Editing MPTP (section)

{{Short description|Tetrahydropyridine, a chemical causing Parkinson's disease symptoms}}
{{about|the chemical|the mitochondrial pore|Mitochondrial permeability transition}}
{{Distinguish|text=[[MPPP]] or [[MPP+|MPP<sup>+</sup>]]}}
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 464192606
|ImageFile = MPTP.svg
|ImageSize = 200px
|ImageAlt = Skeletal formula
|ImageFile1 = MPTP molecule ball.png
|ImageSize1 = 210
|ImageAlt1 = Ball-and-stick model of MPTP
|PIN=1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
|Section1={{Chembox Identifiers
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C04599
|InChI = 1/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3
|InChIKey = PLRACCBDVIHHLZ-UHFFFAOYAV
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 24172
|UNII_Ref = {{fdacite|changed|FDA}}
|UNII = 9P21XSP91P
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = PLRACCBDVIHHLZ-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo=28289-54-5
|PubChem=1388
|IUPHAR_ligand = 280
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 1346
|EINECS=248-939-7
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 17963
|SMILES = c2ccccc2/C1=C/CN(C)CC1
|MeSHName = 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
}}
|Section2={{Chembox Properties
|C=12|H=15|N=1
|MeltingPtC= 40
|MeltingPt_ref = <ref>{{cite web | url = http://chem.sis.nlm.nih.gov/chemidplus/ProxyServlet?objectHandle=DBMaint&actionHandle=default&nextPage=jsp/chemidlite/ResultScreen.jsp&TXTSUPERLISTID=0028289545 | title = 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine | publisher = ChemIDplus}}</ref>
|BoilingPtC= 128 to 132 
|BoilingPt_notes = 12 Torr<ref>{{cite journal | author = Buchi, I. J. | journal = Helvetica Chimica Acta | year = 1952 | volume = 35 | issue = 5 | pages = 1527–1536 | doi = 10.1002/hlca.19520350514 | title = Synthese und analgetische Wirkung einiger 1-Methyl-4-phenyl-piperidin-(4)-alkylsulfone. 1. Mitteilung }}</ref>
|Solubility= Slightly soluble
}}
|Section3={{Chembox Hazards
|NFPA-H = 4
|NFPA-F = 0
|NFPA-R = 0
}}
}}

'''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 (chemistry)|precursor]] to the [[monoaminergic neurotoxin]] [[MPP+|MPP<sup>+</sup>]], which causes permanent symptoms of [[Parkinson's disease]] by destroying dopaminergic [[neuron]]s in the [[substantia nigra]] of the [[brain]]. It has been used to study disease models in various animals.<ref>{{cite journal |doi=10.1111/j.1476-5381.2011.01426.x |title=Animal models of Parkinson's disease: A source of novel treatments and clues to the cause of the disease |date=2011 |last1=Duty |first1=Susan |last2=Jenner |first2=Peter |journal=British Journal of Pharmacology |volume=164 |issue=4 |pages=1357–1391 |pmid=21486284 |pmc=3229766 }}</ref><ref>{{cite journal |doi=10.1016/j.neubiorev.2022.104792 |title=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 |date=2022 |last1=Narmashiri |first1=Abdolvahed |last2=Abbaszadeh |first2=Mojtaba |last3=Ghazizadeh |first3=Ali |journal=Neuroscience & Biobehavioral Reviews |volume=140 |page=104792 |pmid=35872230 |s2cid=250929452 }}</ref>

While MPTP itself has no [[psychoactive]] effects, the compound may be accidentally produced during the manufacture of [[MPPP]], a synthetic opioid [[recreational drug use|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.