Allylprodine

Allylprodine

Systematic (IUPAC) name
(1-Methyl-4-phenyl-3-prop-2-enylpiperidin-4-yl) propanoate
Clinical data
Legal status	DE: Anlage I (Controlled) UK: Class A US: Schedule I
Identifiers
CAS Number	25384-17-2 Y
ATC code	none
PubChem	CID: 32938
DrugBank	DB01542 Y
ChemSpider	30495 Y
UNII	4343OEZ18O Y
ChEMBL	CHEMBL2103995
Synonyms	Allylprodine
Chemical data
Formula	C18H25NO2
Molecular mass	287.397 g/mol
SMILES O=C(CC)OC1(CCN(C)CC1CC=C)C2=CC=CC=C2
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
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Allylprodine 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. 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.

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.