2′-CH3-MPTP

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.^[1][2] It is a considerably more potent dopaminergic neurotoxin than MPTP in mice but is less potent than MPTP in primates.^[3][1][4][5] MPTP and 2′-CH₃-MPTP produce a Parkinson's disease-like condition in animals.^[6][7]

2′-CH₃-MPTP

Clinical data
Other names	2′-Methyl-MPTP
Drug class	Dopaminergic neurotoxin
Identifiers
IUPAC name 1-methyl-4-(2-methylphenyl)-3,6-dihydro-2H-pyridine
CAS Number	102417-86-7 Y
PubChem CID	91767
ChemSpider	82864
UNII	HGQ85CV4U5
ChEMBL	ChEMBL60303
CompTox Dashboard (EPA)	DTXSID70877241
Chemical and physical data
Formula	C13H17N
Molar mass	187.286 g·mol−1
3D model (JSmol)	Interactive image
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 is metabolized by monoamine oxidase A (MAO-A) and B (MAO-B) and this biotransformation is required for its dopaminergic neurotoxicity.^[1][8] 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.^[8][9]

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.^[10] Numerous other neurotoxic MPTP analogues have also been synthesized.^[8]

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