Mesoridazine (CHEM002304)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:59 UTC
Update Date2016-11-09 01:08:44 UTC
Accession NumberCHEM002304
Identification
Common NameMesoridazine
ClassSmall Molecule
DescriptionMesoridazine is only found in individuals that have used or taken this drug. It is a phenothiazine antipsychotic with effects similar to chlorpromazine. [PubChem]Based upon animal studies, mesoridazine, as with other phenothiazines, acts indirectly on reticular formation, whereby neuronal activity into reticular formation is reduced without affecting its intrinsic ability to activate the cerebral cortex. In addition, the phenothiazines exhibit at least part of their activities through depression of hypothalamic centers. Neurochemically, the phenothiazines are thought to exert their effects by a central adrenergic blocking action.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Phenothiazine
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
10-(2(1-Methyl-2-piperidyl)ethyl)-2-(methylsulfinyl)phenothiazineChEBI
10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulfinyl phenothiazineChEBI
2-Methanesulfinyl-10-[2-(1-methyl-piperidin-2-yl)-ethyl]-10H-phenothiazineChEBI
MesoridazinaChEBI
MesoridazinumChEBI
Thioridazine thiomethyl sulfoxideChEBI
Thioridazine-2-sulfoxideChEBI
TPS-23ChEBI
LidanarKegg
10-(2(1-Methyl-2-piperidyl)ethyl)-2-(methylsulphinyl)phenothiazineGenerator
10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulphinyl phenothiazineGenerator
2-Methanesulphinyl-10-[2-(1-methyl-piperidin-2-yl)-ethyl]-10H-phenothiazineGenerator
Thioridazine thiomethyl sulphoxideGenerator
Thioridazine-2-sulphoxideGenerator
Thioridazien thiomethyl sulfoxideHMDB
Thioridazine monosulfoxide analogHMDB
TPS23HMDB
SerentilHMDB
Chemical FormulaC21H26N2OS2
Average Molecular Mass386.574 g/mol
Monoisotopic Mass386.149 g/mol
CAS Registry Number5588-33-0
IUPAC Name2-methanesulfinyl-10-[2-(1-methylpiperidin-2-yl)ethyl]-10H-phenothiazine
Traditional Namemesoridazine
SMILESCN1CCCCC1CCN1C2=CC=CC=C2SC2=C1C=C(C=C2)S(C)=O
InChI IdentifierInChI=1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
InChI KeySLVMESMUVMCQIY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Para-thiazine
  • Piperidine
  • Benzenoid
  • Sulfoxide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Sulfinyl compound
  • Azacycle
  • Amine
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility7.67e-02 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.077 g/LALOGPS
logP3.83ALOGPS
logP3.57ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)19.36ChemAxon
pKa (Strongest Basic)8.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity115.13 m³·mol⁻¹ChemAxon
Polarizability43.83 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, Positivesplash10-006t-9113000000-c43ca99a239d882aaec0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0119000000-fffe496e2ff640e0c935Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-009j-4409000000-1ac2768cf2aedf0c606dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0109000000-34ffca607374cc2d3dadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-3419000000-8395b65edb5ff6d5cb3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002g-8912000000-af14b6ff98df3cb285e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2009000000-a670d5fab14237f10c3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4195000000-c1fd7e13d41cc4d31064Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9320000000-f0c0d591d683e0031797Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-ea6eb7f211262d8b7c60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-5419000000-67a5e726504808a7f165Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0032-9342000000-55bdb60e5caa2bf4c40cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-ae73409bcb6436484a74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0039000000-5b62f5f508c6b499a5f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9082000000-3b94eddc2f178347c05eSpectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9331000000-8e14cb597ee411174c3eSpectrum
Toxicity Profile
Route of ExposureOral; Intramuscular injection. Well absorbed from the gastrointestinal tract.
Mechanism of ToxicityBased upon animal studies, mesoridazine, as with other phenothiazines, acts indirectly on reticular formation, whereby neuronal activity into reticular formation is reduced without affecting its intrinsic ability to activate the cerebral cortex. In addition, the phenothiazines exhibit at least part of their activities through depression of hypothalamic centers. Neurochemically, the phenothiazines are thought to exert their effects by a central adrenergic blocking action.
Metabolism Half Life: 24 to 48 hours
Toxicity ValuesOral LD50 is 560 ± 62.5 mg/kg and 644 ± 48 mg/kg in mouse and rat, respectively.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed in the treatment of schizophrenia, organic brain disorders, alcoholism and psychoneuroses.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose may include emesis, muscle tremors, decreased food intake and death associated with aspiration of oral-gastric contents into the respiratory system.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00933
HMDB IDHMDB0015068
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMesoridazine
Chemspider ID3936
ChEBI ID6780
PubChem Compound ID4078
Kegg Compound IDC07143
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSNot Available
General ReferencesNot Available