1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE Property

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)

pka

8.66±0.40(Predicted)

form 

Solid

color 

Pale Yellow to Light Yellow

Merck 

13,6319

Stability:

Stable. Incompatible with strong oxidizing agents.

Safety

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.

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H370Causes damage to organs

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P307+P311IF exposed: call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE Chemical Properties,Usage,Production

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.