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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:18 UTC
Update Date2023-02-21 17:29:04 UTC
HMDB IDHMDB0041945
Secondary Accession Numbers
  • HMDB41945
Metabolite Identification
Common NameN-Ethylglycine
DescriptionN-Ethylglycine, also known as EG, belongs to the family of compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). N-ethylglyicne is a known metabolite of the anesthesia drug lidocaine (PMID: 25932687 ). N-ethylglyicne is also an endogenously produced metabolite and appears in normal subjects’ urine in small amounts, but its presence is significantly higher in patients with metastatic bone disease (PMID: 16962088 ). Research has shown that it is lidocaine’s metabolites, n-ethylglycine and monoethylglycinexylidide inhibit GlyT1-mediated uptake of glycine. N-ethylglycine acts as a substrate for the glycine transporter GlyT1 (PMID: 22133759 , 25932687 ).
Structure
Thumb
Synonyms
ValueSource
EtGlyChEBI
2-Ethylaminoacetic acidHMDB
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name2-(ethylamino)acetic acid
Traditional NameN-ethylglycine
CAS Registry Number627-01-0
SMILES
CCNCC(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-2-5-3-4(6)7/h5H,2-3H2,1H3,(H,6,7)
InChI KeyYPIGGYHFMKJNKV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111681
KNApSAcK IDC00053549
Chemspider ID280126
KEGG Compound IDC11735
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlpha-Aminobutyric acid
METLIN IDNot Available
PubChem Compound6992079
PDB IDNot Available
ChEBI ID15620
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. Tsuruta Y, Matsumoto M, Inoue H, Munemura S, Ishizu T, Yamano S, Iguchi H: Identification of N-ethylglycine in urine of cancer patients with metastatic bone disease. Clin Chim Acta. 2007 Feb;376(1-2):226-8. Epub 2006 Jul 28. [PubMed:16962088 ]
  2. Werdehausen R, Mittnacht S, Bee LA, Minett MS, Armbruster A, Bauer I, Wood JN, Hermanns H, Eulenburg V: The lidocaine metabolite N-ethylglycine has antinociceptive effects in experimental inflammatory and neuropathic pain. Pain. 2015 Sep;156(9):1647-59. doi: 10.1097/j.pain.0000000000000206. [PubMed:25932687 ]
  3. Werdehausen R, Kremer D, Brandenburger T, Schlosser L, Jadasz J, Kury P, Bauer I, Aragon C, Eulenburg V, Hermanns H: Lidocaine metabolites inhibit glycine transporter 1: a novel mechanism for the analgesic action of systemic lidocaine? Anesthesiology. 2012 Jan;116(1):147-58. doi: 10.1097/ALN.0b013e31823cf233. [PubMed:22133759 ]