Cannabinoids naturally occurring

Revision Problem 8 TM 406 is a synthetic intermediate related to the cannabinoids, naturally occurring hallucinogenic compounds. How could it be synthesised ... 

Monoclonal antibodies against naturally occurring cannabinoids, partly saturated annelated pyrans, marichuana components 99YGK708. 

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). 

Knobloch. Comparative analgesic activity of various naturally occurring cannabinoids in mice and rats. Psychopharmacologia 1975 40 285. 

Some naturally occurring neurotransmitters may be similar to drugs we use. For example, it is well known that the brain makes its own morphine (i.e., beta endorphin), and its own marijuana (i.e., anandamide). The brain may even make its own antidepressants, it own anxiolytics, and its own hallucinogens. Drugs often mimic the brain s natural neurotransmitters. Often, drugs are discovered prior to the natural neurotransmitter. Thus, we knew about morphine before the discovery of beta-endorphin marijuana before the discovery of cannabinoid receptors and anandamide the benzodiazepines diazepam (Valium) and alprazolam (Xanax) before the discovery of benzodiazepine receptors and the antidepressants amitriptyline (Elavil) and fluoxetine (Prozac) before the discovery of the serotonin transporter site. This un-... 

Among the long list of diverse structures reported to possess central antitussive activity is Ahtetrahydrocannabinol (THC) [1972-08-3] (68), the principal psychoactive component of marijuana (see PSYCHOPHARMACOLOGICALAGENTS). This compound was found to be comparable to codeine against electrically induced cough in the anesthetized cat (90). Two other naturally occurring cannabinoids, cannabidiol and cannabinol, are inactive. 

Cannabinoids may also cause effects via mechanisms distinct from the cannabinoid receptor pathways. The most extensively investigated compound is (+)-HU 211, a synthetic cannabinoid with a stereochemistry opposite to that present in the naturally occurring compounds. It does not produce THC-type effects in animals and shows insignificant binding to the CB, receptor. However, HU 211 blocks A-methyl-n-aspartate (NMDA) receptors and calcium uptake through the NMDA-receptor-ion channel in primary cell cultures. HU 211 is a potent blocker of NMDA-induced tremor, seizures, and lethality in mice. It may therefore prove useful as a nonpsychoactive drug that protects against NMDA-receptor-mediated neurotoxicity. This is supported by the potent attenuation of NMDA-receptor-mediator neurotoxicity in cell cultures by HU 211. 

Figure 19.1. Chemical structure of main active ingredient of Cannabis sativa, A9-tetrahydrocannabinol (THC) and the naturally occurring ligand for cannabinoid receptors anandamide (arachidonyl ethanolamide).

Pure polyunsaturated fatty acid amides and their derivatives. These synthcally produced compounds are able to mimic naturally occuring anandamides in the brain and bind the cannabinoid receptor. The compounds exhibit physiological activity and are useful as active ingredients in pharmaceutical compositions for the treatment of inflammation, migraines, spasticity activity, glaucoma, multiple sclerosis. 

Tetrahydrocannabinol (THC), the psychoactive marijuana plant- derived cannabinoid, and numerous synthetic derivatives have been shown to bind to a specific brain receptor, cannabinoid receptor 1 (CBl) (Howlett et al. 1990 Matsuda et al. 1990 Herkenham et al. 1990 Mailleux and Vanderhagen 1992). Arachidonoyl ethanolamide (anandamide), homo—linolenyl ethanolamide, and docosatetraenyl ethanolamide are naturally occurring brain constituents that bind to CBl and as a class are called the anandamides (Mechoulam et al. 

The southern aliphatic hydroxyl (SAH) pharmacophore is absent in the naturally occurring cannabinoids. To study more precisely the stereochemical requirements of this new pharmacophore, Makriyannis and co-workers designed a group of hybrid ligands that incorporated all of the structural features of both classical and non-classical cannabinoids (Drake et al. 1998 Tins et al. 1995,1994). 

Fig. 1. Some naturally occurring cannabinoids. The top three compounds are by far the most important, with the set of three compounds below being identical except that the side chain is shortened by 2 carbon atoms in the cannabidivarol series. Later in the text look for a discussion of the series with the propyl side chain, and see the Appendix for the numbering system used. (Reprinted, by permission, from R. Mechoulam, Mar/yt/ana, 1973.)...

Fig. 2. Other naturally occurring cannabinoids. (Reprinted, by permission, from R. Mechoulam, Marijuana, 1973.)...

Dronabinol (delta-9-tetrahydrocannabinol marinol) is a naturally occurring cannabinoid that can be synthesized chemically or extracted from the marijuana plant. Cannabis sativa. The antiemetic action of dronabinol probably relates to stimulation of the CBj subtype of cannabinoid receptors on neurons in and around the vomiting center. 

One important discovery took place during the 1990s when scientists found naturally occurring cannabinoid molecules in mammals, including humans, and cannabinoid receptors in the brain and the body. Researchers identified about half a dozen of these cannabinoids in the human body, which made them want to look more closely at the hundreds of cannabinoids found in marijuana. Scientists want to learn more about why the body has these natural relatives of the cannabinoids in marijuana. Further, pharmaceutical companies want to know if the cannabinoids in marijuana can help the body s own cannabinoids for some therapeutic purposes. Recent research has found, for instance, evidence that some cannabinoids, both the body s own and those found in marijuana, can control some movement disorders, such as Parkinson s disease and Tourette s syndrome, and researchers have also found indications... 

Cannabis Cannabis sativa) has a long history of medicinal and non-medicinal use and records date back 4,000 years. Naturally occurring cannabis contains a unique class of compounds known as cannabinoids. Over 60 members of this family have been identified but only a few have been well studied. The two best known and most studied cannabinoids are delta-9-tet-rahydrocannabinol (THC) and cannabidiol (CBD) (Fig. 1). These two compoimds show markedly different pharmacological activity. THC is best known for its psycho-activity but also displays analgesic, anti-spasmodic, anti-tremor, anti-inflammatory, and anti-emetic activity. CBD... 

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