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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-23 15:22:02 UTC

Update Date

2023-02-21 17:17:20 UTC

HMDB ID

HMDB0006543

Secondary Accession Numbers

HMDB06543

Metabolite Identification

Common Name

Debrisoquine

Description

Debrisoquine 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4840                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       6.574   0.212   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       3.907   0.212   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.241  -2.098   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.908   2.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.574   1.752   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.908  -0.558   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.242   1.752   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.242   0.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.618   2.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.618  -0.611   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.241  -0.558   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.014   1.784   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.014   0.180   0.000  0.00  0.00           C+0
CONECT    1    5    6   11                                                  
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    5    7                                                       
CONECT    5    1    4                                                       
CONECT    6    1    8                                                       
CONECT    7    4    8    9                                                  
CONECT    8    6    7   10                                                  
CONECT    9    7   12                                                       
CONECT   10    8   13                                                       
CONECT   11    1    2    3                                                  
CONECT   12    9   13                                                       
CONECT   13   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Debrisochinum	ChEBI
Debrisoquina	ChEBI
Debrisoquinum	ChEBI
Isocaramidine	ChEBI
3,4-dihydro-2(1H)-Isoquinolinecarboximidamide	HMDB
Debrisoquin sulfate	HMDB
Debrisoquin sulphate	HMDB
Tendor	MeSH, HMDB
Debrisoquin	MeSH, HMDB
Debrisoquine	ChEBI

Chemical Formula

C₁₀H₁₃N₃

Average Molecular Weight

175.2303

Monoisotopic Molecular Weight

175.110947431

IUPAC Name

1,2,3,4-tetrahydroisoquinoline-2-carboximidamide

Traditional Name

debrisoquin

CAS Registry Number

1131-64-2

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 Key

JWPGJSVJDAJRLW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
Benzenoid
Guanidine
Azacycle
Carboximidamide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Imine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carboxamidine (CHEBI:34665 )
isoquinolines (CHEBI:34665 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006543)
Extracellular (HMDB: HMDB0006543)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006543)

Source

Endogenous

Endogenous (HMDB: HMDB0006543)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0006543)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	278 - 280 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	0.75	SANGSTER (1994)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	138.655	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000957

