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PubMedDate not supplied

Metabolism of dimethylamine in the nasal mucosa of the Fischer 344 rat.

The metabolism of dimethylamine (DMA) in the nasal mucosa of the male Fischer 344 rat was investigated in vitro and in vivo. Microsomes were prepared from liver, and from respiratory and olfactory nasal mucosa. All microsomal preparations metabolized DMA to formaldehyde (CH2O), though DMA was a poor substrate for the N-demethylation reaction when compared to benzphetamine. Phenobarbital-induced microsomes metabolized DMA at a rate less than that of control. The results indicated that DMA was a substrate for both cytochrome P-450 and FAD-containing monooxygenase, and that both enzyme activities were present in all microsomal preparations. Finally, unextractable radioactivity was observed in DNA, RNA, and protein isolated from respiratory and olfactory mucosa of rats exposed to either 10 or 175 ppm of [14C]DMA, suggesting metabolism of [14C]DMA to 14CH20 with subsequent incorporation of 14C into macromolecules. The results demonstrate that the respiratory and olfactory nasal mucosa have the capability to metabolize DMA to CH2O, and indicate that such metabolism occurs in vivo.

Aniline Compounds↗
PubMed1984

Enzymatic activity of activated sludge in biological treatment of wastewater containing dimethylamine, dimethylformamide and methylethylketone.

Activated sludge treating synthetic wastewater carrying dimethylamine (DMA), dimethylformamide (DMF) and methylethylketone (MEK) was examined. The compounds in question were found to affect the enzymatic activity of the activated sludge. Dehydrogenase activity was higher than in control activated sludge and stabilization of this activity was achieved on the twelfth day of the run. Alkaline phosphatase activity was lower than in the control sludge. No correlation between activity of the studied enzymes and biodegradation of DMA, DMF and MEK was observed.

Alkaline Phosphatase↗
PubMed1984

Absorption, secretion and excretion of dimethylamine in rats.

The dimethylamine (DMA) concentration in the gastrointestinal tract of Wistar male rats fed a commercial diet containing 23.6 mg/kg DMA was highest (11.2 +/- 2.1 mg/kg) in the stomach and decreased from the upper region to the lower region. In contrast, the highest DMA concentration (6.6 +/- 2.5 mg/kg) in the upper small intestine was observed in rats fed a low-DMA diet containing 1.0 mg/kg DMA. DMA absorption was observed in the intestines and the absorbtion curves were monoexponential. The biological half-lives (t1/2) of DMA in the ligated stomach, upper and lower small intestine, caecum and large intestine were 198, 8.3, 11.6, 31.5 and 11.0 min, respectively. The DMA concentration in blood increased from 0.3 +/- 0.1 mg/kg to 3.0 +/- 1.0 mg/kg 5 min after injection of 250 micrograms DMA into the ligated upper small intestine. The disappearance curve of DMA in blood was monoexponential and the half-life for the initial 15 min was 12.5 min when 250 micrograms DMA were injected through a femoral vein. Intestinal secretion of DMA (15.6 +/- 12.6 mg/kg) was observed 15 min after the injection. Urinary DMA increased from 17.3 +/- 9.4 to 139 +/- 23 mg/kg within 30 min of intravenous injection of DMA. These results show that the behaviour of DMA in rats is as follows: (Formula: see text)

Animals↗
PubMed1983

Gas chromatographic determination of dimethylamine and trimethylamine in seafoods.

The volatile amines dimethylamine (DMA) and trimethylamine (TMA) are common degradation products of TMA-oxide in marine fish. Both compounds are used as important indicators of quality in seafoods. DMA is produced along with an equimolar quantity of formaldehyde by action of an endogenous enzyme found primarily in gadoid fish. TMA is produced in fresh, but not frozen seafoods by a bacterial enzyme. The current AOAC method for determination of TMA in fish is based on the colorimetric estimation of TMA as a picrate salt. This method is not specific for TMA; ammonia, monomethylamine, and DMA also form corresponding picrate salts. Gas chromatography provides a means of separating and quantitating the individual volatile amines. A simple perchloric acid extract of fish is neutralized with potassium hydroxide and extracted with benzene. The amines are then separated by gas chromatography on a porous polymer packed column and detected by using a nitrogen-phosphorus-specific flame ionization detector. The method provides simple, rapid simultaneous quantitation of DMA and TMA, and is applicable to a wide variety of seafoods.

