cas 92292-84-7, 4-Acetoxy-N,N-dimethyltryptamine

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Improvements to the synthesis of psilocybin and a facile method for preparing the O-acetyl prodrug of psilocin
An improved procedure to accomplish the O-phosphorylation of 4-hydroxy- N,N-dimethyltryptamine (psilocin 5) is reported that utilizes reaction between the O-lithium salt of 5 and tetra-O-benzylpyrophosphate. The O- benzyl groups were removed by catalytic hydrogenation over palladium on carbon to afford N,N-dimethyl-4-phosphoryloxytryptamine (psilocybin, 1). In view of difficulties encountered in the preparation of 1, it is suggested that 4-acetoxy-N,N-dimethyltryptamine (2) may be a useful alternative for pharmacological studies. The latter was obtained following catalytic O- debenzylation of 4-benzyloxy-N,N-dimethyltryptamine in the presence of acetic anhydride and sodium acetate.
Nichols, David E.,Frescas, Stewart
p. 935 - 938
(1999)
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Synthesis and in vitro evaluation of anti-inflammatory activity of ester and amine derivatives of indoline in RAW 264.7 and peritoneal macrophages
A prolonged increase in pro-inflammatory cytokines, TNF-α and IL-6 occurs in inflammatory diseases. Although existing therapies like steroids and TNF-α antagonists are effective they may cause serious adverse effects. We describe the preparation and evaluation for anti-inflammatory activity of 11 novel derivatives of indoline carbamates with a propionic ester, 2-aminoethyl, 3-aminopropyl 2-(dimethylamino)ethyl or 3-(dimethylamino)propyl group in positions 3 or 1. Compounds 25, 26 and 29 were previously shown to inhibit acetylcholinesterase with IC50s ranging from 0.4 to 55 μM and to prevent cytotoxicity induced by reactive oxygen species in a concentration range of 100 pM-1 μM. Compounds 25, 26, 29, 9, 10, 17 and 18, reduced NO, TNF-α and IL-6 at concentrations of 1-10 pM in LPS-activated RAW-264.7 and mouse peritoneal macrophages. The reduction in cytokines by compound 25 was associated with an increase in IκBα degradation and a decrease in the phosphorylation of p38 but not that of ERK. Conclusion: Indoline derivatives substituted at position 3 with chains carrying ester or amino groups may have potential for the treatment of chronic inflammatory and neurodegenerative diseases.
Furman, Svetlana,Nissim-Bardugo, Elinor,Zeeli, Shani,Weitman, Michal,Nudelman, Abraham,Finkin-Groner, Efrat,Moradov, Dorit,Shifrin, Helena,Schorer-Apelbaum, Donna,Weinstock, Marta
p. 2283 - 2287
(2014/05/20)