5-{[methyl(prop-2-yn-1-yl)amino]methyl}quinolin-8-ol dihydrochloride

• ChemBase ID: 153254
• Molecular Formular: C14H16Cl2N2O
• Molecular Mass: 299.19564
• Monoisotopic Mass: 298.0639685
• SMILES: CN(CC#C)Cc1ccc(c2c1cccn2)O.Cl.Cl
• Canonical SMILES: C#CCN(Cc1ccc(c2c1cccn2)O)C.Cl.Cl
• InChI: InChI=1S/C14H14N2O.2ClH/c1-3-9-16(2)10-11-6-7-13(17)14-12(11)5-4-8-15-14;;/h1,4-8,17H,9-10H2,2H3;2*1H
• InChIKey: XJNICPXVRPOSSO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[methyl(prop-2-yn-1-yl)amino]methyl}quinolin-8-ol dihydrochloride
• IUPAC Traditional name: 5-{[methyl(prop-2-yn-1-yl)amino]methyl}quinolin-8-ol dihydrochloride
• Synonyms: 5-[N-methyl-N-propargylaminomethyl]-8-hydroxyquinoline dihydrochloride; M-30 dihydrochloride; VAR10300 dihydrochloride; M30 dihydrochloride

Database IDs

• CAS Number: 64821-19-8
• MDL Number: MFCD20488063
• PubChem SID: 162247393
• PubChem CID: 71311622

CALCULATED PROPERTIES

• Acid pKa: 8.992044
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.8254321
• LogD (pH = 7.4): 0.9211066
• Log P: 1.5016537
• Molar Refractivity: 68.0831 cm^3
• Polarizability: 27.237415 Å^3
• Polar Surface Area: 36.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO, heptane and xylene: ≥21 mg/mL
• Apperance: green-yellow powder

Safety Information

• Storage Condition: desiccated
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H14N2O · 2HCl

DETAILS

Sigma Aldrich - SML0128

Biochem/physiol Actions
M30 is a site-activated iron chelator and monoamine oxidase (MAO) inhibitor; with neuroprotective and anti-apoptotic activity. It is a multifunctional non-toxic, brain permeable iron chelator possessing a neuroprotective propargylamine moiety and an antioxidant-iron chelator moiety. M30 is a selective irreversible inhibitor of mitochondrial brain monoamine oxidases A and B (MAO-A and -B), providing for improved levels of neurotransmitters. It reduces oxidative damage and shows neuroprotective and neurorestorative effects in various neurodegenerative models of ALS, Alzheimer′s and Parkinson′s diseases, and is being investigated in other diseases where oxidative stress is a problem.