Animals↗
PubMed1983

Susceptibility of germ-free rats to the hepatotoxic effects of dimethylnitrosamine or dimethylamine plus sodium nitrite administered orally.

The influence of intestinal microflora on the hepatotoxic effects of dimethylnitrosamine (DMN) or dimethylamine (DMA) plus NaNO2 was studied by comparing the degree of liver necrosis and the levels of serum alanine aminotransferase (GPT) and aspartate aminotransferase (GOT) in germ-free and conventional male Wistar rats (320 to 340 g). In one experiment, both germ-free and conventional rats were intubated with DMN in respective doses of 8, 9, and 10 mg/kg of body weight, while in another experiment, both groups were intubated with DMA (1500 mg/kg) plus NaNO2 (100 mg/kg). In both experiments, 48 hr after intubation, there was a marked difference in the degree of liver necrosis and the levels of serum GPT and GOT between the groups. In particular, a dose of 8 mg of DMN or 1500 mg of DMA plus 100 mg of NaNO2 produced severe liver necrosis in the majority of germ-free rats, while the same dose did not produce any detectable liver necrosis in the majority of conventional rats. At a dose of 8 mg, serum GPT and GOT levels were raised to 22 and 15 times normal values, respectively, in germ-free rats, but only to about twice the normal values for both levels in conventional rats. At the combination dose of DMA plus NaNO2, the levels of serum GPT and GOT were raised to 40 and 30 times normal values, respectively, in germ-free rats, while both levels remained almost normal in conventional rats. Thus, the results indicated that the liver of the germ-free state was far more susceptible to the acute toxic effects of DMN as well as DMA plus NaNO2 administration at a certain dose range than was the liver of the conventional state, suggesting the influence of the absence of microflora.

Administration, Oral↗
PubMed1981

Biosynthesis of dimethylnitrosamine in dimethylamine-treated mice after exposure to nitrogen dioxide.

These studies demonstrate the nitrosating potential of NO2 in vivo in ICR mice. Groups of mice were gavaged with 2 mg dimethylamine (DMA) and exposed to NO2 at levels from 0.04 to 44.5 ppm for periods up to 4 hours. Mice were individually frozen and blended to a powder, aliquots of which were homogenized in ice-cold dicholoromethane and 35% aqueous methanol. Concentrates of organic extracts were analyzed or dimethylnitrosamine (DMN) by a Thermal Energy Analyzer with a gas chromatograph interface. Biosynthesis of DMN was dose- and time-dependent with relation to NO2 exposure, reaching a maximum yield of 60-70 ng/mouse (0.0035% DMA conversion) at 2 hours. DMN biosynthesis was inhibited by sodium ascorbate and, more effectively, by ammonium sulfamate.

Animals↗
PubMed1981

[Blastomogenic action of low concentrations of nitrosodimethylamine, dimethylamine and nitrogen dioxide].

The round-the clock inhalation of the mixture of nitrosodimethylamine (NDMA), dimethylamine (DMA) and nitrogen dioxide, with NDMA concentrations varying within 0.66-0.0026 mg/m3, was followed by development of tumors in the kidney, liver, lungs and at other sites in albino nonbred rats, after a year of exposure. Application of DMA and nitrogen dioxide modified the carcinogenic effect of NDMA. In male rats, the blastogenic effect of the mixture was higher, as compared with that of inhalation of NDMA alone. NDMA inhalation resulted in a lower tumor yield in female rats.

Animals↗
PubMedDate not supplied

[Possibility of endogenous dimethylnitrosamine synthesis in rats administered dimethylamine and nitrite with the food].

