Diethylenetriamine/nitric oxide

The source of nitric oxide was diethylenetriamine/nitric oxide, DETA/ NO (Scheme 20.4) a compound that has been used in studies of the cytostatic, vasodilatory and other pharmacological properties of NO [65-67]. DETA/NO is a 1-substituted diazen-l-ium-l,2-diolate containing the [N(0)N0] functional group that has been proved to be useful for the reliable generation of nitric oxide in homogenous solutions [68]. When dissolved in blood, cell culture medium or buffer this compound dissociates to generate NO leaving the nucleophilic structure as a by-product. 

FIGURE 4 Effects of candidate cytostatic agents on DNA synthesis by rat aorta smooth muscle cells in culture. (A) The diethylamine/nitric oxide adduct (DEA/NO), whose half-life for NO release is 2.1 min under the conditions used (B) The diethylenetriamine/nitric oxide adduct (DETA/NO), with a half-life of 20 hr. Cells were incubated at 37°C for 22 hr after addition of the given drug at the indicated concentrations, whereupon [ H]thymidine was added. After an additional 2-hr incubation DNA was isolated from the cells and subjected to scintillation counting to provide a quantitative measure of DNA synthesis by these cells. [Adapted from Mooradian et al. (1995) with permission.]... 

FIGURE 5 Antiproliferative effect of the diethylenetriamine/nitric oxide adduct (DETA/ NO) on rat aorta smooth muscle cells in culture over a 7-day observation period. Cells were allowed to attach in a serum-free medium for 24 hr, then cultured in a medium containing 10% fetal bovine serum. On days 1, 3, 5, and 7, cells were counted with a hemocytometer the medium was replaced on each of these days with a fresh medium containing 500 /uAl DETA/NO on days 1, 3, and 5 (V) on days 1 and 3 only (V) on day 1 only ( ) or not at all (O). [Reprinted from Mooradian et al. (1995) with permission.]... 

NITROCARBOL (75-52-5) Forms explosive mixture with air (flash point 95°F/35°C). Thermally unstable. Shock, friction, pressure, or elevated temperature above 599°F/315°C can cause explosive decomposition, especially if confined. Violent reaction with strong oxidizers, alkyl metal halides, diethylaluminum bromide, formic acid, methylzinc iodide. Contact with acids, bases, acetone, aluminum powder, amines, bis(2-aminoethyl)amine, haolforms make this material more sensitive to explosion. Reacts, possibly violently, with ammonium hydroxide, calcium hydroxide, calcium hypochlorite, 1,2-diaminomethane, formaldehyde, hexamethylbenzene, hydrocarbons, hydroxides, lithium perchlorite, m-methyl aniline, nickel peroxide, nitric acid, metal oxides, potassium hydride, potassium hydroxide, sodium hydride. Mixtures with ammonia, aniline, diethylenetriamine, metal oxides, methyl amine, morpholine, phosphoric acid, silver nitrate form shock-sensitive compounds. Forms high-explosive compound with urea perchlorate. Mixtures with hydrocarbons and other combustible materials can cause fire and explosions. Attacks some plastics, rubber, and coatings. 

FIGURE 3 Structures of candidate antirestenosis agents used in the series of experiments described herein. DEA, Diethylamine NO, nitric oxide DETA, diethylenetriamine MAHMA, methylaminohexylmethylamine. 

F/79°C cc Fire Rating 2). Violent reaction with strong oxidizers, alkalis. Incompatible with sulfuric acid, nitric acid, caustic materials, aliphatic amines, isocyanates, boranes. On small fires, use dry chemical powder (such as Purple-K-Powder), alcohol-resistant foam, or CO2 extinguishers, DETA (111-40-0) see diethylenetriamine. DIACETATO de ETILENGLICOL (Spanish) (111-55-7) see ethylene glycol diacetate. 

DIETHYLENETRIAMINE (111 -40-0) C4HJ3N3 Combustible liquid [explosion limits in air (vol %) 1 to 10.0 flash point 216°F/102°C cc autoignition temp 676°F/358°C Fire Rating 1]. An organic base. Ignites spontaneously with cellulose nitrate and possibly with other nitrogen compounds. Silver, cobalt, or chromium compounds may cause explosions. Contact with nitromethane forms a heat-, fiiction-, and shock-sensitive e losive. Violent reaction with strong oxidizers nitric acid. May form heat-sensitive explosive materials... 

Five grams (0.017 mol) of trinitro(diethylenetriamine)-cobalt(III) is warmed with 5 ml. of concentrated nitric acid (sp. gr. 1.42) nitrogen(IV) oxide is evolved and a deep violet solution is formed. This solution is allowed to evaporate to a slurry at room temperature. By mixing 25 ml. of acetone with the slurry and filtering on a Buchner funnel, violet crystals of trinitrato(diethylenetriamine)-cobalt(III) are left on the paper. These are washed with acetone and dried at 110°. The yield is 5.2 g. (90%). Anal. Calcd. for [Co(dien)(N03)3] Co, 16.95 C, 13.80. Found Co, 17.00 C, 13.70. 

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