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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-06-18 17:42:33 UTC
Update Date2020-02-26 16:25:52 UTC
HMDB IDHMDB0060656
Secondary Accession Numbers
  • HMDB60656
Metabolite Identification
Common NameMonoethylglycinexylidide
DescriptionMonoethylglycinexylidide, also known as norlidocaine or MEGX, belongs to the class of organic compounds known as alpha-amino acid amides. These are amide derivatives of alpha-amino acids. Monoethylglycinexylidide is a very strong basic compound (based on its pKa). Monoethylglycinexylidide is a metabolite of lidocaine, also known as lignocaine. Lidocaine (trade name: Xylocaine) is a common local anesthetic and antiarrhythmic drug. Lidocaine is used topically to relieve itching, burning, and pain from skin inflammations, is injected as a dental anesthetic, or is injected as a local anesthetic for minor surgery (Wikipedia). Monoethylglycinexylidide and formaldehyde can be biosynthesized from lidocaine via the enzymes cytochrome P450 1A2 and cytochrome P450 3A4.
Structure
Data?1574099599
Synonyms
ValueSource
2-Ethylamino-2',6'-acetoxylidideChEBI
2-Ethylamino-2,6-acetoxylidineChEBI
EthylglycylxylidideChEBI
Lidocaine N-de-ethylated metaboliteChEBI
N-(2,6-Dimethylphenyl)-2-(ethylamino)acetamideChEBI
N-EthylglycinexylidideChEBI
NorlidocaineChEBI
Omega-(ethylamino)-2',6'-dimethylacetanilideChEBI
MEGXHMDB
Monoethylglycinexylidide, 3H,1-(14)C-labeledHMDB
Monoethylglycinexylidide monohydrochlorideHMDB
2-(Ethylamino)-2',6'-acetoxylidideHMDB
2-(Ethylamino)-2’,6’-acetoxylidideHMDB
MonoethylglycinexylidideHMDB
MonoethylglycylxylidideHMDB
N-(N-Ethylglycyl)-2,6-xylidineHMDB
omega-Ethylamino-2',6'-dimethylacetanilideHMDB
ω-Ethylamino-2',6'-dimethylacetanilideHMDB
ω-Ethylamino-2’,6’-dimethylacetanilideHMDB
Chemical FormulaC12H18N2O
Average Molecular Weight206.2841
Monoisotopic Molecular Weight206.141913208
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number7728-40-7
SMILESNot Available
InChI Identifier
InChI=1S/C12H18N2O/c1-4-13-8-11(15)14-12-9(2)6-5-7-10(12)3/h5-7,13H,4,8H2,1-3H3,(H,14,15)
InChI KeyWRMRXPASUROZGT-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
  • Anilide
  • N-arylamide
  • M-xylene
  • Xylene
  • 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

