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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 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
Data?1582753309
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 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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00096 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available168.392http://allccs.zhulab.cn/database/detail?ID=AllCCS00000739
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.41531661259
DarkChem[M-H]-170.08931661259
DeepCCS[M+H]+169.51230932474
DeepCCS[M-H]-167.15430932474
DeepCCS[M-2H]-200.0430932474
DeepCCS[M+Na]+175.60530932474
AllCCS[M+H]+171.832859911
AllCCS[M+H-H2O]+168.332859911
AllCCS[M+NH4]+175.032859911
AllCCS[M+Na]+175.932859911
AllCCS[M-H]-177.132859911
AllCCS[M+Na-2H]-177.332859911
AllCCS[M+HCOO]-177.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AlverineCCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C12802.3Standard polar33892256
AlverineCCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C12162.6Standard non polar33892256
AlverineCCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C12199.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alverine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ox-7920000000-c8c9f49008d42192bf432017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alverine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alverine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 10V, Positive-QTOFsplash10-001i-0190000000-fa5d943a706cbacc29662016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 20V, Positive-QTOFsplash10-001i-2590000000-5670c74b8576969d473e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 40V, Positive-QTOFsplash10-00kf-9700000000-0ca8414132b5d9b38dc02016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 10V, Negative-QTOFsplash10-001i-0090000000-3436180aa1a55dae3c0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 20V, Negative-QTOFsplash10-001i-0190000000-4f76075ca6910a6f99f92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 40V, Negative-QTOFsplash10-0hgo-4920000000-8a9772388b6011f2db4f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 10V, Positive-QTOFsplash10-001i-0090000000-6c46192dea07b99770572021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 20V, Positive-QTOFsplash10-001i-0190000000-116fee06af3fb48655ac2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 40V, Positive-QTOFsplash10-0006-9710000000-88ece644f51433dcc79c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 10V, Negative-QTOFsplash10-001i-0090000000-78e4f4cb0fda655af8842021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 20V, Negative-QTOFsplash10-001i-0290000000-8bc76e555b532b4d0ea22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alverine 40V, Negative-QTOFsplash10-0006-9740000000-30aa7cd1d162b50b60bc2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01616 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01616 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01616
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]