665:
2038:
1983:
1956:
1920:
1884:
1847:
1821:
1732:
1681:
1562:
1424:
1383:
1316:
1280:
1183:
1089:
908:
2022:
1948:
1912:
1876:
1813:
1724:
1715:
1661:
1554:
1527:
1414:
1373:
1363:
1308:
1270:
1262:
1217:
931:
819:
637:
610:
489:
430:
2600:
2595:
2421:
2354:
2156:
1101:
1093:
852:
Dopaminergic neurons are selectively vulnerable to MPP because DA neurons exhibit dopamine
324:
102:
2554:
2544:
2514:
2288:
2273:
1789:. National Institute of Neurological Disorders and Stroke. 9 February 2005. Archived from
1447:"Chapter 30 The Impact of MPTP on Parkinson's Disease Research: Past, Present, and Future"
1116:
982:
935:
873:
865:
186:
2103:
2018:
1359:
357:
208:
146:
1952:
1677:
1275:
1250:
1149:
1139:
1019:
In 2000, another animal model for Parkinson's disease was found. It was shown that the
561:
2659:
2378:
2346:
2311:
2258:
2207:
2189:
1916:
1670:
1665:
1558:
1378:
1343:
1328:
1266:
1188:
815:
785:
478:
468:
197:
2050:
1769:
1744:
1574:
1312:
2485:
2148:
1639:
1178:
835:
831:
808:
778:
648:
2085:
738:
61:
1490:"The Establishment of Chronic Parkinson's Disease in Mouse Model Induced by MPTP"
923:
and destruction of dopaminergic neurons in the substantia nigra were discovered.
304:
2490:
2398:
2316:
2263:
2213:
1787:"Summary of the Article by Dr. Greenamyre on Pesticides and Parkinson's Disease"
1531:
1134:
1112:
1024:
1002:
680:
1446:
2331:
2203:
2091:
1880:
994:
846:
804:
455:
235:
177:
1635:"How tainted drugs "froze" young people—but kickstarted Parkinson's research"
1221:
651:
effects, the compound may be accidentally produced during the manufacture of
2413:
2109:
2026:
1419:
1368:
1074:
1070:
1047:
1031:
1020:
1009:
990:
920:
905:
823:
664:
1987:
1825:
1736:
1728:
1428:
1320:
1284:
2042:
1960:
1924:
1888:
1387:
781:, hence users of MPPP contaminated with MPTP will develop these symptoms.
2403:
2326:
2321:
2278:
2248:
2228:
1566:
1078:
1066:
1027:
986:
985:
resulted in Parkinsonism, symptoms of which were subsequently reduced by
912:
897:
853:
660:
546:
539:
532:
505:
1817:
1142:, MPTP is used as a means of inducing Parkinsonism in another character.
1012:
research, all of which have demonstrated initial provisional successes.
989:, the drug-of-choice in the treatment of Parkinson's disease along with
2223:
2218:
2034:
916:
880:
869:
811:
705: in this section. Unsourced material may be challenged and removed.
291:
217:
381:
InChI=1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3
2099:
https://openvault.wgbh.org/catalog/V_474CF2C8A20B4173988486AC4C605A3C
1077:. While cyperquat is not used anymore, the closely related substance
939:
884:
793:
633:
391:
InChI=1/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3
157:
856:
which is mediated by DAT, which also has high-affinity for MPP. The
560:
Except where otherwise noted, data are given for materials in their
27:
This article is about the chemical. For the mitochondrial pore, see
2509:
2293:
2268:
1120:
625:
483:
128 to 132 °C (262 to 270 °F; 401 to 405 K) 12 Torr
265:
39:
2388:
2283:
641:
137:
125:
115:
540:
834:
metabolism, which leads to cell death and causes the buildup of
652:
256:
35:
2113:
838:, toxic molecules that contribute further to cell destruction.
644:. It has been used to study disease models in various animals.
52:
960:
674:
864:
The gross depletion of dopaminergic neurons severely affects
792:. Once inside the brain, MPTP is metabolized into the toxic
341:
1488:
Luo Qin; Peng Guoguang; Wang Jiacai; Wang Shaojun (2010).
