N-Deacetyl Colchicine is a structurally related impurity of Colchiceine, characterized by the absence of an acetyl group at the N-1 position, exposing a primary amine functionality. Its core structure comprises a fused isoquinoline and pyridine ring system substituted with a 8-hydroxy-9-methoxy group and a methylene bridge connecting to a cyclohexenone moiety. The deacetylated nitrogen introduces a basic center, altering its solubility and reactivity compared to the parent compound. This impurity arises via non-enzymatic hydrolysis of the acetyl ester in Colchiceine under acidic conditions. It serves as a critical HPLC reference standard for quantifying deacetylation-related degradation in pharmaceutical formulations.
On RequestCOC1=CC=C2C(=CC1=O)[C@H](CCC3=CC(=C(C(=C32)OC)OC)OC)N
InChI=1S/C20H23NO5/c1-23-16-8-6-12-13(10-15(16)22)14(21)7-5-11-9-17(24-2)19(25-3)20(26-4)18(11)12/h6,8-10,14H,5,7,21H2,1-4H3/t14-/m0/s1
HFPMXDMZJUJZBX-AWEZNQCLSA-N