MPTP

MPTP
Names

IUPAC name 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Identifiers
CAS Number	28289-54-5^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17963^Y
ChemSpider	1346^Y
ECHA InfoCard	100.044.475
EC Number	248-939-7
IUPHAR/BPS	280
KEGG	C04599^Y
MeSH	1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
PubChem CID	1388
UNII	9P21XSP91P^N
InChI InChI=1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3^Y Key: PLRACCBDVIHHLZ-UHFFFAOYSA-N^Y InChI=1/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3 Key: PLRACCBDVIHHLZ-UHFFFAOYAV
SMILES c2ccccc2/C1=C/CN(C)CC1
Properties
Chemical formula	C₁₂H₁₅N
Molar mass	173.26 g·mol⁻¹
Melting point	40 °C (104 °F; 313 K)
Boiling point	128 to 132 °C (262 to 270 °F; 401 to 405 K) 12 Torr
Solubility in water	Slightly soluble
Hazards
NFPA 704	0 4 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) is a prodrug to the neurotoxin MPP+, which causes permanent symptoms of Parkinson's disease by destroying dopaminergic neurons in the substantia nigra of the brain. It has been used to study disease models in various animal studies.

While MPTP itself has no psychoactive effects, the compound may be accidentally produced during the manufacture of MPPP, a synthetic opioid drug with effects similar to those of morphine and pethidine (meperidine). The Parkinson-inducing effects of MPTP were first discovered following accidental ingestion as a result of contaminated MPPP.

Injection of MPTP causes rapid onset of Parkinsonism, hence users of MPPP contaminated with MPTP will develop these symptoms.

MPTP itself is not toxic, and as a lipophilic compound can cross the blood–brain barrier. Once inside the brain, MPTP is metabolized into the toxic cation 1-methyl-4-phenylpyridinium (MPP+) by the enzyme MAO-B of glial cells. MPP+ kills primarily dopamine-producing neurons in a part of the brain called the pars compacta of the substantia nigra. MPP+ interferes with complex I of the electron transport chain, a component of metabolism, which leads to cell death and causes the buildup of free radicals, toxic molecules that contribute further to cell destruction.

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