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

| 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 = {{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}}

| 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

| routes_of_administration =

| bioavailability =

| metabolism =

| 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.{{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 }}{{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 }}{{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 }}{{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 }}{{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 }}{{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 }}