1325:
31:
762:
Subramanyam B, Pond SM, Eyles DW, Whiteford HA, Fouda HG, Castagnoli N (December 1991). "Identification of potentially neurotoxic pyridinium metabolite in the urine of schizophrenic patients treated with haloperidol".
665:
Castagnoli N, Castagnoli KP, Van der Schyf CJ, Usuki E, Igarashi K, Steyn SJ, et al. (1999). "Enzyme-catalyzed bioactivation of cyclic tertiary amines to form potential neurotoxins".
651:
311:
63:
489:
HPP was first identified as a neurotoxic metabolite of haloperidol in 1990 and 1991, many years after haloperidol was introduced clinically and following the discovery of MPTP.
1370:
816:
46:
Haloperidol pyridinium; Haloperidol pyridinium ion; Haloperidol pyridinium cation; BCPP; 4-CFOBP; 4-(4-Chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)pyridinium
325:
692:
Subramanyam B, Rollema H, Woolf T, Castagnoli N (January 1990). "Identification of a potentially neurotoxic pyridinium metabolite of haloperidol in rats".
1307:
727:
Subramanyam B, Woolf T, Castagnoli N (1991). "Studies on the in vitro conversion of haloperidol to a potentially neurotoxic pyridinium metabolite".
1414:
1389:
1363:
1299:
546:
579:
Igarashi K (1998). "The
Possible Role of an Active Metabolite Derived from the Neuroleptic Agent Haloperidol in Drug-Induced Parkinsonism".
1303:
809:
529:
Kostrzewa RM (2022). "Survey of
Selective Monoaminergic Neurotoxins Targeting Dopaminergic, Noradrenergic, and Serotoninergic Neurons".
1429:
1419:
1394:
1356:
1202:
1050:
1007:
345:
474:(EPS) in patients undergoing long-term haloperidol therapy. An alternative theory posits that these symptoms result from long-term
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1192:
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1409:
1103:
909:
846:
87:
1197:
802:
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Górska A, Marszałł M, Sloderbach A (October 2015). "" [The neurotoxicity of pyridinium metabolites of haloperidol].
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1182:
1060:
353:
InChI=1S/C21H18ClFNO/c22-19-7-3-16(4-8-19)17-11-14-24(15-12-17)13-1-2-21(25)18-5-9-20(23)10-6-18/h3-12,14-15H,1-2,13H2/q+1
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and has been detected in the brain following haloperidol administration in both animals and humans.
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16:
Monoaminergic neurotoxin related to MPTP and metabolites of haloperidol
459:
451:-like symptoms in humans. HPP is a neurotoxin specifically affecting
409:
229:
964:
444:
1055:
954:
413:
406:
310:
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533:. Cham: Springer International Publishing. pp. 159–198.
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78:
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37:
650:: CS1 maint: DOI inactive as of September 2024 (
462:, and its neurotoxicity resembles that of MPTP.
333:C1=CC(=CC=C1C2=CC=(C=C2)CCCC(=O)C3=CC=C(C=C3)F)Cl
137:
524:
522:
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112:
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8:
21:
1371:
1357:
817:
803:
795:
177:
29:
627:
616:Postepy Higieny I Medycyny Doswiadczalnej
470:HPP may contribute to the development of
197:
395:HPP is formed from haloperidol, and its
514:
350:
330:
157:
92:
643:
20:
237:
217:
7:
1321:
1319:
581:Journal of Toxicology: Toxin Reviews
481:, rather than direct neurotoxicity.
128:
1343:. You can help Knowledge (XXG) by
14:
1323:
277:
274:
271:
265:
95:4--1-(4-fluorophenyl)butan-1-one
1308:Monoamine metabolism modulators
729:Chemical Research in Toxicology
505:, has been detected in humans.
358:Key:KAPIKUHBALFONG-UHFFFAOYSA-N
1415:Human pathological metabolites
1390:Drugs not assigned an ATC code
667:Polish Journal of Pharmacology
280:
259:
1:
1300:Monoamine reuptake inhibitors
1280:Receptor/signaling modulators
466:Extrapyramidal symptoms (EPS)
416:. The compound can cross the
777:10.1016/0006-291x(91)91228-5
706:10.1016/0006-291x(90)91936-m
539:10.1007/978-3-031-15080-7_53
501:metabolite of haloperidol,
1446:
1318:
1304:Monoamine releasing agents
249:Chemical and physical data
1430:Nervous system drug stubs
1420:Monoaminergic neurotoxins
1272:
826:Monoaminergic neurotoxins
593:10.3109/15569549809006488
531:Handbook of Neurotoxicity
341:
321:
83:
28:
1395:4-Fluorophenyl compounds
1335:article relating to the
629:10.5604/17322693.1175009
391:Formation and metabolism
377:monoaminergic neurotoxin
57:Monoaminergic neurotoxin
632:(inactive 2024-09-15).
472:extrapyramidal symptoms
1410:Human drug metabolites
493:Additional metabolites
373:haloperidol pyridinium
1203:MDMA (midomafetamine)
497:Besides HPP, another
1425:Pyridinium compounds
1066:Oxidopamine (6-OHDA)
988:Oxidopamine (6-OHDA)
978:-Methylnorsalsolinol
430:structurally related
1188:MDA (tenamfetamine)
1119:4-CAB (α-ethyl-PCA)
1061:MDA (tenamfetamine)
741:10.1021/tx00019a017
449:Parkinson's disease
418:blood–brain barrier
25:
856:-Cysteinyldopamine
1352:
1351:
1316:
1315:
1311:
1148:-Dimethyldopamine
1139:α-Me-DA (3,4-DHA)
548:978-3-031-15079-1
476:dopamine receptor
447:), which induces
442:active metabolite
432:to the selective
366:
365:
312:Interactive image
1437:
1373:
1366:
1359:
1327:
1320:
1274:
925:Dopamine quinone
819:
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805:
796:
789:
788:
759:
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752:
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479:supersensitivity
371:, also known as
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1377:
1317:
1312:
1268:
1242:
1218:Norfenfluramine
1208:Methamphetamine
1075:
1012:
965:MPP (cyperquat)
960:Methamphetamine
871:ALDH inhibitors
828:
823:
793:
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1337:nervous system
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866:6-OHDA quinone
863:
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838:
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829:
824:
822:
821:
814:
807:
799:
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771:(2): 573–578.
