2-(2,2-dicyclohexylethyl)piperidine; but-2-enedioic acid

• ChemBase ID: 153260
• Molecular Formular: C23H39NO4
• Molecular Mass: 393.56006
• Monoisotopic Mass: 393.28790873
• SMILES: C1CCC(CC1)C(CC1CCCCN1)C1CCCCC1.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: C1CCC(NC1)CC(C1CCCCC1)C1CCCCC1.OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C19H35N.C4H4O4/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18;5-3(6)1-2-4(7)8/h16-20H,1-15H2;1-2H,(H,5,6)(H,7,8)
• InChIKey: JDZOTSLZMQDFLG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,2-dicyclohexylethyl)piperidine; but-2-enedioic acid
• IUPAC Traditional name: butenedioic acid; perhexiline
• Synonyms: 2-(2,2-Dicyclohexylethyl)piperidine; Perhexiline maleate salt

Database IDs

• CAS Number: 6724-53-4
• MDL Number: MFCD00057329
• PubChem SID: 162247399
• PubChem CID: 21896623

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.2955542
• LogD (pH = 7.4): 2.6224937
• Log P: 5.5313087
• Molar Refractivity: 87.2286 cm^3
• Polarizability: 35.12344 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H35N · C4H4O4

DETAILS

Sigma Aldrich - SML0120

Biochem/physiol Actions
Perhexiline maleate is an anti-anginal metabolic modulator. It inhibits the mitochondrial enzyme carnitine palmitoyltransferase CPT-1 and to a lesser extent CPT-2. This causes a shift in myocardial substrate utilisation from long chain fatty acids to carbohydrates, resulting in increased glucose and lactate utilization and increased ATP production for the same O2 consumption as before and consequently increases myocardial efficiency. Perhexiline maleate was also recently found to inhibit the activity of mTORC1.