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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:53 UTC
Secondary Accession NumbersNone
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.
Monomethyl guanidinChEBI
Chemical FormulaC2H7N3
Average Molecular Weight73.0971
Monoisotopic Molecular Weight73.063997239
IUPAC Name1-methylguanidine
Traditional Namemethylguanidine
CAS Registry Number471-29-4
InChI Identifier
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 ClassOrganonitrogen compounds
Sub ClassNot Available
Direct ParentGuanidines
Alternative Parents
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Hydrocarbon derivative
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.78 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility15.7 mg/mLALOGPS
pKa (Strongest Basic)12.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.9 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.63 m3·mol-1ChemAxon
Polarizability7.57 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
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
MSMass Spectrum (Electron Ionization)splash10-007o-9000000000-9397702dbb559840626eView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Brain
  • Liver
PathwaysNot Available
Normal Concentrations
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
SalivaDetected and Quantified5.25+/- 3.24 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
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 QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineDetected and Quantified9.073 +/- 5.348 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    • Mordechai, Hien, ...
UrineDetected but not QuantifiedNot ApplicableAdult (>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...
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
Abnormal Concentrations
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 QuantifiedNot ApplicableAdult (>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, ...
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. [7296840 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB005421
KNApSAcK IDNot Available
Chemspider ID9707
KEGG Compound IDC02294
BioCyc IDCPD-593
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01522
Metagene LinkHMDB01522
PubChem Compound10111
ChEBI ID16628
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. [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. [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. [8520461 ]
  4. Lazdins I, Dawborn JK: Concentration of guanidines in normal human plasma. Clin Exp Pharmacol Physiol. 1978 Jan-Feb;5(1):75-80. [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. [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. [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. [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. [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. [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. [8459881 ]
  11. Giovannetti S, Barsotti G: Uremic intoxication. Nephron. 1975;14(2):123-33. [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. [236102 ]