Ethylmorphine

{{Short description|Opioid analgesic and antitussive drug}} {{Drugbox | Watchedfields = changed | verifiedrevid = 447189889 | IUPAC_name = 7,8-didehydro-4,5-α-epoxy- 3-ethoxy-17-methylmorphinan-6-α-ol | image = Ethylmorphine.svg | image_class = skin-invert-image | alt = Structural formula | width = 210 | image2 = Ethylmorphine molecule ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model | width2 = 220

| tradename = Cosylan, Diolan, Dionina, Diosan, Solvipect, Trachyl | Drugs.com = {{drugs.com|international|ethylmorphine}} | pregnancy_category = | legal_BR = A2 | 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=2023-08-03 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}</ref> | legal_CA = Schedule I | legal_UK = Class B | legal_US = Schedule II | legal_US_comment = and Schedule III (In Combination Products) | legal_DE = Prescription only (Anlage II for higher doses) | legal_UN_comment = Narcotic Schedule III | legal_status = SE: Förteckning III<ref>https://fass.se/health/product/19641222000010/fass-text#:~:text=Om%20l%C3%A4kemedlet-,Narkotikaklass%20III,-Recept%20kr%C3%A4vs</ref> | routes_of_administration = Oral  | bioavailability = | metabolism = Hepatic, specifically CYP2D6<ref>https://go.drugbank.com/drugs/DB01466#:~:text=After%20ingestion%2C%20ethylmorphine%20is%20converted%20to%20morphine%20in%20the%20human%20liver%20by%20the%20CYP450%2Disozyme%20CYP2D6%2C%20similarly%20to%20codeine.</ref> | excretion =  | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 76-58-4 | ATC_prefix = R05 | ATC_suffix = DA01 | ATC_supplemental = {{ATC|S01|XA06}} | PubChem = 5359271 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01466 | KEGG = D07929 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4514250 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = RWO67D87EU  | C=19 | H=23 | N=1 | O=3 | smiles = O[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(OCC)ccc3C4)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C19H23NO3/c1-3-22-15-7-4-11-10-13-12-5-6-14(21)18-19(12,8-9-20(13)2)16(11)17(15)23-18/h4-7,12-14,18,21H,3,8-10H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OGDVEMNWJVYAJL-LEPYJNQMSA-N }} '''Ethylmorphine''' (also known as '''codethyline''', '''dionine''', and '''ethyl morphine''') is an opioid analgesic and antitussive.<ref>{{cite journal | vauthors = Xu BQ, Aasmundstad TA, Lillekjendlie B, Bjørneboe A, Christophersen AS, Mørland J | title = Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model | journal = Pharmacology & Toxicology | volume = 80 | issue = 4 | pages = 171–81 | date = April 1997 | pmid = 9140136 | doi = 10.1111/j.1600-0773.1997.tb00392.x | doi-access = free }}</ref><ref>{{cite journal | vauthors = Jonasson B, Jonasson U, Holmgren P, Saldeen T | title = Fatal poisonings where ethylmorphine from antitussive medications contributed to death | journal = International Journal of Legal Medicine | volume = 112 | issue = 5 | pages = 299–302 | date = August 1999 | pmid = 10460420 | doi = 10.1007/s004140050253 | s2cid = 24384512 }}</ref><ref>{{cite journal | vauthors = Popa C, Beck O, Brodin K | title = Morphine formation from ethylmorphine: implications for drugs-of-abuse testing in urine | journal = Journal of Analytical Toxicology | volume = 22 | issue = 2 | pages = 142–7 | date = March–April 1998 | pmid = 9547411 | doi = 10.1093/jat/22.2.142 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Amacher DE, Schomaker SJ | title = Ethylmorphine N-demethylase activity as a marker for cytochrome P450 CYP3A activity in rat hepatic microsomes | journal = Toxicology Letters | volume = 94 | issue = 2 | pages = 115–25 | date = January 1998 | pmid = 9574808 | doi = 10.1016/S0378-4274(97)00108-2 }}</ref><ref>{{cite journal | vauthors = Aasmundstad TA, Xu BQ, Johansson I, Ripel A, Bjørneboe A, Christophersen AS, Bodd E, Mørland J | display-authors = 6 | title = Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose | journal = British Journal of Clinical Pharmacology | volume = 39 | issue = 6 | pages = 611–20 | date = June 1995 | pmid = 7654478 | pmc = 1365072 | doi = 10.1111/j.1365-2125.1995.tb05720.x }}</ref><ref>{{cite journal | vauthors = Liu Z, Mortimer O, Smith CA, Wolf CR, Rane A | title = Evidence for a role of cytochrome P450 2D6 and 3A4 in ethylmorphine metabolism | journal = British Journal of Clinical Pharmacology | volume = 39 | issue = 1 | pages = 77–80 | date = January 1995 | pmid = 7756104 | pmc = 1364985 | doi = 10.1111/j.1365-2125.1995.tb04413.x }}</ref>

==Side effects== Adverse effects are similar to other opioids and include drowsiness, constipation, vertigo, nausea, vomiting, and respiratory depression. Contraindications include asthma, respiratory insufficiency, and age under 8. Ethylmorphine may affect the user's ability to drive and operate heavy machinery, and may cause chemical dependence or addiction at high doses.<ref name="DAA">{{cite book |isbn=0-8103-7177-4 |title=Drugs Available Abroad, 1st Edition |date=1991 |page=79 | vauthors = Schlesser JL |publisher=Derwent Publications Ltd.}}</ref>

==Society and culture== Ethylmorphine was first marketed in France in 1953 by Houde, and in Norway and Spain in 1960. It is not marketed in the United States and is a Schedule II controlled substance.<ref name="DAA" /><ref>{{Cite web |last=PubChem |title=Ethylmorphine |url=https://pubchem.ncbi.nlm.nih.gov/compound/5359271 |access-date=2023-09-08 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>

== References == {{Reflist|2}}

Category:Secondary alcohols Category:Antitussives Category:4,5-Epoxymorphinans Category:Semisynthetic opioids Category:Phenol ethers Category:Mu-opioid receptor agonists Category:Ophthalmology drugs Category:Ethoxy compounds