Revision as of 05:43, 2 September 2011 editBogBot (talk | contribs)Bots53,132 edits populated new fields in {{drugbox}} and reordered per bot approval. Report errors and suggestions to User_talk:BogBot← Previous edit |
Latest revision as of 16:20, 11 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
(40 intermediate revisions by 23 users not shown) |
Line 1: |
Line 1: |
|
|
{{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 |
|
|
|
|
Line 11: |
Line 12: |
|
| 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--> |
Line 22: |
Line 27: |
|
| 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 |
Line 33: |
Line 39: |
|
| 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 |
Line 49: |
Line 52: |
|
}} |
|
}} |
|
|
|
|
|
'''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 == |
|
|
*] |
|
|
*] |
|
|
*] |
|
|
|
|
|
⚫ |
== References == |
|
|
{{Reflist|2}} |
|
|
|
|
|
|
{{Analgesics}} |
|
|
{{Opioidergics}} |
|
|
|
|
⚫ |
] |
|
⚫ |
] |
|
⚫ |
] |
|
|
] |
|
|
] |
|
] |
|
] |
⚫ |
] |
|
|
] |
|
⚫ |
] |
|
⚫ |
] |
|
|
|
|
|
⚫ |
{{analgesic-stub}} |
|
|
|
|
|
|
⚫ |
{{analgesic-stub}} |
|
] |
|