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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-12-07 02:51:46 UTC
HMDB IDHMDB0015554
Secondary Accession Numbers
  • HMDB15554
Metabolite Identification
Common NameAlverine
DescriptionAlverine is a smooth muscle relaxant. Smooth muscle is a type of muscle that is not under voluntary control; it is the muscle present in places such as the gut and uterus. Alverine acts directly on the muscle in the gut, causing it to relax. This prevents the muscle spasms which occur in the gut in conditions such as irritable bowel syndrome and diverticular disease. It is used to relieve cramps or spasms of the stomach and intestines. It is also useful in treating irritable bowel syndrome (IBS) and similar conditions. It can also be used to help relieve period pain. Alverine is formulated as the citrate salt (5982-87-6).
Structure
Thumb
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
SpasmonalMeSH
Alverine citrateMeSH
SpasmaverineMeSH
United drug brand OF alverine citrateMeSH
Alverine hydrochlorideMeSH
Norgine brand OF alverine citrateMeSH
Chemical FormulaC20H27N
Average Molecular Weight281.4351
Monoisotopic Molecular Weight281.214349869
IUPAC Nameethylbis(3-phenylpropyl)amine
Traditional Namealverine
CAS Registry Number150-59-4
SMILES
CCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities known as phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00096 g/LNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ox-7920000000-c8c9f49008d42192bf43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-fa5d943a706cbacc2966View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2590000000-5670c74b8576969d473eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9700000000-0ca8414132b5d9b38dc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-3436180aa1a55dae3c0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0190000000-4f76075ca6910a6f99f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0hgo-4920000000-8a9772388b6011f2db4fView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01616 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01616 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01616
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3550
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlverine
METLIN IDNot Available
PubChem Compound3678
PDB IDNot Available
ChEBI ID518413
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:17934514 ]
  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. [PubMed:19148544 ]
  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. [PubMed:20003095 ]
  4. Spasmonal Package Insert [Link]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
References
  1. Coelho AM, Jacob L, Fioramonti J, Bueno L: Rectal antinociceptive properties of alverine citrate are linked to antagonism at the 5-HT1A receptor subtype. J Pharm Pharmacol. 2001 Oct;53(10):1419-26. [PubMed:11697552 ]