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;
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

^ ^a ^b ^c ^d ^e 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.
^ ^a ^b ^c ^d 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 1 November 2024). PMID 26561842.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)
^ ^a ^b ^c ^d 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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v t e Monoaminergic neurotoxins
Dopaminergic	2′-CH₃-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 5-S-Cysteinyldopamine 5,6-DHT 6-Hydroxydopa 6-OHDA quinone ALDH inhibitors (e.g., disulfiram, methylmercury) Amphetamine Benomyl Daidzin Dieldrin DOPA quinone DOPAL DOPAL quinone Dopamine Dopamine quinone Fenpropathrin Haloperidol HPP HPTP Mancozeb Maneb Mephedrone Methamphetamine Methyone MPP (cyperquat) MPTP N-Methylnorsalsolinol Norsalsolinol Oxidopamine (6-OHDA) Paraquat Rotenone Salsolinol Ziram
Noradrenergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4,5-THA 5,6-DHT 5,7-DHT 6-Hydroxydopa DOPEGAL DSP-4 MDA (tenamfetamine) Oxidopamine (6-OHDA) Xylamine
Serotonergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4-DCA 2,4,5-THA 2,4,5-THMA 3-CA 3,4-DCA 4-CAB (α-ethyl-PCA) 4-CMA 5-IAI 5,6-DHT 5,7-DHT αET Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PCA PIA
Unsorted	5-HIAL RHPP RHPTP
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators