Triprolidine (CED0009267)

Record Information
Version1.0
Creation Date2016-05-22 03:47:45 UTC
Update Date2026-08-20 03:20:44 UTC
Accession NumberCHEM016924
Identification
Common NameTriprolidine
ClassSmall Molecule
Description
Triprolidine is an organic compound with the chemical formula C19H22N2 and an average molecular weight of 278.39 g/mol. Triprolidine belongs to the styrenes, a subclass of benzene and substituted derivatives within the organic compounds. In terms of biological activity, it is recorded as an antagonist of the Histamine H1 receptor (HRH1). The substance is identified in seven recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an antihistamine. It is also found in household cleaning and consumer products, specifically soap dispensers, and in electrical and electronic equipment, including antennas, amplifiers, video games, electric hearing aids, and gas filled discharge tubes with solid cathode. The recorded route of exposure for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-2-[3-(1-Pyrrolidinyl)-1-p-toluenepropenyl]pyridineChEBI
trans-1-(2-Pyridyl)-3-pyrrolidino-1-p-tolylprop-1-eneChEBI
trans-1-(4-Methylphenyl)-1-(2-pyridyl)-3-pyrrolidinoprop-1-eneChEBI
trans-2-(3-(1-Pyrrolidinyl)-1-p-tolylpropenyl)pyridineChEBI
TripolidinaChEBI
TriprolidinumChEBI
Hydrochloride anhydrous, triprolidineHMDB
Triprolidine hydrochloride anhydrousHMDB
Hydrochloride, triprolidineHMDB
Triprolidine monohydrochlorideHMDB
Triprolidine monohydrochloride, monohydrateHMDB
Triprolidine oxalate, (trans)-isomerHMDB
Triprolidine hydrochlorideHMDB
Triprolidine monohydrochloride, (Z)-isomerHMDB
ActidilHMDB
Anhydrous, triprolidine hydrochlorideHMDB
Pro actidilHMDB
Triprolidine oxalateHMDB
Triprolidine, (Z)-isomerHMDB
Wellcome brand OF triprolidineHMDB
Chemical FormulaC19H22N2
Average Molecular Mass278.391 g/mol
Monoisotopic Mass278.178 g/mol
CAS Registry Number486-12-4
IUPAC Name2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine
Traditional Nametriprolidine
SMILESCC1=CC=C(C=C1)C(=C/CN1CCCC1)\C1=CC=CC=N1
InChI IdentifierInChI=1S/C19H22N2/c1-16-7-9-17(10-8-16)18(19-6-2-3-12-20-19)11-15-21-13-4-5-14-21/h2-3,6-12H,4-5,13-15H2,1H3/b18-11+
InChI KeyCBEQULMOCCWAQT-WOJGMQOQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassStyrenes
Direct ParentStyrenes
Alternative Parents
Substituents
  • Styrene
  • Toluene
  • Pyridine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
logP4.14ALOGPS
logP4.05ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.53 m³·mol⁻¹ChemAxon
Polarizability33.09 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0a4i-2690000000-a4b47440bb135b0a9addNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-2690000000-a4b47440bb135b0a9addNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-9550000000-61fa9fbbd86c1d8132d5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-57d0a53f4f4fbf44333eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0560-3190000000-e5e446529606f5e3e26cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ae9-9760000000-9bf046a80ce2090309e5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-f32aa6a085f862b1f8e5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00b9-6190000000-81f7c9adb1e5c8d01951Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9010000000-f391092305f35968f4a2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-0090000000-1bd83ede0cbeecafcb5fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0190000000-f7eb5282af1d309096f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a5c-5790000000-dd4dd9f6e9e6f3da20c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0290000000-ba238a298ca7561c0f88Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-2590000000-f5506cf2d6662537e1c9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6u-2950000000-7eac67d12b72f0fe7d93Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
573.0Log mg/kg[320:1000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
393AntihistaminesHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
Pathways
7 pathways
Triprolidine H1-Antihistamine Action
Triprolidine H1-Antihistamine Action
Triprolidine Drug Metabolism Action Pathway
Triprolidine Drug Metabolism Action Pathway
Triprolidine H1 Antihistamine Neurological Sleep Action Pathway
Triprolidine H1 Antihistamine Neurological Sleep Action Pathway
Triprolidine Predicted Metabolism Pathway
Triprolidine Predicted Metabolism Pathway
Triprolidine H1 Antihistamine Smooth Muscle Relaxation Action Pathway
Triprolidine H1 Antihistamine Smooth Muscle Relaxation Action Pathway
Triprolidine H1-Antihistamine Blood Vessel Constriction Action Pathway
Triprolidine H1-Antihistamine Blood Vessel Constriction Action Pathway
Triprolidine H1-Antihistamine Immune Response Action Pathway
Triprolidine H1-Antihistamine Immune Response Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)627.309
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)399.678
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)758.485
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)666.701
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)268.035
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)571.725
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)611.194
Click to view 3D structureLuciferin 4-monooxygenaseP08659Photinus pyralisPredicted (SEA)147.68
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)861.557
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)335.452
Click to view 3D structureNonstructural protein 1Q194T2Influenza A virusPredicted (SEA)46.8652
Histamine H3 receptor structureClick to view 3D structureHistamine H3 receptorQ9Y5N1HumansPredicted (SEA)408.008
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)903.129
Krueppel-like factor 5 structureClick to view 3D structureKrueppel-like factor 5Q13887HumansPredicted (SEA)37.6012
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)1990.22
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)873.079
Click to view 3D structureHistamine H3 receptorQ9QYN8Rattus norvegicusPredicted (SEA)145.656
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)949.293
D(1A) dopamine receptor structureClick to view 3D structureD(1A) dopamine receptorP21728HumansPredicted (SEA)660.628
Click to view 3D structureHeat shock factor protein 1P38532Mus musculusPredicted (SEA)261.34
Click to view 3D structureTransient receptor potential cation channel subfamily V member 3Q8K424Mus musculusPredicted (SEA)72.8669
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)662.653
Click to view 3D structureSigma non-opioid intracellular receptor 1Q60492Cavia porcellusPredicted (SEA)589.864
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)940.263
Click to view 3D structureDNA damage-inducible transcript 3 proteinP35639Mus musculusPredicted (SEA)328.524
Concentrations
Not Available
External Links
DrugBank IDDB00427
HMDB IDHMDB0014571
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTriprolidine
Chemspider ID4445597
ChEBI ID84116
PubChem Compound ID5282443
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44.
2. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97.
3. Telekes A, Holland RL, Withington DA, Peck AW: Effects of triprolidine and dipipanone in the cold induced pain test, and the central nervous system of healthy volunteers. Br J Clin Pharmacol. 1987 Jul;24(1):43-50.
4. Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80.
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=1362947
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1362948
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3944383
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6509877
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7258744
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=8529817