User:Savannaj13/Cannabinol

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Cannabis sativa has been used since ancient times for agricultural, ceremonial and medicinal purposes. In traditional medicine, the plant has been used as an analgesic, anticonvulsant, anti-asthmatic, antimalarial or anti-rheumatic agent.[1] Cannabinol (CBN) is a mildly psychoactive cannabinoid that binds to the cannabinoid receptors with more selectivity for CB2 over CB1[2][3][4] found in trace amounts from Cannabis[5]. CBN is mostly found in cannabis that is aged and stored, and is derived from the plant's main psychoactive chemical, tetrahydrocannabinol (THC)[6].

Cannabis contains over 700 different chemicals, among which a group of compounds called cannabinoids stands out.[1] One of the most prominent cannabinoids has been commonly referred to as cannabinol. It was the first cannabis compound to be isolated from cannabis extract in the late 1800s. Then by the 1930s, the first to have its structure determined and in 1940, to have scientists achieve its chemical synthesis.

Formation[edit]

Delta-9-THC can degrade into CBN from oxidation[7][8]. Manufacturers expose THC to heat and light, which breaks it down, leaving behind CBN [9].Unlike more prevalent cannabinoids such as THC and cannabidiol (CBD), CBN is not produced by the plant in significant quantities. CBN is mainly formed from the degradation of THC and other cannabinoids, when they are exposed to heat, UV light and/or oxygen. This is the reason why higher levels of CBN can be found in aged, dry Cannabis. The graphic below shows the chemical structure and production of CBN and other cannabinoids in the plant.[10] Unlike many other cannabinoids, cannabinol (CBN) does not stem from cannabigerol (CBG). Instead, CBN is a tetrahydrocannabinol (THC) metabolite formed as cannabis ages. THC degrades into CBN over time and exposure to ultraviolet (UV) light.[11].

Pharmacology[edit]

CBN acts as a partial agonist at the CB1 receptors, but has a higher affinity to CB2 receptors; however, it has lower affinities relative to THC[12][13][14]. Both THC and CBN activate the CB1 (Ki = 211.2 nM) and CB2 (Ki = 126.4 nM) receptors[15]. It is metabolised to 11-OH-CBN, which is a more potent CB1 agonist than CBN but acts as a weak antagonist at CB2[16].

Molecular Structure of Cannabinol

Chemistry[edit]

Early Depiction of Cannabinol

In contrast to THC, CBN has no double bond isomers or stereoisomers.CBN can degrade into HU-345 from oxidation. CBN is molecularly similar to THC, but is not psychoactive.[17] THC acts on the CB1 endocannabinoid receptors, which is what creates the high associated with cannabis. CBN also binds to the CB1 receptor, but at a much lower strength than THC.[18]

Legal Status[edit]

CBN is not listed in the schedules set out by the United Nations' Single Convention on Narcotic Drugs from 1961 nor their Convention on Psychotropic Substances from 1971[19], so the signatory countries to these international drug control treaties are not required by these treaties to control CBN. This compound is less regulated by the FDA compared to THC and CBD[17]. However, this can make it harder to access legally.

United States[edit]

Cannabinol 10 mg transdermal patches are sold at marijuana dispensaries in Colorado, U.S. As of 2021 in the United States, CBN and other cannabis extracts remain illegal under federal law to prescribe for medical use or to use as an ingredient in dietary supplements or other foods[20][21], and sales or possession of CBN could potentially be prosecuted under the Federal Analogue Act. In December 2016, the Drug Enforcement Administration added marijuana extracts, which are defined as any "extract containing one or more cannabinoids that has been derived from any plant of the genus Cannabis,

other than the separated resin", to Schedule I.

