R1317

R1317
Clinical data
Other names	1-Cinnamyl-4-phenyl-4-piperidinol propionate
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.

References

^ ^a ^b J., Paul A.; Eddy, Nathan B. (1960). "Compounds Related to Pethidine--IV. New Genaral Chemical Methods of Increading the Analgesic Activity of Pethidine". Journal of Medicinal and Pharmaceutical Chemistry. 2: 31–45. doi:10.1021/jm50008a003. PMID 14406754.
^ Elpern, Bill; Wetterau, William; Carabateas, Philip; Grumbach, Leonard (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.

[Eddy-1] J., Paul A.; Eddy, Nathan B. (1960). "Compounds Related to Pethidine--IV. New Genaral Chemical Methods of Increading the Analgesic Activity of Pethidine". Journal of Medicinal and Pharmaceutical Chemistry. 2: 31–45. doi:10.1021/jm50008a003. PMID 14406754.

[2] Elpern, Bill; Wetterau, William; Carabateas, Philip; Grumbach, Leonard (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.

[1]

[2]