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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 09:40:01 UTC
HMDB IDHMDB0001522
Secondary Accession Numbers
  • HMDB01522
Metabolite Identification
Common NameMethylguanidine
DescriptionMethylguanidine (MG) is a guanidine compound deriving from protein catabolism. It is also a product of putrefaction. Methylguanidine is a suspected uraemic toxin that accumulates in renal failure, however it also exhibits anti-inflammatory effects. Methylguanidine is synthesized from creatinine concomitant with the synthesis of hydrogen peroxide from endogenous substrates in peroxisomes. Recent evidence suggests that methylguanidine significantly inhibits iNOS activity and TNF- release. This means that methylguandine can attenuate the degree of inflammation and tissue damage associated with endotoxic shock.
Structure
Thumb
Synonyms
ValueSource
1-METHYLGUANIDINEChEBI
MethylguanidinChEBI
MGXChEBI
Monomethyl guanidinChEBI
MonomethylguanidineChEBI
N-MethylguanidineChEBI
N1-MethylguanidineChEBI
Chemical FormulaC2H7N3
Average Molecular Weight73.0971
Monoisotopic Molecular Weight73.063997239
IUPAC Name1-methylguanidine
Traditional Namemethylguanidine
CAS Registry Number471-29-4
SMILES
CNC(N)=N
InChI Identifier
InChI=1S/C2H7N3/c1-5-2(3)4/h1H3,(H4,3,4,5)
InChI KeyCHJJGSNFBQVOTG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as guanidines. These are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentGuanidines
Alternative Parents
Substituents
  • Guanidine
  • Carboximidamide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.78 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.7 g/LALOGPS
logP-1.3ALOGPS
logP-0.96ChemAxon
logS-0.67ALOGPS
pKa (Strongest Basic)12.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.9 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.63 m³·mol⁻¹ChemAxon
Polarizability7.57 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-0b42b86da8534391928aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-9000000000-534633b3b3a72158d516View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-ee83bc75360621d86cc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-7c1f479fe12182b55b74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-9000000000-44511a31625f714234e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-c221ed32014cd06b0bfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-83eaeeade889a9c4fad4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dl-9000000000-afe740e2160d95afdac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-9000000000-471b2da48f84e67fff62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-193b559c768749fc6b0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3661661b88220d227907View in MoNA
MSMass Spectrum (Electron Ionization)splash10-007o-9000000000-9397702dbb559840626eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Brain
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.10 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.025 (0.0-0.05) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified < 0.050 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected and Quantified5.25+/- 3.24 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.34 +/- 0.14 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
UrineDetected and Quantified9.073 +/- 5.348 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected and Quantified1.25 +/- 0.72 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.5 (0.29-0.87) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.7 (1.2-6.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.3 +/- 1.3 uMAdult (>18 years old)BothChronic renal failure details
BloodDetected and Quantified1.91 +/- 0.82 uMAdult (>18 years old)Bothuremia details
BloodDetected but not Quantified Adult (>18 years old)BothPancreatic Cancer details
UrineDetected and Quantified10.32 +/- 7.817 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Chronic renal failure
  1. Kikuchi T, Orita Y, Ando A, Mikami H, Fujii M, Okada A, Abe H: Liquid-chromatographic determination of guanidino compounds in plasma and erythrocyte of normal persons and uremic patients. Clin Chem. 1981 Nov;27(11):1899-902. [PubMed:7296840 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Pancreatic cancer
  1. Xie G, Lu L, Qiu Y, Ni Q, Zhang W, Gao YT, Risch HA, Yu H, Jia W: Plasma metabolite biomarkers for the detection of pancreatic cancer. J Proteome Res. 2015 Feb 6;14(2):1195-202. doi: 10.1021/pr501135f. Epub 2014 Dec 8. [PubMed:25429707 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005421
KNApSAcK IDNot Available
Chemspider ID9707
KEGG Compound IDC02294
BioCyc IDCPD-593
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3768
PubChem Compound10111
PDB IDMGX
ChEBI ID16628
References
Synthesis ReferencePhilippi, E.; Morsch, K. Preparation of methylguanidine according to Werner-Bell. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1927), 60B 2120-2.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  2. Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [PubMed:3433275 ]
  3. De Deyn PP, Marescau B, D'Hooge R, Possemiers I, Nagler J, Mahler C: Guanidino compound levels in brain regions of non-dialyzed uremic patients. Neurochem Int. 1995 Sep;27(3):227-37. [PubMed:8520461 ]
  4. Lazdins I, Dawborn JK: Concentration of guanidines in normal human plasma. Clin Exp Pharmacol Physiol. 1978 Jan-Feb;5(1):75-80. [PubMed:639360 ]
  5. De Deyn PP, Marescau B, Cuykens JJ, Van Gorp L, Lowenthal A, De Potter WP: Guanidino compounds in serum and cerebrospinal fluid of non-dialyzed patients with renal insufficiency. Clin Chim Acta. 1987 Jul 30;167(1):81-8. [PubMed:3665089 ]
  6. Orita Y, Ando A, Tsubakihara Y, Mikami H, Kikuchi T, Nakata K, Abe H: Tissue and blood cell concentration of methylguanidine in rats and patients with chronic renal failure. Nephron. 1981;27(1):35-9. [PubMed:7219635 ]
  7. Hiraga Y, Kinoshita T: High-performance liquid chromatographic analysis of guanidino compounds using ninhydrin reagent. II. Guanidino compounds in blood of patients on haemodialysis therapy. J Chromatogr. 1985 Aug 9;342(2):269-75. [PubMed:4055949 ]
  8. Boppana VK, Rhodes GR, Brooks DP: Determination of methylguanidine in plasma and urine by high-performance liquid chromatography with fluorescence detection following postcolumn derivatization. Anal Biochem. 1990 Feb 1;184(2):213-8. [PubMed:2327567 ]
  9. Nohara Y, Hanai T, Suzuki J, Matsumoto G, Iinuma F, Kubo H, Kinoshita T, Watanabe M: Automatic system for the assay of guanidino compounds to assess uremic status. Biol Pharm Bull. 2000 Sep;23(9):1015-20. [PubMed:10993196 ]
  10. Fujitsuka N, Yokozawa T, Oura H, Akao T, Kobashi K, Ienaga K, Nakamura K: L-gulono-gamma-lactone oxidase is the enzyme responsible for the production of methylguanidine in the rat liver. Nephron. 1993;63(4):445-51. [PubMed:8459881 ]
  11. Giovannetti S, Barsotti G: Uremic intoxication. Nephron. 1975;14(2):123-33. [PubMed:1093053 ]
  12. Shainkin R, Berkenstadt Y, Giat Y, Berlyne GM: An automated technique for the analysis of plasma guanidino acids, and some findings in chronic renal disease. Clin Chim Acta. 1975 Apr 2;60(1):45-50. [PubMed:236102 ]