347:
198:
51:
508:
670:
42:
513:
559:
986:. 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.
876:
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
849:
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
511:
1004:
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.
989:
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,
1245:
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".
1182:
877:
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.
1465:
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".
1051:. 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.
919:, 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
512:
865:, 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.
923:
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
572:
1291:"Implanted fibroblasts genetically engineered to produce brain-derived neurotrophic factor prevent 1-methyl-4-phenylpyridinium toxicity to dopaminergic neurons in the rat"
1818:
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".
900:
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
514:
1492:
Davis GC, Williams AC, Markey SP, Ebert MH, Caine ED, Reichert CM, Kopin IJ (1979). "Chronic parkinsonism secondary to intravenous injection of meperidine analogs".
1944:
1581:
1115:
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.
889:, 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
396:
1733:
1871:
1436:
2435:
536:
2427:
1798:
1632:
17:
656:(meperidine). The Parkinson-inducing effects of MPTP were first discovered following accidental injection as a result of contaminated MPPP.
1111:
271:
2431:
1937:
890:
2471:
1751:
Lee, J.; Ziering, A.; Heineman, S. D.; Berger, L. (1947). "Piperidine
Derivatives. Part II. 2-Phenyl- and 2-Phenylalkyl-Piperidines".
1647:"The Case of the Frozen Addicts" first broadcast 7 April 1986 and "Awakening the Frozen Addicts" first broadcast 4 January 1993. See
2330:
2178:
2135:
753:
361:
838:. MAOIs prevent the metabolism of MPTP to MPP by inhibiting the action of MAO-B, minimizing toxicity, and preventing neural death.
2340:
2320:
1998:
1535:
2231:
2037:
1974:
1705:
1155:
Buchi, I. J. (1952). "Synthese und analgetische
Wirkung einiger 1-Methyl-4-phenyl-piperidin-(4)-alkylsulfone. 1. Mitteilung".
2325:
1930:
1019:
causes
Parkinsonism in rats by killing dopaminergic neurons in the substantia nigra. Like MPP, rotenone also interferes with
916:
830:
Because MPTP itself is not directly harmful, toxic effects of acute MPTP poisoning can be mitigated by the administration of
691:
234:
2315:
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2188:
579:
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2407:
304:
2381:
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2226:
2158:
1969:
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831:
785:
325:
1561:
931:, the motor symptoms of two of the three patients were successfully treated, and the third showed partial recovery.
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1101:
734:
115:
680:
2466:
1737:
939:
885:
The neurotoxicity of MPTP was hinted at in 1976 after Barry Kidston, a 23-year-old chemistry graduate student in
706:
205:
1993:
1953:
1648:
1024:
816:
611:
265:
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cell, which is not the case in SNc neurons due to their high-calcium-dependent autonomous pacemaker activity.
778:
2221:
1879:
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522:
2285:
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1988:
1044:
713:
2102:
1979:
193:
2423:
2419:
2415:
2355:
2271:
1198:"Animal models of Parkinson's disease: A source of novel treatments and clues to the cause of the disease"
994:
953:
857:
control of complex movements. The direction of complex movement is based from the substantia nigra to the
618:
2236:
2350:
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1911:
1887:
687:
645:
607:
155:
2216:
2153:
1660:
Jackson-Lewis, V.; Przedborski, S. (2007). "Protocol for the MPTP Mouse Model of Parkinson's Disease".
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63:
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81:
2032:
1859:
1843:
1687:
1566:
1517:
1350:"Richardson, Jason R., et al. "Paraquat neurotoxicity is distinct from that of MPTP and rotenone"
1271:
702:
603:
1289:
Frim, D. M.; Uhler, T. A.; Galpern, W. R.; Beal, M. F.; Breakefield, X. O.; Isacson, O. (1994).
