Triprolidine (CHEM016924)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:47:45 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016924
Identification
Common NameTriprolidine
ClassSmall Molecule
DescriptionFirst generation histamine H1 antagonist used in allergic rhinitis; asthma; and urticaria. It is a component of cough and cold medicines. It may cause drowsiness.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
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)splash10-0a4i-2690000000-a4b47440bb135b0a9addSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-2690000000-a4b47440bb135b0a9addSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9550000000-61fa9fbbd86c1d8132d5Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-57d0a53f4f4fbf44333eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-3190000000-e5e446529606f5e3e26cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ae9-9760000000-9bf046a80ce2090309e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f32aa6a085f862b1f8e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-6190000000-81f7c9adb1e5c8d01951Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9010000000-f391092305f35968f4a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0090000000-1bd83ede0cbeecafcb5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0190000000-f7eb5282af1d309096f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-5790000000-dd4dd9f6e9e6f3da20c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0290000000-ba238a298ca7561c0f88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2590000000-f5506cf2d6662537e1c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-2950000000-7eac67d12b72f0fe7d93Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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