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.84 g/L	ALOGPS
logP	0.58	ALOGPS
logP	1.07	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	12.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.11 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	63.85 m³·mol⁻¹	ChemAxon
Polarizability	19.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.539	31661259
DarkChem	[M-H]-	135.884	31661259
DeepCCS	[M+H]+	138.133	30932474
DeepCCS	[M-H]-	135.387	30932474
DeepCCS	[M-2H]-	171.754	30932474
DeepCCS	[M+Na]+	147.291	30932474
AllCCS	[M+H]+	138.3	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	142.4	32859911
AllCCS	[M+Na]+	143.6	32859911
AllCCS	[M-H]-	140.7	32859911
AllCCS	[M+Na-2H]-	141.3	32859911
AllCCS	[M+HCOO]-	142.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Debrisoquine	NC(=N)N1CCC2=CC=CC=C2C1	3232.2	Standard polar	33892256
Debrisoquine	NC(=N)N1CCC2=CC=CC=C2C1	1789.7	Standard non polar	33892256
Debrisoquine	NC(=N)N1CCC2=CC=CC=C2C1	1888.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Debrisoquine,1TMS,isomer #1	C[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C1	2039.1	Semi standard non polar	33892256
Debrisoquine,1TMS,isomer #1	C[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C1	1786.0	Standard non polar	33892256
Debrisoquine,1TMS,isomer #1	C[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C1	2581.5	Standard polar	33892256
Debrisoquine,1TMS,isomer #2	C[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C1	1955.0	Semi standard non polar	33892256
Debrisoquine,1TMS,isomer #2	C[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C1	1744.1	Standard non polar	33892256
Debrisoquine,1TMS,isomer #2	C[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C1	2719.0	Standard polar	33892256
Debrisoquine,2TMS,isomer #1	C[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C	2066.9	Semi standard non polar	33892256
Debrisoquine,2TMS,isomer #1	C[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C	2002.0	Standard non polar	33892256
Debrisoquine,2TMS,isomer #1	C[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C	2617.9	Standard polar	33892256
Debrisoquine,2TMS,isomer #2	C[Si](C)(C)N=C(N[Si](C)(C)C)N1CCC2=CC=CC=C2C1	2022.0	Semi standard non polar	33892256
Debrisoquine,2TMS,isomer #2	C[Si](C)(C)N=C(N[Si](C)(C)C)N1CCC2=CC=CC=C2C1	1857.4	Standard non polar	33892256
Debrisoquine,2TMS,isomer #2	C[Si](C)(C)N=C(N[Si](C)(C)C)N1CCC2=CC=CC=C2C1	2558.9	Standard polar	33892256
Debrisoquine,3TMS,isomer #1	C[Si](C)(C)N=C(N1CCC2=CC=CC=C2C1)N([Si](C)(C)C)[Si](C)(C)C	2039.2	Semi standard non polar	33892256
Debrisoquine,3TMS,isomer #1	C[Si](C)(C)N=C(N1CCC2=CC=CC=C2C1)N([Si](C)(C)C)[Si](C)(C)C	2043.2	Standard non polar	33892256
Debrisoquine,3TMS,isomer #1	C[Si](C)(C)N=C(N1CCC2=CC=CC=C2C1)N([Si](C)(C)C)[Si](C)(C)C	2381.6	Standard polar	33892256
Debrisoquine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C1	2279.3	Semi standard non polar	33892256
Debrisoquine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C1	2092.7	Standard non polar	33892256
Debrisoquine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=N)N1CCC2=CC=CC=C2C1	2723.7	Standard polar	33892256
Debrisoquine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C1	2191.3	Semi standard non polar	33892256
Debrisoquine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C1	2016.6	Standard non polar	33892256
Debrisoquine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N)N1CCC2=CC=CC=C2C1	2866.6	Standard polar	33892256
Debrisoquine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C(C)(C)C	2453.3	Semi standard non polar	33892256
Debrisoquine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C(C)(C)C	2508.8	Standard non polar	33892256
Debrisoquine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=N)N1CCC2=CC=CC=C2C1)[Si](C)(C)C(C)(C)C	2735.6	Standard polar	33892256
Debrisoquine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CCC2=CC=CC=C2C1	2416.5	Semi standard non polar	33892256
Debrisoquine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CCC2=CC=CC=C2C1	2389.1	Standard non polar	33892256
Debrisoquine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CCC2=CC=CC=C2C1	2707.5	Standard polar	33892256
Debrisoquine,3TBDMS,isomer #1	CC(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)C	2640.1	Semi standard non polar	33892256
Debrisoquine,3TBDMS,isomer #1	CC(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)C	2761.2	Standard non polar	33892256
Debrisoquine,3TBDMS,isomer #1	CC(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)C	2625.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Debrisoquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-2900000000-5f2dcf1ab6da5e83a08a	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Debrisoquine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 10V, Positive-QTOF	splash10-004i-0900000000-f06d895d1fcd72887575	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 20V, Positive-QTOF	splash10-004i-1900000000-303f4d1056319a7af379	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 40V, Positive-QTOF	splash10-0006-9600000000-23a3b1c9891fa4ed0d48	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 10V, Negative-QTOF	splash10-0089-0900000000-de5f6c454f33dfa49631	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 20V, Negative-QTOF	splash10-001i-0900000000-345411615860de4e9f9c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 40V, Negative-QTOF	splash10-0006-9200000000-97c195947a62b5ad1914	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 10V, Negative-QTOF	splash10-00di-0900000000-197f016c597f3f68820e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 20V, Negative-QTOF	splash10-001i-0900000000-404d46b163e905d93c5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 40V, Negative-QTOF	splash10-000x-5900000000-e17ff20314593cc52ea6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 10V, Positive-QTOF	splash10-004i-0900000000-00288a7f5daf602f9bc5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 20V, Positive-QTOF	splash10-053r-0900000000-6b0a6356c1254214f4db	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Debrisoquine 40V, Positive-QTOF	splash10-05mo-5900000000-74557ed99dab28c73eb8	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.149 +/- 0.087 uM	Adult (>18 years old)	Both	Normal	12814461	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04840

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023967

KNApSAcK ID

Not Available

Chemspider ID

2860

KEGG Compound ID

C13650

BioCyc ID

Not Available

BiGG ID

2299980

Wikipedia Link

Debrisoquine

METLIN ID

Not Available

PubChem Compound

2966

PDB ID

Not Available

ChEBI ID

34665

Food Biomarker Ontology

Not Available

VMH ID

DEBRISOQUINE

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Alvan G, Dahl ML: [Knowledge about metabolic capacity is important in drug therapy]. Lakartidningen. 1992 Feb 5;89(6):382, 387-90. [PubMed:1738265 ]
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 ]

Showing metabocard for Debrisoquine (HMDB0006543)

MOL for HMDB0006543 (Debrisoquine)

3D MOL for HMDB0006543 (Debrisoquine)

3D SDF for HMDB0006543 (Debrisoquine)

3D-SDF for HMDB0006543 (Debrisoquine)

PDB for HMDB0006543 (Debrisoquine)

3D PDB for HMDB0006543 (Debrisoquine)

SMILES for HMDB0006543 (Debrisoquine)

INCHI for HMDB0006543 (Debrisoquine)

Structure for HMDB0006543 (Debrisoquine)

3D Structure for HMDB0006543 (Debrisoquine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra