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Usage

Uses

Used in Pharmaceutical Industry:
Cannabidiol is used as a therapeutic agent for various medical conditions due to its potential anti-inflammatory, analgesic, and neuroprotective properties. It has shown promise in treating conditions such as epilepsy, anxiety, chronic pain, and neurodegenerative diseases like Alzheimer's and Parkinson's.
Used in Cosmetics Industry:
Cannabidiol is used as an ingredient in skincare products for its potential anti-inflammatory and antioxidant properties. It is believed to help with skin conditions like acne, eczema, and psoriasis by reducing inflammation and promoting skin health.
Used in Nutraceutical Industry:
Cannabidiol is used as a supplement in the form of oils, capsules, and edibles for its potential health benefits. It is believed to support overall well-being and may help with sleep, stress reduction, and general health maintenance.
Used in Veterinary Medicine:
Cannabidiol is used as a treatment option for pets, particularly for conditions like anxiety, arthritis, and epilepsy. It is believed to provide relief and improve the quality of life for animals suffering from these conditions.
Used in Drug Delivery Systems:
Cannabidiol can be incorporated into various drug delivery systems, such as transdermal patches, inhalers, and oral sprays, to improve its bioavailability and targeted delivery to specific areas of the body. This can enhance the therapeutic effects of CBD and minimize potential side effects.

Reactivity Profile

CANNABINOL is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Fire Hazard

Flash point data for CANNABINOL are not available, but CANNABINOL is probably combustible.

Biological Activity

CB 1 and CB 1 receptor agonist (K i values are 126 and 211 nM respectively). Inhibits adenylyl cyclase (EC 50 values are 120 and 261 nM for CB 1 and CB 2 receptors respectively) and suppresses immune cell function. Major constituent of cannabis; displays little or no psychotropic activity.

Purification Methods

Cannabinol crystallises from pet ether and sublimes in a vacuum. [Meitzer et al. Synthesis 985 1981, Beilstein 17 II 151, 17 III/IV 1652.]

InChI:InChI=1/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 61595-80-0 cannabinol tert-butyldimethylsilyl ether 
• 63839-83-8 1-hydroxy-9-methyl-3-pentyl-6H-dibenzopyran-6-one 
• 23978-85-0 tetrahydrocannabinolic acid 
• 41935-92-6 cannabinol monomethyl ether 
• 1352573-54-6 8-(2-propenyl)-1-methoxy-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran 
• 1352573-55-7 8-acetyl-1-methoxy-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran 
• 63839-82-7 2'-(1-Hydroxy-1-methyl-ethyl)-5'-methyl-4-pentyl-biphenyl-2,6-diol 
• 1433988-22-7 2-(4-pentylphenyl)-4-methylbenzoic acid 
• 1433988-23-8 3-pentyl-9-methyl-6H-benzo[c]chromen-6-one 
• 1433988-24-9 2-(2-methoxy-4-pentyl)-4-methylbenzoic acid 
• 7697-27-0 2-bromo-4-methylbenzoic acid 
• 121219-12-3 (4-pentylphenyl)boronic acid 
• 1601476-43-0 9-methyl-3-pentyl-1-(prop-2-yn-1-yloxy)-6H-benzo[c]chromene 

Downstream Products

• 2808-39-1 cannabinolic acid 

Relevant academic research and scientific papers

Iodine-Promoted Aromatization of p -Menthane-Type Phytocannabinoids

Treatment with iodine cleanly converts various p-menthane-type phytocannabinoids and their carboxylated precursors into cannabinol (CBN, 1a). The reaction is superior to previously reported protocols in terms of simplicity and substrate range, which inclu

METHODS FOR SELECTIVE AROMATIZATION OF CANNABINOIDS

The present invention relates to methods of selective aromatization of cannabinoids. Such methods may be used, among other purposes, for the removal of delta-9-tetrahydrocannabinol from hemp extracts or other samples by selectively converting delta-9-tetrahydrocannabinol to cannabinol using ortho-quinone catalysts.

APPARATUS FOR CANNABINOL GENERATION AND METHODS OF USING THE SAME

The present disclosure methods for producing cannabinol from Cannabis compositions. The present disclosure further provides apparatuses for the production of cannabinol from Cannabis compositions.

METHODS OF PREPARING SYNTHETIC CANNABINOL AND HOMOLOGS THEREOF

The present disclosure relates to the preparation of synthetic cannabinol and homologs thereof having the structure of Formula (I), wherein, n is 1, 2, 3 or 4. The methods described herein provide for high yields and purity in a one-pot synthesis or high yields and purity without the need for lengthy column chromatography. The present disclosure also relates to solid forms of cannabinol.

