Propiomazine (CHEM002271)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:38 UTC
Update Date2016-11-09 01:08:43 UTC
Accession NumberCHEM002271
Identification
Common NamePropiomazine
ClassSmall Molecule
DescriptionPropiomazine, an atypical antipsychotic agent, is used to treat both negative and positive symptoms of schizophrenia, acute mania with bipolar disorder, agitation, and psychotic symptoms in dementia. Future uses may include the treatment of obsessive-compulsive disorder and severe behavioral disorders in autism. Structurally and pharmacologically similar to clozapine, propiomazine binds to alpha(1), dopamine, histamine H1, muscarinic, and serotonin type 2 (5-HT2) receptors.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Amine
  • Antiemetic
  • Drug
  • Ester
  • Ether
  • Histamine Antagonist
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
10-(2-Dimethylaminopropyl)-2-propionylphenothiazineChEBI
2-Propionyl-10-(2-(dimethylamino)propyl)phenothiazineChEBI
3-Propionyl-10-dimethylaminoisopropylphenothiazineChEBI
PropiomazinaChEBI
PropiomazinumChEBI
LargonHMDB
Chemical FormulaC20H24N2OS
Average Molecular Mass340.482 g/mol
Monoisotopic Mass340.161 g/mol
CAS Registry Number362-29-8
IUPAC Name1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}propan-1-one
Traditional Namepropiomazine
SMILESCCC(=O)C1=CC2=C(SC3=CC=CC=C3N2CC(C)N(C)C)C=C1
InChI IdentifierInChI=1S/C20H24N2OS/c1-5-18(23)15-10-11-20-17(12-15)22(13-14(2)21(3)4)16-8-6-7-9-19(16)24-20/h6-12,14H,5,13H2,1-4H3
InChI KeyUVOIBTBFPOZKGP-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
  • Aryl alkyl ketone
  • Aryl ketone
  • Para-thiazine
  • Benzenoid
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • 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
Solubility0.454 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.007 g/LALOGPS
logP4.53ALOGPS
logP4.55ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)16.64ChemAxon
pKa (Strongest Basic)8.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity103.53 m³·mol⁻¹ChemAxon
Polarizability38.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9100000000-976e369803cbbc61ad7aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9100000000-976e369803cbbc61ad7aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-9032000000-8ac8d90dc51b6244aecfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3129000000-8a45d39e43f3fcf55fd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-9082000000-53493e52601db97df35bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-9410000000-7fe35b6626b933c91bbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-feea6c99c610382d5059Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1893000000-516b36aec603eac0bc93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pba-9870000000-ff2d57285ef106d3c73fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0019000000-fe1a7766d0ed20f6cd54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9043000000-fb6cfea0a368597116ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9240000000-9f301a72de3beafb7b1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-f17a13bc04340efdfe2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014u-1094000000-7053530da24323a19772Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvl-0290000000-cc131874e5924b29218cSpectrum
MSMass Spectrum (Electron Ionization)splash10-00di-9220000000-31dfa9c2a3e2a6046ef7Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityPropiomazine is an antagonist at types 1, 2, and 4 dopamine receptors, serotonin (5-HT) receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Its main use as a sedative is due to its antihistamine effect.
MetabolismUnknown, but most likely hepatic as with other phenothiazines.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPropiomazine is largely used for its antihistamininc sleep inducing effects in treating insomnia.
Minimum Risk LevelNot Available
Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
SymptomsRare, serious side effects include convulsions (seizures); difficult or unusually fast breathing; fast or irregular heartbeat or pulse; fever (high); high or low blood pressure; loss of bladder control; muscle stiffness (severe); unusual increase in sweating; unusually pale skin; and unusual tiredness or weakness.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00777
HMDB IDHMDB0014915
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPropiomazine
Chemspider ID4771
ChEBI ID8491
PubChem Compound ID4940
Kegg Compound IDC07405
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available