Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 UTC
HMDB IDHMDB0014668
Secondary Accession Numbers
  • HMDB14668
Metabolite Identification
Common NameDibucaine
DescriptionDibucaine, also known as cinchocainum or dibucaine base, belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group. Dibucaine is a drug which is used for production of local or regional anesthesia by infiltration techniques such as percutaneous injection and intravenous regional anesthesia by peripheral nerve block techniques such as brachial plexus and intercostal and by central neural techniques such as lumbar and caudal epidural blocks. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions. Dibucaine is a very strong basic compound (based on its pKa). In humans, dibucaine is involved in dibucaine action pathway. A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid.
Structure
Data?1582753206
Synonyms
ValueSource
2-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamideChEBI
2-Butoxy-N-(alpha-diethylaminoethyl)cinchoninamideChEBI
2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamideChEBI
2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamideChEBI
2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amideChEBI
2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamideChEBI
2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamideChEBI
alpha-Butyloxycinchonic acid-gamma-diethylethylenediamineChEBI
alpha-Butyloxycinchoninic acid diethylethylenediamideChEBI
CinchocainumChEBI
CincocainioChEBI
Dibucaine baseChEBI
N-(2-(Diethylamino)ethyl)-2-butoxycinchoninamideChEBI
CinchocaineKegg
NupercaineKegg
2-Butoxy-N-(a-diethylaminoethyl)cinchoninamideGenerator
2-Butoxy-N-(α-diethylaminoethyl)cinchoninamideGenerator
2-Butoxy-N-(b-diethylaminoethyl)cinchoninamideGenerator
2-Butoxy-N-(β-diethylaminoethyl)cinchoninamideGenerator
2-Butoxy-quinoline-4-carboxylate (2-diethylamino-ethyl)-amideGenerator
2-Butoxyquinoline-4-carboxylate diethylaminoethylamideGenerator
a-Butyloxycinchonate-g-diethylethylenediamineGenerator
a-Butyloxycinchonic acid-g-diethylethylenediamineGenerator
alpha-Butyloxycinchonate-gamma-diethylethylenediamineGenerator
Α-butyloxycinchonate-γ-diethylethylenediamineGenerator
Α-butyloxycinchonic acid-γ-diethylethylenediamineGenerator
a-Butyloxycinchoninate diethylethylenediamideGenerator
a-Butyloxycinchoninic acid diethylethylenediamideGenerator
alpha-Butyloxycinchoninate diethylethylenediamideGenerator
Α-butyloxycinchoninate diethylethylenediamideGenerator
Α-butyloxycinchoninic acid diethylethylenediamideGenerator
CincainHMDB
NupercainalHMDB
SovcaineHMDB
Chemical FormulaC20H29N3O2
Average Molecular Weight343.4632
Monoisotopic Molecular Weight343.225977187
IUPAC Name2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
Traditional Namedibucaine
CAS Registry Number85-79-0
SMILES
CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
InChI Identifier
InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)
InChI KeyPUFQVTATUTYEAL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentQuinolones and derivatives
Alternative Parents
Substituents
  • Quinolone
  • Alkyl aryl ether
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point99 - 101 °C (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.039 g/LNot Available
LogP4.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM196.230932474
[M+H]+Not Available195.466http://allccs.zhulab.cn/database/detail?ID=AllCCS00000992
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP3.79ALOGPS
logP3.7ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)14.57ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity102.12 m³·mol⁻¹ChemAxon
Polarizability40.78 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]+181.77231661259
DarkChem[M-H]-179.4931661259
DeepCCS[M+H]+182.34630932474
DeepCCS[M-H]-179.98830932474
DeepCCS[M-2H]-213.14630932474
DeepCCS[M+Na]+188.43930932474
AllCCS[M+H]+185.032859911
AllCCS[M+H-H2O]+182.332859911
AllCCS[M+NH4]+187.632859911
AllCCS[M+Na]+188.332859911
AllCCS[M-H]-186.432859911
AllCCS[M+Na-2H]-187.032859911
AllCCS[M+HCOO]-187.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DibucaineCCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC3544.0Standard polar33892256
DibucaineCCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC2776.2Standard non polar33892256
DibucaineCCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC2732.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dibucaine,1TMS,isomer #1CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C)=C2C=CC=CC2=N12766.2Semi standard non polar33892256
Dibucaine,1TMS,isomer #1CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C)=C2C=CC=CC2=N12824.4Standard non polar33892256
Dibucaine,1TMS,isomer #1CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C)=C2C=CC=CC2=N13505.6Standard polar33892256
Dibucaine,1TBDMS,isomer #1CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=N12995.6Semi standard non polar33892256
Dibucaine,1TBDMS,isomer #1CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=N13002.6Standard non polar33892256
Dibucaine,1TBDMS,isomer #1CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=N13573.