Sars for the antiparasitic plant metabolite pulchrol. 3. combinations of new substituents in a/b-rings and a/c-rings

The natural products pulchrol and pulchral, isolated from the roots of the Mexican plant Bourreria pulchra, have previously been shown to possess antiparasitic activity towards Try-panosoma cruzi, Leishmania braziliensis and L. amazonensis, which are protozoa responsible for Chagas disease and leishmaniasis. These infections have been classified as neglected diseases, and still require the development of safer and more efficient alternatives to their current treatments. Recent SARs studies, based on the pulchrol scaffold, showed which effects exchanges of its substituents have on the antileishmanial and antitrypanosomal activity. Many of the analogues prepared were shown to be more potent than pulchrol and the current drugs used to treat leishmaniasis and Chagas disease (miltefosine and benznidazole, respectively), in vitro. Moreover, indications of some of the possible interactions that may take place in the binding sites were also identified. In this study, 12 analogues with modifications at two or three different positions in two of the three rings were prepared by synthetic and semi-synthetic procedures. The molecules were assayed in vitro towards T. cruzi epimastigotes, L. braziliensis promastigotes, and L. amazonensis promastigotes. Some compounds had higher antiparasitic activity than the parental compound pulchrol, and in some cases even benznidazole and miltefosine. The best combinations in this subset are with carbonyl functionalities in the A-ring and isopropyl groups in the C-ring, as well as with alkyl substituents in both the A-and C-rings combined with a hydroxyl group in position 1 (C-ring). The latter corresponds to cannabinol, which indeed was shown to be potent towards all the parasites.

METHODS FOR CONVERTING TETRAHYDROCANNABINOLIC ACID INTO CANNABINOLIC ACID

Disclosed herein is a method for converting tetrahydrocannabinolic acid (THCA) to cannabinolic acid (CBNA). The method comprises contacting an input material comprising THCA with a benzoquinone reagent under reaction conditions comprising: (i) a reaction temperature that is within a target reaction-temperature range; and (ii) a reaction time that is within a target reaction-time range, to provide an output material in which at least a portion of the THCA from the input material has been converted into CBNA.

Conversion of Δ9-THC to Δ10-THC

Methods of converting Δ9-THC to Δ10-THC are described and the products disclosed. The methods do not affect existing CBD or CBG in the extract. Various adjustments can be made to the reactions resulting in increased or decreased product and by-product.

Photochemistry of Cannabidiol (CBD) Revised. A Combined Preparative and Spectrometric Investigation

Cannabis is a plant with an astonishing ability to biosynthesize cannabinoids, and more than 100 molecules belonging to this class have been isolated. Among them in recent years cannabidiol (CBD) has received the interest of pharmacology as the major nonpsychotropic cannabinoid with many potential clinical applications. Although the reactivity of CBD has been widely investigated, only little attention has been given to the possible photodegradation of this cannabinoid, and the data available in the literature are outdated and, in some cases, conflicting. The aim of the present work is providing a characterization of the photochemical behavior of CBD in organic solvents, through a detailed GC-MS analyses, isolation, and NMR characterization of the photoproducts obtained.

Activity of THC, CBD, and CBN on Human ACE2 and SARS-CoV1/2 Main Protease to Understand Antiviral Defense Mechanism

THC, CBD, and CBN were reported as promising candidates against SARS-CoV2 infection, but the mechanism of action of these three cannabinoids is not understood. This study aims to determine the mechanism of action of THC, CBD, and CBN by selecting two essential targets that directly affect the coronavirus infections as viral main proteases and human angiotensin-converting enzyme2. Tested THC and CBD presented a dual-action action against both selected targets. Only CBD acted as a potent viral main protease inhibitor at the IC 50value of 1.86 ± 0.04 μM and exhibited only moderate activity against human angiotensin-converting enzyme2 at the IC 50value of 14.65 ± 0.47 μM. THC acted as a moderate inhibitor against both viral main protease and human angiotensin-converting enzymes2 at the IC 50value of 16.23 ± 1.71 μM and 11.47 ± 3.60 μM, respectively. Here, we discuss cannabinoid-associated antiviral activity mechanisms based on in silico docking studies and in vitro receptor binding studies.

Antioxidant function of phytocannabinoids: Molecular basis of their stability and cytoprotective properties under UV-irradiation

In this contribution, a comprehensive study of the redox transformation, electronic structure, stability and photoprotective properties of phytocannabinoids is presented. The non-psychotropic cannabidiol (CBD), cannabigerol (CBG), cannabinol (CBN), cannabichromene (CBC), and psychotropic tetrahydrocannabinol (THC) isomers and iso-THC were included in the study. The results show that under aqueous ambient conditions at pH 7.4, non-psychotropic cannabinoids are slight or moderate electron-donors and they are relatively stable, in the following order: CBD > CBG ≥ CBN > CBC. In contrast, psychotropic Δ9-THC degrades approximately one order of magnitude faster than CBD. The degradation (oxidation) is associated with the transformation of OH groups and changes in the double-bond system of the investigated molecules. The satisfactory stability of cannabinoids is associated with the fact that their OH groups are fully protonated at pH 7.4 (pKa is ≥ 9). The instability of CBN and CBC was accelerated after exposure to UVA radiation, with CBD (or CBG) being stable for up to 24 h. To support their topical applications, an in vitro dermatological comparative study of cytotoxic, phototoxic and UVA or UVB photoprotective effects using normal human dermal fibroblasts (NHDF) and keratinocytes (HaCaT) was done. NHDF are approx. twice as sensitive to the cannabinoids’ toxicity as HaCaT. Specifically, toxicity IC50 values for CBD after 24 h of incubation are 7.1 and 12.8 μM for NHDF and HaCaT, respectively. None of the studied cannabinoids were phototoxic. Extensive testing has shown that CBD is the most effective protectant against UVA radiation of the studied cannabinoids. For UVB radiation, CBN was the most effective. The results acquired could be used for further redox biology studies on phytocannabinoids and evaluations of their mechanism of action at the molecular level. Furthermore, the UVA and UVB photoprotectivity of phytocannabinoids could also be utilized in the development of new cannabinoid-based topical preparations.