Chemistry:R1317
R1317 is a desmethylprodine analog in which the N-methyl group is replaced by a cinnamyl group. This change in sidechain endows the compound with an increase in potency. The compound is 261 times more potent[clarification needed] than meperidine in mice[1] and 1100 times more potent in rats. In another article it was stated to be 785 times more potent than meperidine.[2]
Despite this high potency, it is not the most potent 4-phenylpiperidine-reverse ester ever created. The most potent 4-phenylpiperidine-reverse ester ever created is R1480.[1] R1480 is stated to have a potency 1500-3180 times higher than meperidine in mice and 3040 times higher in rats.
It was investigated as a candidate for a non-lethal incapacitating agent, but was discarded due to its high toxicity in primates. The substituted 2-nitrocinnamyl, EA 2475, is 282 times more potent (analgesic potency = 28000) and have a therapeutic index superior to remifentanil, in mices, but it is highly toxic and ineffective for primates.[3]
None of these compounds were adopted as incapacitating agents, with the likely agent adopted being the EA 3382.[4]
References
- ↑ 1.0 1.1 "Compounds related to pethidine-IV. New general chemical methods of increasing the analgesic activity of pethidine". Journal of Medicinal and Pharmaceutical Chemistry 2: 31–45. February 1960. doi:10.1021/jm50008a003. PMID 14406754.
- ↑ "Strong Analgesics. The Preparation of Some 4-Acyloxy-1-aralkyl-4-phenylpiperidines". Journal of the American Chemical Society 80 (18): 4916–4918. 1958. doi:10.1021/ja01551a038. Bibcode: 1958JAChS..80.4916E.
- ↑ James W King; William R Hydro; W James Lennox. Some Physicochemical and Pharmacologiall Characteristics of 1-Substituted-4-Phenyl-4-Piperidinols and their Esters. ERDEC-SP-002. June 1993
- ↑ "Crowd Control Technologies (An Appraisal of Technologies for Political Control) | Think Tank | European Parliament" (in en). https://www.europarl.europa.eu/thinktank/en/document/DG-4-JOIN_ET(2000)168394.
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