Chemistry:8,9-Dihydrocannabidiol

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8,9-Dihydrocannabidiol
New H2CBD.png
Names
Preferred IUPAC name
2-[(1S,6S)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
Other names
H2CBD, DiHydroCBD
Identifiers
3D model (JSmol)
ChemSpider
Properties
C21H32O2
Molar mass 316.485 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

8,9-Dihydrocannabidiol (also known as H2CBD, DiHydroCBD, Delta-1-H2CBD, or Delta-1-DiHydroCBD) is a synthetic cannabinoid that is closely related to cannabidiol (CBD) itself.[1][2]

Pharmacology

It may have certain advantages over CBD, in that it is fully synthetic, inexpensive to produce, and it is not a scheduled drug (cannabis extracts are controlled substances in most parts of the world). In addition, there is no path to synthesize the psychoactive substance tetrahydrocannabinol (THC) from H2CBD. CBD has been shown to convert to some extent to THC in the gastric tract,[3][4] and the deliberate laboratory conversion of CBD to THC is straightforward.[5][6] H2CBD has therefore been studied for its potential use as an alternative to CBD in terms of its lack of abuse liability and absence of psychotropic effects.[1][7][8]

It was shown to have anti-seizure activity essentially identical to that of CBD in tests with rats.[9]

In 2006 it was reported that 8,9-Dihydrocannabidiol binds very weakly to the CB1 receptor with a binding affinity higher than 1µM but was noted to have potential anti-inflammatory effects independent of its cannabinoid receptor action.[10]

See also

References

  1. ↑ 1.0 1.1 "Synthetic, non-intoxicating 8,9-dihydrocannabidiol for the mitigation of seizures". Scientific Reports 9 (1): 7778. May 2019. doi:10.1038/s41598-019-44056-y. PMID 31123271. Bibcode: 2019NatSR...9.7778M. 
  2. ↑ "Overview of cannabidiol (CBD) and its analogues: Structures, biological activities, and neuroprotective mechanisms in epilepsy and Alzheimer's disease". European Journal of Medicinal Chemistry 192: 112163. April 2020. doi:10.1016/j.ejmech.2020.112163. PMID 32109623. 
  3. ↑ "Identification of Psychoactive Degradants of Cannabidiol in Simulated Gastric and Physiological Fluid". Cannabis and Cannabinoid Research 1 (1): 102–112. 2016. doi:10.1089/can.2015.0004. PMID 28861485. 
  4. ↑ "Conversion of cannabidiol to Δ9-tetrahydrocannabinol and related cannabinoids in artificial gastric juice, and their pharmacological effects in mice". Forensic Toxicology 25: 16–21. 2007. doi:10.1007/s11419-007-0021-y. 
  5. ↑ "Structure of Cannabidiol. VI. Isomerization of Cannabidiol to Tetrahydrocannabinol, a Physiologically Active Product. Conversion of Cannabidiol to Cannabinol". Journal of the American Chemical Society 62 (9): 2402–2405. 1940. doi:10.1021/ja01866a040. 
  6. ↑ "Structure of Cannabidiol. XII. Isomerization to Tetrahydrocannabinols1". Journal of the American Chemical Society 63 (8): 2209–2213. 1941. doi:10.1021/ja01853a052. 
  7. ↑ Mascal M, Shevchenko N, "Use of 8,9-dihydrocannabidiol compounds.", WO patent 2020/185661, assigned to University of California
  8. ↑ Delta 9 Edibles, 1 August 2023
  9. ↑ Mascal, Mark; Hafezi, Nema; Wang, Deping; Hu, Yuhan; Serra, Gessica; Dallas, Mark L.; Spencer, Jeremy P. E. (2019). "Synthetic, non-intoxicating 8,9-dihydrocannabidiol for the mitigation of seizures". Scientific Reports 9 (1): 7778. doi:10.1038/s41598-019-44056-y. PMID 31123271. Bibcode: 2019NatSR...9.7778M. 
  10. ↑ Ben-Shabat, Shimon; Hanuš, Lumír O.; Katzavian, Galia; Gallily, Ruth (2006). "New Cannabidiol Derivatives: Synthesis, Binding to Cannabinoid Receptor, and Evaluation of Their Antiinflammatory Activity". Journal of Medicinal Chemistry 49 (3): 1113–1117. doi:10.1021/jm050709m. PMID 16451075. https://pubs.acs.org/doi/10.1021/jm050709m. 



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