1065:
MPTP is used in industry as a chemical intermediate; the
973:
Contribution of MPTP to research into Parkinson's disease
517:
1759:"Pesticides and Parkinson's Disease - A Critical Review"
1615:"Success reported using fetal tissue to repair a brain"
578:
1451:
Parkinson's Disease. Diagnosis and Clinical Management
1081:
is still being used as a herbicide in some countries.
2088:- Contains information regarding MPTP as a neurotoxin
1147:
MPTP-induced Parkinson's disease is featured in the
2583:
2412:
2345:
2147:
244:
1669:
2075:"How a Junkie's Brain Helps Parkinson's Patients"
303:
1348:Proceedings of the National Academy of Sciences
807:, specifically astrocytes. MPP kills primarily
521:
101:
1236:"1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine"
945:Langston documented the case in his 1995 book
2125:
8:
607:1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
283:1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
79:1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
18:1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
2132:
2118:
2110:
1589:"Bogus Heroin Brings Illness on the Coast"
1449:. In Factor, S. A.; Weiner, W. J. (eds.).
1046:MPTP was first synthesized as a potential
356:
207:
185:
44:
1846:. Elsevier Health Sciences. p. 369.
1837:
1835:
1440:
1438:
1418:
1377:
1367:
1274:
765:Learn how and when to remove this message
323:
2096:episode, "The Case of the Frozen Addict"
1301:Neuroscience & Biobehavioral Reviews
981:(1984) found that injections of MPTP in
777:Injection of MPTP causes rapid onset of
2104:"The MPTP Story" by J. William Langston
1764:. Institute of Environment and Health,
1494:Journal of Chongqing Medical University
1200:
412:
377:
352:
281:
784:MPTP itself is not toxic, but it is a
198:
788:compound and can therefore cross the
628:, which causes permanent symptoms of
473:40 °C (104 °F; 313 K)
384:Key: PLRACCBDVIHHLZ-UHFFFAOYSA-N
165:
145:
29:Mitochondrial permeability transition
7:
1842:Vinken, P. J.; Bruyn, G. W. (1994).
1165:The Metamorphosis of Prime Intellect
703:adding citations to reliable sources
1844:Intoxications of the Nervous System
1520:The New England Journal of Medicine
1249:Duty, Susan; Jenner, Peter (2011).
1115:-derived monoaminergic neurotoxins
915:but he died 18 months later from a
902:National Institute of Mental Health
892:Discovery in users of illicit drugs
394:Key: PLRACCBDVIHHLZ-UHFFFAOYAV
294:
264:
1953:10.1111/j.1471-4159.1993.tb03271.x
1123:are structurally related to MPTP.
949:, which was later featured in two
814:in a part of the brain called the
25:
659:with effects similar to those of
2059:"Surprising Clue to Parkinson's"
1267:10.1111/j.1476-5381.2011.01426.x
679:
568:
448:
442:
60:
51:
2645:Monoamine metabolism modulators
1470:. Neuro Detective International
1313:10.1016/j.neubiorev.2022.104792
1255:British Journal of Pharmacology
904:found traces of MPTP and other
690:needs additional citations for
564:(at 25 °C , 100 kPa).
2065:. 24 June 2001. Archived from
1768:. October 2005. Archived from
1672:The Case of the Frozen Addicts
947:The Case of the Frozen Addicts
928:Santa Clara County, California
436:
1:
2637:Monoamine reuptake inhibitors
2617:Receptor/signaling modulators
1069:of the toxic metabolite MPP,
1917:10.1016/0006-8993(89)90065-6
1806:Journal of Organic Chemistry
1559:10.1016/0165-1781(79)90006-4
1465:"Parkinson's Disease Models"
959:, re-aired in the UK on the
879:MPTP causes Parkinsonism in
843:monoamine oxidase inhibitors
1532:10.1056/NEJM199612263352618
1453:. Demos Medical Publishing.
797:1-methyl-4-phenylpyridinium
632:by destroying dopaminergic
2697:
2641:Monoamine releasing agents
1401:Richardson, Jason (2005).
