Alverine (CHEM022327)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:28:22 UTC
Update Date2016-11-09 01:17:28 UTC
Accession NumberCHEM022327
Identification
Common NameAlverine
ClassSmall Molecule
DescriptionA tertiary amine having one ethyl and two 3-phenylprop-1-yl groups attached to the nitrogen. An antispasmodic that acts directly on intestinal and uterine smooth muscle, it is used (particularly as the citrate salt) in the treatment of irritable bowel syndrome.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AlverinaChEBI
AlverinumChEBI
Bis(gamma-phenylpropyl)ethylamineChEBI
Di(phenylpropyl)ethylamineChEBI
N,N-Bis(3-phenylpropyl)ethylamineChEBI
N-Ethyl-3,3'-diphenyldipropylamineChEBI
N-Ethyl-3-phenyl-N-(3-phenylpropyl)-1-propanamineChEBI
N-Ethyl-N-(3-phenylpropyl)benzenepropanamineChEBI
PhenopropamineChEBI
PhenpropamineChEBI
Bis(g-phenylpropyl)ethylamineGenerator
Bis(γ-phenylpropyl)ethylamineGenerator
N-Ethyl-bis(3-phenylpropyl)aminHMDB
SpasmonalHMDB
Alverine citrateHMDB
SpasmaverineHMDB
United drug brand OF alverine citrateHMDB
Alverine hydrochlorideHMDB
Norgine brand OF alverine citrateHMDB
Chemical FormulaC20H27N
Average Molecular Mass281.435 g/mol
Monoisotopic Mass281.214 g/mol
CAS Registry Number150-59-4
IUPAC Nameethylbis(3-phenylpropyl)amine
Traditional Namealverine
SMILESCCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1
InChI IdentifierInChI=1S/C20H27N/c1-2-21(17-9-15-19-11-5-3-6-12-19)18-10-16-20-13-7-4-8-14-20/h3-8,11-14H,2,9-10,15-18H2,1H3
InChI KeyZPFXAOWNKLFJDN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpropylamines. Phenylpropylamines are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropylamines
Direct ParentPhenylpropylamines
Alternative Parents
Substituents
  • Phenylpropylamine
  • Aralkylamine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.00096 g/LALOGPS
logP5.73ALOGPS
logP5.46ChemAxon
logS-5.5ALOGPS
pKa (Strongest Basic)10.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity92.67 m³·mol⁻¹ChemAxon
Polarizability35.42 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ox-7920000000-c8c9f49008d42192bf43Spectrum
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, Positivesplash10-001i-0190000000-fa5d943a706cbacc2966Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2590000000-5670c74b8576969d473eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9700000000-0ca8414132b5d9b38dc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-3436180aa1a55dae3c0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0190000000-4f76075ca6910a6f99f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0hgo-4920000000-8a9772388b6011f2db4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-6c46192dea07b9977057Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0190000000-116fee06af3fb48655acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9710000000-88ece644f51433dcc79cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-78e4f4cb0fda655af884Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0290000000-8bc76e555b532b4d0ea2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9740000000-30aa7cd1d162b50b60bcSpectrum
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 IDDB01616
HMDB IDHMDB0015554
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlverine
Chemspider ID3550
ChEBI ID518413
PubChem Compound ID3678
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hayase M, Hashitani H, Suzuki H, Kohri K, Brading AF: Evolving mechanisms of action of alverine citrate on phasic smooth muscles. Br J Pharmacol. 2007 Dec;152(8):1228-38. Epub 2007 Oct 15.
2. Ju D, Wang X, Xie Y: Dyclonine and alverine citrate enhance the cytotoxic effects of proteasome inhibitor MG132 on breast cancer cells. Int J Mol Med. 2009 Feb;23(2):205-9.
3. Wittmann T, Paradowski L, Ducrotte P, Bueno L, Andro Delestrain MC: Clinical trial: the efficacy of alverine citrate/simeticone combination on abdominal pain/discomfort in irritable bowel syndrome--a randomized, double-blind, placebo-controlled study. Aliment Pharmacol Ther. 2010 Mar;31(6):615-24. doi: 10.1111/j.1365-2036.2009.04216.x. Epub 2009 Dec 10.
4. Spasmonal Package Insert: http://www.medicines.org.uk/EMC/medicine/24562/SPC/