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dibucaine EI-B (Non-derivatized)splash10-000i-9000000000-11b0b035aed1c901a8272017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibucaine CI-B (Non-derivatized)splash10-0006-5009000000-4623c33d494376e699f32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibucaine EI-B (Non-derivatized)splash10-000i-9000000000-11b0b035aed1c901a8272018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dibucaine CI-B (Non-derivatized)splash10-0006-5009000000-4623c33d494376e699f32018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dibucaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05br-9272000000-3d2ab0479ffb92d2501b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dibucaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOFsplash10-0006-0009000000-396529f9f1539ca4f5d22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOFsplash10-00di-0091000000-f6ba1af6a7e8fcdfaa162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOFsplash10-00xr-0190000000-9cd7408320081da0e4352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOFsplash10-01b9-0960000000-48d5c97824dd28e11f732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-cbd25496ff6fc8a2fa362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-b4f898603ef48a2b9e292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine , positive-QTOFsplash10-00xr-3980000000-e5e0b2d6136d950b770a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 60V, Positive-QTOFsplash10-01bc-0930000000-f9d20a9fdaa804f3c0c22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 40V, Positive-QTOFsplash10-00xr-0190000000-226cb2826cf33c4cb0bc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 45V, Positive-QTOFsplash10-00xr-0290000000-99941cc61989e5a21fad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 35V, Positive-QTOFsplash10-00di-0090000000-e3109e7f0063b8d26ac22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 55V, Positive-QTOFsplash10-01b9-0960000000-48f69614630fb349afad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 50V, Positive-QTOFsplash10-01b9-0590000000-66ea2193e7e219589c8c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 30V, Positive-QTOFsplash10-00di-0090000000-cece5add8c5b72bebe672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 70V, Positive-QTOFsplash10-014i-0900000000-d7a2dd0e46b7abe92e462021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 75V, Positive-QTOFsplash10-014i-0900000000-fb9b59d77fc5a1720e6b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 65V, Positive-QTOFsplash10-014l-0910000000-3fbd1b08182eb4cfad022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 5V, Positive-QTOFsplash10-00dl-0096000000-94c62fffc37698ecddd62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dibucaine 60V, Positive-QTOFsplash10-01bc-0930000000-6e8fbc14f543ed77b6452021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibucaine 10V, Positive-QTOFsplash10-0006-3559000000-63b39814c87e3867b4c82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibucaine 20V, Positive-QTOFsplash10-0zmi-8891000000-b554e300f3adf4d3ece42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibucaine 40V, Positive-QTOFsplash10-0pi0-9310000000-e2dff930dc76d57522082016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibucaine 10V, Negative-QTOFsplash10-0006-2069000000-55885f8ff7612dc6aaeb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibucaine 20V, Negative-QTOFsplash10-0006-8396000000-06d05a3147875a59f5b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dibucaine 40V, Negative-QTOFsplash10-0006-5910000000-c55a93ba4d932f2362ab2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00527 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00527 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00527
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2917
KEGG Compound IDC07879
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDibucaine
METLIN IDNot Available
PubChem Compound3025
PDB IDNot Available
ChEBI ID247956
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. [PubMed:15910814 ]
  2. Nounou MM, El-Khordagui LK, Khalafallah N: Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles. Acta Pol Pharm. 2005 Sep-Oct;62(5):369-79. [PubMed:16459486 ]
  3. Souto-Padron T, Lima AP, Ribeiro Rde O: Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res. 2006 Sep;99(4):317-20. Epub 2006 Apr 13. [PubMed:16612626 ]

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Elamin B: Dibucaine inhibition of serum cholinesterase. J Biochem Mol Biol. 2003 Mar 31;36(2):149-53. [PubMed:12689511 ]
General function:
Involved in calcium ion binding
Specific function:
Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:
CALM1
Uniprot ID:
P62158
Molecular weight:
16837.5
References
  1. Muto Y, Kudo S, Nozawa Y: Effects of local anesthetics on calmodulin-dependent guanylate cyclase in the plasma membrane of Tetrahymena pyriformis. Biochem Pharmacol. 1983 Dec 1;32(23):3559-63. [PubMed:6140014 ]
  2. Volpi M, Sha'afi RI, Epstein PM, Andrenyak DM, Feinstein MB: Local anesthetics, mepacrine, and propranolol are antagonists of calmodulin. Proc Natl Acad Sci U S A. 1981 Feb;78(2):795-9. [PubMed:6262771 ]
  3. Liu SH, Fu WM, Lin-Shiau SY: Studies on the inhibition by chlorpromazine of myotonia induced by ion channel modulators in mouse skeletal muscle. Eur J Pharmacol. 1993 Jan 26;231(1):23-30. [PubMed:7680317 ]
  4. Sambandam T, Gunasekaran M: Purification and properties of calmodulin from Phymatotrichum omnivorum. Microbios. 1993;73(294):61-74. [PubMed:8382768 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Oka M, Itoh Y, Fujita T: Halothane attenuates the cerebroprotective action of several Na+ and Ca2+ channel blockers via reversal of their ion channel blockade. Eur J Pharmacol. 2002 Oct 4;452(2):175-81. [PubMed:12354567 ]
  4. Louro SR, Anteneodo C, Wajnberg E: Carboxyl groups at the membrane interface as molecular targets for local anesthetics. Biophys Chem. 1998 Aug 4;74(1):35-43. [PubMed:9742684 ]
  5. Ryan SE, Demers CN, Chew JP, Baenziger JE: Structural effects of neutral and anionic lipids on the nicotinic acetylcholine receptor. An infrared difference spectroscopy study. J Biol Chem. 1996 Oct 4;271(40):24590-7. [PubMed:8798723 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular weight:
220623.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Louro SR, Anteneodo C, Wajnberg E: Carboxyl groups at the membrane interface as molecular targets for local anesthetics. Biophys Chem. 1998 Aug 4;74(1):35-43. [PubMed:9742684 ]
  4. Ryan SE, Demers CN, Chew JP, Baenziger JE: Structural effects of neutral and anionic lipids on the nicotinic acetylcholine receptor. An infrared difference spectroscopy study. J Biol Chem. 1996 Oct 4;271(40):24590-7. [PubMed:8798723 ]