33:
26:
2681:Monoaminergic neurotoxins
2609:
2501:HHMA (α-methylepinine, α,
2141:Monoaminergic neurotoxins
1881:10.3109/03602539009041087
1162:In Roger Williams' novel
647:While MPTP itself has no
617:. It is of interest as a
558:
499:
423:
403:
368:
85:
73:
68:
59:
50:
1702:List of Horizon episodes
1445:Langston, J. W. (2002).
1222:10.1002/hlca.19520350514
1036:electron transport chain
936:Lund University Hospital
926:In 1983, four people in
919:overdose. Upon autopsy,
828:electron transport chain
623:monoaminergic neurotoxin
613:. It is classified as a
34:Not to be confused with
2027:10.1126/science.6823561
1369:10.1073/pnas.91.11.5104
1060:1-methyl-4-piperidinone
1056:phenylmagnesium bromide
972:
2496:HHA (α-methyldopamine)
2161:-MPTP (2′-methyl-MPTP)
1729:10.1038/nprot.2006.342
1407:Toxicological Sciences
1210:Helvetica Chimica Acta
1006:electrical stimulation
822:. MPP interferes with
528:
415:c2ccccc2/C1=C/CN(C)CC1
2540:MDMA (midomafetamine)
2426:-MPTP (2′-amino-MPTP)
2359:-MPTP (2′-amino-MPTP)
1775:on February 27, 2008.
1420:10.1093/toxsci/kfi304
1073:, has been used as a
655:, a synthetic opioid
527:
2399:Oxidopamine (6-OHDA)
2317:Oxidopamine (6-OHDA)
2307:-Methylnorsalsolinol
2081:. 21 September 2007.
1793:on October 16, 2007.
1766:Cranfield University
1100:(2′-amino-MPTP) and
883:, including humans.
858:dopamine transporter
799:(MPP) by the enzyme
699:improve this article
510:(fire diamond)
75:Preferred IUPAC name
2671:Tetrahydropyridines
2525:MDA (tenamfetamine)
2456:4-CAB (α-ethyl-PCA)
2394:MDA (tenamfetamine)
2019:1983Sci...219..979L
1818:10.1021/jo01170a021
1623:. 26 November 1992.
1547:Psychiatry Research
1360:1994PNAS...91.5104F
1050:in 1947 by Ziering
932:J. William Langston
801:monoamine oxidase B
790:blood–brain barrier
630:Parkinson's disease
490:Solubility in water
463: g·mol
47:
2505:-dimethyldopamine)
2180:-Cysteinyldopamine
2069:on March 30, 2005.
1620:The New York Times
1593:The New York Times
1127:In popular culture
1108:(2′-methyl-MPTP).
1042:Synthesis and uses
809:dopamine-producing
615:tetrahydropyridine
591:Infobox references
529:
45:
2653:
2652:
2648:
2086:Erowid MPTP Vault
2013:(4587): 979–980.
1853:978-0-444-81284-1
1687:978-0-679-42465-9
1595:. 9 December 1983
1526:(26): 2002–2003.
1354:(11): 5104–5108.
1184:6-Hydroxydopamine
830:, a component of
775:
774:
767:
749:
599:Chemical compound
597:
596:
495:Slightly soluble
337:CompTox Dashboard
127:Interactive image
16:(Redirected from
2688:
2676:Phenyl compounds
2611:
2254:Dopamine quinone
2134:
2127:
2120:
2111:
2082:
2070:
2054:
1992:
1991:
1971:
1965:
1964:
1947:(3): 1167–1170.
1935:
1929:
1928:
1899:
1893:
1892:
1864:
1858:
1857:
1839:
1830:
1829:
1801:
1795:
1794:
1783:
1777:
1776:
1774:
1763:
1755:
1749:
1748:
1716:Nature Protocols
1710:
1704:
1698:
1692:
1691:
1675:
1658:
1652:
1651:
1649:
1647:
1631:
1625:
1624:
1611:
1605:
1604:
1602:
1600:
1585:
1579:
1578:
1542:
1536:
1535:
1515:
1509:
1508:
1506:
1505:
1485:
1479:
1478:
1476:
1475:
1469:
1461:
1455:
1454:
1442:
1433:
1432:
1422:
1398:
1392:
1391:
1381:
1371:
1339:
1333:
1332:
1295:
1289:
1288:
1278:
1261:(4): 1357–1391.