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419:
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2386:
841:
Dopaminergic neurons are selectively vulnerable to MPP because DA neurons exhibit dopamine
313:
91:
2345:
2335:
2305:
2087:
2072:
1736:. National Institute of Neurological Disorders and Stroke. 9 February 2005. Archived from
1394:"Chapter 30 The Impact of MPTP on Parkinson's Disease Research: Past, Present, and Future"
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924:
862:
854:
175:
1916:
1831:
1306:
346:
197:
135:
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1222:
1197:
1096:
1086:
1008:
In 2000, another animal model for Parkinson's disease was found. It was shown that the
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2006:
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186:
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824:
820:
797:
767:
637:
1898:
727:
50:
1437:"The Establishment of Chronic Parkinson's Disease in Mouse Model Induced by MPTP"
912:
and destruction of dopaminergic neurons in the substantia nigra were discovered.
293:
2295:
2193:
2115:
2062:
2012:
1734:"Summary of the Article by Dr. Greenamyre on Pesticides and Parkinson's Disease"
1478:
1081:
1013:
991:
669:
1393:
2130:
2002:
1904:
983:
835:
793:
444:
224:
166:
1582:"How tainted drugs "froze" young people—but kickstarted Parkinson's research"
1168:
640:
effects, the compound may be accidentally produced during the manufacture of
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1922:
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1366:
1315:
1063:
1059:
1036:
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998:
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812:
653:
1772:
1683:
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1375:
1267:
1231:
1855:
1334:
770:, hence users of MPPP contaminated with MPTP will develop these symptoms.
2198:
2125:
2120:
2077:
2047:
2027:
1513:
1067:
1055:
1016:
975:
974:
resulted in Parkinsonism, symptoms of which were subsequently reduced by
901:
886:
842:
649:
535:
528:
521:
494:
1764:
1089:, MPTP is used as a means of inducing Parkinsonism in another character.
1001:
research, all of which have demonstrated initial provisional successes.
978:, the drug-of-choice in the treatment of Parkinson's disease along with
2022:
2017:
1847:
905:
869:
858:
800:
694: in this section. Unsourced material may be challenged and removed.
280:
206:
370:
InChI=1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3
1912:
https://openvault.wgbh.org/catalog/V_474CF2C8A20B4173988486AC4C605A3C
1066:. While cyperquat is not used anymore, the closely related substance
928:
873:
782:
622:
380:
InChI=1/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3
146:
845:
which is mediated by DAT, which also has high-affinity for MPP. The
549:
Except where otherwise noted, data are given for materials in their
16:
This article is about the chemical. For the mitochondrial pore, see
2300:
2092:
2067:
614:
472:
128 to 132 °C (262 to 270 °F; 401 to 405 K) 12 Torr
254:
28:
2183:
2082:
630:
126:
114:
104:
529:
823:
metabolism, which leads to cell death and causes the buildup of
641:
245:
24:
1926:
827:, toxic molecules that contribute further to cell destruction.
633:. It has been used to study disease models in various animals.
41:
949:
663:
853:
The gross depletion of dopaminergic neurons severely affects
781:. Once inside the brain, MPTP is metabolized into the toxic
330:
1435:
Luo Qin; Peng Guoguang; Wang Jiacai; Wang Shaojun (2010).
1054:
MPTP is used in industry as a chemical intermediate; the
962:
Contribution of MPTP to research into Parkinson's disease
506:
1706:"Pesticides and Parkinson's Disease - A Critical Review"
1562:"Success reported using fetal tissue to repair a brain"
567:
1398:
Parkinson's Disease. Diagnosis and Clinical Management
1070:
is still being used as a herbicide in some countries.
1901:- Contains information regarding MPTP as a neurotoxin
1094:
MPTP-induced Parkinson's disease is featured in the
2374:
2207:
2144:
1960:
233:
1616:
1888:"How a Junkie's Brain Helps Parkinson's Patients"
292:
1295:Proceedings of the National Academy of Sciences
796:, specifically astrocytes. MPP kills primarily
510:
90:
1183:"1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine"
934:Langston documented the case in his 1995 book
1938:
8:
596:1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
272:1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
68:1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
1945:
1931:
1923:
1536:"Bogus Heroin Brings Illness on the Coast"
1396:. In Factor, S. A.; Weiner, W. J. (eds.).
