Allylprodine

Title: Allylprodine
CAS Registry Number: 25384-17-2
CAS Name: 1-Methyl-4-phenyl-3-(2-propenyl)-4-piperidinol propanoate
Additional Names: a-3-allyl-1-methyl-4-phenyl-4-propionoxypiperidine; a-3-allyl-1-methyl-4-phenyl-4-piperidinol propionate
Manufacturers' Codes: NIH-7440; Ro-2-7113
Molecular Formula: C18H25NO2
Molecular Weight: 287.40
Percent Composition: C 75.22%, H 8.77%, N 4.87%, O 11.13%
Literature References: Narcotic analgesic. Prepn: Ziering et al., J. Org. Chem. 22, 1521 (1957); Lee, Ziering, US 2798073 (1957 to Hoffmann-La Roche).
Derivative Type: Hydrochloride
Molecular Formula: C18H25NO2.HCl
Molecular Weight: 323.86
Percent Composition: C 66.75%, H 8.09%, N 4.32%, O 9.88%, Cl 10.95%
Properties: Crystals from acetone + methanol, mp 186-187°.
Melting point: mp 186-187°
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.11.
Allylurea Almagate Alminoprofen Almond, Bitter Almond, Sweet

Allylprodine
Allylprodine.svg
Systematic (IUPAC) name
(1-methyl-4-phenyl-3-prop-2-enylpiperidin-4-yl) propanoate
Clinical data
Legal status Class A (UK) Schedule I (US)
Identifiers
CAS number 25384-17-2 YesY
ATC code None
PubChem CID 32938
DrugBank DB01542
ChemSpider 30495 YesY
UNII 4343OEZ18O YesY
Synonyms Allylprodine
Chemical data
Formula C18H25NO2 
Mol. mass 287.397 g/mol
 YesY (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 (the 3R,4S isomer is 23 times more potent than morphine) than 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.