Terpenes (general)

Hashishene: The Mysterious Terpene Formed While Making Hashish

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Written by Paul James

If you’ve ever consumed hashish, you’re well aware that it produces a taste, smell, and feeling unlike any cannabis bud. Of course, the cannabinoids and terpenes are more concentrated in hash, but interestingly, the process of making hash has been shown to create a new terpene.

In 2014, a study released by the Journal of Chromatography A discovered that hashish characteristics are thanks to the degradation of a terpene common to the cannabis plant. [1] Resin extracts oxidize to produce high amounts of a rare monoterpene known as 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane. The researchers of the study coined the catchier name “hashishene” for their newly discovered terpene.

During the hashish manufacturing process, beta-myrcene (a natural hydrocarbon found in the cannabis plant) is rearranged. This occurs through photo-oxidation in the presence of light and oxygen. [1]

β-Myrcene is found in a number of plants and is known for its pleasant smell. Another notable trait is the fact that it’s a starting terpene for the synthesis of several other terpenes. [2] In terms of cannabis, β-myrcene has been found as one of the most common terpenes within the plant. [3,4] Due to the ensemble effect, myrcene may help modulate or improve the medical properties of cannabinoids and the terpene provides potential medical benefits, including anti-inflammatory and sedative effects. [4,5]

Within the above-mentioned study, 7 out of the 10 cannabis flower samples investigated had high amounts of β-myrcene (between 19.5% and 28.7%). Since myrcene degrades to hashishene, its abundance in cannabis buds plays a fundamental role in everything we love about hash. The researchers also noted that “most of the major terpenes present in fresh cannabis herb undergo various transformations during hashish manufacture…” [1]

The research provided on hashishene gives us new insights into how the cannabis plant works its magic. However, even more importantly, it can build the steppingstones for further research concerning terpene profiles and how they may be used to help for particular ailments.

Image Credit: Wikipedia

References

  1. Marchini M, Charvoz MC, Dujourdy L, Baldovini N, Filippi JJ. Multidimensional analysis of cannabis volatile constituents: Identification of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L. The Journal of Chromatography A. 2014;1370:200-15. [Impact Factor: 4.049; Times Cited: 28 (Semantic Scholar)]
  2. Behr A, Johnen L. Myrcene as a natural base chemical in sustainable chemistry: A critical review. ChemSusChem. 2009;2(12):1072-1095. https://doi.org/10.1002/cssc.200900186. [Impact Factor: 7.962; Times Cited: 165 (Semantic Scholar)]
  3. Mediavilla V, Steinemann S. Essential oil of Cannabis sativa L. strains. Journal of the International Hemp Association. 1997;4(2):80-82. [Impact Factor: n/a; Times Cited: 53 (Semantic Scholar]
  4. Russo EB. Taming THC: Potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. Br J Pharmacol. 2011;163(7):1344-1364. doi:10.1111/j.1476-5381.2011.01238.x. [Impact Factor: 7.73; Times Cited: 642 (Semantic Scholar)]
  5. Lupoi, J. The Cannabis Terpene Experience. Mace Media Group, 2020.

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Paul James

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