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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:43:35 UTC
Update Date2019-07-23 14:38:56 UTC
HMDB IDHMDB0240245
Secondary Accession NumbersNone
Metabolite Identification
Common NameBamipine
DescriptionBamipine, also known as soventol or taumidrine, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. No clinically relevant contraindications or interactions with other drugs are known. These effects are rare when bamipine is applied topically as an ointment. Bamipine (trade name Soventol) is a pharmaceutical drug acting as an H1 antihistamine with anticholinergic properties. Bamipine is a very strong basic compound (based on its pKa). In humans, bamipine is involved in bamipine h1-antihistamine action. Bamipine is not absorbed through intact skin in relevant doses. Side effects are typical of an old (first-generation) antihistamine: tiredness in adults, agitation in children, mydriasis (dilation of the pupils). No oral use is known. When applied topically, the maximal effect is reached after 20 to 60 minutes and lasts up to 48 hours. Acute eczema can be worsened by bamipine ointment.
Structure
Data?1563892736
Synonyms
ValueSource
BamipinHMDB
SoventolHMDB
TaumidrineHMDB
BamipineHMDB
Chemical FormulaC19H24N2
Average Molecular Weight280.415
Monoisotopic Molecular Weight280.193948781
IUPAC Name1-(1,2-diphenylethyl)-4-methylpiperazine
Traditional Name1-(1,2-diphenylethyl)-4-methylpiperazine
CAS Registry Number4945-47-5
SMILES
CN1CCN(CC1)C(CC1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C19H24N2/c1-20-12-14-21(15-13-20)19(18-10-6-3-7-11-18)16-17-8-4-2-5-9-17/h2-11,19H,12-16H2,1H3
InChI KeyNXTSFMFOSFAEGA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Amphetamine or derivatives
  • Aralkylamine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.74ALOGPS
logP3.83ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)8.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.69 m³·mol⁻¹ChemAxon
Polarizability33.02 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-2f5abac1da038e6e1a2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-4960000000-b9fd52d24d4f5cdb6bc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9610000000-194594bb6a12328c4f29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-763a440a4cfae734b23eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090000000-6abc99ab8b6c04c6e2d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0097-9650000000-31846b8b6fb35b04014dSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID184818
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBamipine
METLIN IDNot Available
PubChem Compound213142
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Weis R, Schweiger K, Faist J, Rajkovic E, Kungl AJ, Fabian WM, Schunack W, Seebacher W: Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives. Bioorg Med Chem. 2008 Dec 15;16(24):10326-31. doi: 10.1016/j.bmc.2008.10.042. Epub 2008 Oct 22. [PubMed:18977145 ]