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2′-CH3-MPTP

From Wikipedia, the free encyclopedia
Dopaminergic neurotoxin

Pharmaceutical compound
2′-CH3-MPTP
Clinical data
Other names2′-Methyl-MPTP
Drug classDopaminergic neurotoxin
Identifiers
  • 1-methyl-4-(2-methylphenyl)-3,6-dihydro-2H-pyridine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H17N
Molar mass187.286 g·mol−1
3D model (JSmol)
  • CC1=CC=CC=C1C2=CCN(CC2)C
  • InChI=1S/C13H17N/c1-11-5-3-4-6-13(11)12-7-9-14(2)10-8-12/h3-7H,8-10H2,1-2H3
  • Key:BORHNVHYIYTKKC-UHFFFAOYSA-N

2′-CH3-MPTP, also known as2′-methyl-MPTP, is a selectivedopaminergic neurotoxin related toMPTP which is used inscientific research to lesiondopaminergicneurons.[1][2] It is a considerably morepotent dopaminergic neurotoxin than MPTP in mice but is less potent than MPTP in primates.[3][1][4][5] MPTP and 2′-CH3-MPTP produce aParkinson's disease-like condition in animals.[6][7]

2′-CH3-MPTP ismetabolized bymonoamine oxidaseA (MAO-A) andB (MAO-B) and thisbiotransformation is required for its dopaminergic neurotoxicity.[1][8] Whereas the dopaminergic neurotoxicity of MPTP is completely prevented by theMAO-B inhibitorselegiline, complete prevention of 2′-CH3-MPTP's dopaminergic neurotoxicity requires combined treatment with both selegiline and theMAO-A inhibitorclorgyline.[8][9]

A closeanalogue of 2′-CH3-MPTP is2′-NH2-MPTP, which, in contrast to 2′-CH3-MPTP and MPTP, is aserotonergic andnoradrenergic neurotoxin with no effect ondopaminergicneurons.[10] Numerous other neurotoxic MPTP analogues have also beensynthesized.[8]

2′-CH3-MPTP was first described in thescientific literature by 1986.[4]

References

[edit]
  1. ^abcMaret G, Testa B, Jenner P, el Tayar N, Carrupt PA (1990). "The MPTP story: MAO activates tetrahydropyridine derivatives to toxins causing parkinsonism".Drug Metabolism Reviews.22 (4):291–332.doi:10.3109/03602539009041087.PMID 2253555.
  2. ^Manaye KF, Sonsalla PK, Barnett G, Heikkila RE, Woodward DJ, Smith WK, et al. (July 1989). "1-Methyl-4-(2'-methylphenyl)-1,2,3,6-tetrahydropyridine (2'CH3-MPTP)-induced degeneration of mesostriatal dopaminergic neurons in the mouse: biochemical and neuroanatomical studies".Brain Research.491 (2):307–315.doi:10.1016/0006-8993(89)90065-6.PMID 2765888.
  3. ^Heikkila RE, Sieber BA, Manzino L, Sonsalla PK (June 1989). "Some features of the nigrostriatal dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in the mouse".Molecular and Chemical Neuropathology.10 (3):171–183.doi:10.1007/BF03159727.PMID 2669769.
  4. ^abYoungster SK, Duvoisin RC, Hess A, Sonsalla PK, Kindt MV, Heikkila RE (March 1986). "1-Methyl-4-(2'-methylphenyl)-1,2,3,6-tetrahydropyridine (2'-CH3-MPTP) is a more potent dopaminergic neurotoxin than MPTP in mice".European Journal of Pharmacology.122 (2):283–287.doi:10.1016/0014-2999(86)90115-9.PMID 3486770.
  5. ^Rose S, Nomoto M, Jackson EA, Gibb WR, Jenner P, Marsden CD (May 1990). "1-Methyl-4-(2'-methylphenyl)-1,2,3,6-tetrahydropyridine (2'-methyl-MPTP) is less neurotoxic than MPTP in the common marmoset".European Journal of Pharmacology.181 (1–2):97–103.doi:10.1016/0014-2999(90)90249-6.PMID 2117541.
  6. ^Meredith GE, Rademacher DJ (2011)."MPTP mouse models of Parkinson's disease: an update".Journal of Parkinson's Disease.1 (1):19–33.doi:10.3233/JPD-2011-11023.PMC 3530193.PMID 23275799.
  7. ^Herlinger AL, Almeida AR, Presti-Silva SM, Pereira EV, Andrich F, Pires RG, et al. (March 2018). "Behavioral, Biochemical and Molecular Characterization of a Parkinson's Disease Mouse Model Using the Neurotoxin 2'-CH3-MPTP: A Novel Approach".Neuromolecular Medicine.20 (1):73–82.doi:10.1007/s12017-018-8476-z.PMID 29332269.
  8. ^abcSinger TP, Ramsay RR (November 1990). "Mechanism of the neurotoxicity of MPTP. An update".FEBS Letters.274 (1–2):1–8.doi:10.1016/0014-5793(90)81315-f.PMID 2253761.
  9. ^Chiueh CC, Huang SJ, Murphy DL (August 1992). "Enhanced hydroxyl radical generation by 2'-methyl analog of MPTP: suppression by clorgyline and deprenyl".Synapse.11 (4):346–348.doi:10.1002/syn.890110410.PMID 1323883.
  10. ^Andrews AM, Murphy DL (March 1993). "Sustained depletion of cortical and hippocampal serotonin and norepinephrine but not striatal dopamine by 1-methyl-4-(2'-aminophenyl)-1,2,3,6-tetrahydropyridine (2'-NH2-MPTP): a comparative study with 2'-CH3-MPTP and MPTP".Journal of Neurochemistry.60 (3):1167–1170.doi:10.1111/j.1471-4159.1993.tb03271.x.PMID 8094744.
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