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Piperidines, Cannabinoids

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Rimonabant (168273-06-1, 158681-13-1)  
Rimonabant (also known as SR141716; trade names Acomplia, Zimulti) was an anorectic antiobesity drug that was first approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious psychiatric side effects; it was never approved in the United States. Rimonabant is an inverse agonist for the cannabinoid receptor CB1 and was the first drug approved in that class.
AM251 (183232-66-8)  
AM 251  ·  N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxamide  ·  N-(piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide
AM-251 is an inverse agonist at the CB1 cannabinoid receptor. AM-251 is structurally very close to SR141716A (rimonabant); both are biarylpyrazole cannabinoid receptor antagonists. In AM-251 the p-chloro group attached to the phenyl substituent at C-5 of the pyrazole ring is replaced with a p-iodo group.
NABITAN (66556-74-9)  
Nabitan (Nabutam, Benzopyranoperidine, SP-106, Abbott 40656) is a synthetic cannabinoid analog of dronabinol (Marinol). It exhibits antiemetic and analgesic effects, most likely by binding to and activating the CB1 and CB2 cannabinoid receptors, and reduced intraocular pressure in animal tests, making it potentially useful in the treatment of glaucoma. Nabitan has the advantage of being water-soluble, unlike most cannabinoid derivatives, and was researched for potential use as an analgesic or sedative, although it was never developed for clinical use and is not currently used in medicine, as dronabinol or nabilone were felt to be more useful.
MENABITAN (83784-21-8)  
Menabitan (INN; SP-204), or menabitan hydrochloride (USAN), is a synthetic drug which acts as a potent cannabinoid receptor agonist. It is closely related to natural cannabinoids of the tetrahydrocannabinol (THC) group, differing mainly by its longer and branched side chain, and the replacement of the 9-position carbon with a nitrogen. It was studied as an analgesic in the 1970s and was found to possess antinociceptive effects in both humans and animals but was never marketed.
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Piperidines
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