HPTP

HPTP
Clinical data
Drug class	Serotonergic and dopaminergic neurotoxin
Identifiers
	IUPAC name 4-[4-(4-chlorophenyl)-3,6-dihydro-2H-pyridin-1-yl]-1-(4-fluorophenyl)butan-1-one;
CAS Number	52669-92-8;
PubChem CID	171187;
ChemSpider	149659;
ChEBI	CHEBI:177523;
ChEMBL	ChEMBL3544895;
CompTox Dashboard (EPA)	DTXSID80200642 ;
Chemical and physical data
Formula	C21H21ClFNO
Molar mass	357.85 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CC=C1C2=CC=C(C=C2)Cl)CCCC(=O)C3=CC=C(C=C3)F;
	InChI InChI=1S/C21H21ClFNO/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/h3-11H,1-2,12-15H2; Key:ZNOLNAPJKOYTHY-UHFFFAOYSA-N;

HPTP is a monoaminergic neurotoxin related to MPTP.^[1]^[2]^[3]^[4] It is the dehydration product of haloperidol.^[1]^[2]^[4] The agent is specifically a dopaminergic and serotonergic neurotoxin.^[1] HPTP is a prodrug of HPP⁺, which mediates its monoaminergic neurotoxicity.^[1]^[2]^[4] This is analogous to how MPP⁺ mediates the neurotoxicity of MPTP.^[1]^[2]^[4] Other related compounds include RHPTP and RHPP⁺.^[5]

References

1 2 3 4 5 Kostrzewa RM (2022). "Survey of Selective Monoaminergic Neurotoxins Targeting Dopaminergic, Noradrenergic, and Serotoninergic Neurons". Handbook of Neurotoxicity. Cham: Springer International Publishing. pp. 159–198. doi:10.1007/978-3-031-15080-7_53. ISBN 978-3-031-15079-1.
1 2 3 4 Igarashi, Kazuo (1998). "The Possible Role of an Active Metabolite Derived from the Neuroleptic Agent Haloperidol in Drug-Induced Parkinsonism". Journal of Toxicology: Toxin Reviews. 17 (1): 27–38. doi:10.3109/15569549809006488. ISSN 0731-3837.
↑ Górska A, Marszałł M, Sloderbach A (October 2015). "[The neurotoxicity of pyridinium metabolites of haloperidol]" [The neurotoxicity of pyridinium metabolites of haloperidol]. Postepy Higieny I Medycyny Doswiadczalnej (in Polish). 69: 1169–1175. doi:10.5604/17322693.1175009 (inactive 12 July 2025). PMID 26561842.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)
1 2 3 4 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". Pol J Pharmacol. 51 (1): 31–38. PMID 10389142.
↑ Avent KM, DeVoss JJ, Gillam EM (July 2006). "Cytochrome P450-mediated metabolism of haloperidol and reduced haloperidol to pyridinium metabolites". Chem Res Toxicol. 19 (7): 914–920. doi:10.1021/tx0600090. PMID 16841959.

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[Kostrzewa2022-1] 1 2 3 4 5 Kostrzewa RM (2022). "Survey of Selective Monoaminergic Neurotoxins Targeting Dopaminergic, Noradrenergic, and Serotoninergic Neurons". Handbook of Neurotoxicity. Cham: Springer International Publishing. pp. 159–198. doi:10.1007/978-3-031-15080-7_53. ISBN 978-3-031-15079-1.

[Igarashi1998-2] 1 2 3 4 Igarashi, Kazuo (1998). "The Possible Role of an Active Metabolite Derived from the Neuroleptic Agent Haloperidol in Drug-Induced Parkinsonism". Journal of Toxicology: Toxin Reviews. 17 (1): 27–38. doi:10.3109/15569549809006488. ISSN 0731-3837.

[GórskaMarszałłSloderbach2015-3] Górska A, Marszałł M, Sloderbach A (October 2015). "[The neurotoxicity of pyridinium metabolites of haloperidol]" [The neurotoxicity of pyridinium metabolites of haloperidol]. Postepy Higieny I Medycyny Doswiadczalnej (in Polish). 69: 1169–1175. doi:10.5604/17322693.1175009 (inactive 12 July 2025). PMID 26561842.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)

[CastagnoliCastagnoliVanderSchyf1999-4] 1 2 3 4 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". Pol J Pharmacol. 51 (1): 31–38. PMID 10389142.

[AventDeVossGillam2006-5] Avent KM, DeVoss JJ, Gillam EM (July 2006). "Cytochrome P450-mediated metabolism of haloperidol and reduced haloperidol to pyridinium metabolites". Chem Res Toxicol. 19 (7): 914–920. doi:10.1021/tx0600090. PMID 16841959.

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v t e Monoaminergic neurotoxins
Dopaminergic	2′-CH₃-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 4-MMA 5-S-Cysteinyldopamine 5,6-DHT 6-Hydroxydopa 6-OHDA quinone 6,7-DHT ALDH inhibitors (e.g., disulfiram, methylmercury) Amphetamine V-61 Benomyl Daidzin Dieldrin DOPA quinone DOPAL DOPAL quinone Dopamine Dopamine quinone Fenpropathrin Haloperidol HPP⁺ HPTP Imidazole propionate (ImP) Mancozeb Maneb Mephedrone Methamphetamine Methcathinone Methylone MPP⁺ (cyperquat) MPTP N-Methylnorsalsolinol Norsalsolinol Oxidopamine (6-OHDA) Paraquat Rotenone Salsolinol TaClo (1-TCMTC) Ziram
Noradrenergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4,5-THA 4,5-DHT 5,6-DHT 5,7-DHT 6-Hydroxydopa DOPEGAL DSP-4 MDA (tenamfetamine) Oxidopamine (6-OHDA) Xylamine V-61
Serotonergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4-DCA 2,4,5-THA 2,4,5-THMA pCPE 3-CA 3,4-DCA 4-CAB (α-ethyl-PCA) 4-CMA 4-HO-5-MeO-T 4,5-DHT 5-IAI 5-MAPB 5-MeO-DiPT 5,6-DHT 5,7-DHT 6,7-DHT αET ETAI Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP⁺ HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PBMA PCA PCMA PIA TAI
Unsorted	2,5-DDM-DOM 5-HIAL RHPP⁺ RHPTP
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators

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References