Allylprodine

Allylprodine

Systematic (IUPAC) name
(1-methyl-4-phenyl-3-prop-2-enylpiperidin-4-yl) propanoate
Clinical data
Pregnancy cat.	?
Legal status	? (UK) Schedule I (US)
Identifiers
CAS number	25384-17-2 Y
ATC code	None
PubChem	CID 32938
DrugBank	DB01542
ChemSpider	30495 Y
UNII	4343OEZ18O Y
Synonyms	Allylprodine
Chemical data
Formula	C18H25NO2
Mol. mass	287.397 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C18H25NO2/c1-4-9-16-14-19(3)13-12-18(16,21-17(20)5-2)15-10-7-6-8-11-15/h4,6-8,10-11,16H,1,5,9,12-14H2,2-3H3 Y Key:KGYFOSCXVAXULR-UHFFFAOYSA-N Y
Y(what is this?)  (verify)

Allylprodine^[1] is an opioid analgesic that is an analogue 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 (23 times morphine) 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.^[2][3]

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.

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References

1. ^ US Patent 2798073 - PIPERIDINE DERIVATIVES AND PREPARATION
2. ^ 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.
3. ^ 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.