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Allylprodine
Systematic (IUPAC) name
(1-methyl-4-phenyl-3-prop-2-enylpiperidin-4-yl) propanoate
Identifiers
CAS number 25384-17-2
ATC code none
PubChem 32938
ChemSpider 30495
Chemical data
Formula C 18H25NO2  
Mol. mass 287.397 g/mol
SMILES eMolecules & PubChem
Synonyms Allylprodine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Class A (UK)
Routes  ?

Allylprodine is an opioid analgesic that is an analogue of prodine. It was developed in the 1970s during research into the related drug pethidine.

Allylprodine is more potent as an analgesic than other similar drugs such as α-prodine, 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.[1][2]

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

  1. ^ Portoghese PS, Shefter E. 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 Medicinal Chemistry. 1976 Jan;19(1):55-7.
  2. ^ Portoghese PS, Alreja BD, Larson DL. Allylprodine analogues as receptor probes. Evidence that phenolic and nonphenolic ligands interact with different subsites on identical opioid receptors. Journal of Medicinal Chemistry. 1981 Jul;24(7):782-7.
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