Detail of "109-11-5"

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Evaluation of morpholine, 3-morpholinone, and N-substituted morpholines in the rat hepatocyte primary culture/DNA repair test: Evaluation of morpholine, 3-morpholinone, and N-substituted morpholines in the rat hepatocyte primary culture/DNA repair test. Conaway, C. Clifford; Tong, Charles; Williams, Gary M. (Texaco Res. Cent., Beacon, NY 12508, USA). Mutat. Res., 136(2), 153-7 (English) 1984. CODEN: MUREAV. ISSN: 0027-5107. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) Morpholine [110-91-8] and a series of morpholine derivs. were assayed for the potential to induce DNA repair in the rat hepatocyte primary culture/DNA repair assay. Morpholine did not induce DNA repair at dose concns. which were not toxic (0.0001-0.1 mg/mL). Two metabolites of morpholine, N-methylmorpholine oxide [7529-22-8] and N-hydroxymorpholine (I) [5765-63-9], also did not induce DNA repair at the nontoxic concns. tested (0.0001-10 and 0.0001-1 mg/mL, resp.). A putative metabolite of morpholine, 3-morpholinone [109-11-5], was inactive (0.001-10 mg/mL) and a polyurethane foam catalyst, N-butylmorpholine [1005-67-0] (0.0001-0.1 mg/mL) was also inactive. The chem. intermediate N-hydroxyethylmorpholine [622-40-2] induced DNA repair in the dose range 1-5 mg/mL. Thus genotoxicity of substituted morpholines is a function of the substituent moiety rather than morpholine itself.

The structure of a human metabolite of pholcodine: The structure of a human metabolite of pholcodine. Gore, Jeff; Kasum, Bruno; Holman, Michelle A.; Scharfbillig, Ilse M.; Ward, A. David (Dep. of Chemistry, The University of Adelaide, Adelaide 5005, Australia). Australian Journal of Chemistry, 49(11), 1235-1242 (English) 1996 Commonwealth Scientific and Industrial Research Organization. CODEN: AJCHAS. ISSN: 0004-9425. DOCUMENT TYPE: Journal CA Section: 31 (Alkaloids) The structure of a metabolite of pholcodine produced by humans is shown, by spectroscopic and synthetic data, to be a morpholin-3-one (amide) deriv. I rather than the alternative morpholin-2-one (lactone) isomer. Acylation of diethanolamine leads to an N,O-diacyl product even when only 1 equiv. 109-11-5 and 52-26-6 are also in the experiment. of acylating agent is used. A mechanism is proposed to account for this observation. The appropriately substituted diacyl product can be cyclized to give a morpholin-3-one deriv. which can be coupled to morphine by using cesium carbonate to give the metabolite. Suitable morpholin-2-one systems were coupled with morphine in basic conditions to give the alternative metabolite structure whose lactone group hydrolyzed on standing to form a hydroxy acid deriv. .