1035:MPTP was first synthesized as a potential
345:
196:
174:
33:
1793:. Elsevier Health Sciences. p. 369.
1784:
1782:
1387:
1385:
1365:
1324:
1314:
1221:
754:Learn how and when to remove this message
312:
1909:episode, "The Case of the Frozen Addict"
1248:Neuroscience & Biobehavioral Reviews
970:(1984) found that injections of MPTP in
766:Injection of MPTP causes rapid onset of
1917:"The MPTP Story" by J. William Langston
1711:. Institute of Environment and Health,
1441:Journal of Chongqing Medical University
1147:
401:
366:
341:
270:
773:MPTP itself is not toxic, but it is a
187:
777:compound and can therefore cross the
617:, which causes permanent symptoms of
462:40 °C (104 °F; 313 K)
373:Key: PLRACCBDVIHHLZ-UHFFFAOYSA-N
154:
134:
18:Mitochondrial permeability transition
7:
1789:Vinken, P. J.; Bruyn, G. W. (1994).
1112:The Metamorphosis of Prime Intellect
692:adding citations to reliable sources
1791:Intoxications of the Nervous System
1467:The New England Journal of Medicine
1196:Duty, Susan; Jenner, Peter (2011).
904:but he died 18 months later from a
891:National Institute of Mental Health
881:Discovery in users of illicit drugs
383:Key: PLRACCBDVIHHLZ-UHFFFAOYAV
283:
253:
938:, which was later featured in two
803:in a part of the brain called the
14:
648:with effects similar to those of
1872:"Surprising Clue to Parkinson's"
1214:10.1111/j.1476-5381.2011.01426.x
668:
557:
437:
431:
49:
40:
2436:Monoamine metabolism modulators
1417:. Neuro Detective International
1260:10.1016/j.neubiorev.2022.104792
1202:British Journal of Pharmacology
893:found traces of MPTP and other
679:needs additional citations for
553:(at 25 °C , 100 kPa).
1878:. 24 June 2001. Archived from
1715:. October 2005. Archived from
1619:The Case of the Frozen Addicts
936:The Case of the Frozen Addicts
917:Santa Clara County, California
425:
1:
2428:Monoamine reuptake inhibitors
2408:Receptor/signaling modulators
1058:of the toxic metabolite MPP,
1753:Journal of Organic Chemistry
1506:10.1016/0165-1781(79)90006-4
1412:"Parkinson's Disease Models"
948:, re-aired in the UK on the
868:MPTP causes Parkinsonism in
832:monoamine oxidase inhibitors
1479:10.1056/NEJM199612263352618
1400:. Demos Medical Publishing.
786:1-methyl-4-phenylpyridinium
621:by destroying dopaminergic
2488:
2432:Monoamine releasing agents
1348:Richardson, Jason (2005).
22:
15:
2472:Monoaminergic neurotoxins
2400:
1954:Monoaminergic neurotoxins
1109:In Roger Williams' novel
636:While MPTP itself has no
606:. It is of interest as a
547:
488:
412:
392:
357:
74:
62:
57:
48:
39:
1649:List of Horizon episodes
1392:Langston, J. W. (2002).
1169:10.1002/hlca.19520350514
1025:electron transport chain
925:Lund University Hospital
915:In 1983, four people in
908:overdose. Upon autopsy,
817:electron transport chain
612:monoaminergic neurotoxin
602:. It is classified as a
23:Not to be confused with
1840:10.1126/science.6823561
1316:10.1073/pnas.91.11.5104
1049:1-methyl-4-piperidinone
1045:phenylmagnesium bromide
961:
1676:10.1038/nprot.2006.342
1354:Toxicological Sciences
1157:Helvetica Chimica Acta
995:electrical stimulation
811:. MPP interferes with
517:
404:c2ccccc2/C1=C/CN(C)CC1
2331:MDMA (midomafetamine)
1722:on February 27, 2008.