1246:
1240:
1239:
1232:
1226:
1225:
1216:(5): 1527–1536.
1205:
1092:of MPTP include
983:squirrel monkeys
845:(MAOIs) such as
820:substantia nigra
770:
763:
759:
756:
750:
748:
707:
683:
675:
638:substantia nigra
611:organic compound
581:
575:
572:
571:
549:
542:
535:
520:
462:
450:
444:
438:
431:Chemical formula
361:
360:
345:
343:
327:
307:
296:
285:
268:
248:
219:
211:
200:
189:
169:
149:
129:
105:
64:
55:
48:
21:
2696:
2695:
2691:
2690:
2689:
2687:
2686:
2685:
2656:
2655:
2654:
2649:
2605:
2579:
2555:Norfenfluramine
2545:Methamphetamine
2425:
2408:
2358:
2341:
2294:MPP (cyperquat)
2289:Methamphetamine
2200:ALDH inhibitors
2160:
2143:
2138:
2073:
2057:
2004:
2001:
1996:
1995:
1976:Pol J Pharmacol
1973:
1972:
1968:
1937:
1936:
1932:
1901:
1900:
1896:
1866:
1865:
1861:
1854:
1841:
1840:
1833:
1803:
1802:
1798:
1785:
1784:
1780:
1772:
1761:
1757:
1756:
1752:
1712:
1711:
1707:
1699:
1695:
1688:
1662:Langston, J. W.
1660:
1659:
1655:
1645:
1643:
1633:
1632:
1628:
1613:
1612:
1608:
1598:
1596:
1587:
1586:
1582:
1544:
1543:
1539:
1517:
1516:
1512:
1503:
1501:
1487:
1486:
1482:
1473:
1471:
1467:
1463:
1462:
1458:
1444:
1443:
1436:
1400:
1399:
1395:
1341:
1340:
1336:
1297:
1296:
1292:
1248:
1247:
1243:
1234:
1233:
1229:
1207:
1206:
1202:
1197:
1175:
1150:Law & Order
1129:
1105:
1097:
1087:
1054:by reaction of
1044:
975:
963:science series
955:productions by
894:
874:caudate nucleus
771:
760:
754:
751:
708:
706:
696:
684:
673:
600:
593:
588:
587:
586: ?)
577:
573:
569:
565:
554:
553:
552:
551:
544:
537:
530:
526:
518:
492:
460:
447:
441:
433:
419:
416:
411:
410:
399:
396:
395:
392:
386:
385:
382:
376:
375:
364:
346:
339:
330:
310:
297:
271:
251:
238:
229:
192:
172:
152:
132:
119:
108:
95:
81:
80:
43:
32:
23:
22:
15:
12:
11:
5:
2694:
2692:
2684:
2683:
2678:
2673:
2668:
2658:
2657:
2651:
2650:
2610:
2607:
2606:
2604:
2603:
2598:
2593:
2587:
2585:
2581:
2580:
2578:
2577:
2572:
2567:
2562:
2557:
2552:
2547:
2542:
2537:
2532:
2527:
2522:
2517:
2512:
2507:
2498:
2493:
2488:
2483:
2478:
2473:
2468:
2463:
2458:
2453:
2448:
2443:
2438:
2433:
2428:
2423:
2418:
2416:
2410:
2409:
2407:
2406:
2401:
2396:
2391:
2386:
2381:
2376:
2371:
2366:
2361:
2356:
2351:
2349:
2343:
2342:
2340:
2339:
2334:
2329:
2324:
2319:
2314:
2309:
2301:
2296:
2291:
2286:
2281:
2276:
2271:
2266:
2261:
2256:
2251:
2246:
2241:
2236:
2231:
2226:
2221:
2216:
2211:
2197:
2195:6-OHDA quinone
2192:
2187:
2182:
2173:
2168:
2163:
2158:
2153:
2151:
2145:
2144:
2139:
2137:
2136:
2129:
2122:
2114:
2108:
2107:
2101:
2089:
2083:
2071:
2055:
2000:
1999:External links
1997:
1994:
1993:
1966:
1930:
1911:(2): 307–315.
1894:
1875:(4): 291–332.
1869:Drug Metab Rev
1859:
1852:
1831:
1812:(6): 885–893.
