Perhexiline (CHEM002337)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:18 UTC
Update Date2026-03-31 16:41:22 UTC
Accession NumberCHEM002337
Identification
Common NamePerhexiline
ClassSmall Molecule
DescriptionPerhexiline is only found in individuals that have used or taken this drug. It is a coronary vasodilator used especially for angina of effort. It may cause neuropathy and hepatitis. [PubChem]Perhexiline binds to the mitochondrial enzyme carnitine palmitoyltransferase (CPT)-1 and CPT-2. It acts by shifting myocardial substrate utilisation from long chain fatty acids to carbohydrates through inhibition of CPT-1 and, to a lesser extent, CPT-2, resulting in increased glucose and lactate utilization. This results in increased ATP production for the same O2 consumption as before and consequently increases myocardial efficiency.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Calcium Channel Blocker
  • Cardiovascular Agent
  • Drug
  • Metabolite
  • Organic Compound
  • Synthetic Compound
  • Vasodilator Agent
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PerhexileneChEBI
(+)-2-(2,2-Dicyclohexylethyl)piperidineHMDB
(-)-2-(2,2-Dicyclohexylethyl)piperidineHMDB
2-(2,2-Dicyclohexylethyl)piperidineHMDB
PerhexillineHMDB
Chemical FormulaC19H35N
Average Molecular Mass277.488 g/mol
Monoisotopic Mass277.277 g/mol
CAS Registry Number6621-47-2
IUPAC Name2-(2,2-dicyclohexylethyl)piperidine
Traditional Nameperhexiline
SMILESC(C(C1CCCCC1)C1CCCCC1)C1CCCCN1
InChI IdentifierInChI=1S/C19H35N/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18/h16-20H,1-15H2
InChI KeyCYXKNKQEMFBLER-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassNot Available
Direct ParentPiperidines
Alternative Parents
Substituents
  • Piperidine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility0.0608 mg/L
Predicted Properties
PropertyValueSource
Water Solubility2.7e-05 g/LALOGPS
logP5.87ALOGPS
logP5.53ChemAxon
logS-7ALOGPS
pKa (Strongest Basic)10.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.23 m³·mol⁻¹ChemAxon
Polarizability36.22 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9240000000-7d469dd2b3d8bdb97f5cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1090000000-f6b8ccc29365a1b9553fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057i-4190000000-e00b24bda85621e90894Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-5290000000-6389e823b74d83649abeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-956a531f36ba4bf82719Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-6374e56bfc2eb8609794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9170000000-3d144881a6a7aec9d111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-745fd042a988e5d1440bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2190000000-9d556eceea83c2bc4021Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9200000000-2793cdd7988a27b7095eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f4712ee2d57b7f19751dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-4b2ad669814aa4255d88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0090000000-8d81ed304a7cf5c905eaSpectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-e8335ba9964dd32ada29Spectrum
Toxicity Profile
Route of ExposureWell absorbed (>80%) from the gastrointestinal tract following oral administration.
Mechanism of ToxicityPerhexiline binds to the mitochondrial enzyme carnitine palmitoyltransferase (CPT)-1 and CPT-2. It acts by shifting myocardial substrate utilisation from long chain fatty acids to carbohydrates through inhibition of CPT-1 and, to a lesser extent, CPT-2, resulting in increased glucose and lactate utilization. This results in increased ATP production for the same O2 consumption as before and consequently increases myocardial efficiency.
MetabolismThe principal metabolites of perhexiline in man are monohydroxyperhexiline (which is excreted, in part, conjugated with glucuronic acid) and dihydroxyperhexiline that accounts for a relatively small proportion of the total metabolites. Two unidentified metabolites have also been found in the faeces. The pharmacological activity of the metabolites is not known. Hydroxylation of perhexiline is controlled by cytochrome P450 2D6 (CY P450 2D6). Half Life: Variable and non-linear. Some reports show a half-life of 2-6 days, others indicate it could be as high as 30 days.
Toxicity ValuesLD50: 2150 mg/kg (Oral, Rat) (1) LD50: 2641 mg/kg (Oral, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the management of severe angina pectoris.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsShort term adverse effects include nausea, transient dizziness, hypoglycaemia in diabetic patients, and torsade de pointes (rare).
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01074
HMDB IDHMDB0015207
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPerhexiline
Chemspider ID4584
ChEBI ID35553
PubChem Compound ID4746
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Stephen W. Horgan, Frank P. Palopoli, Edward J. Schwoegler, “Process for preparing 2-(2,2-dicyclohexylethyl)piperidine.” U.S. Patent US4069222, issued August, 1950.

MSDSLink
General ReferencesNot Available