The phytocannabinoids derived from Cannabis sativa L. are described to therapeutically treat a myriad of diseases but also have psychoactive and immunosuppressive side effects. The discovery of the endocannabinoid system (ECS) revealed the G-protein coupled cannabinoid receptors CB1 and CB2 are primarily expressed in the nervous and immune systems, respectively. THC and CBD are the decarboxylated products after heating of the natural acid compounds (THCA and CBDA) found in the plant. Importantly, cannabinoid acids have low affinity for the CB1 and CB2 receptors but are active on other targets such as TRPV1 and PPARγ. Creating novel synthetic derivatives of cannabinoid acids provides an opportunity to selectively agonize receptors involved in altering T cell function. These compounds have the potential to treat diseases of both hypo- and hyperactive immune responses. Using hydrogenation, we chemically transformed the unsaturated phytocannabinoids to develop a library of hydrogenated compounds. Saturation of a double bond in the ring of THCA results in both R and S stereoisomers at the 9-position of hexahydrocannabinolic acid (HHCA). We hypothesize that the hydrogenated phytocannabinoids will exhibit altered receptor binding, presenting a promising avenue for drug discovery. This hypothesis was assessed by measuring T cell survival and function in the Jurkat T cell line. Using flow cytometry, we found significant differences in cell viability between the 9R and 9S stereoisomers of HHCA. Consistent with this, we uncovered significantly lower ATP levels in cells treated with the 9S-HHCA isomer compared to the 9R-HHCA isomer. In addition, we have assessed the effects of hydrofluorinated compounds and found them less cytotoxic than their hydrogenated counterparts. We continue to assess T cell function and distinguish receptor-independent effects from receptor-mediated effects. This research addresses the urgent need for therapeutics with minimal immunosuppressive side effects. By developing novel, chemically transformed derivatives, we can improve treatments for autoimmune, inflammatory diseases, and more; all while maintaining the established inherent safety of phytocannabinoid compounds. Ultimately, this research contributes to advancing drug discovery and enhancing public health.