1796:
1778:
1750:
1723:(1): 141–151.
1705:
1693:
1686:
1678:Pantheon Books
1653:
1626:
1606:
1580:
1553:(3): 249–254.
1537:
1510:
1500:(8): 1149–1151
1480:
1456:
1434:
1413:(1): 193–201.
1393:
1334:
1290:
1241:
1227:
1199:
1198:
1196:
1193:
1192:
1191:
1186:
1181:
1174:
1171:
1170:
1169:
1159:
1158:
1144:
1143:
1140:William Gibson
1138:, authored by
1128:
1125:
1103:
1095:
1086:
1083:
1043:
1040:
974:
971:
893:
890:
773:
772:
687:
685:
678:
672:
669:
598:
595:
594:
589:
567:
566:
562:standard state
559:
556:
555:
545:
538:
531:
516:
515:
514:
513:
511:
502:
501:
497:
496:
493:
488:
485:
484:
481:
475:
474:
471:
465:
464:
458:
452:
451:
445:
439:
434:
429:
426:
425:
421:
420:
418:
417:
414:
406:
405:
404:
401:
400:
398:
397:
393:
390:
389:
387:
383:
380:
379:
371:
370:
369:
366:
365:
363:
362:
349:
347:
335:
332:
331:
329:
328:
320:
318:
312:
311:
309:
308:
300:
298:
290:
287:
286:
279:
273:
272:
270:
269:
261:
259:
253:
252:
250:
249:
241:
239:
234:
231:
230:
228:
227:
223:
221:
213:
212:
202:
194:
193:
191:
190:
182:
180:
174:
173:
171:
170:
162:
160:
154:
153:
151:
150:
142:
140:
134:
133:
131:
130:
122:
120:
113:
110:
109:
107:
106:
98:
96:
91:
88:
87:
83:
82:
78:
77:
71:
70:
66:
65:
57:
56:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2693:
2682:
2679:
2677:
2674:
2672:
2669:
2667:
2664:
2663:
2661:
2647:
2646:
2642:
2638:
2634:
2633:Serotonergics
2630:
2629:Melatonergics
2626:
2625:Dopaminergics
2622:
2618:
2615:
2608:
2602:
2599:
2597:
2594:
2592:
2589:
2588:
2586:
2582:
2576:
2573:
2571:
2568:
2566:
2563:
2561:
2558:
2556:
2553:
2551:
2548:
2546:
2543:
2541:
2538:
2536:
2533:
2531:
2528:
2526:
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2506:
2504:
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:
2420:
2419:
2417:
2415:
2411:
2405:
2402:
2400:
2397:
2395:
2392:
2390:
2387:
2385:
2382:
2380:
2379:6-Hydroxydopa
2377:
2375:
2372:
2370:
2367:
2365:
2362:
2360:
2353:
2352:
2350:
2348:
2347:Noradrenergic
2344:
2338:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2312:Norsalsolinol
2310:
2308:
2306:
2302:
2300:
2297:
2295:
2292:
2290:
2287:
2285:
2282:
2280:
2277:
2275:
2272:
2270:
2267:
2265:
2262:
2260:
2259:Fenpropathrin
2257:
2255:
2252:
2250:
2247:
2245:
2244:DOPAL quinone
2242:
2240:
2237:
2235:
2232:
2230:
2227:
2225:
2222:
2220:
2217:
2215:
2212:
2209:
2208:methylmercury
2205:
2201:
2198:
2196:
2193:
2191:
2190:6-Hydroxydopa
2188:
2186:
2183:
2181:
2179:
2174:
2172:
2169:
2167:
2164:
2162:
2155:
2154:
2152:
2150:
2146:
2142:
2135:
2130:
2128:
2123:
2121:
2116:
2115:
2112:
2105:
2102:
2100:
2097:
2095:
2090:
2087:
2084:
2080:
2076:
2072:
2068:
2064:
2063:Time Magazine
2060:
2056:
2052:
2048:
2044:
2040:
2036:
2032:
2028:
2024:
2020:
2016:
2012:
2008:
2003:
2002:
1998:
1989:
1985:
1981:
1977:
1970:
1967:
1962:
1958:
1954:
1950:
1946:
1942:
1934:
1931:
1926:
1922:
1918:
1914:
1910:
1906:
1898:
1895:
1890:
1886:
1882:
1878:
1874:
1870:
1863:
1860:
1855:
1849:
1845:
1838:
1836:
1832:
1827:
1823:
1819:
1815:
1811:
1807:
1800:
1797:
1792:
1788:
1782:
1779:
1771:
1767:
1760:
1754:
1751:
1746:
1742:
1738:
1734:
1730:
1726:
1722:
1718:
1717:
1709:
1706:
1703:
1697:
1694:
1689:
1683:
1679:
1674:
1673:
1667:
1666:Palfreman, J.
