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2′-CH3-MPTP

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Dopaminergic neurotoxin

Pharmaceutical compound
2′-CH3-MPTP
Clinical data
Other names2′-Methyl-MPTP
Drug classDopaminergic neurotoxin
Identifiers
IUPAC name
  • 1-methyl-4-(2-methylphenyl)-3,6-dihydro-2H-pyridine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H17N
Molar mass187.286 g·mol
3D model (JSmol)
SMILES
  • CC1=CC=CC=C1C2=CCN(CC2)C
InChI
  • 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 as 2′-methyl-MPTP, is a selective dopaminergic neurotoxin related to MPTP which is used in scientific research to lesion dopaminergic neurons. It is a considerably more potent dopaminergic neurotoxin than MPTP in mice but is less potent than MPTP in primates. MPTP and 2′-CH3-MPTP produce a Parkinson's disease-like condition in animals.

2′-CH3-MPTP is metabolized by monoamine oxidase A (MAO-A) and B (MAO-B) and this biotransformation is required for its dopaminergic neurotoxicity. Whereas the dopaminergic neurotoxicity of MPTP is completely prevented by the MAO-B inhibitor selegiline, complete prevention of 2′-CH3-MPTP's dopaminergic neurotoxicity requires combined treatment with both selegiline and the MAO-A inhibitor clorgyline.

A close analogue of 2′-CH3-MPTP is 2′-NH2-MPTP, which, in contrast to 2′-CH3-MPTP and MPTP, is a serotonergic and noradrenergic neurotoxin with no effect on dopaminergic neurons. Numerous other neurotoxic MPTP analogues have also been synthesized.

2′-CH3-MPTP was first described in the scientific literature by 1986.

References

  1. ^ Maret 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. ^ Youngster 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. ^ Singer 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.
Monoaminergic neurotoxins
Dopaminergic
Noradrenergic
Serotonergic
Unsorted
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators
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