8,9-Dihydrocannabidiol

8,9-Dihydrocannabidiol
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
CAS Number
  • 23050-49-9
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9891398
PubChem CID
  • 11716677
InChI
  • InChI=1S/C21H32O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-14,17-18,22-23H,5-10H2,1-4H3/t17-,18+/m0/s1
    Key: PCXRACLQFPRCBB-ZWKOTPCHSA-N
  • CCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(C)C)C)O
Properties
Chemical formula
 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
Chemical compound

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] that was first synthesized by Alexander R. Todd in 1940 derived from the catalytic hydrogenation of cannabidiol.[3]

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,[4][5] and the deliberate laboratory conversion of CBD to THC is straightforward.[6][7] 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][8][9]

It was shown to have anti-seizure activity essentially identical to that of CBD in tests with rats.[10]

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.[11]

See also

References

  1. ^ a b Mascal M, Hafezi N, Wang D, Hu Y, Serra G, Dallas ML, Spencer JP (May 2019). "Synthetic, non-intoxicating 8,9-dihydrocannabidiol for the mitigation of seizures". Scientific Reports. 9 (1): 7778. Bibcode:2019NatSR...9.7778M. doi:10.1038/s41598-019-44056-y. PMC 6533278. PMID 31123271.
  2. ^ Li H, Liu Y, Tian D, Tian L, Ju X, Qi L, et al. (April 2020). "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. doi:10.1016/j.ejmech.2020.112163. PMID 32109623. S2CID 211564148.
  3. ^ Jacob, A.; Todd, A. R. (1940). "119. Cannabis indica. Part II. Isolation of cannabidiol from Egyptian hashish. Observations on the structure of cannabinol". J. Chem. Soc. 119: 649–653. doi:10.1039/jr9400000649.
  4. ^ Merrick J, Lane B, Sebree T, Yaksh T, O'Neill C, Banks SL (2016). "Identification of Psychoactive Degradants of Cannabidiol in Simulated Gastric and Physiological Fluid". Cannabis and Cannabinoid Research. 1 (1): 102–112. doi:10.1089/can.2015.0004. PMC 5576596. PMID 28861485.
  5. ^ Watanabe K, Itokawa Y, Yamaori S, Funahashi T, Kimura T, Kaji T, Usami N, Yamamoto I (2007). "Conversion of cannabidiol to Δ9-tetrahydrocannabinol and related cannabinoids in artificial gastric juice, and their pharmacological effects in mice". Forensic Toxicology. 25: 16–21. doi:10.1007/s11419-007-0021-y. S2CID 2890977.
  6. ^ Adams R, Pease DC, Cain CK, Clark JH (1940). "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. doi:10.1021/ja01866a040.
  7. ^ Adams R, Cain CK, McPhee WD, Wearn RB (1941). "Structure of Cannabidiol. XII. Isomerization to Tetrahydrocannabinols1". Journal of the American Chemical Society. 63 (8): 2209–2213. doi:10.1021/ja01853a052.
  8. ^ WO 2020/185661, Mascal M, Shevchenko N, "Use of 8,9-dihydrocannabidiol compounds.", assigned to University of California 
  9. ^ Delta 9 Edibles, 1 August 2023
  10. ^ 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. Bibcode:2019NatSR...9.7778M. doi:10.1038/s41598-019-44056-y. PMC 6533278. PMID 31123271.
  11. ^ 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.
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