Allylprodine

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Allylprodine
Allylprodine.svg
Systematic (IUPAC) name
(1-Methyl-4-phenyl-3-prop-2-enylpiperidin-4-yl) propanoate
Clinical data
Legal status
Identifiers
CAS Number 25384-17-2 YesY
ATC code None
PubChem CID 32938
DrugBank DB01542 YesY
ChemSpider 30495 YesY
UNII 4343OEZ18O YesY
ChEMBL CHEMBL2103995
Synonyms Allylprodine
Chemical data
Formula C18H25NO2
Molar mass 287.397 g/mol
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Allylprodine[1] is an opioid analgesic that is an analog of prodine. It was discovered in 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 bind at different sites of the opiate receptor.

Allylprodine is more potent as an analgesic than similar drugs such as α-prodine, and the 3R,4S-isomer is 23 times more potent than morphine, due to the allyl group binding to an additional amino acid target in the binding site on the μ-opioid receptor. It is also stereoselective, with one isomer being much more active.[2][3] When modeled in three dimensions, the alkene overlays the alkenes found in 14-cinnamoyloxycodeinone and in 14-allyloxycodeinone, re-enforcing the presence of an interaction of the alkene.[citation needed]

Allylprodine produces similar effects to other opioids, such as analgesia and sedation, along with side effects such as nausea, itching, vomiting and respiratory depression which may be harmful or fatal.

References[edit]

  1. ^ U.S. Patent 2,798,073 - PIPERIDINE DERIVATIVES AND PREPARATION
  2. ^ Portoghese, P. S.; Shefter, E (1976). "Stereochemical studies on medicinal agents. 19. X-ray crystal structures of two (+/-)-allylprodine diastereomers. The role of the allyl group in conferring high stereoselectivity and potency at analgetic receptors". Journal of Medical Chemistry 19 (1): 55–7. doi:10.1021/jm00223a012. PMID 1246054. 
  3. ^ Portoghese, P. S.; Alreja, B. D.; Larson, D. L. (1981). "Allylprodine analogues as receptor probes. Evidence that phenolic and nonphenolic ligands interact with different subsites on identical opioid receptors". Journal of Medical Chemistry 24 (7): 782–7. doi:10.1021/jm00139a004. PMID 6268787.