Allylprodine

Allylprodine
Clinical data
Other names	Allylprodine
ATC code	none;
Legal status
Legal status	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-enylpiperidin-4-yl) propanoate;
CAS Number	25384-17-2 ;
PubChem CID	32938;
DrugBank	DB01542 ;
ChemSpider	30495 ;
UNII	4343OEZ18O;
ChEMBL	ChEMBL2103995;
CompTox Dashboard (EPA)	DTXSID80865210 ;
ECHA InfoCard	100.291.534
Chemical and physical data
Formula	C18H25NO2
Molar mass	287.397 g/mol 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 ; Key:KGYFOSCXVAXULR-UHFFFAOYSA-N ;
	(verify)

Allylprodine^[1] 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.^[2]^[3] 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.

Allylprodine is regulated in most countries as is morphine, including being in Schedule I of the US Controlled Substances Act 1970 as a Narcotic with ACSCN 9602 and a 2014 annual aggregate manufacturing quota of 2 grammes.^[4]

References

^ U.S. patent 2,798,073 - PIPERIDINE DERIVATIVES AND PREPARATION
^ Portoghese, P. S.; Shefter, E (1976). "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. 19 (1): 55–7. doi:10.1021/jm00223a012. PMID 1246054.
^ Portoghese, P. S.; Alreja, B. D.; Larson, D. L. (1981). "Allylprodine analogues as receptor probes. Evidence that phenolic and nonphenolic ligands interact with different subsites on identical opioid receptors". Journal of Medicinal Chemistry. 24 (7): 782–7. doi:10.1021/jm00139a004. PMID 6268787.
^ http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm

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[1] U.S. patent 2,798,073 - PIPERIDINE DERIVATIVES AND PREPARATION

[2] Portoghese, P. S.; Shefter, E (1976). "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. 19 (1): 55–7. doi:10.1021/jm00223a012. PMID 1246054.

[3] Portoghese, P. S.; Alreja, B. D.; Larson, D. L. (1981). "Allylprodine analogues as receptor probes. Evidence that phenolic and nonphenolic ligands interact with different subsites on identical opioid receptors". Journal of Medicinal Chemistry. 24 (7): 782–7. doi:10.1021/jm00139a004. PMID 6268787.

[4] ttp://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm

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