MPTP

This article is about the chemical. For the mitochondrial pore, see Mitochondrial permeability transition.
Not to be confused with MPPP or MPP+.
MPTP
Skeletal formula
Ball-and-stick model of MPTP
Names
Preferred IUPAC name
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.044.475 Edit this at Wikidata
EC Number
  • 248-939-7
KEGG
MeSH 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
UNII
  • InChI=1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3 checkY
    Key: PLRACCBDVIHHLZ-UHFFFAOYSA-N checkY
  • 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
  • c2ccccc2/C1=C/CN(C)CC1
Properties
C12H15N
Molar mass 173.259 g·mol−1
Melting point 40 °C (104 °F; 313 K)[2]
Boiling point 128 to 132 °C (262 to 270 °F; 401 to 405 K) 12 Torr[1]
Slightly soluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) is an organic compound. It is classified as a tetrahydropyridine. It is of interest as a precursor to the monoaminergic 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 animals.[3][4]

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 injection as a result of contaminated MPPP.

  1. ^ Buchi, I. J. (1952). "Synthese und analgetische Wirkung einiger 1-Methyl-4-phenyl-piperidin-(4)-alkylsulfone. 1. Mitteilung". Helvetica Chimica Acta. 35 (5): 1527–1536. doi:10.1002/hlca.19520350514.
  2. ^ "1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine". ChemIDplus.
  3. ^ Duty, Susan; Jenner, Peter (2011). "Animal models of Parkinson's disease: A source of novel treatments and clues to the cause of the disease". British Journal of Pharmacology. 164 (4): 1357–1391. doi:10.1111/j.1476-5381.2011.01426.x. PMC 3229766. PMID 21486284.
  4. ^ Narmashiri, Abdolvahed; Abbaszadeh, Mojtaba; Ghazizadeh, Ali (2022). "The effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) on the cognitive and motor functions in rodents: A systematic review and meta-analysis". Neuroscience & Biobehavioral Reviews. 140: 104792. doi:10.1016/j.neubiorev.2022.104792. PMID 35872230. S2CID 250929452.