Concurrent peroral administration of dimethylamine (DMA) and sodium nitrite to rats produced necrosis of liver parenchyma and increased the activity of glutamicoalanine transaminase. Similar changes were recorded after administering dimethylnitrosamine (DMNA) that points to potential synthesis of this carcinogen from the precursors. Prolonged (over 2.5 years) feeding with DMA and nitrite resulted in part of the rats in tumours of the lungs and in other neoplasms. Ascorbic acid that blocks the endogenous synthesis of DMNA interfered with the development of tumour and pretumour lesions that emerged as a result of concurrent feeding with DMA and nitrite.

Animal Feed↗
PubMed1997

Effect of N-lauryl-N,N-dimethylamine N-oxide on dimyristoyl phosphatidylcholine bilayer thickness: a small-angle neutron scattering study.

Small-angle neutron scattering on large extruded unilamellar dimyristoyl phosphatidylcholine (DMPC) liposomes was used to determine the DMPC bilayer thickness dL and its change in the presence of N-lauryl-N,N-dimethylamine N-oxide (LDAO). At 36 degrees C, the values of dL are dL = 3.44 +/- 0.10 nm and dL = 2.90 +/- 0.10 nm in pure DMPC bilayers and in bilayers at DMPC:LDAO = 2:1 molar ratio, respectively. Using the specific volumes of DMPC and LDAO and supposing that the molecular volumes and surface areas in the bilayer are additive, the surface areas of DMPC (ADMPC) and of LDAO (ALDAO) were found to be at 36 degrees C: ADMPC = 0.644 +/- 0.018 nm2 and ALDAO = 0.25 +/- 0.05 nm2.

Dimethylamines↗
PubMed2003

Myristyl dimethylamine oxide surfactant solutions: model systems for rheological research.

Aqueous surfactant solutions of entangled, rod-shaped micelles are often characterized by monoexponential stress-relaxation processes. This special phenomenon leads to relatively simple theoretical descriptions, and viscoelastic surfactant solutions can, therefore, also be used as simple model systems for studying fundamental principles of flow. Herein, we present a detailed study of the nonlinear rheological properties of aqueous myristyl dimethylamine oxide surfactant solutions. In the regime of small deformations, shear stresses, or shear rates, the dynamic features of the viscoelastic solutions are characterized by the simple equations of a Maxwell material. At elevated values of shear stresses or deformations, however, this simple model fails and nonlinear features, such as normal stresses, stress overshoots, or shear-thinning properties occur. All these phenomena can be described by a Maxwell-type differential constitutive equation, which was first proposed by Giesekus. It turns out that the experimental results are in fairly good agreement with the theoretical predictions, if the anisotropy factor alpha is equal to 0.5. Besides transient data and nonlinear steady-state measurements, many semiempirical laws, such as the Cox-Merz rule, the Yamamoto relation, the Laun equation, and the Gleissble mirror relationships are approximately satisfied. The dynamic properties discussed in this paper are of general importance and they are equally observed in different materials such as polymer, dye, or protein solutions.

Journal Article↗
PubMed1979

Mutagenicity detection of in vivo nitrosation of dimethylamine by nitrite.

In vivo nitrosation of dimethylamine by nitrite was measured with an intrahepatic host-mediated mutagenicity assay using Salmonella typhimurium as the detecting organism. It was possible to detect the product, N-nitrosodimethylamine, at much lower doses with this system than with previously reported in vivo systems. This and other improvements made it possible to detect the formation of nitrosodimethylamine from relatively low levels of gavaged precursors.

Animals↗
PubMed1989

Mutational specificities of environmental carcinogens in the lacl gene of Escherichia coli. II: A host-mediated approach to N-nitroso-N,N-dimethylamine and endogenous mutagenesis in vivo.

