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28289-54-5

28289-54-5 Structure

28289-54-5 Structure
IdentificationBack Directory
[Name]

1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROXPYRIDINE
[CAS]

28289-54-5
[Synonyms]

MPTP
NSC 139654
1-METHYL-4-PHENYL-PIPERIDINE-3-EN
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridin
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-TETRAHYDRO-PYRIDINE
1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROXPYRIDINE
N-METHYL-4-PHENYL-1,2,3,6-TETRAHYDRO-PYRIDINE
Pyridine,1,2,3,6-tetrahydro-1-methyl-4-phenyl-
1-METHYL-4-PHENYL-1,2,3,6-TETRA-*HYDROPY RIDINE FREE
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine)ochloride
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine, free base
[EINECS(EC#)]

248-939-7
[Molecular Formula]

C12H15N
[MDL Number]

MFCD00006120
[MOL File]

28289-54-5.mol
[Molecular Weight]

173.25
Chemical PropertiesBack Directory
[Appearance]

Light Yellow Solid
[Melting point ]

aprox. 36°C
[Boiling point ]

128-132 °C12 mm Hg(lit.)
[density ]

1.001±0.06 g/cm3(Predicted)
[storage temp. ]

-20°C Freezer
[solubility ]

Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
[form ]

Solid
[pka]

8.66±0.40(Predicted)
[color ]

Pale Yellow to Light Yellow
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[Merck ]

13,6319
Hazard InformationBack Directory
[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.
Safety DataBack Directory
[Symbol(GHS) ]

Health Hazard (GHS08)Skull and Crossbones (GHS06)
GHS08,GHS06
[Signal word ]

Danger
[Hazard statements ]

H370-H301
[Precautionary statements ]

P264-P270-P301+P310-P321-P330-P405-P501-P260-P264-P270-P307+P311-P321-P405-P501
[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.
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