R1317

R1317
Clinical data
Other names	1-Cinnamyl-4-phenyl-4-piperidinol propionate; EA 2219
Identifiers
	IUPAC name [4-phenyl-1-[(E)-3-phenylprop-2-enyl]piperidin-4-yl] propanoate;
CAS Number	6849-00-9;
PubChem CID	6444553;
ChemSpider	4948442;
Chemical and physical data
Formula	C23H27NO2
Molar mass	349.474 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)OC1(CCN(CC1)C/C=C/C2=CC=CC=C2)C3=CC=CC=C3;
	InChI InChI=1S/C23H27NO2/c1-2-22(25)26-23(21-13-7-4-8-14-21)15-18-24(19-16-23)17-9-12-20-10-5-3-6-11-20/h3-14H,2,15-19H2,1H3/b12-9+; Key:STWAFYHWLNRRHY-FMIVXFBMSA-N;

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 and 1100 times more potent in rats. In another article it was stated to be 785 times more potent than meperidine.

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. 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.

None of these compounds were adopted as incapacitating agents, with the likely agent adopted being the EA 3382.

References

1 2 Janssen PA, Eddy NB (February 1960). "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. doi:10.1021/jm50008a003. PMID 14406754.
↑ Elpern B, Wetterau W, Carabateas P, Grumbach L (1958). "Strong Analgesics. The Preparation of Some 4-Acyloxy-1-aralkyl-4-phenylpiperidines". Journal of the American Chemical Society. 80 (18): 4916–4918. Bibcode:1958JAChS..80.4916E. doi:10.1021/ja01551a038.
↑ 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". Archived from the original on 2025-12-04. Retrieved 2026-07-01.

[Eddy-1] 1 2 Janssen PA, Eddy NB (February 1960). "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. doi:10.1021/jm50008a003. PMID 14406754.

[2] Elpern B, Wetterau W, Carabateas P, Grumbach L (1958). "Strong Analgesics. The Preparation of Some 4-Acyloxy-1-aralkyl-4-phenylpiperidines". Journal of the American Chemical Society. 80 (18): 4916–4918. Bibcode:1958JAChS..80.4916E. doi:10.1021/ja01551a038.

[3] 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

[4] "Crowd Control Technologies (An Appraisal of Technologies for Political Control) | Think Tank | European Parliament". Archived from the original on 2025-12-04. Retrieved 2026-07-01.