1367:10.1093/toxsci/kfi304
1062:, has been used as a
644:, a synthetic opioid
516:
2194:Oxidopamine (6-OHDA)
2116:Oxidopamine (6-OHDA)
2106:-Methylnorsalsolinol
1894:. 21 September 2007.
1740:on October 16, 2007.
1713:Cranfield University
872:, including humans.
847:dopamine transporter
788:(MPP) by the enzyme
688:improve this article
499:(fire diamond)
64:Preferred IUPAC name
2462:Tetrahydropyridines
2316:MDA (tenamfetamine)
2247:4-CAB (α-ethyl-PCA)
2189:MDA (tenamfetamine)
1832:1983Sci...219..979L
1765:10.1021/jo01170a021
1570:. 26 November 1992.
1494:Psychiatry Research
1307:1994PNAS...91.5104F
1039:in 1947 by Ziering
921:J. William Langston
790:monoamine oxidase B
779:blood–brain barrier
619:Parkinson's disease
479:Solubility in water
452: g·mol
36:
1984:-Cysteinyldopamine
1882:on March 30, 2005.
1567:The New York Times
1540:The New York Times
1074:In popular culture
1031:Synthesis and uses
798:dopamine-producing
604:tetrahydropyridine
580:Infobox references
518:
34:
2444:
2443:
2439:
2276:-Dimethyldopamine
2267:α-Me-DA (3,4-DHA)
1899:Erowid MPTP Vault
1826:(4587): 979–980.
1800:978-0-444-81284-1
1634:978-0-679-42465-9
1542:. 9 December 1983
1473:(26): 2002–2003.
1301:(11): 5104–5108.
1131:6-Hydroxydopamine
819:, a component of
764:
763:
756:
738:
588:Chemical compound
586:
585:
484:Slightly soluble
326:CompTox Dashboard
116:Interactive image
2479:
2467:Phenyl compounds
2402:
2053:Dopamine quinone
1947:
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1663:Nature Protocols
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1208:(4): 1357–1391.
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1187:
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1179:
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1172:
1163:(5): 1527–1536.
1152:
972:squirrel monkeys
834:(MAOIs) such as
809:substantia nigra
759:
752:
748:
745:
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627:substantia nigra
600:organic compound
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420:Chemical formula
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2396:
2370:
2346:Norfenfluramine
2336:Methamphetamine
2203:
2140:
2093:MPP (cyperquat)
2088:Methamphetamine
1999:ALDH inhibitors
1956:
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1609:Langston, J. W.
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1097:Law & Order
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1043:by reaction of
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952:science series
944:productions by
883:
863:caudate nucleus
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2217:2'-Amino-MPTP
2215:
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2206:
2200:
2197:
2195:
2192:
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2174:6-Hydroxydopa
2172:
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2167:
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2162:
2160:
2157:
2155:
2154:2'-Amino-MPTP
2152:
2151:
2149:
2147:
2146:Noradrenergic
2143:
2137:
2134:
2132:
2129:
2127:
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2119:
2117:
2114:
2112:
2111:Norsalsolinol
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2058:Fenpropathrin
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2043:DOPAL quinone
2041:
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2019:
2016:
2014:
2011:
2008:
2007:methylmercury
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1185:. ChemIDplus.