1663:
1657:
1654:
1642:
1641:
1636:
1630:
1627:
1622:
1621:
1616:
1610:
1607:
1594:
1590:
1584:
1581:
1576:
1572:
1568:
1564:
1560:
1556:
1552:
1548:
1541:
1538:
1533:
1529:
1525:
1521:
1514:
1511:
1499:
1495:
1491:
1484:
1481:
1466:
1460:
1457:
1452:
1448:
1441:
1439:
1435:
1430:
1426:
1421:
1416:
1412:
1408:
1404:
1397:
1394:
1389:
1385:
1380:
1375:
1370:
1365:
1361:
1357:
1353:
1349:
1345:
1338:
1335:
1330:
1326:
1322:
1318:
1314:
1310:
1306:
1302:
1294:
1291:
1286:
1282:
1277:
1272:
1268:
1264:
1260:
1256:
1252:
1245:
1242:
1238:. ChemIDplus.
1237:
1231:
1228:
1223:
1219:
1215:
1211:
1204:
1201:
1194:
1190:
1189:Norsalsolinol
1187:
1185:
1182:
1180:
1177:
1176:
1172:
1167:
1166:
1161:
1160:
1156:
1152:
1151:
1146:
1145:
1141:
1137:
1136:
1132:In the novel
1131:
1130:
1126:
1124:
1122:
1118:
1114:
1109:
1107:
1099:
1091:
1084:
1082:
1080:
1076:
1072:
1068:
1063:
1061:
1057:
1053:
1049:
1041:
1039:
1037:
1033:
1029:
1026:
1022:
1017:
1013:
1011:
1007:
1004:
998:
996:
992:
988:
984:
980:
970:
968:
967:
962:
958:
954:
953:
948:
943:
941:
937:
933:
929:
924:
922:
918:
914:
910:
907:
903:
899:
891:
889:
886:
882:
877:
875:
871:
867:
862:
859:
855:
850:
848:
844:
839:
837:
836:free radicals
833:
832:mitochondrial
829:
825:
821:
817:
816:pars compacta
813:
810:
806:
802:
798:
795:
791:
787:
782:
780:
769:
766:
758:
755:December 2022
747:
744:
740:
737:
733:
730:
726:
723:
719:
716: –
715:
711:
710:Find sources:
704:
700:
694:
693:
688:This section
686:
682:
677:
676:
670:
668:
666:
662:
658:
654:
650:
645:
643:
639:
635:
631:
627:
624:
620:
616:
612:
608:
604:
592:
585:
580:
563:
557:
550:
543:
536:
512:
509:
508:
504:
503:
498:
494:
491:
487:
486:
482:
480:
479:Boiling point
477:
476:
472:
470:
469:Melting point
467:
466:
459:
457:
454:
453:
435:
432:
428:
427:
422:
413:
409:
402:
388:
378:
374:
367:
359:
355:
354:DTXSID8040933
351:
350:
348:
338:
334:
333:
326:
322:
321:
319:
317:
314:
313:
306:
302:
301:
299:
293:
289:
288:
284:
280:
278:
275:
274:
267:
263:
262:
260:
258:
255:
254:
247:
243:
242:
240:
237:
233:
232:
225:
224:
222:
220:
215:
214:
210:
206:
203:
201:
199:ECHA InfoCard
196:
195:
188:
184:
183:
181:
179:
176:
175:
168:
164:
163:
161:
159:
156:
155:
148:
144:
143:
141:
139:
136:
135:
128:
124:
123:
121:
117:
112:
111:
104:
100:
99:
97:
94:
90:
89:
84:
76:
72:
67:
63:
58:
54:
49:
41:
37:
30:
19:
2613:
2612:
2502:
2486:Fenfluramine
2414:Serotonergic
2304:
2298:
2234:DOPA quinone
2177:
2149:Dopaminergic
2093:
2078:
2067:the original
2062:
2010:
2006:
1982:(1): 31–38.
