ContaminantDB: Triflupromazine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:04 UTC

Update Date

2026-05-14 16:40:46 UTC

Accession Number

CHEM002213

Identification

Common Name

Triflupromazine

Class

Small 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 (5HT_2B).

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
10-(3-(Dimethylamino)propyl)-2-(trifluoromethyl)phenothiazine	ChEBI
2-(Trifluoromethyl)promazine	ChEBI
2-Trifluoromethyl-10-(gamma-dimethylaminopropyl)phenothiazine	ChEBI
Trifluopromazine	ChEBI
Triflupromazina	ChEBI
Triflupromazinum	ChEBI
Vesprin	Kegg
2-Trifluoromethyl-10-(g-dimethylaminopropyl)phenothiazine	Generator
2-Trifluoromethyl-10-(γ-dimethylaminopropyl)phenothiazine	Generator
Bristol myers squibb brand OF triflupromazine hydrochloride	HMDB
Bristol-myers squibb brand OF triflupromazine hydrochloride	HMDB
Fluopromazine	HMDB
Siquil	HMDB

Chemical Formula

C₁₈H₁₉F₃N₂S

Average Molecular Mass

352.417 g/mol

Monoisotopic Mass

352.122 g/mol

CAS Registry Number

146-54-3

IUPAC Name

dimethyl({3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl})amine

Traditional Name

triflupromazine

SMILES

CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(C=C2)C(F)(F)F

InChI Identifier

InChI=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 Key

XSCGXQMFQXDFCW-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:9711 )
organofluorine compound (CHEBI:9711 )
tertiary amine (CHEBI:9711 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

dopaminergic antagonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	176°C at 7.00E-01 mm Hg
Solubility	1.80e-03 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0018 g/L	ALOGPS
logP	4.95	ALOGPS
logP	4.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.93 m³·mol⁻¹	ChemAxon
Polarizability	35.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9013000000-ef47630a3d0764a3497f	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-3019000000-dc3f041820258623fda5	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9013000000-ef47630a3d0764a3497f	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-3019000000-dc3f041820258623fda5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9164000000-703823624001a2ee0881	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1009000000-402ec2217df80aa43bad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zg0-6029000000-663c0786be1041e99933	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05to-9320000000-703e4677286a0641417a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-0596ba7ec1a1788b8961	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-0394000000-0cec2482504ddb1495d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2490000000-5e52f7ffca021b6f2581	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1009000000-11c5b880304e09474c3b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-9001000000-cd3fd91d666cb8f359e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9010000000-66877469a710d5429303	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-f23473e82dccb4a9df2f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uxr-0049000000-fda20f1ed08674d7aec5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01b9-0390000000-dec7333be9a90fa4471f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9121000000-0dfbd5aaf88b987dbe84	Spectrum

Toxicity Profile

Route of Exposure

Absorption may be erratic and peak plasma concentrations show large interindividual differences.

Mechanism of Toxicity

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 (5HT_2B).

Metabolism

Hepatic.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used mainly in the management of psychoses. Also used to control nausea and vomiting.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms 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.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00508

HMDB ID

HMDB0014650

FooDB ID

Not Available

Phenol Explorer ID