An intrasanguineous host-mediated assay was used to determine the mutational specificity of the hepatocarinogen N-nitroso-N,N-dimethylamine metabolized in vivo. A total of 114 forward mutations in the lacl gene of Escherichia coli reisolated from the livers of treated Swiss albino mice were characterized at the DNA sequence level. Consistent with the methylating ability of this compound and the demonstrated mutagenic specificity of O6-methylguanine, the predominant mutation was the G:C----A:T transition. These were recovered, on average, seven times more frequently at guanines flanked (5') by a purine residue than at those preceded by a pyrimidine residue--a specificity similar to that reported for many direct-acting SN1 alkylating agents. This nitrosamine appears to be distinguished from related N-nitroso methylating compounds by the induction of additional mutational events. Here, the exceptions consisted of four A:T----G:C transitions, four A:T site transversions, and a single G:C----T:A transversion. In addition, the DNA sequence alterations of 34 I- mutants of E. coli reisolated from otherwise untreated mice were identified. The predominant mutation was the G:C----A:T transition, which accounted for almost half of all background mutations. The sites at which these mutations were recovered appear to indicate that some of these mutations may have arisen as a result of an accelerated rate of cytosine deamination. These data suggest that many of the additional "spontaneous" mutations observed under in vivo conditions resulted from genotoxic events occurring during the host-defense (immune) reaction.

Animals↗
PubMed2006

Chiral dimethylamine flutamide derivatives--modeling, synthesis, androgen receptor affinities and carbon-11 labeling.

Most prostate cancers are androgen dependent upon initial diagnosis. On the other hand, some very aggressive forms of prostate cancer were shown to have lost the expression of the androgen receptor (AR). Although the AR is routinely targeted in endocrine treatment, the clinical outcome remains suboptimal. Therefore, it is crucial to demonstrate the presence and activity of the AR in each case of prostate cancer, before and after treatment. While noninvasive positron emission tomography (PET) has the potential to determine AR expression of tumor cells in vivo, fully optimized PET imaging agents are not yet available. Based on molecular modeling, three novel derivatives of hydroxyflutamide (Compounds 1-3) were designed and synthesized. They contain an electron-rich group (dimethylamine) located on the methyl moiety, which may confer a better stability to the molecule in vivo. Compounds 1-3 have AR binding that is similar or higher than that of the currently used commercial drugs. An automated carbon-11 radiolabeling route was developed, and the compounds were successfully labeled with a 10-15% decay-corrected radiochemical yield, 99% radiochemical purity and a specific activity of 4Ci/mumol end of bombardment (n=15). These labeled biomarkers may facilitate the future quantitative molecular imaging of AR-positive prostate cancer using PET and may also allow for image-guided treatment of prostate cancer.

Carbon Radioisotopes↗
PubMed1989

Effect of long-term inhalation of N-nitroso-dimethylamine (NDMA) and SO2/NOx in rats.

This report focusses on preliminary results of a long-term inhalation assay with N-nitroso-dimethylamine (NDMA) at low concentrations. Chronic inhalation of 1 ppm of NDMA (4 h/day, 5 days/week) was found to be toxic in rats and diminished life expectancy by about 8 months compared to the control group. Mostly tumors of the nasal region (25/36) were observed. Inhalation of 0.2 ppm of NDMA lead to a high tumor yield in rats (20/36). At a concentration of 0.04 ppm (= 0.12 mg/m3 in air) 3 tumors of the nasal region have been found until now. In addition, a combined inhalation study of other air pollutants SO2 or NOx together with NDMA at the 0.2 ppm level is being performed. Tumors of the nasal region have been observed in the groups with SO2 + NDMA and NOx + NDMA as well as with NDMA alone. Differences in tumor response of the groups treated with NDMA alone or in combination with SO2/NOx cannot be assessed yet. The additional treatment with the air pollutants SO2 or NOx has not affected the body weight gain or any other observable parameters of the life quality of the rats.

Administration, Inhalation↗
PubMed2003

Muscarinic subtypes profile modulation within a series of new antagonists, bridged bicyclic derivatives of 2,2-diphenyl-[1,3]-dioxolan-4-ylmethyl-dimethylamine.