Europe[edit]

Europe's government does not support legalisation of cannabis sale for recreational use, and all countries have prison sentences for illegal use. In contrast, nearly half of all European citizens support the recreational use of Cannabis and its properties, such as CBN. Several laws have been proposed to national parliaments in the last few years, as well as some initiatives in different cities. These have all been rejected by European lawmakers. Certain countries, such as the Netherlands and Amsterdam, are referred to as a "back door problem" due to creating legally anomalies for the public sale of Cannabis products.[22]

South America[edit]

Recently,[when?] the cannabis market has emerged in many South American countries and has begun to attract the attention of many companies and international investors. Slowly, states are decriminalizing the possession, consumption and cultivation of marijuana and its properties. Simultaneously, they are legalizing and increasing the production of cannabis for therapeutic or recreational purposes.[23]

Asia[edit]

Compared to the United States, Asia's laws are much stricter. Taiwan, China, Malaysia, Korea, Thailand, and the Philippines allow CBD to be used in certain medical circumstances, while others still carry severe prison sentences for cannabis possession. Many legally consider the death penalty as mandatory punishment[24]. Slowly, the medical use of CBD and its properties is being explored scientifically. Some countries allow citizens to grow small amounts for personal use.

Benefits[edit]

A study by Salk scientists shows how Cannabinol can protect nerve cells from oxidative damage, a major pathway to cell death. Cannabinol protects neurons from oxidative stress and cell death, two of the major contributors to Alzheimer’s. This discovery could one day lead to the development of new therapeutics for treating this disease and other neurodegenerative disorders, like Parkinson’s disease.CBN works by protecting mitochondria, the cell’s powerhouses, within the neurons.[17]. CBN can act with higher potency when interacting with certain receptor systems in the body, while acting with lower potency for others when compared to other cannabinoids.[25]

CBN is expected to maintain its structural integrity/stability under external stresses (e.g. heat, light) for a longer period of time.[25] This characteristic allows for a very long shelf life. CBN has been tested as an effective sleep aid and pain reliever.[26]

Future Development[edit]

The use of CBN and other properties found in Cannabis will likely continue to develop. Research on the medical benefits of cannabis properties continues to expand daily. An estimated 147 million people around the world use some form of Cannabis regularly[27]. The number is certainly much larger than this report due to the legal complexities surrounding marijuana use. Relaxed laws and extensive medical research are becoming more common in numerous countries. The use of CBN is becoming less taboo, and will eventually become a more common treatment for medical ailments. Additionally, destigmatizing its use will lead to recreational expansion.

References[edit]

