Disease relevance of N-methylmethanamine

• Trimethylamine dehydrogenases from bacterium W3A1 and Hyphomicrobium X and the dimethylamine dehydrogenase from Hyphomicrobium X were found to contain only one kind of subunit [1].
• Axonal polyneuropathy after acute dimethylamine borane intoxication [2].
• In addition, although lactate, citrate, alanine, and hippurate concentrations increased with increasing glycosuria and glycohemoglobin, trimethylamine-N-oxide and dimethylamine were present at high concentrations even in diabetics with good metabolic control [3].
• Case report: the clinical toxicity of dimethylamine borane [4].
• The other member, identified as Stenotrophomonas maltophilia, was able to degrade dimethylamine, the product of the former [5].

Psychiatry related information on N-methylmethanamine

• 5) Preliminary tests of behavior modification in a rat model by direct instillation of amines into the brain are positive for TMA but negative for DMA, but no DMA entry into brain cells is demonstrated in the latter [6].

High impact information on N-methylmethanamine

• In addition, the metabolism of ADMA, but not SDMA, occurs via hydrolytic degradation to citrulline and dimethylamine by the enzyme dimethylarginine dimethylaminohydrolase (DDAH) [7].
• Methylamine, dimethylamine, trimethylamine, and ethyldimethylamine were fermented by pure cultures of Methanosarcina barkeri; except for ethyldimethylamine, these amines are considered important substrates of this methanogenic microorganism [8].
• Following a 2-day anaerobic incubation of feces with either a secondary amine (dimethylamine, dipropylamine, or morpholine) or nitrite, no nitrosamine was formed [9].
• Methyl transfer from dimethylamine to coenzyme M was reconstituted in vitro for the first time using only highly purified proteins [10].
• MtbB1 methylated either corrinoid bound to MtbC or free cob(I)alamin with dimethylamine, indicating MtbB1 carries an active site for dimethylamine demethylation and corrinoid methylation [10].

Chemical compound and disease context of N-methylmethanamine

• Of 38 pure cultures of microorganisms tested, only one, Pseudomonas stutzeri, was capable of forming dimethylnitrosamine from dimethylamine and nitrite during growth [11].
• Determinations of methylamine and dimethylamine in the fecal samples from normal subjects (n = 22), nonhemodialysis patients (n = 10), and hemodialysis patients (n = 14) with chronic renal failure have been made by high-performance liquid chromatography of their 2,4-dinitrophenyl derivatives [12].
• We have compared some photochemical properties of the reaction-center complex of Rhodopseudomonas spheroides (wild-type) treated with various amounts of either sodium dodecyl sulfate (SDS) or dodecyl dimethylamine N-oxide [13].
• The genetic toxicity in vitro of the dimethylamine salt of 2,4-DB was examined by employing a range of end points including gene mutation in bacteria (Ames test) and mammalian cell cultures (CHO/HGPRT assay), cytogenetic abnormalities in mammalian cells (CHO/chromosomal aberration assay), and induction of DNA damage and repair in rat hepatocytes [14].
• Our present finding that squid and other seafoods contain unusually high levels of dimethylamine and other amines adds to the evidence that dietary factors may have an important role in the aetiology of stomach cancer and other gastro-intestinal tumours [15].

Biological context of N-methylmethanamine

• Immunodepletion of MMCP from the extract inhibited CoM methylation with monomethylamine but not dimethylamine [16].
• Lauryl dimethylamine oxide activates ATP hydrolysis by the mitochondrial H+-ATPase [17].
• In both species we observed similar kinetics of dimethylamine distribution into biologic fluids [18].
• In an attempt to switch the substrate specificity of TMADH so that the enzyme operates more efficiently with dimethylamine, three mutant proteins of TMADH were isolated [19].
• Most of the compounds were synthesized by alkylation of 6-chloro-2-(trifluoromethyl)-9H-purine with the appropriate benzyl halide followed by displacement of the chloro group with dimethylamine [20].