Source

Route of exposure

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 PropertiesNot Available
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.78331661259
DarkChem[M-H]-148.22131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MonoethylglycinexylidideCCNCC(=O)NC1=C(C)C=CC=C1C2338.2Standard polar33892256
MonoethylglycinexylidideCCNCC(=O)NC1=C(C)C=CC=C1C1786.5Standard non polar33892256
MonoethylglycinexylidideCCNCC(=O)NC1=C(C)C=CC=C1C1841.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Monoethylglycinexylidide,1TMS,isomer #1CCN(CC(=O)NC1=C(C)C=CC=C1C)[Si](C)(C)C1936.9Semi standard non polar33892256
Monoethylglycinexylidide,1TMS,isomer #1CCN(CC(=O)NC1=C(C)C=CC=C1C)[Si](C)(C)C1872.7Standard non polar33892256
Monoethylglycinexylidide,1TMS,isomer #1CCN(CC(=O)NC1=C(C)C=CC=C1C)[Si](C)(C)C2466.2Standard polar33892256
Monoethylglycinexylidide,1TMS,isomer #2CCNCC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C1702.4Semi standard non polar33892256
Monoethylglycinexylidide,1TMS,isomer #2CCNCC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C1781.9Standard non polar33892256
Monoethylglycinexylidide,1TMS,isomer #2CCNCC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2157.5Standard polar33892256
Monoethylglycinexylidide,2TMS,isomer #1CCN(CC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C)[Si](C)(C)C1797.1Semi standard non polar33892256
Monoethylglycinexylidide,2TMS,isomer #1CCN(CC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C)[Si](C)(C)C1921.8Standard non polar33892256
Monoethylglycinexylidide,2TMS,isomer #1CCN(CC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C)[Si](C)(C)C2134.6Standard polar33892256
Monoethylglycinexylidide,1TBDMS,isomer #1CCN(CC(=O)NC1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2150.4Semi standard non polar33892256
Monoethylglycinexylidide,1TBDMS,isomer #1CCN(CC(=O)NC1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2078.4Standard non polar33892256
Monoethylglycinexylidide,1TBDMS,isomer #1CCN(CC(=O)NC1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2559.2Standard polar33892256
Monoethylglycinexylidide,1TBDMS,isomer #2CCNCC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C1923.2Semi standard non polar33892256
Monoethylglycinexylidide,1TBDMS,isomer #2CCNCC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C1994.0Standard non polar33892256
Monoethylglycinexylidide,1TBDMS,isomer #2CCNCC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2292.7Standard polar33892256
Monoethylglycinexylidide,2TBDMS,isomer #1CCN(CC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2325.8Semi standard non polar33892256
Monoethylglycinexylidide,2TBDMS,isomer #1CCN(CC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2322.8Standard non polar33892256
Monoethylglycinexylidide,2TBDMS,isomer #1CCN(CC(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2389.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Monoethylglycinexylidide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9700000000-59871f7e43874a6af7532017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoethylglycinexylidide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoethylglycinexylidide 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 - Monoethylglycinexylidide 15V, Positive-QTOFsplash10-0a4i-9030000000-1e8c79f631ca8ed336332021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 30V, Positive-QTOFsplash10-0a4i-9010000000-29c66d7f62e059d77b2c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 45V, Positive-QTOFsplash10-0a4i-9000000000-6c644067087991a7ecb12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 120V, Positive-QTOFsplash10-0a4i-9100000000-e56658554049cc07779c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 90V, Positive-QTOFsplash10-0a4i-9000000000-99b05b954ee15f4eefb02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 30V, Positive-QTOFsplash10-0fk9-0900000000-ae83455c6a9a99b200ce2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 75V, Positive-QTOFsplash10-0a4i-9000000000-cf90d6186b3be90f24022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 20V, Positive-QTOFsplash10-0a4i-9000000000-218972f5c57a26404e712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 40V, Positive-QTOFsplash10-0a4i-9000000000-893dde12a40737b946032021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 10V, Positive-QTOFsplash10-0a4i-9010000000-638af66bdbd0035ebd752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 50V, Positive-QTOFsplash10-014i-0900000000-eda489b5d46d0c4748022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 40V, Positive-QTOFsplash10-00di-0900000000-f8983882a261ea7ea6a82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 10V, Positive-QTOFsplash10-0a4i-0090000000-47b1e77b7eac9395636e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 30V, Positive-QTOFsplash10-0fk9-0900000000-cbf2c13b2a6f321172bb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 20V, Positive-QTOFsplash10-0kmi-0930000000-96aab8eb554bbefb57842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethylglycinexylidide 40V, Positive-QTOFsplash10-00di-0900000000-b6ca77499d9c16e445222021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethylglycinexylidide 10V, Positive-QTOFsplash10-0a4i-9030000000-b30eeaf4741641f186822017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethylglycinexylidide 20V, Positive-QTOFsplash10-0a4i-9100000000-7bcf920a7c1f71061bd32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethylglycinexylidide 40V, Positive-QTOFsplash10-0a6r-9000000000-67742f48ee8088bdd5232017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethylglycinexylidide 10V, Negative-QTOFsplash10-0a4i-0290000000-01db66bd1dc1702ff20a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethylglycinexylidide 20V, Negative-QTOFsplash10-0ab9-5980000000-47d25e48c36e75d3740c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethylglycinexylidide 40V, Negative-QTOFsplash10-00dl-4900000000-26847048db306bbbfda52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethylglycinexylidide 10V, Positive-QTOFsplash10-0a4i-9050000000-c8d0835038a41fabcccc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethylglycinexylidide 20V, Positive-QTOFsplash10-0a4i-9000000000-1da382a29feac05620022021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethylglycinexylidide 40V, Positive-QTOFsplash10-0a4l-9000000000-fd74ebb510c03728eb092021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Sepsis
details
Associated Disorders and Diseases
Disease References
Sepsis
  1. Stewart CJ, Embleton ND, Marrs ECL, Smith DP, Fofanova T, Nelson A, Skeath T, Perry JD, Petrosino JF, Berrington JE, Cummings SP: Longitudinal development of the gut microbiome and metabolome in preterm neonates with late onset sepsis and healthy controls. Microbiome. 2017 Jul 12;5(1):75. doi: 10.1186/s40168-017-0295-1. [PubMed:28701177 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID22824
KEGG Compound IDC16561
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24415
PDB IDNot Available
ChEBI ID222828
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]