95969-40-7

Basic information

• Product Name: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-oxide
• Synonyms: pyridine, 1,2,3,6-tetrahydro-1-methyl-4-phenyl-, 1-oxide
• CAS NO: 95969-40-7
• Molecular Formula: C₁₂H₁₅NO
• Molecular Weight: 189.25
• Mol File: 95969-40-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-oxide(95969-40-7)
• EPA Substance Registry System: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-oxide(95969-40-7)

Safety Data

• Hazardous Substances Data: 95969-40-7(Hazardous Substances Data)

Usage

Classification

Synthetic compound

Discovery

Accidentally created

Effect on humans

Causes severe and irreversible Parkinson's disease-like symptoms

Toxic metabolite

MPP+ (formed by the enzyme monoamine oxidase-B)

Mechanism of action

Damages dopamine-producing neurons in the substantia nigra region of the brain, leading to a depletion of dopamine

Use in research

To study the mechanisms of Parkinson's disease and potential treatments for the condition.

Upstream product

• 28289-54-5 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine 
• 1445-73-4 1-Methyl-4-piperidone 
• 591-51-5 phenyllithium 
• 4972-68-3 1-methyl-4-phenyl-piperidin-4-ol 
• 23007-85-4 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride 

Downstream Products

• 76113-47-8 1,2,5,6-tetrahydro-1-methyl-4-phenyl-2-pyridine carbonitrile 
• 36913-39-0 4-phenyl-N-methylpyridinium iodide 

Relevant articles and documents

Preferential Extracellular Generation of the Active Parkinsonian Toxin MPP+ by Transporter-Independent Export of the Intermediate MPDP+

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.

Conversion of 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and its 5-Methyl Analog into Pyridinium Salts

Monoamine oxidase B metabolizes 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP; 1) first to 1-methyl-4-phenyl-2,3-dihydropyridinium salt (MPDP+; 5), and then to 1-methyl-4-phenylpyridinium salt (MPP+; 7).Chemical synthesis of MPD