morpheridine

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 447992382

| IUPAC_name = ethyl 1-(2-morpholin-4-ylethyl)-4-phenyl-piperidine-4-carboxylate

| image = Morpheridine2DCSD.svg

| image_class = skin-invert-image

| width = 160

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU = S9

| legal_BR = A1

| legal_BR_comment = {{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=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule I

| legal_UK = CD

| legal_US = Schedule I

| legal_DE = Anlage I

| legal_UN = P I

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 469-81-8

| ATC_prefix = none

| ATC_suffix =

| PubChem = 61121

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 55069

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1854GKB41Y

| C=20 | H=30 | N=2 | O=3

| smiles = O=C(OCC)C3(c1ccccc1)CCN(CCN2CCOCC2)CC3

| 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = JDEDMCKQPKGSAX-UHFFFAOYSA-N

| synonyms =

}}

Morpheridine (Morpholinoethylnorpethidine){{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}} is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine). It is a strong analgesic with around 4 times the potency of pethidine,{{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 }} and unlike pethidine, does not cause convulsions, although it produces the standard opioid side effects such as sedation and respiratory depression.{{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 }}

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

Synthesis

File:Normeperidine synthesis.svg

The key intermediate, normeperidine, is obtained by a scheme closely akin to the parent molecule. Thus, alkylation of benzyl cyanide (1) with the tosyl 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 sulfuric acid in ethanol serves both to esterify the acid and to remove the tosyl group to yield the secondary amine (5).

Alkylation of that amine by means of N-(2-chloroethyl)morpholine gives morpheridine.{{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 }}

See also

References