Allylprodine

Other namesAllylprodine

ATC code

• none

Legal status

• AU: S9 (Prohibited substance)
• BR: Class A1 (Narcotic drugs)^[1]
• CA: Schedule I
• DE: Anlage I (Authorized scientific use only)
• UK: Class A
• US: Schedule I

CAS Number

• 25384-17-2 ^N

Allylprodine

Clinical data
Other names	Allylprodine
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs)[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I
Identifiers
IUPAC name 1-Methyl-4-phenyl-3-(prop-2-en-1-yl)piperidin-4-yl propanoate
CAS Number	25384-17-2 N
PubChem CID	32938
DrugBank	DB01542 Y
ChemSpider	30495 Y
UNII	4343OEZ18O
KEGG	D12662 Y
ChEMBL	ChEMBL2103995 N
CompTox Dashboard (EPA)	DTXSID80865210
ECHA InfoCard	100.291.534
Chemical and physical data
Formula	C18H25NO2
Molar mass	287.403 g·mol−1
3D model (JSmol)	Interactive image
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
NY (what is this?)  (verify)

Allylprodine^[2] 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.^[3][4] 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.^{[citation needed]}

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.