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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:43:43 UTC
Update Date2022-03-07 03:18:14 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. In humans, deptropine is involved in the deptropine h1-antihistamine action pathway. Deptropine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Deptropine.
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 Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M-H]-187.39431661259
AllCCS[M+H]+186.24831661259
DeepCCS[M-2H]-207.11730932474
DeepCCS[M+Na]+182.68330932474
AllCCS[M+H]+186.232859911
AllCCS[M+H-H2O]+183.332859911
AllCCS[M+NH4]+188.932859911
AllCCS[M+Na]+189.732859911
AllCCS[M-H]-187.432859911
AllCCS[M+Na-2H]-187.232859911
AllCCS[M+HCOO]-187.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DeptropineCN1C2CCC1CC(C2)OC1C2=CC=CC=C2CCC2=CC=CC=C123475.8Standard polar33892256
DeptropineCN1C2CCC1CC(C2)OC1C2=CC=CC=C2CCC2=CC=CC=C122685.1Standard non polar33892256
DeptropineCN1C2CCC1CC(C2)OC1C2=CC=CC=C2CCC2=CC=CC=C122625.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Deptropine 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 - Deptropine 10V, Positive-QTOFsplash10-001i-0209000000-e7f7b21e212b15d6d4632019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 20V, Positive-QTOFsplash10-008c-0916000000-3e0eca10c286608d83ef2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 40V, Positive-QTOFsplash10-0f7p-8900000000-ea0f66a28c1738ddcc652019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 10V, Negative-QTOFsplash10-001i-0019000000-ca1fbe878822065f87522019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 20V, Negative-QTOFsplash10-001i-0229000000-81a002f6b363312ddccd2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 40V, Negative-QTOFsplash10-0a6r-0940000000-2cf07325a00a010d394b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 10V, Positive-QTOFsplash10-001i-0009000000-31218f01f8f5afd00f202021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 20V, Positive-QTOFsplash10-001i-0709000000-a352b39984d6877fe93d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 40V, Positive-QTOFsplash10-0006-2910000000-828c08b876bb95cc51ad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 10V, Negative-QTOFsplash10-001i-0009000000-0747f0d99ffa085d09ea2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 20V, Negative-QTOFsplash10-001i-0309000000-4dd60ee42dbc8c1ee8dc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deptropine 40V, Negative-QTOFsplash10-0ac3-1976000000-e47a0369c8ee0f712e212021-09-24Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1461671
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 ]