Movatterモバイル変換

[0]ホーム

Jump to content

Picenadol

Edit links

From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Picenadol
Clinical data

ATC code	none
Identifiers
IUPAC name 3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol
CAS Number	79201-85-7^Y
PubChemCID	53077
ChemSpider	47943^Y
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^Y Key:RTOHPIRUUAKHOZ-BBRMVZONSA-N^Y
(verify)

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

Picenadol is an effective analgesic with similar efficacy topethidine (meperidine). It has been investigated for some applications such asobstetrics^[2] anddentistry,^[3] but never commercialised.

It is unusual in that oneenantiomer is a pureμ-opioid agonist, while the other is anantagonist.^[4] The (3R,4R) isomer is the agonist, while (3S,4S) is antagonist.^[5] This means that the racemic mix of the two enantiomers is a mixed agonist-antagonist, with relatively lowabuse potential, and little of theκ-opioid activity that tends to cause problems with other opioid mixed agonist-antagonists such aspentazocine.^[6]

Synthesis

[edit]

References

[edit]

^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.doi:10.1016/S0022-3565(25)22088-2.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.