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;

R 1317 is a Desmethylprodine analog in which the N-Methyl group was replaced by a cinnamyl group. This change in sidechain endows the compound with a great increase in potency.

The compound was stated to be 261 x meperidine in mice.^[1] While it was stated to be 1100 times meperidine in rats.

In another article it was stated to be 785 times meperidine.^[2]

Despite this high potency, it was not the most potent 4-phenylpiperidine-reverse ester ever created.

The most potent 4-phenylpiperidine-reverse ester ever created was R1480.^[1] However, this agent was not in the pubchem/chemspider database and does not have a cas number. R 1480 is stated to have a potency 1.5K-3180 times meperidine in mouse. ~3040 xs meperidine in rat.

References

^ ^a ^b J., Paul A; Eddy, Nathan B. (1960). "Compounds Related to Pethidine--IV. New General Chemical Methods of Increasing the Analgesic Activity of Pethidine". Journal of Medicinal and Pharmaceutical Chemistry. 2 (1): 31–45. doi:10.1021/jm50008a003.
^ 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. doi:10.1021/ja01551a038.

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

[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. doi:10.1021/ja01551a038.

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