Methotrimeprazine (CHEM002393)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (20)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:48 UTC
Update Date2026-04-05 10:50:06 UTC
Accession NumberCHEM002393
Identification
Common NameMethotrimeprazine
ClassSmall Molecule
DescriptionMethotrimeprazine is only found in individuals that have used or taken this drug. It is a phenothiazine with pharmacological activity similar to that of both chlorpromazine and promethazine. It has the histamine-antagonist properties of the antihistamines together with central nervous system effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604). Methotrimeprazine's antipsychotic effect is largely due to its antagonism of dopamine receptors in the brain. In addition, its binding to 5HT2 receptors may also play a role.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Analgesic, Non-Narcotic
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(2R)-3-(2-Methoxy-10H-phenothiazin-10-yl)-N,N,2-trimethylpropan-1-amineChEBI
(-)-10-(3-(Dimethylamino)-2-methylpropyl)-2-methoxyphenothiazineChEBI
2-MethoxytrimeprazineChEBI
LevomepromazinaChEBI
LevomepromazineChEBI
LevomepromazinumChEBI
LevopromeKegg
LevopromazineHMDB
TisercinHMDB
LevomeprazinHMDB
TizertsinHMDB
TizercineHMDB
Chemical FormulaC19H24N2OS
Average Molecular Mass328.472 g/mol
Monoisotopic Mass328.161 g/mol
CAS Registry Number60-99-1
IUPAC Name[(2R)-3-(2-methoxy-10H-phenothiazin-10-yl)-2-methylpropyl]dimethylamine
Traditional Namemethotrimeprazine
SMILESCOC1=CC2=C(SC3=C(C=CC=C3)N2C[C@H](C)CN(C)C)C=C1
InChI IdentifierInChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1
InChI KeyVRQVVMDWGGWHTJ-CQSZACIVSA-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
  • Anisole
  • Tertiary aliphatic/aromatic amine
  • Alkyl aryl ether
  • Para-thiazine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Azacycle
  • Thioether
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen 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 Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility20 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.0052 g/LALOGPS
logP4.84ALOGPS
logP4.25ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)9.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area15.71 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.83 m³·mol⁻¹ChemAxon
Polarizability36.77 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-0a4i-9272000000-663ed1e564555c7e8faeSpectrum
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0009000000-292add600a1d733c3662Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0319000000-9bcdb870e16f29c42cc7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-2920000000-f73fff6b08acc61ea5b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0zfr-6920000000-dc5968beb0d112813d55Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9410000000-0d1f6734452bedc68d3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0910000000-10fe32fa41981fcda652Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0469000000-698db513d68f8238a284Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-3983000000-0963d25ff0f442a1b819Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc3-9420000000-45332e32eecba186d700Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-783dfd7af7ab08cc7337Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00p0-0494000000-78a58d14f5fb19218ba8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-3960000000-d1127cf211de0694b952Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1109000000-34d749e2d87b91114995Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9344000000-c57c58a83df0fed1de87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9010000000-9234afceb922b3e5fbf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-30741f7748d9c6819aaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0095000000-978af20f8f7527c06c88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-0190000000-60e894c19f034f06f29dSpectrum
MSMass Spectrum (Electron Ionization)splash10-056r-9356000000-bb17e4980980d336d337Spectrum
Toxicity Profile
Route of ExposureOral; parental (intramuscular). Methotrimeprazine has an incomplete oral bioavailability, because it undergoes considerable first-pass-metabolism in the liver. Oral bioavailability is approximately 50 to 60%.
Mechanism of ToxicityMethotrimeprazine's antipsychotic effect is largely due to its antagonism of dopamine receptors in the brain. In addition, its binding to 5HT2 receptors may also play a role. Methotrimeprazine exerts its actions through a central adrenergic-blocking, a dopamine-blocking, a serotonin-blocking, and a anticholinergic blocking.
MetabolismHepatic. Methotrimeprazine is metabolized in the liver and degraded to a sulfoxid-, a glucuronid- and a demethyl-moiety. Half Life: Approximately 20 hours.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of psychosis, particular those of schizophrenia, and manic phases of bipolar disorder. As a potentiator of anesthetics: In general anesthesia where it can be used as both a pre- and post-operative sedative and analgesic. (3) As an anti-emetic: For the treatment of nausea and vomiting of central origin.(3) As a sedative: For the management of insomnia. (3)
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include convulsions, spastic movements, and coma.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01403
HMDB IDHMDB0015474
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLevomepromazine
Chemspider ID65239
ChEBI ID6838
PubChem Compound ID72287
Kegg Compound IDC07192
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Christian Berger, “Process for preparing levomepromazine hydrogen maleate.” U.S. Patent US4798895, issued January 17, 1989.

MSDSNot Available
General References
1. Doctissimo: http://www.doctissimo.fr/medicament-NOZINAN.htm
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11026079
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11260766
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15700129
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20825390