  1. ^ a b Kicman, Aleksandra; Toczek, Marek (2020). "The Effects of Cannabidiol, a Non-Intoxicating Compound of Cannabis, on the Cardiovascular System in Health and Disease". International Journal of Molecular Sciences. 21 (18): 6740. doi:10.3390/ijms21186740. ISSN 1422-0067.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  2. ^ Rhee, Man-Hee; Vogel, Zvi; Barg, Jacob; Bayewitch, Michael; Levy, Rivka; Hanuš, Lumir; Breuer, Aviva; Mechoulam, Raphael (1997-09-01). "Cannabinol Derivatives: Binding to Cannabinoid Receptors and Inhibition of Adenylylcyclase". Journal of Medicinal Chemistry. 40 (20): 3228–3233. doi:10.1021/jm970126f. ISSN 0022-2623.
  3. ^ Sampson, Peter B. (2021-01-22). "Phytocannabinoid Pharmacology: Medicinal Properties of Cannabis sativa Constituents Aside from the "Big Two"". Journal of Natural Products. 84 (1): 142–160. doi:10.1021/acs.jnatprod.0c00965. ISSN 0163-3864.
  4. ^ "NCI Thesaurus". ncithesaurus.nci.nih.gov. Retrieved 2022-07-29.
  5. ^ Morales, Paula; Hurst, Dow P.; Reggio, Patricia H. (2017), Kinghorn, A. Douglas; Falk, Heinz; Gibbons, Simon; Kobayashi, Jun'ichi (eds.), "Molecular Targets of the Phytocannabinoids: A Complex Picture", Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa, Cham: Springer International Publishing, pp. 103–131, doi:10.1007/978-3-319-45541-9_4, ISBN 978-3-319-45541-9, PMC 5345356, PMID 28120232, retrieved 2022-07-29
  6. ^ Andre, Christelle M.; Hausman, Jean-Francois; Guerriero, Gea (2016). "Cannabis sativa: The Plant of the Thousand and One Molecules". Frontiers in Plant Science. 7. doi:10.3389/fpls.2016.00019/full. ISSN 1664-462X.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  7. ^ Garrett, Edward R.; Gouyette, Alain J.; Roseboom, Hendrik (1978-01-01). "Stability of Tetrahydrocannabinols II". Journal of Pharmaceutical Sciences. 67 (1): 27–32. doi:10.1002/jps.2600670108. ISSN 0022-3549.
  8. ^ Cannabinoid Pharmacology. Academic Press. 2017-08-18. ISBN 978-0-12-811233-5.
  9. ^ "CBD vs. CBN: Effects, similarities, and differences". www.medicalnewstoday.com. 2020-08-29. Retrieved 2022-07-30.
  10. ^ "Cannabinol 101: The Science of Cannabinol (CBN)". InMed Pharmaceuticals. Retrieved 2022-07-30.
  11. ^ "What Is CBN? Health Benefits, Uses, Risks, and More". Leafwell. Retrieved 2022-07-30.
  12. ^ Mahadevan, Anu; Siegel, Craig; Martin, Billy R.; Abood, Mary E.; Beletskaya, Irina; Razdan, Raj K. (2000-10-01). "Novel Cannabinol Probes for CB1 and CB2 Cannabinoid Receptors". Journal of Medicinal Chemistry. 43 (20): 3778–3785. doi:10.1021/jm0001572. ISSN 0022-2623.
  13. ^ Petitet, François; Jeantaud, Bernadette; Reibaud, Michel; Imperato, Assunta; Dubroeucq, Marie-Christine (1998-05-29). "Complex pharmacology of natural cannabivoids: Evidence for partial agonist activity of Δ9-tetrahydrocannabinol and antagonist activity of cannabidiol on rat brain cannabinoid receptors". Life Sciences. 63 (1): PL1–PL6. doi:10.1016/S0024-3205(98)00238-0. ISSN 0024-3205.
  14. ^ "NCI Thesaurus". ncit.nci.nih.gov. Retrieved 2022-07-29.
  15. ^ Russo, Ethan B.; Marcu, Jahan (2017-01-01), Kendall, David; Alexander, Stephen P. H. (eds.), "Chapter Three - Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads", Advances in Pharmacology, Cannabinoid Pharmacology, vol. 80, Academic Press, pp. 67–134, retrieved 2022-07-29
  16. ^ Rhee, Man-Hee; Vogel, Zvi; Barg, Jacob; Bayewitch, Michael; Levy, Rivka; Hanuš, Lumir; Breuer, Aviva; Mechoulam, Raphael (1997-09-01). "Cannabinol Derivatives: Binding to Cannabinoid Receptors and Inhibition of Adenylylcyclase". Journal of Medicinal Chemistry. 40 (20): 3228–3233. doi:10.1021/jm970126f. ISSN 0022-2623.
  17. ^ a b c "Active ingredient in cannabis protects aging brain cells". Salk Institute for Biological Studies. Retrieved 2022-07-30.
  18. ^ "CBD vs. CBN: Effects, similarities, and differences". www.medicalnewstoday.com. 2020-08-29. Retrieved 2022-07-30.
  19. ^ "Conventions". United Nations : Office on Drugs and Crime. Retrieved 2022-07-30.
  20. ^ Mead, Alice (2019). "Legal and Regulatory Issues Governing Cannabis and Cannabis-Derived Products in the United States". Frontiers in Plant Science. 10. doi:10.3389/fpls.2019.00697/full. ISSN 1664-462X.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  21. ^ Mead, Alice (2017-05-01). "The legal status of cannabis (marijuana) and cannabidiol (CBD) under U.S. law". Epilepsy & Behavior. 70: 288–291. doi:10.1016/j.yebeh.2016.11.021. ISSN 1525-5050. PMID 28169144.
  22. ^ "Cannabis policy: status and recent developments". www.emcdda.europa.eu. Retrieved 2022-07-31.
  23. ^ Cammarata, Luca (2019-04-24). "The great Cannabis revolution in South America: step towards legalization". CBWEED. Retrieved 2022-07-31.
  24. ^ "What are the Legalities of Weed and CBD in Asia?". Qrius. 2021-02-10. Retrieved 2022-07-31.
  25. ^ a b "Cannabinol CBN - A New Potential Therapeutic for Unmet Medical Needs". InMed Pharmaceuticals. Retrieved 2022-07-30.
  26. ^ Sreenivas, Shishira. "CBD vs CBN: What's the Difference?". WebMD. Retrieved 2022-07-30.
  27. ^ "Cannabis". www.who.int. Retrieved 2022-07-31.
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