One-Step and Gram-Scale Synthesis of Caffeine-d9
One-Step, Gram-Scale Synthesis of Caffeine-d9 from Xanthine and CD3I: M. V. Tarasca, C. J. Tomlinson, P. Gris, G. K. Murphy
Synthesis 2022, DOI: 10.1055/a-1972-3819
Caffeine is a naturally occurring alkaloid present in relatively high concentration in the leaves, fruit, or nuts of a variety of plant species such as coffee, tea and cacao. It has psychoactive properties and can serve as a mild stimulant, for increasing alertness and concentration. Furthermore, caffeine is being studied as a therapeutic for a number of conditions. However, it is well known that it has side effects, such as causing heart palpitation and insomnia, whereas at higher concentrations it can cause nausea, vomiting and even death. Considering its widespread consumption, there is strong interest in identifying caffeine analogues devoid of these undesired effects. Among them, there are deuterated caffeine analogues, which could also be used for important metabolic studies. Recently, a collaborative effort between the groups of Professor Graham K. Murphy (Universtity of Waterloo, Canada) and Dr. Pavel Gris (DeutraMed, Collingwood, Canada) resulted in the one-step, gram-scale synthesis of caffeine-d9 from xanthine and CD3I.
Professor Murphy said: “Developing strategies to efficiently synthesize deuterated analogues of bioactive, small-molecule organics is important to support modern drug discovery efforts.”