Triflupromazine (CHEM002213)

Record Information
Version1.0
Creation Date2009-07-21 20:27:04 UTC
Update Date2026-05-14 16:40:46 UTC
Accession NumberCHEM002213
Identification
Common NameTriflupromazine
ClassSmall Molecule
Description
Triflupromazine is only found in individuals that have used or taken this drug. It is a phenothiazine used as an antipsychotic agent and as an antiemetic. Triflupromazine binds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. The mechanism of the anti-emetic effect is due predominantly to blockage of the dopamine D2 neurotransmitter receptors in the chemoreceptor trigger zone (CTZ) and vomiting centre. Triflupromazine blocks the neurotransmitter dopamine and the vagus nerve in the gastrointestinal tract. Triflupromazine also binds the muscarinic acetylcholine receptors (M1 and M2) and the tryptamine D receptors (5HT2B).
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antiemetic
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ether
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
10-(3-(Dimethylamino)propyl)-2-(trifluoromethyl)phenothiazineChEBI
2-(Trifluoromethyl)promazineChEBI
2-Trifluoromethyl-10-(gamma-dimethylaminopropyl)phenothiazineChEBI
TrifluopromazineChEBI
TriflupromazinaChEBI
TriflupromazinumChEBI
VesprinKegg
2-Trifluoromethyl-10-(g-dimethylaminopropyl)phenothiazineGenerator
2-Trifluoromethyl-10-(γ-dimethylaminopropyl)phenothiazineGenerator
Bristol myers squibb brand OF triflupromazine hydrochlorideHMDB
Bristol-myers squibb brand OF triflupromazine hydrochlorideHMDB
FluopromazineHMDB
SiquilHMDB
Chemical FormulaC18H19F3N2S
Average Molecular Mass352.417 g/mol
Monoisotopic Mass352.122 g/mol
CAS Registry Number146-54-3
IUPAC Namedimethyl({3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl})amine
Traditional Nametriflupromazine
SMILESCN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(C=C2)C(F)(F)F
InChI IdentifierInChI=1S/C18H19F3N2S/c1-22(2)10-5-11-23-14-6-3-4-7-16(14)24-17-9-8-13(12-15(17)23)18(19,20)21/h3-4,6-9,12H,5,10-11H2,1-2H3
InChI KeyXSCGXQMFQXDFCW-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
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • 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 Point176°C at 7.00E-01 mm Hg
Solubility1.80e-03 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP4.95ALOGPS
logP4.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)9.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.93 m³·mol⁻¹ChemAxon
Polarizability35.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureAbsorption may be erratic and peak plasma concentrations show large interindividual differences.
Mechanism of ToxicityTriflupromazine binds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. The mechanism of the anti-emetic effect is due predominantly to blockage of the dopamine D2 neurotransmitter receptors in the chemoreceptor trigger zone (CTZ) and vomiting centre. Triflupromazine blocks the neurotransmitter dopamine and the vagus nerve in the gastrointestinal tract. Triflupromazine also binds the muscarinic acetylcholine receptors (M1 and M2) and the tryptamine D receptors (5HT2B).
MetabolismHepatic.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed mainly in the management of psychoses. Also used to control nausea and vomiting.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, and restlessness.
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00508
HMDB IDHMDB0014650
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTriflupromazine
Chemspider ID5367
ChEBI ID9711
PubChem Compound ID5568
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24959397