ContaminantDB: Methylguanidine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:49:01 UTC

Update Date

2026-04-04 19:28:27 UTC

Accession Number

CHEM003130

Identification

Common Name

Methylguanidine

Class

Small Molecule

Description

Methylguanidine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Methylguanidine (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.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amide
Amine
Food Toxin
Metabolite
Natural Compound
Organic Compound
Uremic Toxin

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-METHYLGUANIDINE	ChEBI
Methylguanidin	ChEBI
MGX	ChEBI
Monomethyl guanidin	ChEBI
Monomethylguanidine	ChEBI
N-Methylguanidine	ChEBI
N1-Methylguanidine	ChEBI

Chemical Formula

C₂H₇N₃

Average Molecular Mass

73.097 g/mol

Monoisotopic Mass

73.064 g/mol

CAS Registry Number

471-29-4

IUPAC Name

N-methylguanidine

Traditional Name

methylguanidine

SMILES

CNC(N)=N

InChI Identifier

InChI=1S/C2H7N3/c1-5-2(3)4/h1H3,(H4,3,4,5)

InChI Key

CHJJGSNFBQVOTG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Guanidines

Direct Parent

Guanidines

Alternative Parents

Substituents

Guanidine
Carboximidamide
Organopnictogen compound
Hydrocarbon derivative
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

guanidines (CHEBI:16628 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Brain
Liver

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

EC 1.14.13.39 (nitric oxide synthase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1.78 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	15.7 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-0.96	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Basic)	12.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.63 m³·mol⁻¹	ChemAxon
Polarizability	7.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-0b42b86da8534391928a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-05fr-9000000000-534633b3b3a72158d516	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-ee83bc75360621d86cc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-7c1f479fe12182b55b74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-9000000000-44511a31625f714234e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-b6d964b0cfb37e04aa3a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-18c440680d035ed316d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-ecb092d7f7fa515ac881	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-cc59ab6824edf551244e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-f836ec6360a96bbbd054	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-3b8beb22e673f9fe659e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-7ef3fba0b93f0ffa9dbe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-387fd6ffcb6fd5f260f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-9000000000-d397b15b0bf6997fff62	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-772b7e2aeeb01889ea68	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-b2d8c441679319b6b93b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-f6850e9d0e6cc606dd73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-c221ed32014cd06b0bfc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-83eaeeade889a9c4fad4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06dl-9000000000-afe740e2160d95afdac8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-9000000000-471b2da48f84e67fff62	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-193b559c768749fc6b0b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-3661661b88220d227907	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-dd30b822725ba557254e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-f8ebd4faa807cb8f5321	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-eba2529a06eb90d77ce5	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-007o-9000000000-9397702dbb559840626e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Endogenous, Ingestion, Dermal (contact)

Mechanism of Toxicity

Uremic toxins such as methylguanidine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (4). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (5).

Metabolism

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Naturally produced by the body (endogenous).

Minimum Risk Level

Not Available

Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

Symptoms

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001522

FooDB ID

FDB005421

Phenol Explorer ID

Not Available

KNApSAcK ID

C00052348

BiGG ID

Not Available

BioCyc ID

CPD-593

METLIN ID

3768

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Philippi, E.; Morsch, K. Preparation of methylguanidine according to Werner-Bell. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1927), 60B 2120-2.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14744621

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17190852

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17409514

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19286340

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21090628

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22342614

7. Philippi, E.; Morsch, K. Preparation of methylguanidine according to Werner-Bell. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1927), 60B 2120-2.

8. Philippi, E.; Morsch, K. Preparation of methylguanidine according to Werner-Bell. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1927), 60B 2120-2.

9. 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.