A set of new muscarinic antagonists, bridged bicyclic derivatives of 2,2-diphenyl-[1,3]-dioxolan-4-ylmethyl-dimethylamine (1), was synthesized and tested to evaluate their affinity and selectivity for M(1), M(2), M(3) and M(4) receptor subtypes. The conformational constraint of 1 in a bicyclic structure, and the variation in distance and stereochemistry of the active functions allowed us to modulate the selectivity of interaction with the M(1)-M(3) receptor subtypes. The most interesting compound was (cis,trans)-2-(2,2-diphenylethyl)-5-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole oxalate (6), which is equipotent with Pirenzepine on rabbit vas deferens (M(1)-putative) but shows a better selectivity profile.

Animals↗
PubMed2005

In situ XAFS and NMR study of rhodium-catalyzed dehydrogenation of dimethylamine borane.

In situ X-ray absorption fine structure spectroscopy (XAFS) and 11B NMR were used to study the rhodium-catalyzed dimerization reaction of dimethylaminoborane, (CH3)2NHBH3 or DMAB. XAFS spectra show that the active form of the rhodium catalyst is most likely composed of a six-atom Rh core surrounded by tightly bound external ligands. NMR results show the presence of monomeric dimethylamine borane (CH3)2NBH2, providing evidence that hydrogen formation from the homogeneous Rh species occurs by an intramolecular pathway. This is in contrast to thermal pathways that involve intermolecular B-N concurrent with hydrogen formation. This work shows that in situ XAFS spectroscopy offers a unique experimental tool to differentiate between heterogeneous and homogeneous catalysis.

Journal Article↗
PubMed2005

Control of local ionization and charge transfer in the bifunctional molecule 2-phenylethyl-N,N-dimethylamine using Rydberg fingerprint spectroscopy.

Local photoionization pathways and charge-transfer dynamics of 2-phenylethyl-N,N-dimethylamine (PENNA) are explored using the recently developed Rydberg fingerprint spectroscopy. PENNA, a molecule that derives its biological significance from its relation to neurotransmitters, has two ionization centers that are separated by an ethyl group. We ionize the molecule in various multiphoton ionization processes using different laser wavelengths. The Rydberg fingerprint spectrum reveals the local nature of the ionization process and identifies the center of charge. We discovered that the laser wavelength provides substantial control over the activation of the individual ionization centers. The resonant (2+1) ionization with 400-nm radiation is dominated by the ejection of an electron from the amine moiety. In contrast, the resonant (1+1) ionization with 266-nm radiation leads predominantly to an ion with the charge in the phenyl group. The clean separation of the two ionization processes allows the exploration of ultrafast charge-transfer dynamics ensuing from a specific starting state characterized by a charged phenyl moiety. The width of the corresponding spectral features suggests that the charge transfer proceeds on a femtosecond time scale, suggesting a strong coupling between the two lowest-energy electronic surfaces of the PENNA cation.

Journal Article↗
PubMed2005

Gas electron diffraction study of the vapour over dimethylamine-gallane leading to an improved structure for dimeric dimethylamidogallane, [Me2NGaH2]2: a cautionary tale.

Dimethylamine-gallane is relatively slow to decompose in a closed system and vaporises at low temperature primarily as Me2(H)N.GaH3 molecules which can be trapped in a solid Ar matrix and characterised by their IR spectrum. Under the conditions needed to secure a useful gas electron diffraction (GED) pattern, however, the vapour was found to consist of dimeric dimethylamidogallane molecules, [Me2NGaH2]2, formed from the secondary amine adduct by elimination of H2, and the most reliable structure for which has been determined. Salient structural parameters (r(hl) structure) were found to be: r(Ga-N) 202.6(2), r(Ga-H) 155.6(8), r(N-C) 148.0(3), r(C-H) 111.2(6) pm; Ga-N-Ga 90.7(1), C-N-C 109.3(5), N-C-H 109.9(10) and H-Ga-H 119.4(42) degrees.

Journal Article↗