Structure via PubChem · Public domain (PubChem)
allylprodine
Sign in to saveAllylprodine is an opioid analgesic that is an analog of prodine. It was discovered by Hoffman-La Roche in 1957 during research into the related drug pethidine. Derivatives were tested to prove the theory that phenolic and non-phenolic opioids bind at different sites of the opiate receptor.
Chemical data
- Formula
- C18H25NO2
- Molecular weight
- 287.4 g/mol
- IUPAC name
- (1-methyl-4-phenyl-3-prop-2-enylpiperidin-4-yl) propanoate
- SMILES
- CCC(=O)OC1(CCN(CC1CC=C)C)C2=CC=CC=C2
- InChIKey
- KGYFOSCXVAXULR-UHFFFAOYSA-N
- XLogP
- 3
- Polar surface area
- 29.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 287.188529
Show 3 more facts
- chemical formula
- C₁₈H₂₅NO₂
- canonical SMILES
- CCC(=O)OC1(CCN(CC1CC=C)C)C2=CC=CC=C2
- Commons category
- Allylprodine
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Legal status
- Australia
- Germany
- References
Allylprodine is an opioid analgesic that is an analog of prodine. It was discovered by Hoffman-La Roche in 1957 during research into the related drug pethidine. Derivatives were tested to prove the theory that phenolic and 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.
Excerpted from Wikipedia’s “allylprodine” article, available under the CC BY-SA 4.0 licence.