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]

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.^[8]

Society and culture

Ethylmorphine was first marketed in France in 1953 by Houde, and in Norway and Spain in 1960. It is not available in the United States, where it is a Schedule II controlled substance.^[8]^[9]

References

^ 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.
^ ^a ^b Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 79. ISBN 0-8103-7177-4.
^ PubChem. "Ethylmorphine". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-09-08.

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[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.

[DAA-8] Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 79. ISBN 0-8103-7177-4.

[9] PubChem. "Ethylmorphine". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-09-08.

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Side effects

Society and culture

See also

References