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			{{Short description|Opioid analgesic and antitussive drug}}
	{{Drugbox		{{Drugbox
			| Watchedfields = changed
	| verifiedrevid = 443745429		| verifiedrevid = 447189889
	| IUPAC_name = 7,8-didehydro-4,5-α-epoxy- 3-ethoxy-17-methylmorphinan-6-α-ol		| IUPAC_name = 7,8-didehydro-4,5-α-epoxy- 3-ethoxy-17-methylmorphinan-6-α-ol
	| image = Ethylmorphine.svg		| image = Ethylmorphine.svg
			| image_class = skin-invert-image
			| alt = Structural formula
	| width = 210		| width = 210
			| image2 = Ethylmorphine molecule ball.png
			| alt2 = Ball-and-stick model
			| width2 = 220
	<!--Clinical data-->		<!--Clinical data-->
	| tradename =		| tradename = Cosylan, Diolan, Dionina, Diosan, Solvipect, Trachyl
	| Drugs.com = {{drugs.com|international|ethylmorphine}}		| Drugs.com = {{drugs.com|international|ethylmorphine}}
	| pregnancy_category =		| pregnancy_category =
			| legal_BR = A2
⚫	| legal_status = Schedule II (Single-Entity), Schedule III (In Combination Products)
			| 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=] |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 (] for higher doses)
			| legal_UN_comment = Narcotic Schedule III<!-- exected: N I and II, or II and III -->
	| routes_of_administration =		| routes_of_administration =
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	| bioavailability =		| bioavailability =
	| metabolism =		| metabolism =
	| excretion =		| excretion =
	<!--Identifiers-->		<!--Identifiers-->
	| CASNo_Ref = {{cascite|correct|CAS}}		| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 76-58-4		| CAS_number = 76-58-4
	| ATC_prefix = R05		| ATC_prefix = R05
	| ATC_suffix = DA01		| ATC_suffix = DA01
			| ATC_supplemental = {{ATC|S01|XA06}}
	| PubChem = 5359271		| PubChem = 5359271
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB01466		| DrugBank = DB01466
			| KEGG = D07929
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4514250		| ChemSpiderID = 4514250
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = RWO67D87EU		| UNII = RWO67D87EU
	<!--Chemical data-->		<!--Chemical data-->
	| C=19 | H=23 | N=1 | O=3		| C=19 | H=23 | N=1 | O=3
	| molecular_weight = 313.391
	| smiles = O2\C=C/54N(CC51c3c(O12)c(OCC)ccc3C4)C		| smiles = O2\C=C/54N(CC51c3c(O12)c(OCC)ccc3C4)C
	| InChI = 1/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
	| InChIKey = OGDVEMNWJVYAJL-LEPYJNQMBF
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| 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		| 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
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	| StdInChIKey = OGDVEMNWJVYAJL-LEPYJNQMSA-N		| StdInChIKey = OGDVEMNWJVYAJL-LEPYJNQMSA-N
	}}		}}
			'''Ethylmorphine''' (also known as '''codethyline''', '''dionine''', and '''ethyl morphine''') is an ] ] and ].<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>
	'''Ethylmorphine''' (also known as '''codethyline''', '''dionine''', and '''ethyl morphine''') is an ] ] ] (pain killer).
			==Side effects==
	Ethylmorphine was invented in Germany at ] in 1884 and was used as a weaker alternative to ] for all indications. Chemically, ethylmorphine is a ] ] with a -{{oxygen}}{{carbon}}<sub>2</sub>{{hydrogen}}<sub>5</sub> group substituted for the aromatic 3-{{hydroxyl}} group. Therefore the closest chemical relative of ethylmorphine is ], also known as methylmorphine. Ethylmorphine also has a ] analogue (ethyldihydromorphinone or 3-ethoxy-7,8-dihydro-morphin-6-one), and a dihydromorphine analogue known as ethyldihydromorphine, although none of them appears to be commercially distributed at the current time.
			Adverse effects are similar to other ]s 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 ] 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==
	As is the case with all narcotic analgesics, ethylmorphine is potentially habit-forming and can generate drug dependence of the codeine type. In most countries and internationally ethylmorphine and codeine are regulated much the same way. Like codeine, ] and similar weak ] drugs, ethylmorphine is listed under the international ] in Schedule III, which leads to some ethylmorphine preparations being available over the counter in some countries. In the US, ethylmorphine, like its methyl analog codeine, is controlled under the ], ] as a pure compound and ] when combined with non-opioid analgesics such as ] (akin to US Schedule III paracetamol/codeine combinations sold under the brand name Tylenol 3/4). In theory, cough syrup containing ethylmorphine is listed in US ], meaning that it can be bought without prescription in certain states if the patient presents ID and/or the chemist knows the person and the patient signs a dispensary log that is monitored by the DEA. However, there are currently no ethylmorphine-based pharmaceuticals marketed in the US, making this a moot point; codeine-based products, on the other hand, are still relatively common.
