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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| verifiedrevid = 447992382
| Verifiedfields = changed
| verifiedrevid = 400316378
| IUPAC_name = ethyl 1-(2-morpholin-4-ylethyl)-4-phenyl-piperidine-4-carboxylate | IUPAC_name = ethyl 1-(2-morpholin-4-ylethyl)-4-phenyl-piperidine-4-carboxylate
| image = Morpheridine.svg | image = Morpheridine2DCSD.svg
| image_class = skin-invert-image
| width = 160 | width = 160


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| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = S9
| legal_BR = A1
| legal_CA = <!-- Schedule I -->
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_UK = Class A
| legal_CA = Schedule I
| legal_UK = CD
| legal_US = Schedule I | legal_US = Schedule I
| legal_status = | legal_DE = Anlage I
| legal_UN = P I
| legal_status =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 469-81-8 | CAS_number = 469-81-8
| ATC_prefix = none | ATC_prefix = none
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 55069 | ChemSpiderID = 55069
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1854GKB41Y | UNII = 1854GKB41Y


<!--Chemical data--> <!--Chemical data-->
| C=20 | H=30 | N=2 | O=3 | C=20 | H=30 | N=2 | O=3
| molecular_weight = 346.46 g/mol
| smiles = O=C(OCC)C3(c1ccccc1)CCN(CCN2CCOCC2)CC3 | smiles = O=C(OCC)C3(c1ccccc1)CCN(CCN2CCOCC2)CC3
| InChI = 1/C20H30N2O3/c1-2-25-19(23)20(18-6-4-3-5-7-18)8-10-21(11-9-20)12-13-22-14-16-24-17-15-22/h3-7H,2,8-17H2,1H3
| InChIKey = JDEDMCKQPKGSAX-UHFFFAOYAK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H30N2O3/c1-2-25-19(23)20(18-6-4-3-5-7-18)8-10-21(11-9-20)12-13-22-14-16-24-17-15-22/h3-7H,2,8-17H2,1H3 | StdInChI = 1S/C20H30N2O3/c1-2-25-19(23)20(18-6-4-3-5-7-18)8-10-21(11-9-20)12-13-22-14-16-24-17-15-22/h3-7H,2,8-17H2,1H3
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}} }}


'''Morpheridine''' ('''Morpholinoethylnorpethidine''')<ref>US Patent 2795581 Piperidine Compounds and Their Production</ref> is a 4-]] derivative that is related to the ] ] drug ] (meperidine) developed by J.F. McFarlan. It is a strong analgesic with around 4 times the potency of pethidine,<ref>HOLMES JM. Morpholinoethylnorpethidine hydrochloride in obstetrics. ''Journal of Obstetrics and Gynaecology in the British Empire''. 1958 Feb;65(1):98-9. PMID 13514558</ref> and unlike pethidine, does not cause ]s, although it produces the standard opioid side effects such as ] and ].<ref>GREEN AF, WARD NB. Analgesic and other properties of morpholinoethylnorpethidine. ''British Journal of Pharmacology and Chemotherapy''. 1956 Mar;11(1):32-4. PMID 13304251</ref> '''Morpheridine''' ('''Morpholinoethylnorpethidine''')<ref>{{cite patent | country = US | number = 2795581 | title = Piperidine Compounds and Their Production| inventor = Stern ES, Anderson RJ | assign1 = J.F. McFarlan & Co | gdate = 06/11/1957}}</ref> is a 4-]] derivative that is related to the clinically used ] ] drug ] (meperidine). It is a strong analgesic with around 4 times the potency of pethidine,<ref>{{cite journal | vauthors = Holmes JM | title = Morpholinoethylnorpethidine hydrochloride in obstetrics | journal = The Journal of Obstetrics and Gynaecology of the British Empire | volume = 65 | issue = 1 | pages = 98–9 | date = February 1958 | pmid = 13514558 | doi = 10.1111/j.1471-0528.1958.tb06218.x | s2cid = 1481693 }}</ref> and unlike pethidine, does not cause ]s, although it produces the standard opioid side effects such as ] and ].<ref>{{cite journal | vauthors = Green AF, Ward NB | title = Analgesic and other properties of morpholinoethylnorpethidine | journal = British Journal of Pharmacology and Chemotherapy | volume = 11 | issue = 1 | pages = 32–4 | date = March 1956 | pmid = 13304251 | pmc = 1509567 | doi = 10.1111/j.1476-5381.1956.tb01023.x }}</ref>


Morpheridine is not currently used in medicine and is a ]/] drug which is controlled under UN drug conventions.<ref></ref> Morpheridine is not currently used in medicine and is a ] drug which is controlled under UN drug conventions.<ref>{{ cite web | url = http://www.ukcia.org/pollaw/lawlibrary/singleconventiononnarcoticdrugs1961.php | title = Single convention on drugs 1961 }}</ref>


==Synthesis==
]
The key intermediate, ], is obtained by a scheme closely akin to the parent molecule. Thus, alkylation of ] ('''1''') with the ] analog of the bischloroethylamine ('''2''') leads to the substituted piperidine ('''3'''). Basic hydrolysis serves to convert the nitrile to the acid ('''4'''). Treatment of this last with ] in ] serves both to esterify the acid and to remove the ] group to yield the secondary amine ('''5''').


Alkylation of that amine by means of ''N''-(2-chloroethyl)morpholine gives morpheridine.<ref>{{Cite journal | doi = 10.1039/JR9560004088| title = 788. Some new analogues of pethidine. Part I| journal = Journal of the Chemical Society (Resumed)| pages = 4088| year = 1956| vauthors = Anderson RJ, Frearson PM, Stern ES }}</ref>
== References ==
<references/>


== See also ==
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== References ==
{{Reflist|2}}


{{Analgesics}}
{{Opioidergics}}

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{{analgesic-stub}}
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Morpheridine: Difference between revisions Add topic