Record Information
Version1.0
Creation date2015-10-09 22:28:20 UTC
Update date2017-01-19 02:36:12 UTC
FoodComEx IDPC000101
FoodDB RecordFDB003958
Chemical Information
NameMethylamine
DescriptionMethylamine, also known as aminomethane or methanamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. Methylamine is a strong basic compound (based on its pKa). It has a strong odor similar to fish. Industrially, methylamine is used as a building block for the synthesis of many other commercially available compounds. Methylamine exists in all living organisms, ranging from bacteria to humans. Methylamine is found in relatively high concentrations in a number of plant foods such as wild carrots, carrots, and tea and in a lower concentration in cabbages, corns, and barley. Methylamine has also been detected, but not quantified in, several other plant foods, such as soybeans, wild celeries, french plantains, and common grapes. It has also been detected in cow’s milk. This could make methylamine a potential biomarker for the consumption of these foods. Methylamine occurs endogenously from amine catabolism and its tissue levels increase in some pathological conditions, including diabetes. In the human body methylamine and ammonia levels are reciprocally controlled by a semicarbazide-sensitive amine oxidase activity that deaminates methylamine to formaldehyde with the production of ammonia and hydrogen peroxide ( PMID: 18845121). Methylamine also targets the voltage-operated neuronal potassium channels, probably inducing release of neurotransmitter(s) ( PMID: 16049393). Semicarbazide-sensitive amine oxidase (SSAO) catalyzes the deamination of primary amines. This kind of deamination has been shown capable of regulating glucose transport in adipose cells. Increased serum SSAO activities have been found in patients with diabetic mellitus, vascular disorders, and Alzheimer's disease (PMID: 18691041). The SSAO-catalyzed deamination of endogenous substrates like methylamine is known to lead to the production of toxic formaldehyde. Chronic elevated methylamine increases the excretion of malondialdehyde and microalbuminuria. Amine oxidase substrates such as methylamine have been shown to stimulate glucose uptake by increasing the recruitment of the glucose transporter GLUT4 from vesicles within the cell to the cell surface. Methylamine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
CAS Number74-89-5
Structure
Thumb
Synonyms
SynonymSource
Aminomethanebiospider
CH3-NH2ChEBI
MeNH2ChEBI
Methanaminebiospider
Methylaminebiospider
Monomethylaminebiospider
Chemical FormulaCH5N
IUPAC namemethanamine
InChI IdentifierInChI=1S/CH5N/c1-2/h2H2,1H3
InChI KeyBAVYZALUXZFZLV-UHFFFAOYSA-N
Isomeric SMILESCN
Average Molecular Weight31.0571
Monoisotopic Molecular Weight31.042199165
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentMonoalkylamines
Alternative Parents
Substituents
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-0.57HANSCH,C ET AL. (1995)
Experimental Water Solubility1080 mg/mL at 25 oCSCHWEIZER,AE et al. (1978)
Melting Point-93.4 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Toronto Research Chemicals M285540
Toronto Research Chemicals M285535
Toronto Research Chemicals M330933