23007-85-4 Usage
Description
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride, commonly known as MPTP, is a synthetic chemical compound with a white solid appearance. It is classified as a dopaminergic neurotoxin that has been found to induce severe and irreversible Parkinsonian symptoms in both humans and monkeys.
Uses
Used in Pharmaceutical Research:
MPTP is utilized as a neurotoxin in the creation of animal models for parkinsonism. It is metabolized by monoamine oxidase B to produce MPDP+ and MPP+, with MP+ being the active toxic agent. MPP+ is known to induce neurotoxicity primarily by inhibiting complex I of the mitochondrial electron transport chain, which leads to ATP depletion and increased oxidative stress. This makes MPTP a valuable tool for studying the key features and mechanisms of different neurotoxic models of Parkinson's disease, including the MPTP model itself.
Used in Neurodegenerative Disease Studies:
In the field of neurodegenerative disease research, MPTP serves as a critical compound for understanding the progression and development of Parkinson's disease. By selectively destroying dopaminergic neurons, researchers can gain insights into the underlying causes and potential treatments for this debilitating condition.
Used in Toxicology:
MPTP is also employed in toxicology to study the effects of neurotoxins on the central nervous system. Its role in causing Parkinsonian symptoms provides valuable information on the potential risks and consequences of exposure to similar compounds in various environmental and occupational settings.
Biochem/physiol Actions
Dopaminergic neurotoxin.
Purification Methods
Purify MPTP by recrystallisation from pKEst ~ Me2CO/isoPrOH. The free base has m 40-42o(from heptane), b 99-100o/1.3mm, 128-132o/12mm, (137-142o/0.8mm), n 25 1.5347. The hydrochloride has m 251-252o(from Me2CO/isoPrOH) [Schmidle & Mansfield J Am Chem Soc 78 425 1956, Defeudis Drug Dev Res 15 1 1988, Beilstein 20 III/IV 3240, 20/7 V 121.]
Check Digit Verification of cas no
The CAS Registry Mumber 23007-85-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,0,0 and 7 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 23007-85:
(7*2)+(6*3)+(5*0)+(4*0)+(3*7)+(2*8)+(1*5)=74
74 % 10 = 4
So 23007-85-4 is a valid CAS Registry Number.
InChI:InChI=1/C12H15N.ClH/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11;/h2-7H,8-10H2,1H3;1H
23007-85-4Relevant articles and documents
Preferential Extracellular Generation of the Active Parkinsonian Toxin MPP+ by Transporter-Independent Export of the Intermediate MPDP+
Schildknecht, Stefan,Pape, Regina,Meiser, Johannes,Karreman, Christiaan,Strittmatter, Tobias,Odermatt, Meike,Cirri, Erica,Friemel, Anke,Ringwald, Markus,Pasquarelli, Noemi,Ferger, Boris,Brunner, Thomas,Marx, Andreas,M?ller, Heiko M.,Hiller, Karsten,Leist, Marcel
, p. 1001 - 1016 (2015/11/18)
Aims: 1-Methyl-4-phenyl-tetrahydropyridine (MPTP) is among the most widely used neurotoxins for inducing experimental parkinsonism. MPTP causes parkinsonian symptoms in mice, primates, and humans by killing a subpopulation of dopaminergic neurons. Extrapolations of data obtained using MPTP-based parkinsonism models to human disease are common; however, the precise mechanism by which MPTP is converted into its active neurotoxic metabolite, 1-methyl-4-phenyl-pyridinium (MPP+), has not been fully elucidated. In this study, we aimed to address two unanswered questions related to MPTP toxicology: (1) Why are MPTP-converting astrocytes largely spared from toxicity? (2) How does MPP+ reach the extracellular space? Results: In MPTP-treated astrocytes, we discovered that the membrane-impermeable MPP+, which is generally assumed to be formed inside astrocytes, is almost exclusively detected outside of these cells. Instead of a transporter-mediated export, we found that the intermediate, 1-methyl-4-phenyl-2,3-dihydropyridinium (MPDP+), and/or its uncharged conjugate base passively diffused across cell membranes and that MPP+ was formed predominately by the extracellular oxidation of MPDP+ into MPP+. This nonenzymatic extracellular conversion of MPDP+ was promoted by O2, a more alkaline pH, and dopamine autoxidation products. Innovation and Conclusion: Our data indicate that MPTP metabolism is compartmentalized between intracellular and extracellular environments, explain the absence of toxicity in MPTP-converting astrocytes, and provide a rationale for the preferential formation of MPP+ in the extracellular space. The mechanism of transporter-independent extracellular MPP+ formation described here indicates that extracellular genesis of MPP+ from MPDP is a necessary prerequisite for the selective uptake of this toxin by catecholaminergic neurons. Antioxid. Redox Signal. 23, 1001-1016.
