Comparison of Reactivity of Amphetamine, Methamphetamine, and Dimethylamphetamine with Lactose and Related Compounds

Effect of Milling and Compression on the Solid-State Maillard Reaction

“…Moisture, acidity, and the molecular structure of the amine also have great influence on the rate of the reaction. [11][12][13] Although the Maillard reaction is a widely recognized drug-excipient interaction, [14][15][16] lactose, the reducing sugar used most widely as an excipient, is frequently used to formulate amine drugs. The database of Physicians' Desk Reference 17 gives 72 entries in which amine drugs are formulated with lactose.…”

Interaction of Dextroamphetamine Sulfate with Dextrates in Solution

“…Duvall rt al. (4) reported that amines increased the extent of the browning reaction in tablets prepared from dextrose. The solubility characteristics of the brown material obtained from Solution (b), which had been heated for 2 days at a", differed from those of the brown material obtained from Solution (c).…”

Glycosylation of Aromatic Amines I: Characterization of Reaction Products and Kinetic Scheme

“…Examples of drug instability due to the Maillard reaction include both primary and secondary amines as in the case of amphetamines, insulin, fluoxetine, sulfa drugs, procainamide, metoclopropamide, and daptomycin to name a few (4)(5)(6)(7)(8)(9). For example, Duval et al studied the browning of dextroamphetamine sulfate solutions containing lactose and found that the solution darkens on storage at 50°C with the formation of brownish precipitate (4).…”

“…For example, Duval et al studied the browning of dextroamphetamine sulfate solutions containing lactose and found that the solution darkens on storage at 50°C with the formation of brownish precipitate (4). Using infrared data and thin-layer chromatography, they concluded that the product was a Schiff base formed from the reaction of the primary amine in dextroamphetamine and the carbonyl group of lactose.…”

“…Secondary amines in generic formulations of fluoxetine HCl containing lactose as a common ingredient were shown to be less stable than the formulations containing starch due to the Maillard reaction between the drug and lactose (5). Dextrates obtained by the controlled hydrolysis of starch used as excipients are also known to exhibit the browning reaction due to the presence of varying amounts of dextrose (4,10,11).…”