Methylguanidine
Basic information
- CAS
471-29-4- Standard SMILES
CN=C(N)N- InChIKey
CHJJGSNFBQVOTG-UHFFFAOYSA-N- Molecular formula
- C2H7N3
- Average molar mass
- 73.1 g/mol
- Monoisotopic mass
- 73.06399724
Overview
Methylguanidine is a guanidine in which one of the amino hydrogens of guanidine itself is substituted by a methyl group. It has a role as a metabolite, an EC 1.14.13.39 (nitric oxide synthase) inhibitor and a uremic toxin. It is a conjugate base of a methylguanidinium.
Names & identifiers
- Preferred name
- Methylguanidine
- IUPAC
- 2-methylguanidine
- English name
- methylguanidine
- Molecular formula
- C2H7N3
- Molecular weight
- 73.1
Names & synonyms
METHYLGUANIDINE1-methylguanidineN-Methylguanidine471-29-4MethylguanidinGuanidine, methyl-2-methylguanidineMonomethylguanidineMonomethyl guanidinN1-Methylguanidine5L0H5Q9VAGDTXSID4020872
Show more names
Guanidine, N-methyl-
CHEBI:16628RefChem:925795DTXCID80872207-438-3N-Methylguanidine-d3MGXMethylguanidin [German]Monomethyl guanidin [German]
Database identifiers
- CAS
471-29-4- PubChem CID
- 10111
- DTXSID
DTXSID4020872- ChEBI
CHEBI:16628- UNII
- 5L0H5Q9VAG
- EC Number
- 207-438-3
- Nikkaji
- J403K
Properties
Computed structural properties
- XLogP
- -1.3
- Topological polar surface area
- 64.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 5
- Formal charge
- 0
- Complexity
- 42.9
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
Solubility1.78 mg/mL
Vapor Pressure3.28 [mmHg]
Physical Description
Colorless deliquescent solid; [Merck Index]
Solid
Physicochemical properties
- Melting point
- 180 · 180-200℃
- Boiling point
- 96 ℃ · 96℃
- Density
- 1.19 · 1.19
- refractive index
- 1.5 · 1.5000 (estimate)
- Flash point
- 12 ℃ · 12℃
- pka
- 14.05 · 14.05±0.70(Predicted)
- FDA UNII
- 5 L0H5Q9VAG · 5L0H5Q9VAG
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards SummaryCauses other liver changes, multiple enzyme effects, and effects on inflammation in acute intraperitoneal studies of rats; [RTECS] See Guanidine.
Toxicology
TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary
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) (A7868). 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 (A7869).
Signs and 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.
Chemistry & industry
Pharmacology
Metabolism/MetabolitesUremic 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.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
Produced during putrefaction; [Merck Index]
Naturally produced by the body (endogenous).
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A guanidine in which one of the amino hydrogens of guanidine itself is substituted by a methyl group.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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