Canniprene

Canniprene is an isoprenylated bibenzyl compound with the chemical formula C21H26O4, found in the fan leaves of Cannabis sativa. It has the potential to be vaporized and inhaled from cannabis. Canniprene has been identified as a potent antioxidant, anti-inflammatory, and neuroprotective agent, and it has been studied for its potential therapeutic applications in various conditions[1][2].

Research has shown that canniprene can inhibit the production of pro-inflammatory eicosanoids by targeting the 5-lipoxygenase pathway with an IC50 of 0.4 μM and affecting the generation of prostaglandins via the cyclooxygenase/microsomal prostaglandin E2 synthase pathway with an IC50 of 10 μM[5]. These pathways are involved in the inflammatory response, and their inhibition can be beneficial for treating conditions such as asthma, allergic rhinitis, COPD, and idiopathic pulmonary fibrosis[7].

The concentration of canniprene varies widely among different strains of C. sativa, with no correlation found between its accumulation and a specific phytocannabinoid profile or the concentration of similar polyphenol compounds found in cannabis, such as cannflavin A and B[5][7].

Canniprene was first isolated by Crombie et al. in 1978, and its synthesis was reported two years later, facilitating further research into its properties and potential therapeutic uses[7].

Citations:

[1] https://en.wikipedia.org/wiki/Canniprene

[2] https://www.benchchem.com/product/b564676

[3] https://pubs.acs.org/doi/10.1021/acs.jnatprod.6b01126

[4] https://pubchem.ncbi.nlm.nih.gov/compound/Canniprene

[5] https://pubmed.ncbi.nlm.nih.gov/28165233/

[6] https://pubs.rsc.org/en/content/articlelanding/1982/p1/p19820001467

[7] https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10386382/

[8] https://pubs.acs.org/doi/abs/10.1021/acs.jnatprod.6b01126

[9] https://www.sciencedirect.com/science/article/abs/pii/0040403980802486

[10] https://wikidata.org/wiki/Q48999691

[11] https://www.mdpi.com/1420-3049/23/10/2639

[12] https://www.cannabisclinicians.org/2023/11/18/phytochemical-investigation-of-anti-proliferative-active-fractions-of-cannabis-sativa-leads-to-isolate-a-new-compound-canniprene-a-and-other-bioactive-compounds-through-bioassay-guided-fractionation-a/

[13] https://www.chemfaces.com/natural/Canniprene-CFN97198.html

[14] https://www.bocsci.com/product/canniprene-cas-70677-47-3-423549.html

[15] https://www.researchgate.net/publication/313411614_The_Bibenzyl_Canniprene_Inhibits_the_Production_of_Pro-Inflammatory_Eicosanoids_and_Selectively_Accumulates_in_Some_Cannabis_sativa_Strains