Picenadol

Picenadol
Clinical data
ATC code	none;
Identifiers
	IUPAC name 3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol;
CAS Number	79201-85-7 ;
PubChem CID	53077;
ChemSpider	47943 ;
UNII	TV3535QWTJ;
Chemical and physical data
Formula	C16H25NO
Molar mass	247.382 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC1=CC=CC([C@@]2(CCN(C[C@@H]2C)C)CCC)=C1;
	InChI InChI=1S/C16H25NO/c1-4-8-16(9-10-17(3)12-13(16)2)14-6-5-7-15(18)11-14/h5-7,11,13,18H,4,8-10,12H2,1-3H3/t13-,16-/m0/s1 ; Key:RTOHPIRUUAKHOZ-BBRMVZONSA-N ;
	(verify)

Picenadol (LY-97435) is a 4-phenyl piperidine derivative that is an opioid analgesic drug developed by Eli Lilly in the 1970s.^[1]

Picenadol is an effective analgesic with similar efficacy to pethidine (meperidine). It has been investigated for some applications such as obstetrics^[2] and dentistry,^[3] but never commercialised.

It is unusual in that one enantiomer is a pure μ-opioid agonist, while the other is an antagonist.^[4] The (3S,4R) isomer is the agonist, while (3R,4S) is antagonist.^[5] This means that the racemic mix of the two enantiomers is a mixed agonist-antagonist, with relatively low abuse potential, and little of the κ-opioid activity that tends to cause problems with other opioid mixed agonist-antagonists such as pentazocine.^[6]

Synthesis

References

^ US 4081450, Zimmerman DM, "1,3,4-Trisubstituted-4-arylpiperidines and their preparation", issued 28 April 1978, assigned to Eli Lilly & Company
^ Sherline DM (October 1983). "Picenadol (LY 150720) compared with meperidine and placebo for relief of post-cesarean section pain: a randomized double-blind study". American Journal of Obstetrics and Gynecology. 147 (4): 404–6. doi:10.1016/s0002-9378(16)32234-7. PMID 6624809.
^ Goldstein DJ, Brunelle RL, George RE, Cooper SA, Desjardins PJ, Gaston GW, Jeffers GE, Gallegos LT, Reynolds DC (1994). "Picenadol in a large multicenter dental pain study". Pharmacotherapy. 14 (1): 54–9. doi:10.1002/j.1875-9114.1994.tb02789.x. PMID 8159602. S2CID 24644644.
^ Leander JD, Zimmerman DM (December 1983). "Effects of picenadol and its agonist and antagonist isomers on schedule-controlled behavior". The Journal of Pharmacology and Experimental Therapeutics. 227 (3): 671–5. PMID 6655562.
^ Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. Chirality. 1995;7(7):518-25.
^ Zimmerman DM, Smits SE, Hynes MD, Cantrell BE, Leander JD, Mendelsohn LG, Nickander R (February 1985). "Picenadol". Drug and Alcohol Dependence. 14 (3–4): 381–401. doi:10.1016/0376-8716(85)90069-9. PMID 2986931.
^ US 4499274, Feth G, Mills JE, "Process for preparation of substituted formamidine and substituted N-iminomethyl piperidine", published 1985-02-12, assigned to McNeil Lab Inc.
^ Martinelli MJ, Peterson BC (1990). "A concise, stereoselective synthesis of picenadol". Tetrahedron Letters. 31 (38): 5401–5404. doi:10.1016/S0040-4039(00)97857-2.

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[1] US 4081450, Zimmerman DM, "1,3,4-Trisubstituted-4-arylpiperidines and their preparation", issued 28 April 1978, assigned to Eli Lilly & Company

[pmid6624809-2] Sherline DM (October 1983). "Picenadol (LY 150720) compared with meperidine and placebo for relief of post-cesarean section pain: a randomized double-blind study". American Journal of Obstetrics and Gynecology. 147 (4): 404–6. doi:10.1016/s0002-9378(16)32234-7. PMID 6624809.

[pmid8159602-3] Goldstein DJ, Brunelle RL, George RE, Cooper SA, Desjardins PJ, Gaston GW, Jeffers GE, Gallegos LT, Reynolds DC (1994). "Picenadol in a large multicenter dental pain study". Pharmacotherapy. 14 (1): 54–9. doi:10.1002/j.1875-9114.1994.tb02789.x. PMID 8159602. S2CID 24644644.

[pmid6655562-4] Leander JD, Zimmerman DM (December 1983). "Effects of picenadol and its agonist and antagonist isomers on schedule-controlled behavior". The Journal of Pharmacology and Experimental Therapeutics. 227 (3): 671–5. PMID 6655562.

[5] Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. Chirality. 1995;7(7):518-25.

[pmid2986931-6] Zimmerman DM, Smits SE, Hynes MD, Cantrell BE, Leander JD, Mendelsohn LG, Nickander R (February 1985). "Picenadol". Drug and Alcohol Dependence. 14 (3–4): 381–401. doi:10.1016/0376-8716(85)90069-9. PMID 2986931.

[7] US 4499274, Feth G, Mills JE, "Process for preparation of substituted formamidine and substituted N-iminomethyl piperidine", published 1985-02-12, assigned to McNeil Lab Inc.

[8] Martinelli MJ, Peterson BC (1990). "A concise, stereoselective synthesis of picenadol". Tetrahedron Letters. 31 (38): 5401–5404. doi:10.1016/S0040-4039(00)97857-2.

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Synthesis

See also

References