Norpethidine

Metabolism of pethidine to norpethidine is carried out mainly by the [[Cytochrome P450|CYP]] enzymes, [[CYP2B6]], [[CYP2C19]] and [[CYP3A4]], in the liver, and since the activity of these enzymes can vary between individuals and can be influenced by concurrent use of other drugs, the rate and extent of norpethidine production can be difficult to predict.<ref name="pmid15319333">{{cite journal | vauthors = Ramírez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ | title = CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes | journal = Drug Metabolism and Disposition: The Biological Fate of Chemicals | volume = 32 | issue = 9 | pages = 930–6 | date = September 2004 | pmid = 15319333 | doi = 10.1016/S0090-9556(24)02975-1| url = }}</ref><ref name="pmid10389564">{{cite journal | vauthors = McHugh GJ | title = Norpethidine accumulation and generalized seizure during pethidine patient-controlled analgesia | journal = Anaesthesia and Intensive Care | volume = 27 | issue = 3 | pages = 289–91 | date = June 1999 | pmid = 10389564 | doi = | url = }}</ref>

Metabolism of pethidine to norpethidine is carried out mainly by the [[Cytochrome P450|CYP]] enzymes, [[CYP2B6]], [[CYP2C19]] and [[CYP3A4]], in the liver, and since the activity of these enzymes can vary between individuals and can be influenced by concurrent use of other drugs, the rate and extent of norpethidine production can be difficult to predict.<ref name="pmid15319333">{{cite journal | vauthors = Ramírez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ | title = CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes | journal = Drug Metabolism and Disposition: The Biological Fate of Chemicals | volume = 32 | issue = 9 | pages = 930–6 | date = September 2004 | pmid = 15319333 | doi = 10.1016/S0090-9556(24)02975-1| url = }}</ref><ref name="pmid10389564">{{cite journal | vauthors = McHugh GJ | title = Norpethidine accumulation and generalized seizure during pethidine patient-controlled analgesia | journal = Anaesthesia and Intensive Care | volume = 27 | issue = 3 | pages = 289–91 | date = June 1999 | pmid = 10389564 | doi = | url = }}</ref>

==Precursor Use==

==Precursor Use==

Norpethidine can be used as a precursor in synthesis of other drugs, including [[etoxeridine]],<ref>{{cite patent | country = US | number = 2858316 | url = https://patents.google.com/patent/US2858316 | title = New piperidine derivatives | status = granted | inventor = Henri M | assign1 = UCB SA | pubdate = 28 October 1958 }}</ref> [[benzethidine]],<ref>{{cite journal | vauthors = Frearson PM, Stern ES | title = 622. Some new analogues of pethidine. Part III. 1-Aryloxy-alkylnorpethidines, and close analogues. | journal = Journal of the Chemical Society (Resumed) | date = 1958 | pages = 3065–7 | doi = 10.1039/JR9580003065 }}</ref> [[furethidine]],<ref>{{cite journal | vauthors = Frearson PM, Hardy DG, Stern ES | title = 426. Some new analogues of pethidine. Part IV. Substituents at the 1-position incorporating cyclic ether groups. | journal = Journal of the Chemical Society (Resumed) | date = 1960 | pages = 2103–7 | doi = 10.1039/JR9600002103 }}</ref> [[morpheridine]], [[anileridine]], [[phenoperidine]], [[piminodine]], [[oxpheneridine]], [[pheneridine]] & [https://pubchem.ncbi.nlm.nih.gov/compound/24149 carperidine].

Norpethidine can be used as a precursor in synthesis of other drugs, including [[etoxeridine]],<ref>{{cite patent | country = US | number = 2858316 | url = https://patents.google.com/patent/US2858316 | title = New piperidine derivatives | status = granted | inventor = Henri M | assign1 = UCB SA | pubdate = 28 October 1958 }}</ref> [[benzethidine]],<ref>{{cite journal | vauthors = Frearson PM, Stern ES | title = 622. Some new analogues of pethidine. Part III. 1-Aryloxy-alkylnorpethidines, and close analogues. | journal = Journal of the Chemical Society (Resumed) | date = 1958 | pages = 3065–7 | doi = 10.1039/JR9580003065 }}</ref> [[furethidine]],<ref>{{cite journal | vauthors = Frearson PM, Hardy DG, Stern ES | title = 426. Some new analogues of pethidine. Part IV. Substituents at the 1-position incorporating cyclic ether groups. | journal = Journal of the Chemical Society (Resumed) | date = 1960 | pages = 2103–7 | doi = 10.1039/JR9600002103 }}</ref> [[morpheridine]], [[anileridine]], [[phenoperidine]], [[piminodine]], [[oxpheneridine]], [[pheneridine]] & [https://pubchem.ncbi.nlm.nih.gov/compound/24149 carperidine].

