Cannabis Cannabinol

Cannabinol, A -3,4-trans-tetrahydro-biological activity, 3, 877 Cannabinol, (—)-A -3,4- ran5-tetrahydro-as pharmaceutical, 1, 151 Cannabinolic acid synthesis, 3, 721 Cannabinolic acid, tetrahydro-photochemistry, 3, 721 Cannabis, citrylidene-, 3, 675 Cantharidin synthesis, 1, 440 Capillarin occurrence, 3, 677 ozonolysis, 3, 681... 

Group of compounds which naturally occur in the hemp plant, Cannabis saiiva. Most of them are unsoluble in water. The most abundant cannabinoids are A9--tetrahydrocannabinol (THC), its precursor cannabidiol and cannabinol, which is formed spontaneously from THC. Cannabinoids exert their effects through G-protein coupled cannabinoid receptors (CBi/CB2). 

A few studies have been conducted on cannabis and its derivatives. Alozie et al. (3) measured the radioactivity accumulated in various brain areas following the intravenous injection of 3H-THC, 3H-cannabinol, and 3H-cannabidiol to adult male rats. Five minutes after injection, these three labeled compounds exhibited a homogeneous distribution in brain, suggesting that no specific binding occurred. Such studies must be completed by examining the time course of the evolution of 3H-cannabis derivatives in various brain areas before any firm conclusion can be drawn. 

Gas chromatography coupled to tandem mass spectrometry (GC-MS/MS [49]) prior to analysis of the three primary active components of cannabis (THC, cannabidiol and cannabinol) by this technique, airborne particulates were extracted in an ultrasonic bath with chloroform. The extracts were combined and concentrated under a stream of nitrogen. The residue was filtered through pre-washed disposable PTFE membranes, dried and finally reconstituted with cyclohexane. After separation and solvent partitioning, the extracts were analysed by GC-MS/MS. 

Until the mid 1960 s the only plant cannabinoid whose structure was fully elucidated was cannabinol (CBN) — a constituent which actually may represent an oxidation artifact. However, on the basis of CBN, the main cannabinoid structure skeleton became known. Thus, cannabidiol (CBD), which had been independently isolated in pure form by Adams and by Todd, was correctly assumed to be, like CBN, a terpenoid derivative attached to olivetol. But its exact structure was not elucidated. The psychoactive components of cannabis were assumed to be related tricyclic derivatives. On the basis of the tentatively elucidated constituents, Todd suggested that the cannabinoids may be formed initially in the plant by condensation of a menthatriene with olivetol. 

Yamauchi et al demonstrated that the neutral cannabinoids and cannabinolic acid are artifacts produced from cannabinoid acids during the harvest and storage of cannabis. 

The first successful attempt to identify a typical cannabis constituent (today called cannabinoid) was achieved by Wood who isolated cannabinol... 

A second cannabis constituent, cannabidiol (CBD) was also isolated, but its structure was only partially clarified. Synthetic tetrahydro-cannabinols, which showed cannabis-like activity in animal tests, were prepared, but they obviously differed from the active natural product, on the basis of their UV spectrum. 

Cahn RS, Cannabis indica resin, Part 111. The constitution of Cannabinol, J Chem Soc 1342-1353, 1932. 

Jacob A, Todd AR, Cannabis indica. Part 11. Isolation of Cannabidiol from Egyptian Hashish. Observations on the Structure of Cannabinol, J Chem Soc... 

Ghosh R, Todd AR, Wilkinson S, Cannabis indica. Part v. The synthesis of cannabinol, / Soc, 1393-1396, 1940. 

THC-Delta 9-tetrahydro-cannabinol (cannabis) Cannabinoid receptor Relaxation, euphoria, and enhancement of senses, increase in appetite, sense of time... 

CS004 Shoyama, Y., T. Yamauchi and I. Nishioka. Cannabis. V. Cannab-igerolic acid monomethyl ether and cannabinolic acid. Chem Pharm Bull 1970 18 1327-1332. 

Itokawa, H., K. Takeya and M. Akasu. Studies on the constituents isolated from the callus of Cannabis sativa. Shoyakugaku Zasshi 1975 29 106-112. Stromberg, L. Minor components of cannabis resin. VI. Mass spectrometric data and gas chromatographic retention times of components eluted after cannabinol. J Chromatogr 1976 121 313. 

Gigliano, G. S. Cannabinols in Cannabis sativa L. under different cultivation conditions. Bull Chem Farm 1984 123(7) 352-356. 

