Picenadol

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Picenadol
Picenadol.svg
Systematic (IUPAC) name
3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol
Identifiers
CAS Number 79201-85-7 YesY
ATC code none
PubChem CID: 53077
ChemSpider 47943 YesY
UNII TV3535QWTJ YesY
Chemical data
Formula C16H25NO
Molecular mass 247.38 g/mol
  • OC1=CC=CC([C@@]2(CCN(C[C@@H]2C)C)CCC)=C1
  • 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 YesY
  • Key:RTOHPIRUUAKHOZ-BBRMVZONSA-N YesY
  (verify)

Picenadol (LY-97435) is a 4-phenylpiperidine 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 (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 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

Picenadol synthesis 1: U.S. Patent 4,499,274
Picenadol synthesis 2:[7]

See also

References

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  1. ↑ US Patent 4081450 - 1,3,4-Trisubstituted-4-arylpiperidines and their preparation
  2. ↑ Sherline DM. 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. 1983 Oct 15;147(4):404-6.
  3. ↑ Goldstein DJ, Brunelle RL, George RE, Cooper SA, Desjardins PJ, Gaston GW, Jeffers GE, Gallegos LT, Reynolds DC. Picenadol in a large multicenter dental pain study. Pharmacotherapy. 1994 Jan-Feb;14(1):54-9.
  4. ↑ Leander JD, Zimmerman DM. Effects of picenadol and its agonist and antagonist isomers on schedule-controlled behavior. Journal of Pharmacology and Experimental Therapeutics. 1983 Dec;227(3):671-5.
  5. ↑ Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. Chirality. 1995;7(7):518-25.
  6. ↑ Zimmerman DM, Smits SE, Hynes MD, Cantrell BE, Leander JD, Mendelsohn LG, Nickander R. Picenadol. Drug and Alcohol Dependence. 1985 Feb;14(3-4):381-401.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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