Picenadol

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

Picenadol

Clinical data
ATC code	none
Identifiers
IUPAC name 3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol
CAS Number	79201-85-7 Y
PubChem CID	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
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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:^[7]

Picenadol synthesis 2:^[8]

See also

• Ketobemidone