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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-23 15:22:02 UTC
Update Date2020-02-26 21:26:30 UTC
HMDB IDHMDB0006543
Secondary Accession Numbers
  • HMDB06543
Metabolite Identification
Common NameDebrisoquine
DescriptionDebrisoquine is an adrenergic neuron-blocking drug. Genetic and environmental factors are determinants of the interindividual and interethnic variability in drug metabolism. Thus, interethnic differences in debrisoquine hydroxylation polymorphism (Cytochrome p450, subfamily IID, polypeptide 6, CYP2D6) might be partly responsible for the variation in haloperidol disposition between races. The influence of tobacco, ethanol, caffeine, gender, and oral contraceptive use on the debrisoquine metabolic ratio (MR) has been analyzed in panels of healthy volunteers. About 5-10% of European white population has a genetically determinant defect of the CYP2D6, one of the enzymes of cytochrome P-450. This defect leads to the impaired metabolism of many drugs including various psychopharmacological agents. The measurement of the hydroxylation of debrisoquine is a laboratory test which allows identifying such an individual. Patients who show an impaired hydroxylation of debrisoquine usually demonstrate severe side effects and poor outcome of psychopharmacotherapy. In practice, knowledge of a patient's debrisoquine metabolic phenotype is an advantage when prescribing tricyclic antidepressants and neuroleptics, as the drug concentration will be considerably higher in slow metabolisers than in the average patient. (PMID: 8839686 , 1738265 , 7878155 ).
Structure
Data?1582752390
Synonyms
ValueSource
DebrisochinumChEBI
DebrisoquinaChEBI
DebrisoquinumChEBI
IsocaramidineChEBI
3,4-dihydro-2(1H)-IsoquinolinecarboximidamideHMDB
Debrisoquin sulfateHMDB
Debrisoquin sulphateHMDB
TendorMeSH, HMDB
DebrisoquinMeSH, HMDB
DebrisoquineChEBI
Chemical FormulaC10H13N3
Average Molecular Weight175.2303
Monoisotopic Molecular Weight175.110947431
IUPAC Name1,2,3,4-tetrahydroisoquinoline-2-carboximidamide
Traditional Namedebrisoquin
CAS Registry Number1131-64-2
SMILES
NC(=N)N1CCC2=CC=CC=C2C1
InChI Identifier
InChI=1S/C10H13N3/c11-10(12)13-6-5-8-3-1-2-4-9(8)7-13/h1-4H,5-7H2,(H3,11,12)
InChI KeyJWPGJSVJDAJRLW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • Benzenoid
  • Guanidine
  • Azacycle
  • Carboximidamide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Imine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point278 - 280 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.75SANGSTER (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available138.655http://allccs.zhulab.cn/database/detail?ID=AllCCS00000957
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.84 g/LALOGPS
logP0.58ALOGPS
logP1.07ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)12.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.11 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity63.85 m³·mol⁻¹ChemAxon
Polarizability19.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.53931661259
DarkChem[M-H]-135.88431661259
DeepCCS[M+H]+138.13330932474
DeepCCS[M-H]-135.38730932474
DeepCCS[M-2H]-171.75430932474
DeepCCS[M+Na]+147.29130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DebrisoquineNC(=N)N1CCC2=CC=CC=C2C13232.2Standard polar33892256
DebrisoquineNC(=N)N1CCC2=CC=CC=C2C11789.7Standard non polar33892256
DebrisoquineNC(=N)N1CCC2=CC=CC=C2C11888.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Debrisoquine,1TMS,isomer #1C[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C12039.1Semi standard non polar33892256
Debrisoquine,1TMS,isomer #1C[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C11786.0Standard non polar33892256
Debrisoquine,1TMS,isomer #1C[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C12581.5Standard polar33892256
Debrisoquine,1TMS,isomer #2C[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C11955.0Semi standard non polar33892256
Debrisoquine,1TMS,isomer #2C[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C11744.1Standard non polar33892256
Debrisoquine,1TMS,isomer #2C[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C12719.0Standard polar33892256
Debrisoquine,2TMS,isomer #1C[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C2066.9Semi standard non polar33892256
Debrisoquine,2TMS,isomer #1C[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C2002.0Standard non polar33892256
Debrisoquine,2TMS,isomer #1C[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C2617.9Standard polar33892256
Debrisoquine,2TMS,isomer #2C[Si](C)(C)N=C(N[Si](C)(C)C)N1CCC2=CC=CC=C2C12022.0Semi standard non polar33892256
Debrisoquine,2TMS,isomer #2C[Si](C)(C)N=C(N[Si](C)(C)C)N1CCC2=CC=CC=C2C11857.4Standard non polar33892256
Debrisoquine,2TMS,isomer #2C[Si](C)(C)N=C(N[Si](C)(C)C)N1CCC2=CC=CC=C2C12558.9Standard polar33892256
