This PDF file includes:

• Fig. S1. Radioligand displacement assay using ³HCP55,940 and membranes from CHO cells stably transfected with human CB1R and CB2R, respectively.
• Fig. S2. ³⁵SGTPγS binding curves for THC and PET stereoisomers on human cannabinoid receptors.
• Fig. S3. LC-MS/MS quantifications of the NAEs OEA, PEA, and LEA in the brain of BALB/c male mice 1 hour after intraperitoneal injection of cannabinoids.
• Fig. S4. LC-MS/MS quantification of Δ9-trans-THC, cis-PET, and trans-PET in plasma of BALB/c male mice 1 hour after intraperitoneal injection of cannabinoids.
• Fig. S5. Inhibition of COX-2 activity.
• Fig. S6. Representative LC-MS/MS reaction monitoring chromatogram of reference standards in mouse brain tissue showing LC separation of cis- and trans-PET.
• Table S1. Profiling of THC and PET diastereoisomers on endocannabinoid-degrading enzymes in vitro.
• Synthesis and characterization of products
• Preparation of allylic alcohol 1
• Preparation of (–)-cis-PET (S,R)-PET
• Preparation of (–)-trans-PET (R,R)-PET
• SFC traces

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