			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.<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>
	==Metabolism==		== See also ==
	After ingestion, ethylmorphine is converted to morphine in the human liver by the CYP450-isozyme ], similarly to ]. ] is a powerful ] and the main active compound found in naturally occurring ]. Ethylmorphine's metabolism is hindered by ],<ref>{{cite journal | last1 = Xu | first1 = BQ | last2 = Aasmundstad | first2 = TA | last3 = Lillekjendlie | first3 = B | last4 = Bjørneboe | first4 = A | last5 = Christophersen | first5 = AS | last6 = Mørland | first6 = 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 | year = 1997 | pmid = 9140136 }}</ref> which, being a ] ], also boosts the drug's sedative effect—creating a potentially dangerous combination as both drugs cause depression of the respiratory system that can be mutually amplified.
			* ]
	==Medical uses==
			* ]
	Ethylmorphine is used as an ] to treat dry cough. It is also a moderately strong ]. It is most widely used in ophthalmology for removing inflammation products from the eyes, inducing ] and relief of various symptoms. Ethylmorphine was once used, as was heroin, to attempt to cure morphine addiction, including being present in patent medicines sold for this purpose. Ethylmorphine is being investigated as a possible substitution agent for maintenance treatment of opioid dependence as it can quell withdrawal symptoms and also has a ceiling effect, i.e. additional doses beyond a certain level produce no extra euphoria.
			* ]
			* ]
	===Dosage===		== References ==
			{{Reflist|2}}
	Ethylmorphine is "less potent than morphine" but "more potent than ]" by a small percentage. Medical oral dosages vary from 5 to 30, even 50&nbsp;mg. Like codeine and close chemical relatives, ethylmorphine should not be injected directly into the veins as the sudden histamine release can have dangerous impacts, Naturally, all doses are much lower in ] use. Ethylmorphine shares codeine's good oral bioavailability and is the fifth- or sixth-most-commonly used drug of the codeine-based semi-synthetic group of moderate to strong narcotic analgesics. This series includes ], ], ethylmorphine, dihydroethylmorphine, ] (Peronine), ], ], ], ], ], ], acetylcodone, ] and others.
	The lethal dose is unknown. One source (in Finnish),<ref>Takaisin. {{fi icon}}. Accessed (via the ]) on February 27, 2010.</ref> however, suggests it to be as low as 500&nbsp;mg.
	==Problems==
	] to the drug's effects develops fast. That is why ethylmorphine is normally used only as a temporary medicine to treat e.g. cough. Patients may develop addiction. Side effects, which are rare for medical doses but normal for recreational doses, include the classical opiate side-effects: nausea, vomiting, urinary retention, ] and ]. Also, some people are hypersensitive or ] to ethylmorphine and should never take it. Additionally, the same dose of ethylmorphine can have completely different effects on two different people because of large individual differences in metabolism.
	Opioids are known of causing severe ], in addition to ]. This type of addiction is hard to treat.
	Taking ethylmorphine in combination with ] or other drugs that have a suppressive effect on the central nervous system boosts both drugs' effects, creating a dangerous combination. Possible outcome is death through ].
	In recreational use the most common problem, however, is liver damage and other effects caused by other compounds besides ethylmorphine. Some analgesics with ethylmorphine also contain ] (e.g. Indalgin), which is toxic in high doses.
	Antidepressants such as fluoxetine (]) inhibit the enzyme that metabolizes ethylmorphine. Taking ethylmorphine while using such an antidepressant may therefore lead to major changes in ethylmorphine's effects. Conversely, barbiturate compounds such as ] induce the same enzyme, which rapidly increases the metabolism of ethylmorpine. Other current medications therefore always have to be taken into account when using this compound.
	==Brand names==
	===Analgesics===
	* Indalgin (with indometacin)
	===Antitussives===
	* Cocillana
	* Cosylan
	* Feco Syrup
	* Solvipect Comp.
	== Notes ==
	<references/>
	== External links ==
	*
	{{Cough and cold preparations}}		{{Cough and cold preparations}}
			{{Opioid receptor modulators}}
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			{{respiratory-system-drug-stub}}
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