Picenadol: Difference between revisions

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Title: Erratum: Froimowitz, M., Cody, V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. Chirality 7:518–525, 1995. Series: Chirality vol. 8 iss. 4
 
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 443569052
| verifiedrevid = 447993535
| IUPAC_name = 3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol
| IUPAC_name = 3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol
| image = Picenadol.svg
| image = Picenadol.svg
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 79201-85-7
| CAS_number = 79201-85-7
| ATC_prefix = none
| ATC_prefix = none
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<!--Chemical data-->
<!--Chemical data-->
| C=16 | H=25 | N=1 | O=1
| C=16 | H=25 | N=1 | O=1
⚫
| smiles = OC1=CC=CC([C@@]2(CCN(C[C@@H]2C)C)CCC)=C1
| molecular_weight = 247.38 g/mol
⚫
| smiles = Oc1cccc(c1)[C@@]2(CCC)CCN(C)C[C@@H]2C
| InChI = 1/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
| InChIKey = RTOHPIRUUAKHOZ-BBRMVZONBN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
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}}
}}


'''Picenadol''' ('''LY-97435''') is a 4-[[phenyl]][[piperidine]] derivative that is an [[opioid]] [[analgesic]] drug.
'''Picenadol''' ('''LY-97435''') is a 4-[[phenyl]][[piperidine]] derivative that is an [[opioid]] [[analgesic]] drug developed by Eli Lilly in the 1970s.<ref>{{cite patent | country = US | number = 4081450 | title = 1,3,4-Trisubstituted-4-arylpiperidines and their preparation | inventor = Zimmerman DM | assign1 = Eli Lilly & Company | gdate = 28 April 1978 }}</ref>


Picenadol is an effective analgesic with similar efficacy to [[pethidine]] (meperidine). It has been investigated for some applications such as [[obstetrics]]<ref>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.</ref> and [[dentistry]],<ref>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.</ref> but never commercialised.
Picenadol is an effective analgesic with similar efficacy to [[pethidine]] (meperidine). It has been investigated for some applications such as [[obstetrics]]<ref name="pmid6624809">{{cite journal | vauthors = Sherline DM | title = Picenadol (LY 150720) compared with meperidine and placebo for relief of post-cesarean section pain: a randomized double-blind study | journal = American Journal of Obstetrics and Gynecology | volume = 147 | issue = 4 | pages = 404–6 | date = October 1983 | pmid = 6624809 | doi = 10.1016/s0002-9378(16)32234-7 }}</ref> and [[dentistry]],<ref name="pmid8159602">{{cite journal | vauthors = Goldstein DJ, Brunelle RL, George RE, Cooper SA, Desjardins PJ, Gaston GW, Jeffers GE, Gallegos LT, Reynolds DC | title = Picenadol in a large multicenter dental pain study | journal = Pharmacotherapy | volume = 14 | issue = 1 | pages = 54–9 | date = 1994 | pmid = 8159602 | doi = 10.1002/j.1875-9114.1994.tb02789.x | s2cid = 24644644 }}</ref> but never commercialised.

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It is unusual in that one [[enantiomer]] is a pure [[Mu opioid receptor|μ-opioid]] [[agonist]], while the other is an [[Receptor antagonist|antagonist]].<ref>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.</ref> The (3R,4R) isomer is the agonist, while (3S,4S) is antagonist.<ref>Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. ''Chirality''. 1995;7(7):518-25.</ref> This means that the racemic mix of the two enantiomers is a mixed agonist-antagonist, with relatively low [[Drug abuse|abuse potential]], and little of the [[Kappa opioid receptor|κ-opioid]] activity that tends to cause problems with other opioid mixed agonist-antagonists such as [[pentazocine]].<ref>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.</ref>


⚫
It is unusual in that one [[enantiomer]] is a pure [[Mu opioid receptor|μ-opioid]] [[agonist]], while the other is an [[Receptor antagonist|antagonist]].<ref name="pmid6655562">{{cite journal | vauthors = Leander JD, Zimmerman DM | title = Effects of picenadol and its agonist and antagonist isomers on schedule-controlled behavior | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 227 | issue = 3 | pages = 671–5 | date = December 1983 | pmid = 6655562 }}</ref> The (3S,4R) isomer is the agonist, while (3R,4S) is antagonist.<ref>Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. ''Chirality''. 1995;7(7):518-25.</ref> This means that the racemic mix of the two enantiomers is a mixed agonist-antagonist, with relatively low [[Drug abuse|abuse potential]], and little of the [[Kappa opioid receptor|κ-opioid]] activity that tends to cause problems with other opioid mixed agonist-antagonists such as [[pentazocine]].<ref name="pmid2986931">{{cite journal | vauthors = Zimmerman DM, Smits SE, Hynes MD, Cantrell BE, Leander JD, Mendelsohn LG, Nickander R | title = Picenadol | journal = Drug and Alcohol Dependence | volume = 14 | issue = 3–4 | pages = 381–401 | date = February 1985 | pmid = 2986931 | doi = 10.1016/0376-8716(85)90069-9 }}</ref>
==Synthesis==
[[File:Picenadol synthesis1.svg|thumb|center|500px|Picenadol synthesis 1:<ref>{{cite patent | country = US | number = 4499274 | title = Process for preparation of substituted formamidine and substituted N-iminomethyl piperidine | inventor = Feth G, Mills JE | assign1 = McNeil Lab Inc. | pubdate = 1985-02-12 }}</ref>]]
[[File:Picenadol synthesis 2.svg|thumb|center|500px|Picenadol synthesis 2:<ref>{{cite journal | vauthors = Martinelli MJ, Peterson BC | title = A concise, stereoselective synthesis of picenadol| journal = Tetrahedron Letters| volume = 31| issue = 38| pages = 5401–5404| year = 1990| doi = 10.1016/S0040-4039(00)97857-2 }}</ref>]]
==See also==
*[[Ketobemidone]]
== References ==
== References ==
{{Reflist|2}}
<references/>



{{opioids}}
{{Opioidergics}}


[[Category:Synthetic opioids]]
[[Category:Synthetic opioids]]
[[Category:Piperidines]]
[[Category:4-Phenylpiperidines]]
[[Category:phenols]]
[[Category:Phenols]]
[[Category:Mu-opioid agonists]]
[[Category:Mu-opioid receptor agonists]]

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{{pharm-stub}}

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{{analgesic-stub}}
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