You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:43:43 UTC
Update Date2019-07-23 14:38:56 UTC
HMDB IDHMDB0240246
Secondary Accession NumbersNone
Metabolite Identification
Common NameDeptropine
DescriptionDeptropine, also known as brontina or dibenzheptropine, belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring. Deptropine is a very strong basic compound (based on its pKa). In humans, deptropine is involved in deptropine h1-antihistamine action. It is usually marketed as the citrate salt.
Structure
Data?1563892736
Synonyms
ValueSource
BrontinaHMDB
DibenzheptropineHMDB
DeptropineHMDB
Chemical FormulaC23H27NO
Average Molecular Weight333.475
Monoisotopic Molecular Weight333.209264493
IUPAC Name8-methyl-3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yloxy}-8-azabicyclo[3.2.1]octane
Traditional Name8-methyl-3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yloxy}-8-azabicyclo[3.2.1]octane
CAS Registry Number604-51-3
SMILES
CN1C2CCC1CC(C2)OC1C2=CC=CC=C2CCC2=CC=CC=C12
InChI Identifier
InChI=1S/C23H27NO/c1-24-18-12-13-19(24)15-20(14-18)25-23-21-8-4-2-6-16(21)10-11-17-7-3-5-9-22(17)23/h2-9,18-20,23H,10-15H2,1H3
InChI KeyZWPODSUQWXAZNC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassDibenzocycloheptenes
Sub ClassNot Available
Direct ParentDibenzocycloheptenes
Alternative Parents
Substituents
  • Dibenzocycloheptene
  • Tropane alkaloid
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary amine
  • Tertiary aliphatic amine
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Amine
  • 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
logP5.05ALOGPS
logP4.75ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity102.52 m³·mol⁻¹ChemAxon
Polarizability38.94 ųChemAxon
Number of Rings5ChemAxon
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-0209000000-e7f7b21e212b15d6d463Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008c-0916000000-3e0eca10c286608d83efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7p-8900000000-ea0f66a28c1738ddcc65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-ca1fbe878822065f8752Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0229000000-81a002f6b363312ddccdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-0940000000-2cf07325a00a010d394bSpectrum
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 ID15716
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDeptropine
METLIN IDNot Available
PubChem Compound16576
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. Cam JF, Gleave CM: A comparison of deptropine citrate (Brontina) with atropine for premedication. Br J Anaesth. 1968 Nov;40(11):885-9. [PubMed:4883647 ]