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^[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 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.

[1]

[2]

[3]

[4]