1184:
1178:
1175:
1170:
1166:
1162:
1158:
1151:
1148:
1141:
1137:
1136:Norsalsolinol
1134:
1132:
1129:
1127:
1124:
1123:
1119:
1114:
1113:
1108:
1107:
1103:
1099:
1098:
1093:
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1084:
1083:
1079:In the novel
1078:
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828:
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825:free radicals
822:
821:mitochondrial
818:
814:
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805:pars compacta
802:
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744:December 2022
736:
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705: –
704:
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699:Find sources:
693:
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677:This section
675:
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468:Boiling point
466:
465:
461:
459:
458:Melting point
456:
455:
448:
446:
443:
442:
424:
421:
417:
416:
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398:
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377:
367:
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343:DTXSID8040933
340:
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188:ECHA InfoCard
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52:
47:
43:
38:
30:
26:
19:
2404:
2403:
2291:Fenfluramine
2273:
2209:Serotonergic
2103:
2097:
2033:DOPA quinone
1981:
1962:Dopaminergic
1906:
1891:
1880:the original
1875:
1823:
1819:
1790:
1756:
1752:
1746:
1738:the original
1728:
1717:the original
1700:
1667:
1661:
1655:
1643:
1618:
1615:(May 1995).
1603:
1591:. Retrieved
1587:Ars Technica
1585:
1576:
1565:
1556:
1544:. Retrieved
1539:
1530:
1497:
1493:
1487:
1470:
1466:
1460:
1449:. Retrieved
1444:
1440:
1430:
1419:. Retrieved
1406:
1397:
1357:
1353:
1343:
1298:
1294:
1284:
1251:
1247:
1240:
1205:
1201:
1191:
1177:
1160:
1156:
1150:
1126:Phenindamine
1110:
1095:
1080:
1053:
1040:
1034:
1007:
1003:
988:
967:
965:
954:
940:
935:
933:
914:
884:
867:
852:
840:
829:
772:
768:Parkinsonism
765:
750:
741:
731:
724:
717:
710:
698:
686:Please help
681:verification
678:
638:psychoactive
635:
595:
591:
590:
495:
75:Identifiers
2412:Adrenergics
2296:Haloperidol
2063:Haloperidol
2013:Amphetamine
1546:3 September
1082:Neuromancer
1014:insecticide
992:subthalamic
910:Lewy bodies
794:glial cells
792:(MAO-B) of
413:Properties
194:100.044.475
156:ChEMBL24172
136:CHEBI:17963
2451:Categories
2232:2,4,5-THMA
2131:Salsolinol
2003:disulfiram
1975:2,4,5-THMA
1919:. nih.gov.
1451:2012-03-06
1421:2012-03-06
1254:: 104792.
1142:References
984:entacapone
836:selegiline
775:lipophilic
714:newspapers
445:Molar mass
314:9P21XSP91P
225:IUPHAR/BPS
167:ChemSpider
103:3D model (
92:28289-54-5
82:CAS Number
2405:See also:
2227:2,4,5-THA
2159:2,4,5-THA
1970:2,4,5-THA
1276:250929452
1100:episode "
1064:herbicide
1060:cyperquat
1037:analgesic
1021:complex I
1010:pesticide
999:stem cell
980:carbidopa
966:Langston
895:pethidine
813:complex I
654:pethidine
608:precursor
215:248-939-7
207:EC Number
2457:Prodrugs
2375:Unsorted
2199:Xylamine
2126:Rotenone
2121:Paraquat
2078:Mancozeb
2048:Dopamine
2028:Dieldrin
1864:31966839
1773:18919741
1692:39743261
1684:17401348
1522:44304872
1376:16141438
1268:35872230
1232:21486284
1120:See also
1068:paraquat
1056:chloride
1017:rotenone
976:levodopa
902:levodopa
887:Maryland
870:primates
855:cortical
843:reuptake
660:Toxicity
650:morphine
598:) is an
496:NFPA 704
489:Hazards
2262:5,7-DHT
2257:5,6-DHT
2242:3,4-DCA
2222:2,4-DCA
2179:DOPEGAL
2169:5,7-DHT
2164:5,6-DHT
2023:Daidzin
2018:Benomyl
2001:(e.g.,
1989:5,6-DHT
1856:6823561
1848:1690734
1828:Bibcode
1820:Science
1335:8197193
1303:Bibcode
1223:3229766
1023:of the
955:Horizon
906:cocaine
898:analogs
874:Rodents
859:putamen
815:of the
807:of the
801:neurons
728:scholar
629:of the
625:in the
623:neurons
610:to the
573:what is
571: (
450:173.259
281:PubChem
2382:5-HIAL
1862:
1854:
1846:
1797:
1771:
1690:
1682:
1631:
1593:21 May
1520:
1514:298352
1512:
1374:
1333:
1323:
1274:
1266:
1230:
1220:
1041:et al.
