Allylprodine is an
opioidAn opioid is a psychoactive chemical that works by binding to opioid receptors, which are found principally in the central and peripheral nervous system and the gastrointestinal tract...
analgesicAn analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
that is an
analogueIn chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...
of
prodineProdine is an opioid analgesic that is an analogue of pethidine .There are two isomers of prodine, Alphaprodine and Betaprodine. Betaprodine is some 5x more potent than alphaprodine, but is metabolised more rapidly, and only alphaprodine was developed for medicinal use...
. It was discovered in by Hoffman-La Roche in 1957 during research into the related drug
pethidinePethidine or meperidine Pethidine (INN) or meperidine (USAN) Pethidine (INN) or meperidine (USAN) (commonly referred to as Demerol but also referred to as: isonipecaine; lidol; pethanol; piridosal; Algil; Alodan; Centralgin; Dispadol; Dolantin; Mialgin (in Indonesia); Petidin Dolargan (in Poland);...
. Derivatives were tested to prove the theory that phenolic & non-phenolic opioids bind at different sites of the opiate receptor.
Allylprodine is more potent as an analgesic (23 times morphine) than other similar drugs such as α-prodine, due to the
allylAn allyl group is a substituent with the structural formula H2C=CH-CH2R, where R is the connection to the rest of the molecule. It is made up of a methylene , attached to a vinyl group . The name is derived from the Latin word for garlic, Allium sativum. Theodor Wertheim isolated an allyl...
group binding to an additional amino acid target in the binding site on the
μ-opioid receptorThe μ-opioid receptors are a class of opioid receptors with high affinity for enkephalins and beta-endorphin but low affinity for dynorphins. They are also referred to as μ opioid peptide receptors. The prototypical μ receptor agonist is the opium alkaloid morphine; μ refers to morphine...
. It is also stereoselective, with one
isomerIn chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
being much more active.
Allylprodine produces similar effects to other opioids, such as analgesia and
sedationSedation is the reduction of irritability or agitation by administration of sedative drugs, generally to facilitate a medical procedure or diagnostic procedure...
, along with side effects such as
nauseaNausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...
, itching,
vomitingVomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose...
and respiratory depression which may be harmful or fatal.