754:
735:(1): 123–128.
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1296:Serotonergics
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1292:Melatonergics
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1288:Dopaminergics
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1112:
1110:
1107:
1105:
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1100:
1097:
1095:
1092:
1090:
1089:2'-Amino-MPTP
1087:
1086:
1084:
1082:
1078:
1072:
1069:
1067:
1064:
1062:
1059:
1057:
1054:
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1049:
1047:
1046:6-Hydroxydopa
1044:
1042:
1039:
1037:
1034:
1032:
1029:
1027:
1026:2'-Amino-MPTP
1024:
1023:
1021:
1019:
1018:Noradrenergic
1015:
1009:
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1004:
1001:
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996:
994:
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989:
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983:Norsalsolinol
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930:Fenpropathrin
928:
926:
923:
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918:
916:
915:DOPAL quinone
913:
911:
908:
906:
903:
901:
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896:
893:
891:
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886:
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880:
879:methylmercury
876:
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688:
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676:
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668:
661:
658:
653:
647:
639:
635:
630:
625:
622:: 1169–1175.
621:
618:(in Polish).
617:
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431:
424:Neurotoxicity
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53:
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41:
38:Clinical data
36:
32:
27:
19:
1405:Chloroarenes
1345:expanding it
1330:
1276:
1275:
1172:
1163:Fenfluramine
1145:
1081:Serotonergic
975:
939:
905:DOPA quinone
853:
834:Dopaminergic
768:
764:
757:
732:
728:
722:
697:
693:
687:
673:(1): 31–38.
670:
666:
660:
646:cite journal
619:
615:
609:
587:(1): 27–38.
584:
580:
530:
496:
488:
469:
457:dopaminergic
453:serotonergic
434:dopaminergic
427:
394:
372:
368:
367:
219:CHEBI:178132
18:
1284:Adrenergics
1168:Haloperidol
935:Haloperidol
885:Amphetamine
436:neurotoxin
397:dehydration
385:haloperidol
295: g·mol
114:125785-69-5
79:Identifiers
43:Other names
1384:Categories
1104:2,4,5-THMA
1003:Salsolinol
875:disulfiram
847:2,4,5-THMA
509:References
381:metabolite
300:3D model (
288:Molar mass
239:ChEMBL1269
199:47Z7A2W953
170:ChemSpider
159:DBMET01212
105:CAS Number
88:IUPAC name
52:Drug class
1400:Alkanones
1277:See also:
1099:2,4,5-THA
1031:2,4,5-THA
842:2,4,5-THA
601:0731-3837
485:Discovery
440:(and its
1247:Unsorted
1071:Xylamine
998:Rotenone
993:Paraquat
950:Mancozeb
920:Dopamine
900:Dieldrin
679:10389142
638:26561842
499:reactive
150:DrugBank
64:ATC code
1134:5,7-DHT
1129:5,6-DHT
1114:3,4-DCA
1094:2,4-DCA
1051:DOPEGAL
1041:5,7-DHT
1036:5,6-DHT
895:Daidzin
890:Benomyl
873:(e.g.,
861:5,6-DHT
785:1755839
749:1912294
714:2302206
460:neurons
428:HPP is
412:in the
410:enzymes
400:product
375:, is a
255:Formula
179:8151055
139:9975463
125:PubChem
1254:5-HIAL
783:
747:
712:
677:
636:
599:
545:
379:and a
326:SMILES
293:354.83
230:ChEMBL
1339:is a
1331:This
1264:RHPTP
1124:5-IAI
1056:DSP-4
1008:Ziram
955:Maneb
910:DOPAL
414:liver
407:CYP3A
405:, by
346:InChI
302:JSmol
210:ChEBI
1341:stub
1333:drug
1259:RHPP
1233:PCMA
1213:MMAI
1198:MDEA
1193:MDAI
1183:MBDB
1178:HPTP
1109:3-CA
970:MPTP
945:HPTP
781:PMID
745:PMID
710:PMID
675:PMID
652:link
634:PMID
597:ISSN
543:ISBN
503:RHPP
455:and
438:MPTP
403:HPTP
190:UNII
71:None
1238:PIA
1228:PCA
1223:PBA
1173:HPP
1158:DCA
1153:αET
940:HPP
773:doi
769:181
737:doi
702:doi
698:166
624:doi
589:doi
535:doi
445:MPP
387:.
383:of
369:HPP
129:CID
23:HPP
1386::
1306:•
1302:•
1298:•
1294:•
1290:•
1286:•
1282:•
1144:α,
877:,
852:5-
779:.
767:.
743:.
731:.
708:.
696:.
671:51
669:.
648:}}
644:{{
620:69
595:.
585:17
583:.
557:^
541:.
517:^
272:Cl
269:18
263:21
1372:e
1365:t
1358:v
1347:.
1146:N
976:N
881:)
854:S
818:e
811:t
804:v
787:.
775::
751:.
739::
733:4
716:.
704::
681:.
654:)
640:.
626::
603:.
591::
551:.
537::
304:)
281:O
278:N
275:F
266:H
260:C
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
