14-Cinnamoyloxycodeinone is the most potent example in a series of
opiate
An opiate, in classical pharmacology, is a substance derived from opium. In more modern usage, the term ''opioid'' is used to designate all substances, both natural and synthetic, that bind to opioid receptors in the brain (including antagonis ...
analgesic
An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...
drugs discovered in the 1960s, with > ×100 times the potency of
morphine
Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a analgesic, pain medication, and is also commonly used recreational drug, recreationally, or to make ...
.
It is a derivative of , being the 14-
cinnamate
Cinnamic acid is an organic compound with the formula C6H5-CH=CH- COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs na ...
ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
.
In another paper, Buckett assigns the potency as 177 with a range (depending on animal and test) of ×101 - ×310.
It may be of interest to researchers that the allyl group in this compound and in
allylprodine
Allylprodine is an opioid analgesic that is an analog of prodine. It was discovered by Hoffman-La Roche in 1957 during research into the related drug pethidine. Derivatives were tested to prove the theory that phenolic & non-phenolic opioids bi ...
overlay very closely.
See also
*
14-Phenylpropoxymetopon
*
7-PET
7-PET is an opioid analgesic drug that has 300 times the potency of morphine by weight. It was discovered by K.W. Bentley and is related to the more well known oripavine derivative etorphine, which is used as a veterinary painkiller and anestheti ...
*
N-Phenethylnormorphine
''N''-Phenethylnormorphine is an opioid analgesic drug derived from morphine by replacing the ''N''-methyl group with β-phenethyl. It is around eight to fourteen times more potent than morphine as a result of this modification, in contrast to m ...
*
N-Phenethyl-14-ethoxymetopon
''N''-Phenethyl-14-ethoxymetopon is a drug that is a derivative of metopon. It is a potent analgesic, around 60 times stronger than morphine and produces significantly less constipation.
''N''-Phenethyl-14-ethoxymetopon acts as an agonist at b ...
*
Phenomorphan
Phenomorphan is an opioid analgesic. It is not currently used in medicine, but has similar side-effects to other opiates, which include itching, nausea and respiratory depression.
Phenomorphan is a highly potent drug due to the N-phenethyl group, ...
*
RAM-378
RAM-378(7,8-Dihydro-14-hydroxy-N-phenethylnormorphine) is an opioid analgesic. It is the N-phenethyl derivative of hydromorphinol.
See also
* 14-Cinnamoyloxycodeinone
* 14-Phenylpropoxymetopon
* 7-PET
* N-Phenethylnormorphine
* N-Phenethyl-14 ...
*
Ro4-1539
Ro4-1539 (furethylnorlevorphanol) is an opioid analgesic drug from the morphinan series that was discovered by the pharmaceutical company Hoffmann–La Roche in the 1950s. It acts as a potent μ-opioid agonist, and was found to be around 30-60 t ...
References
4,5-Epoxymorphinans
Semisynthetic opioids
Mu-opioid receptor agonists
{{Analgesic-stub