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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:41:24 UTC
Update Date2019-07-23 14:38:54 UTC
HMDB IDHMDB0240237
Secondary Accession NumbersNone
Metabolite Identification
Common NameMebhydrolin
DescriptionMebhydrolin, also known as bexidal or diazolin, belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position. Mebhydrolin has been shown to magnify the performance-deficit effects of alcohol. Mebhydrolin is a drug. Mebhydrolin is a very strong basic compound (based on its pKa). In humans, mebhydrolin is involved in mebhydrolin h1-antihistamine action. It is not available in the United States, but it is in various other countries under the brand names Bexidal (BD) and Diazolin (RU). It is used for symptomatic relief of allergic symptoms caused by histamine release, including nasal allergies and allergic dermatosis. Mebhydrolin (INN) or mebhydroline is an antihistamine.
Structure
Data?1563892734
Synonyms
ValueSource
BexidalKegg
MEBHYDROLIN napadisylATEHMDB
MEBHYDROLIN napadisylic acidHMDB
5-Benzyl-1,3,4,5-tetrahydro-2-methyl-2H-pyrido(4,3-b)indoleHMDB
MebhydrolineHMDB
DiazolinHMDB
DiazolinumHMDB
FabahistinHMDB
IncidalHMDB
OmerilHMDB
MebhydrolinHMDB
Chemical FormulaC19H20N2
Average Molecular Weight276.383
Monoisotopic Molecular Weight276.162648652
IUPAC Name5-benzyl-2-methyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indole
Traditional Namemebhydrolin
CAS Registry Number524-81-2
SMILES
CN1CCC2=C(C1)C1=CC=CC=C1N2CC1=CC=CC=C1
InChI Identifier
InChI=1S/C19H20N2/c1-20-12-11-19-17(14-20)16-9-5-6-10-18(16)21(19)13-15-7-3-2-4-8-15/h2-10H,11-14H2,1H3
InChI KeyFQQIIPAOSKSOJM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassN-alkylindoles
Direct ParentN-alkylindoles
Alternative Parents
Substituents
  • N-alkylindole
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Monocyclic benzene moiety
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP3.69ALOGPS
logP3.69ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)7.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area8.17 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.49 m³·mol⁻¹ChemAxon
Polarizability32.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9360000000-9002610ba3e228f59affSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3090000000-40622525da2ce99796faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9060000000-6696356c1054ed8a110dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-d98d9810eda32a0bbd0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-3a3bda3830d86f3d214eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3390000000-22a83e55769bca15edbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02vr-2910000000-ea3f90b4d71454e8f193Spectrum
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 IDDB13808
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMebhydrolin
METLIN IDNot Available
PubChem Compound22530
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. Franks HM, Lawrie M, Schabinsky VV, Starmer GA, Teo RK: Interaction between ethanol and antihistamines: 3. mebhydrolin. Med J Aust. 1981 Oct 31;2(9):477-9. [PubMed:6119605 ]