1979:
1975:
1969:
1944:
1940:
1933:
1908:
1904:
1897:
1872:
1868:
1862:
1843:
1809:
1805:
1799:
1791:the original
1781:
1770:the original
1753:
1720:
1714:
1708:
1696:
1671:
1668:(May 1995).
1656:
1644:. Retrieved
1640:Ars Technica
1638:
1629:
1618:
1609:
1597:. Retrieved
1592:
1583:
1550:
1546:
1540:
1523:
1519:
1513:
1502:. Retrieved
1497:
1493:
1483:
1472:. Retrieved
1459:
1450:
1410:
1406:
1396:
1351:
1347:
1337:
1304:
1300:
1293:
1258:
1254:
1244:
1230:
1213:
1209:
1203:
1179:Phenindamine
1163:
1148:
1133:
1110:
1088:
1064:
1051:
1045:
1018:
1014:
999:
978:
976:
965:
951:
946:
944:
925:
895:
878:
863:
851:
840:
783:
779:Parkinsonism
776:
761:
752:
742:
735:
728:
721:
709:
697:Please help
692:verification
689:
649:psychoactive
646:
606:
602:
601:
506:
86:Identifiers
2621:Adrenergics
2491:Haloperidol
2264:Haloperidol
2214:Amphetamine
1941:J Neurochem
1599:3 September
1135:Neuromancer
1113:haloperidol
1025:insecticide
1003:subthalamic
921:Lewy bodies
805:glial cells
803:(MAO-B) of
424:Properties
205:100.044.475
167:ChEMBL24172
147:CHEBI:17963
2660:Categories
2441:2,4,5-THMA
2332:Salsolinol
2204:disulfiram
2171:2,4,5-THMA
2106:. nih.gov.
1504:2012-03-06
1474:2012-03-06
1307:: 104792.
1195:References
995:entacapone
847:selegiline
786:lipophilic
725:newspapers
456:Molar mass
325:9P21XSP91P
236:IUPHAR/BPS
178:ChemSpider
114:3D model (
103:28289-54-5
93:CAS Number
2614:See also:
2436:2,4,5-THA
2364:2,4,5-THA
2166:2,4,5-THA
1905:Brain Res
1329:250929452
1153:episode "
1090:Analogues
1085:Analogues
1075:herbicide
1071:cyperquat
1048:analgesic
1032:complex I
1021:pesticide
1010:stem cell
991:carbidopa
977:Langston
906:pethidine
824:complex I
665:pethidine
619:precursor
226:248-939-7
218:EC Number
2666:Prodrugs
2584:Unsorted
2404:Xylamine
2327:Rotenone
2322:Paraquat
2279:Mancozeb
2249:Dopamine
2229:Dieldrin
2051:31966839
1988:10389142
1826:18919741
1745:39743261
1737:17401348
1575:44304872
1429:16141438
1321:35872230
1285:21486284
1173:See also
1079:paraquat
1067:chloride
1028:rotenone
987:levodopa
913:levodopa
898:Maryland
881:primates
866:cortical
854:reuptake
671:Toxicity
661:morphine
609:) is an
507:NFPA 704
500:Hazards
2471:5,7-DHT
2466:5,6-DHT
2451:3,4-DCA
2431:2,4-DCA
2384:DOPEGAL
2374:5,7-DHT
2369:5,6-DHT
2224:Daidzin
2219:Benomyl
2202:(e.g.,
2185:5,6-DHT
2043:6823561
2035:1690734
2015:Bibcode
2007:Science
1961:8094744
1925:2765888
1889:2253555
1388:8197193
1356:Bibcode
1276:3229766
1034:of the
966:Horizon
917:cocaine
909:analogs
885:Rodents
870:putamen
826:of the
818:of the
812:neurons
739:scholar
640:of the
636:in the
634:neurons
621:to the
584:what is
582: (
461:173.259
292:PubChem
2591:5-HIAL
2049:
2041:
2033:
1986:
1959:
1923:
1887:
1850:
1824:
1743:
1735:
1684:
1646:21 May
1573:
1567:298352
1565:
1427:
1386:
1376:
1327:
1319:
1283:
1273:
1052:et al.
