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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:46:14 UTC
HMDB IDHMDB0014888
Secondary Accession Numbers
  • HMDB14888
Metabolite Identification
Common NamePrilocaine
DescriptionPrilocaine is only found in individuals that have used or taken this drug. It is a local anesthetic that is similar pharmacologically to lidocaine. Currently, it is used most often for infiltration anesthesia in dentistry. (From AMA Drug Evaluations Annual, 1992, p165)Prilocaine acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers.
Structure
Data?1582753232
Synonyms
ValueSource
2-(Propylamino)-O-propionotoluidideChEBI
2-Methyl-alpha-propylaminopropionanilideChEBI
alpha-N-Propylamino-2-methylpropionanilideChEBI
N-(2-Methylphenyl)-2-(propylamino)propanamideChEBI
O-Methyl-2-propylaminopropionanilideChEBI
O-Methyl-alpha-propylaminopropionanilideChEBI
PrilocainaChEBI
Prilocaine baseChEBI
PrilocainumChEBI
PropitocaineChEBI
2-Methyl-a-propylaminopropionanilideGenerator
2-Methyl-α-propylaminopropionanilideGenerator
a-N-Propylamino-2-methylpropionanilideGenerator
Α-N-propylamino-2-methylpropionanilideGenerator
O-Methyl-a-propylaminopropionanilideGenerator
O-Methyl-α-propylaminopropionanilideGenerator
Astra brand OF prilocaine hydrochlorideHMDB
Citanest octapressinHMDB
Parnell brand OF prilocaine hydrochlorideHMDB
Delvet brand OF prilocaine hydrochlorideHMDB
Prilocaine hydrochlorideHMDB
XylonestHMDB
Inibsa brand OF prilocaine hydrochlorideHMDB
AstraZeneca brand OF prilocaine hydrochlorideHMDB
CitanestHMDB
Chemical FormulaC13H20N2O
Average Molecular Weight220.3107
Monoisotopic Molecular Weight220.157563272
IUPAC NameN-(2-methylphenyl)-2-(propylamino)propanamide
Traditional Nameprilocaine
CAS Registry Number721-50-6
SMILES
CCCNC(C)C(=O)NC1=CC=CC=C1C
InChI Identifier
InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)
InChI KeyMVFGUOIZUNYYSO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Alanine or derivatives
  • Anilide
  • N-arylamide
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary amine
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point37 - 38 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.33 g/LNot Available
LogP2.1Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP1.87ALOGPS
logP2.68ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.51ChemAxon
pKa (Strongest Basic)8.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.86 m³·mol⁻¹ChemAxon
Polarizability25.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available154.25http://allccs.zhulab.cn/database/detail?ID=AllCCS00001289
DarkChem[M+H]+PredictedNot Available152.52931661259
DarkChem[M-H]-PredictedNot Available148.28231661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9800000000-c7980348fde318ec44772017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-1390000000-c8416e476741832b26372017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0290000000-ecb70add14abedae843c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0290000000-44d4259708c3f68cf9fa2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9010000000-62668ab56142315d25c72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9000000000-b24ca970640547e77f452017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9000000000-fa235236a550137d65ac2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9000000000-c5326a5261240ae38b1e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9000000000-6c794305d6cd738a7fa32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9000000000-ee81ed4cf795affc96e82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0290000000-ecb70add14abedae843c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0290000000-44d4259708c3f68cf9fa2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-1390000000-c8416e476741832b26372017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-9000000000-b24ca970640547e77f452021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-000i-9010000000-b031f8cfcb2f5d9250552021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-000i-9000000000-2f951b718ec1c3fb96b02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-000i-9000000000-2e40656cee28569c95342021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-000i-9000000000-29bc00afaed4a8f651102021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-000i-9000000000-439134ebdf51577dd8412021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0abi-9760000000-6466db752ba0441390c82016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4u-9400000000-cf766fd99bb51d64aaac2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-c417e9eda43debe8e2cb2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0290000000-c8d33031e7de066c46c12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0cdi-1940000000-30003dbb848dad517df12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbc-9800000000-4573f7687d90e96645b62016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00750 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00750 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00750
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4737
KEGG Compound IDC07531
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPrilocaine
METLIN IDNot Available
PubChem Compound4906
PDB IDNot Available
ChEBI ID8404
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]