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| | 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE Basic information |
| Product Name: | 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE | | Synonyms: | MPTP;1,2,3,6-tetrahydro-1-methyl-4-phenyl-pyridin;1,2,3,6-tetrahydro-1-methyl-4-phenylpyridine;1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine)ochloride;NSC 139654;1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine, free base;Pyridine,1,2,3,6-tetrahydro-1-methyl-4-phenyl-;1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridin | | CAS: | 28289-54-5 | | MF: | C12H15N | | MW: | 173.25 | | EINECS: | 248-939-7 | | Product Categories: | Neurochemicals;Heterocyclic Compounds | | Mol File: | 28289-54-5.mol |  |
| | 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE Chemical Properties |
| Melting point | aprox. 36°C | | Boiling point | 128-132 °C12 mm Hg(lit.) | | density | 1.001±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly) | | form | Solid | | pka | 8.66±0.40(Predicted) | | color | Pale Yellow to Light Yellow | | Merck | 13,6319 | | Stability: | Stable. Incompatible with strong oxidizing agents. |
| Hazard Codes | T | | Risk Statements | 25-39/23/24/25 | | Safety Statements | 45 | | RIDADR | UN 2811 6.1/PG 2 | | WGK Germany | 3 | | RTECS | UT8358900 | | HazardClass | 6.1(b) | | PackingGroup | III | | Hazardous Substances Data | 28289-54-5(Hazardous Substances Data) | | Toxicity | Human toxicity
originally discovered when it was an unexpected by-product
from the illicit synthesis of a heroin substitute (i.e., meperidine
analog). Currently used experimentally as the primary animal
model for the study of Parkinson’s disease. MPTP is a neurotoxicant
that is activated to 1-methyl-4-phenylpyridinium ion
(MPP1) by the actions of monoamine oxidase B located in the
mitochondria of brain astrocytes. The MPP1 is then transported
into dopamine, and to a lesser extent, other monoaminergic
neurons. Once inside these dopamine neurons in the
substantia nigra, it destroys these neurons by mechanisms that
may involve an oxidative cascade and/or inhibition of electron
transport. Intoxication causes a parkinsonism syndrome almost
identical in signs and symptoms to Parkinson’s disease, including
rigidity, bradykinesia, tremor, and postural instability. In
the event of known ingestion, immediate (but not delayed)
administration of a monoamine oxidase inhibitor (especially
one selective for MAO-B like deprenyl) and dopamine uptake
inhibitor can be therapeutic. |
| | 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE Usage And Synthesis |
| Chemical Properties | Light Yellow Solid | | Uses | 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine is a dopaminergic neurotoxin that reportedly causes a severe and irreversible Parkinsonian condition in humans and monkeys. | | Definition | ChEBI: A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4. | | Metabolic pathway | N-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)
in a rat pheochromocytoma cell line is oxidized to give
the N-methyl-4-phenylpyridinium ion. |
| | 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE Preparation Products And Raw materials |
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