1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine

• ChemBase ID: 128464
• Molecular Formular: C12H15N
• Molecular Mass: 173.2542
• Monoisotopic Mass: 173.12044949
• SMILES: c1c(C2=CCN(C)CC2)cccc1
• Canonical SMILES: CN1CCC(=CC1)c1ccccc1
• InChI: InChI=1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3
• InChIKey: PLRACCBDVIHHLZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
• IUPAC Traditional name: MPTP
• Synonyms: 1,2,3,6-Tetrahydro-1-methyl-4-phenylpyridine; NSC 139654; 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine; MPTP; MPTP; 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Database IDs

• CAS Number: 28289-54-5
• EC Number: 248-939-7
• MDL Number: MFCD00006120
• PubChem SID: 162222771
• PubChem CID: 1388
• CHEBI ID: 17963
• CHEMBL: 24172
• Chemspider ID: 1346
• IUPHAR ligand ID: 280
• KEGG ID: C04599
• MeSH Name: 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
• Wikipedia Title: MPTP

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.5582506
• LogD (pH = 7.4): 1.1854286
• Log P: 2.35042
• Molar Refractivity: 57.4697 cm^3
• Polarizability: 22.088713 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; slightly soluable in water
• Apperance: Light Yellow Solid
• Melting Point: 39°C; aprox. 36°C
• Boiling Point: 128-132 °C/12 mmHg(lit.); 128-132°C@12mm; 130°C
• Flash Point: 235.4 °F

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: UT8358900
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25-39/23/24/25
• Safety Statements: 45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• NFPA704:
  

  0

  4

  0
• GHS Hazard statements: H301-H370
• GHS Precautionary statements: P260-P301 + P310-P307 + P311
• RID/ADR: UN 2811 6.1/PG 2

Product Information

• Empirical Formula (Hill Notation): C12H15N

DETAILS

Sigma Aldrich - M1021

Biochem/physiol Actions
Dopaminergic neurotoxin.
Warning
Reportedly causes a severe and irreversible Parkinsonism condition in humans and monkeys. New Engl. J. Med. 1983, 309, 310. Science 1983, 219, 979. ibid. 1984, 224, 1083, 1451. ibid. 1984, 225, 529. J. Med. Chem. 1985, 28, 997.

Toronto Research Chemicals - M325910

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine is a dopaminergic neurotoxin that reportedly causes a severe and irreversible Parkinsonian condition in humans and monkeys.

REFERENCES

• Burns, R.S., et al.: Proc. Natl. Acad.Sci. USA, 80, 4546 (1983)
• Langston, J.W., et al.: Science, 219, 979 (1983)
• Mogi, M., et al.: Neurosci. Lett., 250, 25 (1983)
• Przedborski, S. and Jackson-Lewis, V., Mov. Disord., 13, 35 (1983)