968:et al.
929:Sweden
783:cation
730:
723:
716:
709:
703:"MPTP"
701:
568:verify
565:
397:SMILES
255:C04599
147:ChEMBL
58:Names
2392:RHPTP
2252:5-IAI
2184:DSP-4
2136:Ziram
2083:Maneb
2038:DOPAL
1892:Wired
1860:S2CID
1844:JSTOR
1720:(PDF)
1709:(PDF)
1688:S2CID
1518:S2CID
1415:(PDF)
1326:43940
1272:S2CID
1102:Stiff
1047:with
735:JSTOR
721:books
631:brain
362:InChI
127:ChEBI
105:JSmol
35:MPTP
2387:RHPP
2361:PCMA
2341:MMAI
2326:MDEA
2321:MDAI
2311:MBDB
2306:HPTP
2237:3-CA
2098:MPTP
2073:HPTP
1907:NOVA
1905:PBS
1852:PMID
1795:ISBN
1769:PMID
1680:PMID
1629:ISBN
1595:2016
1548:2023
1510:PMID
1445:2010
1372:PMID
1331:PMID
1264:PMID
1228:PMID
1012:and
997:and
982:and
941:NOVA
861:and
707:news
652:and
646:drug
642:MPPP
592:MPTP
305:UNII
294:1388
266:MeSH
246:KEGG
176:1346
25:MPPP
2366:PIA
2356:PCA
2351:PBA
2301:HPP
2286:DCA
2281:αET
2068:HPP
1836:doi
1824:219
1761:doi
1672:doi
1502:doi
1475:doi
1471:335
1362:doi
1321:PMC
1311:doi
1256:doi
1252:140
1218:PMC
1210:doi
1206:164
1165:doi
950:BBC
946:PBS
927:in
690:by
615:MPP
331:EPA
284:CID
235:280
29:MPP
27:or
2453::
2434:•
2430:•
2426:•
2422:•
2418:•
2414:•
2410:•
2272:α,
2005:,
1980:5-
1890:.
1874:.
1858:.
1850:.
1842:.
1834:.
1822:.
1781:^
1767:.
1757:12
1755:.
1686:.
1678:.
1666:.
1627:.
1623:.
1611:;
1584:.
1564:.
1538:.
1516:.
1508:.
1496:.
1469:.
1443:.
1439:.
1384:^
1370:.
1358:88
1356:.
1352:.
1329:.
1319:.
1309:.
1299:91
1297:.
1293:.
1270:.
1262:.
1250:.
1226:.
1216:.
1204:.
1200:.
1161:35
1159:.
1104:."
1027:.
958:.
435:15
429:12
2274:N
2104:N
2009:)
1982:S
1946:e
1939:t
1932:v
1866:.
1838::
1830::
1803:.
1775:.
1763::
1694:.
1674::
1668:2
1637:.
1597:.
1550:.
1524:.
1504::
1498:1
1481:.
1477::
1454:.
1424:.
1378:.
1364::
1337:.
1313::
1305::
1278:.
1258::
1234:.
1212::
1171:.
1167::
757:)
751:(
746:)
742:(
732:·
725:·
718:·
711:·
684:.
594:(
563:N
537:0
530:0
523:4
438:N
432:H
426:C
333:)
329:(
107:)
31:.
20:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