El Sohly, M. A., J. H. Holley and C. E. Turner. Constituents of Cannabis sa tiva L. XXVI. The delta-9-tetrahydro-cannabinol content of confiscated marijuana, 1974-1983. Proc Oxford Symp Cannabis 1985 1984 37-42. Morita, M. and H. Ando. Analysis of hashish oil by gas chromatography / mass spectrometry. Kagaku Keisatsu Kenkyusho Hokoku Hokagaku Hen 1984 37(2) 137-140. 

Capillary gas chromatography of natural substances from Cannabis sativa L. I. Cannabinol and cannabinolic acid— Artefacts. Acta Univ Palacki Olomuc EacMed 1985 108(52) 29-38. 

A -3,4-cis-THC has now been found in Cannabis sativa (Phenotype III) other papers reporting the characterization of compounds from Cannabis sativa concern conclusive identification and synthesis of cannabinodiol, " which is known to result from the photochemical irradiation of cannabinol (Vol. 7, p. 51), and the identification of A -tetrahydrocannabinolic acid " and (+)-cannabitriol (263) " (263) and the corresponding C-2 ethyl ether may be epoxide-derived. " ... 

Cannabis chinensis Del. C. sativa L. Huo Ma Ren or Da Ma Ren (Hemp) (fruit, seed) Vitamin Bj, vitamin B2, muscarine, choline, trigonelline, l(d)-isoleucine betaine, cannabinol, tetra-hydrocannobinol, cannabidiol.33-450 Purgative, stimulate intestinal mucosa causing an increase in secretions and peristalsis. 

At least 60 bioactive compounds are contained in herbal cannabis. A9-Tetrahydrocannabinol (A9-THC) (Mechoulam and Gaoni, 1967), cannabidiol and cannabinol are the major psychoactive or adjuvant ingredients. Cannabinoids act through at least two different G-protein coupled receptors named CBi and CB2 receptors. 

Cannabis resin, obtained from the flowering tops of hemp plants, contains a number of dibenzopyrans. The main active constituent is (-)-A1-3,4-numbering system is used). Cannabinol derivatives have slight pharmaceutical potential, e.g. as antiemetics and analgesics, but because of their hallucinatory effects and habituation tendency, which have led to their widespread abuse, they are not prescribed. 

The physiologically active component of cannabis is A -S -rrans-tetrahydrocannabinol, but cannabinol, into which the other less stable cannabinoids change as the plant ages, is inactive. Recent advances in cannabinoids have been reviewed (B-73MI22402) and a survey of the whole area of cannabinoids has been published (76CRV75). 

The opium alkaloids codeine and morphine served as models for the synthesis of naloxone, an important analog used to treat and diagnose opiate addicts, and also led to the discovery of endogenous opioids (enkephalins and endorphins) (see Chapter 47). Similarly, A9-tetrahydro-cannabinol (THC), the component of Cannabis sativa responsible for the central nervous system (CNS) effect, has also been found to reduce nausea associated with cancer chemotherapy (see Chapter 18). 

More than 400 chemical compounds have been identified in marijuana. Approximately 60 of these are unique to the cannabis plant, substances called cannabinoids. Of the cannabinoids, a group of isomers (chemically similar substances) called tetrahydro-cannabinols (THC) are thought to be the most psychoactive. These are Ai-THC (also called A9-THC) and A6-THC (also called A8-THC). Other cannabinoids include cannabidiolic acid (CBDA), cannabidiol (CBD), and cannabinol (CBN). Their role in marijuana intoxication is less well understood. The amount of THC produced depends on the strain of cannabis and on environmental factors such as growth, harvest, and storage conditions. 

The psychoactive and medicinal chemical compounds found in the resin of the marijuana plant are known as cannabinoids. The cannabis plant contains more than 460 known compounds over 60 of these have a cannabinoid structure. The only cannabinoid that is highly psychoactive and present in large amounts in the resin of the cannabis plant is tetrahydrocannabinol, or THC. The other two major cannabinoids are the cannabidiols and the cannabinols. It appears that the cannabis plant first produces the mildly active cannabidiols, which are converted to the more psychoactive THCs and then broken down to relatively inactive... 

The main active ingredients of cannabis are cannabinol, cannabidiol and several isomers of tetrahydrocannabinol, of which delta-9-tetrahydro-cannabinol (THC) is probably responsible for most of the psychoactive effects of the various preparations. It is of interest to note that THC does not contain nitrogen in its three-membered ring system. The structure of THC is shown in Figure 15.8. 

Derivative or preparation from Cannabis sativa. This contains several dozen that are chemically related to cannabinol. 

Phytocannabinoids are natural compounds present in Cannabis sativa, responsible for the pharmacological and toxicological properties of this plant. About 70 compounds belong to this class, the most important are A9-tetrahydrocannabinol (THC), cannabinol (CBN), and cannabidiol (CBD). 

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