The Halogen Bond between Amantadine and Iodine and Its Application in the Determination of Amantadine Hydrochloride in Pharmaceuticals

Abstract

It is proposed that molecular iodine as a donor could form halogen bonding complexes with amantadine (AMD) and amantadine hydrochloride (AMD-HCl) in chloroform and the resultant charge transfer bands (CT band) would be located at 259 and 253 nm, respectively. The halogen bonding interaction was explored by UV absorption, Raman and X-ray crystallography, and a new bonding model named N + ···N lep bond in crystal was observed. The halogen bonding complexes were utilized in the development of simple and accurate spectrophotometry for the analysis of AMD/AMD-HCl. Compared with the traditional method based on the absorption of I3 -at 290 and 365 nm, the new proposed spectrometry based on the CT band of halogen bonding complex was more sensitive and selective for the detection of AMD/AMD-HCl. Linear relationships with good correlation coefficients (>0.9994) were obtained between the absorbance and the AMD/AMD-HCl concentration in the range of 10 -180 μg mL -1 for AMD-HCl and 0.2 -13 μg mL -1 for AMD. The limit of detection (LOD) was 2.23 μg mL -1 and limit of quantification (LOQ) was 7.45 μg mL -1 for AMD-HCl. And because of the stronger bond constant between AMD and iodine than AMD-HCl, the method is more sensitive for AMD; the LOD was 0.02 μg mL -1 and LOQ was 0.08 μg mL -1 which was 100 times lower than that of AMD-HCl. Keywords

Adsorption-based capture of iodine and organic iodides: status and challenges

“…Copyright 2022, Springer Nature. (c and d) The interaction mechanisms between electron donors and I 2 proposed by different researchers [58][59][60][61][62].…”

Synthesis and Structure of Cyclic Trisaccharide with Expanded Glycosidic Linkages

“…We premise that AMT occupies the upper rim of 8 , with the adamantane moiety occupying the macrocycle cavity and amine moiety exposed to the hydroxyl groups and water molecules of the aqueous environment, as in the case of AMT binding to CDs. , Lengths of AMT and 8 , as derived from crystal structure analysis, are given in Figure c. Enhanced binding strength of AMT with 8 , when compared to AMT binding to β-CD, might prove to be useful, as AMT is an antiviral drug and its slow release when complexed with CD is beneficial.…”