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Ethylmorphine: Difference between revisions
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{{DepressantOD|opiates}} | {{headerpanel|{{DepressantOD|opiates}}}} | ||
{{SummarySheet}} | |||
{{SubstanceBox/Ethylmorphine}} | {{SubstanceBox/Ethylmorphine}} | ||
'''Ethylmorphine''', also known as codethyline and dionine, is a semi-synthetic [[chemical class::morphinan]] [[psychoactive class::opioid]] first created by Merck in 1884 and used as a weaker alternative to [[morphine]]. Today, it is most commonly used as an [[antitussive]] which is available in cough syrup preparations like Cocillana, Cosylan, Solvipect comp. (in combination with guaifenesin) and Lepheton (in combination with [[ephedrine]]), or in tablet form sold as Tussipax (in combination with [[codeine]]). Cough syrup preparations commonly include a mild laxative to counter the [[constipation]] which is a common side effect of opioids. | '''Ethylmorphine''', also known as codethyline and dionine, is a semi-synthetic [[chemical class::morphinan]] [[psychoactive class::opioid]] first created by Merck in 1884 and used as a weaker alternative to [[morphine]]. