A group of Italian researchers isolated and fully characterized two naturally occurring cannabinoids, (-)-trans-Δ9-tetrahydrocannabiphoral (Δ9-THCP) and (-)-trans-cannabidiphoral (CBDP). Both Δ9-THCP and CBDP are homologs of the more familiar cannabinoids, (-)-trans-Δ9-tetrahydrocannabinol (THC) and (-)-trans-cannabidiol (CBD). Whereas THC and CBD each have five-term side alkyl chains, the newly discovered cannabinoids each have seven-term side alkyl chains. Surprisingly, the researchers found that the longer side chain affords it a greater binding affinity than THC at both human cannabinoid receptors (CBs). The binding affinity of THC at CB1 and CB2 is approximately 40 nM and 36 nM, respectively, while THCP has a binding affinity of 1.2 nM and 6.2 nM, respectively. It is believed that CBDP, like CBD, has a poor affinity to both CB1 and CB2, but the researchers believe it may have anti-inflammatory, antioxidant, and anti-epileptic effects.
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