Allylprodine

Structural formula
Mixture of four stereoisomers - structural formula without stereochemistry
General
Non-proprietary name	Allylprodine
other names	(3-Allyl-1-methyl-4-phenyl-4-piperidyl) propionate 1-methyl-4-phenyl-3- (2-propenyl) -4-piperidinol propanoate
Molecular formula	C 18 H 25 NO 2
External identifiers / databases
CAS number 25384-17-2 66679-16-1 (3 R , 4 S ) 42013-68-3 (3 R , 4 S ) • HCl 50895-13-1 (3 S , 4 R ) • HCl 53611-18-0 (3 RS , 4 SR ) = (3 R * , 4 S * ) PubChem 32938 ChemSpider 30495 DrugBank DB01542 Wikidata Q4062649
Drug information
Drug class	Analgesic , opioid
Mechanism of action	µ receptor - agonist
properties
Molar mass	287.40 g · mol -1
Physical state	firmly
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Allylprodine (ger .: Allylprodine ) is a fully synthetic opioid - analgesic and a structural analogue to Prodin (ger .: Prodine ). In terms of substance, it belongs to the pethidine group, which also includes alphaprodin (α-prodin) and betaprodin (β-prodin). It was discovered by John Lee and Albert Ziering on behalf of Hoffmann-La Roche in 1957 while researching pethidine, with the aim of further delineating the role of the allyl group in the interaction of allylprodine with pain receptors.

As an analgesic, allylprodine is much stronger than similar drugs such as α-prodine, with the (3 R , 4 S ) isomer being up to 23 times stronger due to the binding of the allyl group to an additional amino acid at the binding site of the μ-opioid receptor than morphine . Furthermore, it is more stereoselectively active with one isomer.

Effects

Allylprodine produces effects similar to other opioids, i.e. analgesia (pain relief) and sedation (calming). Side effects can include nausea, itching, vomiting and constipation (constipation). It can also cause dangerous respiratory depression , which can be harmful or fatal.

Legal status

In Germany, allylprodine is listed as a non-marketable narcotic in Appendix 1 to the Narcotics Act and can therefore not be prescribed.

Trade names

• Allylprodine
• Allylprodine Hydrochloride

Individual evidence

1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
2. ^ PH List, L. Hörhammer: Hager's Handbook of Pharmaceutical Practice ( limited preview in Google book search).
3. ↑ Patent US 2798073 A : Piperidine derivatives and preparation .
4. ^ PS Portoghese, E Shefter: 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 . In: Journal of Medical Chemistry . 19, No. 1, 1976, pp. 55-57. doi : 10.1021 / jm00223a012 . PMID 1246054 .
5. ↑ PS Portoghese, BD Alreja, DL Larson: Allylprodine analogues as receptor probes. Evidence that phenolic and nonphenolic ligands interact with different subsites on identical opioid receptors . In: Journal of Medical Chemistry . 24, No. 7, 1981, pp. 782-787. doi : 10.1021 / jm00139a004 . PMID 6268787 .