MPTP

MPTP
Names
	Preferred IUPAC name 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Identifiers
CAS Number	28289-54-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17963 ;
ChEMBL	ChEMBL24172 ;
ChemSpider	1346 ;
ECHA InfoCard	100.044.475
EC Number	248-939-7;
IUPHAR/BPS	280;
KEGG	C04599 ;
MeSH	1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
PubChem CID	1388;
UNII	9P21XSP91P ;
CompTox Dashboard (EPA)	DTXSID8040933 ;
	InChI InChI=1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3 Key: PLRACCBDVIHHLZ-UHFFFAOYSA-N ; 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	173.259 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 (fire diamond)	4 0 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 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.

^ 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.
^ "1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine". ChemIDplus.
^ 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.
^ 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.

[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.

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