Ethylmorphine

Ethylmorphine
Clinical data
Trade names	Cosylan, Diolan, Dionina, Diosan, Solvipect, Trachyl
AHFS/Drugs.com	International Drug Names
ATC code	R05DA01 (WHO) S01XA06 (WHO);
Legal status
Legal status	BR: Class A2 (Narcotic drugs); CA: Schedule I; DE: Prescription only (Anlage II for higher doses); UK: Class B; US: Schedule II and Schedule III (In Combination Products); UN: Narcotic Schedule III;
Identifiers
	IUPAC name 7,8-didehydro-4,5-α-epoxy- 3-ethoxy-17-methylmorphinan-6-α-ol;
CAS Number	76-58-4 ;
PubChem CID	5359271;
DrugBank	DB01466 ;
ChemSpider	4514250 ;
UNII	RWO67D87EU;
KEGG	D07929;
CompTox Dashboard (EPA)	DTXSID1046760 ;
ECHA InfoCard	100.000.883
Chemical and physical data
Formula	C19H23NO3
Molar mass	313.397 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(OCC)ccc3C4)C;
	InChI InChI=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 ; Key:OGDVEMNWJVYAJL-LEPYJNQMSA-N ;
	(verify)

Ethylmorphine (also known as codethyline, dionine, and ethyl morphine) is an opioid analgesic and antitussive.^[2]^[3]^[4]^[5]^[6]^[7]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.
^ Xu BQ, Aasmundstad TA, Lillekjendlie B, Bjørneboe A, Christophersen AS, Mørland J (April 1997). "Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model". Pharmacology & Toxicology. 80 (4): 171–81. doi:10.1111/j.1600-0773.1997.tb00392.x. PMID 9140136.
^ Jonasson B, Jonasson U, Holmgren P, Saldeen T (August 1999). "Fatal poisonings where ethylmorphine from antitussive medications contributed to death". International Journal of Legal Medicine. 112 (5): 299–302. doi:10.1007/s004140050253. PMID 10460420. S2CID 24384512.
^ Popa C, Beck O, Brodin K (March–April 1998). "Morphine formation from ethylmorphine: implications for drugs-of-abuse testing in urine". Journal of Analytical Toxicology. 22 (2): 142–7. doi:10.1093/jat/22.2.142. PMID 9547411.
^ Amacher DE, Schomaker SJ (January 1998). "Ethylmorphine N-demethylase activity as a marker for cytochrome P450 CYP3A activity in rat hepatic microsomes". Toxicology Letters. 94 (2): 115–25. doi:10.1016/S0378-4274(97)00108-2. PMID 9574808.
^ Aasmundstad TA, Xu BQ, Johansson I, Ripel A, Bjørneboe A, Christophersen AS, et al. (June 1995). "Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose". British Journal of Clinical Pharmacology. 39 (6): 611–20. doi:10.1111/j.1365-2125.1995.tb05720.x. PMC 1365072. PMID 7654478.
^ Liu Z, Mortimer O, Smith CA, Wolf CR, Rane A (January 1995). "Evidence for a role of cytochrome P450 2D6 and 3A4 in ethylmorphine metabolism". British Journal of Clinical Pharmacology. 39 (1): 77–80. doi:10.1111/j.1365-2125.1995.tb04413.x. PMC 1364985. PMID 7756104.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.

[2] Xu BQ, Aasmundstad TA, Lillekjendlie B, Bjørneboe A, Christophersen AS, Mørland J (April 1997). "Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model". Pharmacology & Toxicology. 80 (4): 171–81. doi:10.1111/j.1600-0773.1997.tb00392.x. PMID 9140136.

[3] Jonasson B, Jonasson U, Holmgren P, Saldeen T (August 1999). "Fatal poisonings where ethylmorphine from antitussive medications contributed to death". International Journal of Legal Medicine. 112 (5): 299–302. doi:10.1007/s004140050253. PMID 10460420. S2CID 24384512.

[4] Popa C, Beck O, Brodin K (March–April 1998). "Morphine formation from ethylmorphine: implications for drugs-of-abuse testing in urine". Journal of Analytical Toxicology. 22 (2): 142–7. doi:10.1093/jat/22.2.142. PMID 9547411.

[5] Amacher DE, Schomaker SJ (January 1998). "Ethylmorphine N-demethylase activity as a marker for cytochrome P450 CYP3A activity in rat hepatic microsomes". Toxicology Letters. 94 (2): 115–25. doi:10.1016/S0378-4274(97)00108-2. PMID 9574808.

[6] Aasmundstad TA, Xu BQ, Johansson I, Ripel A, Bjørneboe A, Christophersen AS, et al. (June 1995). "Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose". British Journal of Clinical Pharmacology. 39 (6): 611–20. doi:10.1111/j.1365-2125.1995.tb05720.x. PMC 1365072. PMID 7654478.

[7] Liu Z, Mortimer O, Smith CA, Wolf CR, Rane A (January 1995). "Evidence for a role of cytochrome P450 2D6 and 3A4 in ethylmorphine metabolism". British Journal of Clinical Pharmacology. 39 (1): 77–80. doi:10.1111/j.1365-2125.1995.tb04413.x. PMC 1364985. PMID 7756104.

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