86219-77-4

Usage

Type of Compound

Synthetic neurotoxin

Discovery

Accidentally synthesized in the 1980s during the production of a synthetic opioid

Metabolism

Converted into MPP+ (1-methyl-4-phenylpyridinium) in the body

Target

Selectively destroys dopamine-producing neurons

Brain Region Affected

Substantia nigra

Disease Association

Parkinson's disease

Symptoms

Motor symptoms such as tremors, rigidity, and bradykinesia

Research Significance

Provides insights into the pathophysiology of Parkinson's disease

Application

Used to develop animal models for studying Parkinson's disease and testing potential treatments

InChI:InChI=1/C13H17NO/c1-14-8-7-13(12(9-14)10-15)11-5-3-2-4-6-11/h2-7,12,15H,8-10H2,1H3

Upstream product

• 98-83-9 isopropenylbenzene 
• 28289-54-5 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine 
• 109-77-3 malononitrile 
• 50-00-0 formaldehyd 
• 95835-87-3 1,2,3,6-Tetrahydro-4-phenyl-3-pyridinemethanol 

Downstream Products

• 50373-11-0 trans-1-methyl-4-phenyl-3-(hydroxymethyl)piperidine 
• 50373-11-0 ((3S,4S)-1-Methyl-4-phenyl-piperidin-3-yl)-methanol 
• 95835-89-5 3-(Acetoxymethyl)-1,2,3,6-tetrahydro-1-methyl-4-phenylpyridine 
• 102075-85-4 1-methyl-4-phenyl-3-propionyloxy-1,2,3,6-tetrahydropyridine 
• 939-23-1 p-phenylpyridine 
• 218945-04-1 5-hydroxymethyl-1-methyl-2-oxo-4-phenyl-1,2,3,6-tetrahydropyridine 
• 54088-07-2 (+/-)-cis-3-(4-methoxyphenoxymethyl)-1-methyl-4-phenylpiperidine 
• 54088-07-2 trans-(+)-3-<(4-methoxyphenoxy)methyl>-1-methyl-4-phenylpiperidine hydrochloride 
• 675597-14-5 3,4-dihydroxy-1-methyl-2-oxo-4-phenyl-5-propionyloxymethylpiperidine 
• 218945-10-9 5-acetoxymethyl-3,4-dihydroxy-1-methyl-2-oxo-4-phenylpiperidine 
• 107412-06-6 3-hydroxymethyl-1-methyl-4-phenyl-piperidin-4-ol 

Relevant academic research and scientific papers

Oxidation reactions of azines. 10. Synthesis, structure, and oxodihydroxylation of 3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine

It has been established that oxidation of a mixture of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and dicyanomethane or formaldehyde with manganese dioxide gives 3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, the structure of which was confirmed by X-ray structural analysis. Some oxidative conversions by potassium permanganate of the product formed and its esters have been studied. These included lactamization, aromatization, and oxodihydroxylation.

Prins reaction under manganese dioxide control: The synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde

The course of the acid-catalysed Prins reaction of tetrahydropyridines 1 with formaldehyde, leading to derivatives of piperidino-dioxane 4 and 3-oxa-7-azabicyclononanes 5 and 6, is dramatically changed in the presence of manganese dioxide to give new products, 6-oxa-2-azabicyclo[3.2.1]octan-4-ones 7 and 8.

Isolation and Structure Elucidation of the By-Product Formed in the Aminomethylation of α-Methylstyrene

Aminomethylation of α-Methylstyrene (1) leads to 1,2,3,6-tetrahydro-4-phenylpyridine (3) as main product, together with a significant amount of a previously unknown by-product.The N-methyl, O-acetyl-N-methyl, N,O-diacetyl, N-(4-nitrobenzoyl), and (via N -> O acyl-migration) O-(4-nitrobenzoyl) derivatives of the by-product were synthesized.By aromatization of the heteroring, 4-phenyl-3-pyridinemethanol (8a) was obtained.According to these derivatives and their IR, 1H and 13C NMR spectra, the by-product is 1,2,3,6-tetrahydro-4-phenyl-3-pyridine-methanol (4a).