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MPTP information


MPTP
Skeletal formula
Ball-and-stick model of MPTP
Names
Preferred IUPAC name
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Identifiers
CAS Number
  • 28289-54-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17963 checkY
ChEMBL
  • ChEMBL24172 checkY
ChemSpider
  • 1346 checkY
ECHA InfoCard 100.044.475 Edit this at Wikidata
EC Number
  • 248-939-7
IUPHAR/BPS
  • 280
KEGG
  • C04599 checkY
MeSH 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
PubChem CID
  • 1388
UNII
  • 9P21XSP91P ☒N
CompTox Dashboard (EPA)
  • DTXSID8040933 Edit this at Wikidata
InChI
  • 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
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)[2]
Boiling point 128 to 132 °C (262 to 270 °F; 401 to 405 K) 12 Torr[1]
Solubility in water
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 ?)
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.

  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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MPTP

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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...

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Substantia nigra

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substantia nigra). MPTP, is a neurotoxin specific to dopaminergic cells in the brain, specifically in the substantia nigra. MPTP was brought to the spotlight...

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The mitochondrial permeability transition pore (mPTP or MPTP; also referred to as PTP, mTP or MTP) is a protein that is formed in the inner membrane of...

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transition pore (MPTP), thus preventing MPTP opening. The MPTP is found in the mitochondrial membrane of cardiac muscle cells. MPTP opening signifies...

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transition pore (mPTP) is normally closed during ischemia, but calcium overload and increased reactive oxygen species (ROS) with reperfusion open mPTP allowing...

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3,6-tetrahydropyridine (MPTP) was discovered. MPTP is able to cross the blood brain barrier and enter acidic lysosomes. MPTP is biologically activated...

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temperature. Consequently, MPTP was formed as a major impurity. 1-Methyl-4-phenylpyridinium (MPP+), a metabolite of MPTP, causes rapid onset of irreversible...

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Rotenone

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pathology to Parkinson's disease in aged Rhesus monkeys from MPTP. Therefore, the mechanism behind MPTP as it relates to Parkinson's disease is not fully understood...

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DSP-4 Oxidopamine (6-OHDA) Dopaminergic Fenpropathrin Methamphetamine MPP+ MPTP Norsalsolinol Oxidopamine (6-OHDA) Rotenone Salsolinol Serotonergic 3-CA...

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disease in laboratory animals, for example, by administering a toxin, such as MPTP to cause Parkinson's disease, or through genetic manipulation. Protein structure...

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MPPP byproduct MPTP. It appears that the N-methyl group of MPTP is required for neurotoxic activity. In animal experiments, only MPTP analogues that preserved...

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sports-related concussions, and some forms of chemical poisoning such as MPTP, can lead to substantial cell loss, producing a parkinsonian syndrome that...

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through first-pass metabolism by the liver. Loperamide metabolizes into an MPTP-like compound, but is unlikely to exert neurotoxicity. Efflux by P-glycoprotein...

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metro forms part of the 62-billion-riyal Mecca Public Transport Programme (MPTP), which will include integrated bus services. The four new metro lines will...

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ultimately cell death. MPP+ is produced by monoamine oxidase B as a metabolite of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine), and its toxicity is particularly...

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PPIF

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is a major component of the mitochondrial permeability transition pore (MPTP) and, thus, highly involved in mitochondrial metabolism and apoptosis, as...

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to occupants. MPTP may be accidentally produced during the manufacture of MPPP. 1-Methyl-4-phenylpyridinium (MPP+), a metabolite of MPTP, causes rapid...

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disorder, is thought to be caused by certain neurotoxins. A neurotoxin called MPTP (1[N]-methyl-4-phenyl-1,2,3,6-tetrahydropyridine), the precursor to MPP+...

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and this is often achieved either with oxidopamine or another neurotoxin MPTP. Both these agents likely destroy neurons by generating reactive oxygen species...

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meperidine. One, MPPP, was found in some cases to contain an impurity called MPTP, which caused brain damage that could result in a syndrome identical to late...

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membrane channel of the mitochondrial permeability transition pore, known as MPTP. Bongkrek acid is permeable through this membrane and binds to the surface...

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(January 2001). "[Mexidol potentiates antiparkinsonian effect of L-DOPA in MPTP-induced parkinsonism model]". Eksperimental'naia i Klinicheskaia Farmakologiia...

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