Debrisoquine,3TMS,isomer #1C[Si](C)(C)N=C(N1CCC2=CC=CC=C2C1)N([Si](C)(C)C)[Si](C)(C)C2039.2Semi standard non polar33892256
Debrisoquine,3TMS,isomer #1C[Si](C)(C)N=C(N1CCC2=CC=CC=C2C1)N([Si](C)(C)C)[Si](C)(C)C2043.2Standard non polar33892256
Debrisoquine,3TMS,isomer #1C[Si](C)(C)N=C(N1CCC2=CC=CC=C2C1)N([Si](C)(C)C)[Si](C)(C)C2381.6Standard polar33892256
Debrisoquine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C12279.3Semi standard non polar33892256
Debrisoquine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C12092.7Standard non polar33892256
Debrisoquine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C12723.7Standard polar33892256
Debrisoquine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C12191.3Semi standard non polar33892256
Debrisoquine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C12016.6Standard non polar33892256
Debrisoquine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C12866.6Standard polar33892256
Debrisoquine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C(C)(C)C2453.3Semi standard non polar33892256
Debrisoquine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C(C)(C)C2508.8Standard non polar33892256
Debrisoquine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C(C)(C)C2735.6Standard polar33892256
Debrisoquine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CCC2=CC=CC=C2C12416.5Semi standard non polar33892256
Debrisoquine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CCC2=CC=CC=C2C12389.1Standard non polar33892256
Debrisoquine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CCC2=CC=CC=C2C12707.5Standard polar33892256
Debrisoquine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(N1CCC2=CC=CC=C2C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2640.1Semi standard non polar33892256
Debrisoquine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(N1CCC2=CC=CC=C2C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2761.2Standard non polar33892256
Debrisoquine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(N1CCC2=CC=CC=C2C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2625.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Debrisoquine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-2900000000-5f2dcf1ab6da5e83a08a2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Debrisoquine 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 - Debrisoquine 10V, Positive-QTOFsplash10-004i-0900000000-f06d895d1fcd728875752017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 20V, Positive-QTOFsplash10-004i-1900000000-303f4d1056319a7af3792017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 40V, Positive-QTOFsplash10-0006-9600000000-23a3b1c9891fa4ed0d482017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 10V, Negative-QTOFsplash10-0089-0900000000-de5f6c454f33dfa496312017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 20V, Negative-QTOFsplash10-001i-0900000000-345411615860de4e9f9c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 40V, Negative-QTOFsplash10-0006-9200000000-97c195947a62b5ad19142017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 10V, Negative-QTOFsplash10-00di-0900000000-197f016c597f3f68820e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 20V, Negative-QTOFsplash10-001i-0900000000-404d46b163e905d93c5a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 40V, Negative-QTOFsplash10-000x-5900000000-e17ff20314593cc52ea62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 10V, Positive-QTOFsplash10-004i-0900000000-00288a7f5daf602f9bc52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 20V, Positive-QTOFsplash10-053r-0900000000-6b0a6356c1254214f4db2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Debrisoquine 40V, Positive-QTOFsplash10-05mo-5900000000-74557ed99dab28c73eb82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.149 +/- 0.087 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04840
Phenol Explorer Compound IDNot Available
FooDB IDFDB023967
KNApSAcK IDNot Available
Chemspider ID2860
KEGG Compound IDC13650
BioCyc IDNot Available
BiGG ID2299980
Wikipedia LinkDebrisoquine
METLIN IDNot Available
PubChem Compound2966
PDB IDNot Available
ChEBI ID34665
Food Biomarker OntologyNot Available
VMH IDDEBRISOQUINE
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Llerena A, Cobaleda J, Martinez C, Benitez J: Interethnic differences in drug metabolism: influence of genetic and environmental factors on debrisoquine hydroxylation phenotype. Eur J Drug Metab Pharmacokinet. 1996 Apr-Jun;21(2):129-38. [PubMed:8839686 ]
  2. Alvan G, Dahl ML: [Knowledge about metabolic capacity is important in drug therapy]. Lakartidningen. 1992 Feb 5;89(6):382, 387-90. [PubMed:1738265 ]
  3. Jarema M: [Debrisoquine hydroxylation test as an example of new possibilities of research in psychopharmacology]. Psychiatr Pol. 1995 Jan-Feb;29(1):57-66. [PubMed:7878155 ]