Mazindol (CHEM002224)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:12 UTC
Update Date2016-11-09 01:08:42 UTC
Accession NumberCHEM002224
Identification
Common NameMazindol
ClassSmall Molecule
DescriptionMazindol is only found in individuals that have used or taken this drug. It is a tricyclic anorexigenic agent unrelated to and less toxic than amphetamine, but with some similar side effects. It inhibits uptake of catecholamines and blocks the binding of cocaine to the dopamine uptake transporter. Although the mechanism of action of the sympathomimetics in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Unlike other sympathomimetic appetite suppressants such as phentermine, mazindol is thought to inhibit the reuptake of norepinephrine rather than to cause its release.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Adrenergic Uptake Inhibitor
  • Amide
  • Amine
  • Central Nervous System Stimulant
  • Dopamine Uptake Inhibitor
  • Drug
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SanorexKegg
Mazindol wyeth brandHMDB
Medix brand OF mazindolHMDB
MazanorHMDB
Mazindol searle brandHMDB
Novartis brand OF mazindolHMDB
SanjorexHMDB
TeronacHMDB
DiestetHMDB
Mazindol medix brandHMDB
Searle brand OF mazindolHMDB
TeronakHMDB
Mazindol novartis brandHMDB
MazindoleHMDB
SolucapsHMDB
Wyeth brand OF mazindolHMDB
Chemical FormulaC16H13ClN2O
Average Molecular Mass284.740 g/mol
Monoisotopic Mass284.072 g/mol
CAS Registry Number22232-71-9
IUPAC Name5-(4-chlorophenyl)-2H,3H,5H-imidazo[2,1-a]isoindol-5-ol
Traditional Namemazindol
SMILESOC1(N2CCN=C2C2=CC=CC=C12)C1=CC=C(Cl)C=C1
InChI IdentifierInChI=1S/C16H13ClN2O/c17-12-7-5-11(6-8-12)16(20)14-4-2-1-3-13(14)15-18-9-10-19(15)16/h1-8,20H,9-10H2
InChI KeyZPXSCAKFGYXMGA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindoles
Direct ParentIsoindoles
Alternative Parents
Substituents
  • Isoindoline
  • Isoindole
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Imidolactam
  • Benzenoid
  • 2-imidazoline
  • Alkanolamine
  • Amidine
  • Carboxylic acid amidine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point198-199°C
Boiling PointNot Available
Solubility1.39e-01 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.64ALOGPS
logP3.44ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.61ChemAxon
pKa (Strongest Basic)3.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.42 m³·mol⁻¹ChemAxon
Polarizability29.42 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3920000000-014167a19bc06d4b57ceSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-3090000000-fc6fdc778249a1f313a6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-d3dc6820d6c6134b2013Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0390000000-3cdf028f902955c380faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vo-5920000000-5efd9a158e2afed55e22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-ae73b97007675d68826bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0190000000-7ab5be67a229e84bec41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-2920000000-13bafaed87a47c8871a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-467b34577c9cf5fb314aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-884c24d87555dd9b139fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-0790000000-181f37bd2b8a9227e5eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-ccaa52cef887c66f191bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4090000000-4b24fa7d85c7759e56ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-5890000000-ed80b0de920491d0799eSpectrum
MSMass Spectrum (Electron Ionization)splash10-014i-0390000000-2514253f04060882685bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityAlthough the mechanism of action of the sympathomimetics in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Unlike other sympathomimetic appetite suppressants such as phentermine, mazindol is thought to inhibit the reuptake of norepinephrine rather than to cause its release.
MetabolismHepatic. Half Life: 10-13 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMazindol is used in short-term (a few weeks) treatment of exogenous obesity in conjunction with a regimen of weight reduction based on caloric restriction, exercise, and behavior modification in patients with a body mass index of 30 kg of body weight per height in meters squared (kg/m2) or in patients with a body mass index of 27 kg/m2 in the presence of risk factors such as hypertension, diabetes, or hyperlipidemia.
Minimum Risk LevelNot Available
Health EffectsUsing large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.
SymptomsSymptoms of a mazindol overdose include restlessness, tremor, rapid breathing, confusion, hallucinations, panic, aggressiveness, nausea, vomiting, diarrhea, an irregular heartbeat, and seizures.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00579
HMDB IDHMDB0014718
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMazindol
Chemspider ID3880
ChEBI ID146385
PubChem Compound ID4020
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

U.S. Patents 3,597,445 and 3,763,178.

MSDSNot Available
General ReferencesNot Available