979:et al.
940:Sweden
794:cation
741:
734:
727:
720:
714:"MPTP"
712:
579:verify
576:
408:SMILES
266:C04599
158:ChEMBL
69:Names
2601:RHPTP
2461:5-IAI
2422:2′-NH
2389:DSP-4
2355:2′-NH
2337:Ziram
2284:Maneb
2239:DOPAL
2157:2′-CH
2079:Wired
2047:S2CID
2031:JSTOR
1773:(PDF)
1762:(PDF)
1741:S2CID
1571:S2CID
1468:(PDF)
1379:43940
1325:S2CID
1155:Stiff
1106:-MPTP
1102:2′-CH
1098:-MPTP
1094:2′-NH
1058:with
746:JSTOR
732:books
642:brain
373:InChI
138:ChEBI
116:JSmol
46:MPTP
2596:RHPP
2570:PCMA
2550:MMAI
2535:MDEA
2530:MDAI
2520:MBDB
2515:HPTP
2446:3-CA
2299:MPTP
2274:HPTP
2094:NOVA
2092:PBS
2039:PMID
1984:PMID
1957:PMID
1921:PMID
1885:PMID
1848:ISBN
1822:PMID
1733:PMID
1682:ISBN
1648:2016
1601:2023
1563:PMID
1498:2010
1425:PMID
1384:PMID
1317:PMID
1281:PMID
1119:and
1117:HPTP
1111:The
1023:and
1008:and
993:and
952:NOVA
872:and
718:news
663:and
657:drug
653:MPPP
603:MPTP
316:UNII
305:1388
277:MeSH
257:KEGG
187:1346
36:MPPP
2575:PIA
2565:PCA
2560:PBA
2510:HPP
2481:DCA
2476:αET
2269:HPP
2023:doi
2011:219
1949:doi
1913:doi
1909:491
1877:doi
1814:doi
1725:doi
1555:doi
1528:doi
1524:335
1415:doi
1374:PMC
1364:doi
1309:doi
1305:140
1271:PMC
1263:doi
1259:164
1218:doi
1121:HPP
961:BBC
957:PBS
938:in
701:by
626:MPP
342:EPA
295:CID
246:280
40:MPP
38:or
2662::
2643:•
2639:•
2635:•
2631:•
2627:•
2623:•
2619:•
2206:,
2176:5-
2077:.
2061:.
2045:.
2037:.
2029:.
2021:.
2009:.
1980:51
1978:.
1955:.
1945:60
1943:.
1919:.
1907:.
1883:.
1873:22
1871:.
1834:^
1820:.
1810:12
1808:.
1739:.
1731:.
1719:.
1680:.
1676:.
1664:;
1637:.
1617:.
1591:.
1569:.
1561:.
1549:.
1522:.
1496:.
1492:.
1437:^
1423:.
1411:88
1409:.
1405:.
1382:.
1372:.
1362:.
1352:91
1350:.
1346:.
1323:.
1315:.
1303:.
1279:.
1269:.
1257:.
1253:.
1214:35
1212:.
1157:."
1038:.
969:.
446:15
440:12
2503:N
2424:2
2357:2
2305:N
2210:)
2178:S
2159:3
2133:e
2126:t
2119:v
2053:.
2025::
2017::
1990:.
1963:.
1951::
1927:.
1915::
1891:.
1879::
1856:.
1828:.
1816::
1747:.
1727::
1721:2
1690:.
1650:.
1603:.
1577:.
1557::
1551:1
1534:.
1530::
1507:.
1477:.
1431:.
1417::
1390:.
1366::
1358::
1331:.
1311::
1287:.
1265::
1224:.
1220::
1104:3
1096:2
768:)
762:(
757:)
753:(
743:·
736:·
729:·
722:·
695:.
605:(
574:N
548:0
541:0
534:4
449:N
443:H
437:C
344:)
340:(
118:)
42:.
31:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.