Anatomical context of N-methylmethanamine

• In submitochondrial particles depleted of inhibitor protein, lauryl dimethylamine oxide induced a biphasic response which is characterized by a drop-in activity induced by relatively low concentrations of LDAO; at higher concentrations the detergent activates to an extent never greater than the initial activity [17].
• The most commonly occurring nitrosatable secondary amines found in human saliva, gastric juice, blood, urine and faeces are dimethylamine (DMA), pyrrolidine (PYR) and piperidine (PIP) [21].
• The in vitro oxidation of trimethylamine (TMA) to TMA N-oxide (TMAO) and dimethylamine (DMA) was studied in rat liver microsomes [22].
• Diphenylacetoxypropyldimethylamine and its quaternary trimethylammonium salt are roughly equiactive: the dimethylamine and the piperidine have some selectivity for ileum compared with atria, but are not as active nor as selective as 4-diphenylacetoxy-N-methylpiperidine (4-DAMP) methobromide (MeBr) [23].
• The dehydrogenase has been purified 45-fold from membranes of strain L-57, a non-photosynthetic mutant, by steps involving solubilization with lauryl dimethylamine oxide and three anion-exchange chromatography steps [24].

Associations of N-methylmethanamine with other chemical compounds

• N-nitrosodimethylamine (NDMA) was detected in the cell culture medium in the presence of LPS and L-Arg but without added dimethylamine [25].
• After digestion of glycosylated fiber with endoproteinase GluC, isolation of the glycosylated peptide by reverse-phase HPLC, and chemical derivatization using dimethylamine, the site of glycosylation was located in the fiber shaft at serine 109 by mass spectrometry [26].
• The pH gradient between the extracellular pH and the mean intracellular pH is --0.45, as measured by equilibrium distributions of methylamine and dimethylamine, and --0.05, as determined by equilibrium distributions of 5,5-dimethyloxazolidine-2,4-dione and trimethylacetic acid [27].
• AChE IC(50) values of the optimum dimers decrease significantly as the peripheral site ligand was permuted in the series ammonia > dimethylamine > 4-aminopyridine > 4-aminoquinoline > tacrine [28].
• The 4-(N,N-dimethylamino)phenoxyl radical is quite unstable and decays in a pseudo-first order reaction (k = 0.4 sec-1 at pH 8.5, 22 degrees) with the formation of p-benzoquinone and dimethylamine [29].

Gene context of N-methylmethanamine

• Pretreatment with 1-deprenyl did not affect significantly the rate of incorporation of the radiotracer DMPEA into the brain, suggesting that reduction of the radioactivity in brain by this compound might be due to a decrease in the rate of production of the radioactive metabolite dimethylamine by brain MAO-B [30].
• ADMA is degraded by dimethylarginine dimethylaminohydrolase (DDAH) to dimethylamine and citrulline [31].
• In MS/MS, we observed neutral loss of dimethylamine (m/z 45.05) from which it follows that the dimethylation in FUS/TLS is asymmetric [32].
• In titration experiments at pH 8.5 about 1.0 mol of dimethylamine or 0.5 mol of trimethylamine per mol of the enzyme is required to titrate the enzyme to an endpoint [33].
• The TMA-MT polypeptides, when supplemented with purified methylcorrinoid:CoM methyltransferase (MT2), could effect the demethylation of TMA with the subsequent methylation of CoM and the production of dimethylamine at specific activities of up to 600 nmol/min/mg of TMA-MT protein [34].

Analytical, diagnostic and therapeutic context of N-methylmethanamine

• Dimethylamine concentrations in blood and gastric fluid rose rapidly during the first minutes after treatment [18].
• Sequence analysis of the first 15 residues from the N-terminus of dimethylamine dehydrogenase indicated a single unique sequence [1].
• The mean dimethylamine value of the hemodialysis group was significantly higher than that of the nonhemodialysis group (P less than 0.01) and that of the normal group (P less than 0.005) [12].
• The Mr 10,000 phosphoprotein was purified from photosystem II particles by solubilization of the particles in 5% (w/v) dodecyl dimethylamine oxide, centrifugation in 10% (w/v) sucrose, and three chromatography steps [35].
• Owing to quantitative recoveries following oral administration, urinary dimethylamine levels provide good overall measures of body exposure [36].

References