U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C13H17N
Molecular Weight 187.2808
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,2,3,6-TETRAHYDRO-1-METHYL-4-(2-METHYLPHENYL)PYRIDINE

SMILES

CN1CCC(=CC1)C2=CC=CC=C2C

InChI

InChIKey=BORHNVHYIYTKKC-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C13H17N
Molecular Weight 187.2808
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2888874

2'-CH3-MPTP is an extremely potent dopaminergic neurotoxin, which lead to large decrements in the neostriatal concent of DA and a large loss in the capacity of a neostriatal synaptosomal preparations to take up [3H]DA. 2'CH3-MPTP-induced neurotoxicity, was attenuated by pretreatment of mice with dopamine uptake inhibitor, and non-specific MAO-A and MAO-B inhibitor, but not by a specific MAO-B inhibitor. The mechanism of toxicity is formation of a metabolite 2'CH3-MPP+, which is a potent inhibitor of mitochondrial respiration.

CNS Activity

Curator's Comment: Known to be CNS active in mice. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Characteristics of 1-methyl-4-(2'-methylphenyl)-1,2,3,6-tetrahydropyridine-induced neurotoxicity in the mouse.
1987-09
1-Methyl-4-(2'-methylphenyl)-1,2,3,6-tetrahydropyridine (2'-CH3-MPTP) is a more potent dopaminergic neurotoxin than MPTP in mice.
1986-03-18
Patents

Sample Use Guides

Dopaninergic toxicity of 2'-CH3-MPTP was studied in mice. The mice were injected intraperitoneally with 2'-CH3-MPTP hydrochloride at 9 a.m. and again at 3 p.m.; the dose for each injection was 0.113 mmol/kg. Injections of 2'-CH3-MPTP lead to a very large decrement in neostriatal DA content and a very large and parallel decrement of [3H]DA uptake.
Route of Administration: Intraperitoneal
DA uptake inhibition was shown using resealed bovine chromaffin granule ghosts. Washed membranes were isolated and purified. The released granule ghosts were incubated for 30 °C for 10 min, and the desired concentrations of the inhibitor were adde to the mixture. The uptake reaction was initiated by the addition of the desired concentration of DA. 2'-CH3-MPTP inhbited DA uptake with Ki of 38.4 uM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:52:54 GMT 2025
Edited
by admin
on Mon Mar 31 19:52:54 GMT 2025
Record UNII
HGQ85CV4U5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-METHYL-4-(2'-METHYLPHENYL)-1,2,3,6-TETRAHYDROPYRIDINE
Preferred Name English
1,2,3,6-TETRAHYDRO-1-METHYL-4-(2-METHYLPHENYL)PYRIDINE
Systematic Name English
2'-CH3-MPTP
Common Name English
2'-METHYL-MPTP
Common Name English
PYRIDINE, 1,2,3,6-TETRAHYDRO-1-METHYL-4-(2-METHYLPHENYL)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID70877241
Created by admin on Mon Mar 31 19:52:54 GMT 2025 , Edited by admin on Mon Mar 31 19:52:54 GMT 2025
PRIMARY
FDA UNII
HGQ85CV4U5
Created by admin on Mon Mar 31 19:52:54 GMT 2025 , Edited by admin on Mon Mar 31 19:52:54 GMT 2025
PRIMARY
CAS
102417-86-7
Created by admin on Mon Mar 31 19:52:54 GMT 2025 , Edited by admin on Mon Mar 31 19:52:54 GMT 2025
PRIMARY
PUBCHEM
91767
Created by admin on Mon Mar 31 19:52:54 GMT 2025 , Edited by admin on Mon Mar 31 19:52:54 GMT 2025
PRIMARY