Legitimate research chemical uses include: [https://pubchem.ncbi.nlm.nih.gov/compound/43481 R 951]<ref>{{Cite journal |doi=10.1021/jm50002a008 |title=Compounds Related to Pethidine--I. Mannich Bases Derived from Norpethidine and Acetophenones |date=1959 |last1=Janssen |first1=Paul A. J. |last2=Jageneau |first2=Anton H. M. |last3=Demoen |first3=Paul J. A. |last4=Westeringh |first4=Corn. van De. |last5=Raeymaekers |first5=Alfons H. M. |last6=Wouters |first6=Maria S. J. |last7=Sanczuk |first7=Stefan |last8=Hermans |first8=Bert K. F. |last9=Loomans |first9=Jozef L. M. |journal=Journal of Medicinal and Pharmaceutical Chemistry |volume=1 |issue=1 |pages=105–120 |pmid=13655032 }}</ref><ref>{{Cite journal |doi=10.1021/jm50005a002 |title=Compounds Related to Pethidine--II. Mannich Bases Derived from Various Esters of 4-Carboxy-4-phenylpiperidine and Acetophenones |date=1959 |last1=Janssen |first1=Paul A. J. |last2=Jageneau |first2=Anton H. M. |last3=Demoen |first3=Paul J. A. |last4=Van De Westeringh |first4=Corn. |last5=De Canniere |first5=Julienne H. M. |last6=Raeymaekers |first6=Alfons H. M. |last7=Wouters |first7=Maria S. J. |last8=Sanczuk |first8=Stefan |last9=Hermans |first9=Bert K. F. |journal=Journal of Medicinal and Pharmaceutical Chemistry |volume=1 |issue=4 |pages=309–317 |pmid=14406753 }}</ref><ref>Pohland Albert, US2951080 (1960 to Eli Lilly and Co).</ref><ref>Jr Frank A Cutler & James F Fisher, US2962501 (1960 to Merck and Co Inc).</ref> [https://pubchem.ncbi.nlm.nih.gov/compound/138755414 R 1187],<ref name="Janssen1960">{{Cite journal |doi=10.1021/jm50010a003 |title=Compounds Related to Pethidine--III. Basic Ketones derived from Norpethidine |date=1960 |last1=Janssen |first1=Paul |last2=Jageneau |first2=Anton H. M. |last3=Demoen |first3=Paul J. A. |last4=Van De Westeringh |first4=Corn. |last5=De Canniere |first5=Julienne H. M. |last6=Raeymaekers |first6=Alfons H. M. |last7=Wouters |first7=Maria |last8=Sanczuk |first8=Stefan |last9=Hermans |first9=Bert K. F. |journal=Journal of Medicinal and Pharmaceutical Chemistry |volume=2 |issue=3 |pages=271–280 }}</ref> [https://pubchem.ncbi.nlm.nih.gov/compound/154359674 R 1204],<ref name=Janssen1960/><ref>Elpern Bill, US3093652 (1963 to STWB Inc).</ref> R 1133,<ref name=Janssen1960/> [https://pubchem.ncbi.nlm.nih.gov/compound/138755415 R 960]<ref name=Janssen1960/> PCP-hybrid ([https://pubchem.ncbi.nlm.nih.gov/compound/59334 121019-93-0]),<ref>{{Cite journal |pmid=7241506 |date=1981 |last1=Itzhak |first1=Y. |last2=Kalir |first2=A. |last3=Weissman |first3=B. A. |last4=Cohen |first4=S. |title=New analgesic drugs derived from phencyclidine |journal=Journal of Medicinal Chemistry |volume=24 |issue=5 |pages=496–499 |doi=10.1021/jm00137a004 }}</ref> [https://pubchem.ncbi.nlm.nih.gov/compound/10895908 amitriptyline-hybrid].<ref>{{cite journal | vauthors=((Davis, M. A.)), ((Herr, F.)), ((Thomas, R. A.)), ((Charest, M.-Paule.)) | journal=Journal of Medicinal Chemistry | title=New Psychotropic Agents. VIII. 1 Analogs of Amitriptyline Containing the Normeperidine Group | volume=10 | issue=4 | pages=627–635 | date= July 1967 | doi=10.1021/jm00316a024| pmid=6037052 }}</ref><ref>{{cite journal | vauthors=((Davis, M. A.)), ((Herr, F.)), ((Thomas, R. A.)), ((Charest, M.-Paule.)) | journal=Journal of Medicinal Chemistry | title=Additions and Corrections - New Psychotropic Agents. VIII. Analogs of Amitriptyline Containing the Normeperidine Group. | volume=10 | issue=6 | pages=1197 | date= November 1967 | doi=10.1021/jm00318a607}}</ref><ref>Martin Arnold Davis & Stanley Oscar Winthrop, DE1200300 (1965 to Wyeth Canada Inc).</ref><ref>A. Davis Martin & O. Winthrop Stanley, CA724166A (1965 to Wyeth Canada Inc).</ref><ref>Martin A Davis & Stanley O Winthrop, {{US patent|3074953}} (1963 to Wyeth LLC).</ref> >6 hr duration patent: [https://pubchem.ncbi.nlm.nih.gov/compound/20975957 PC20975957]<ref>Gustav Ehrhart, Leopold Ther, Hans-Georg Alpermann, & Heinrich Ott, {{US patent|3426028}} (1969 to Hoechst AG).</ref> (c.f. [[3,3-Diphenylpropylamine]])

==See also==

==See also==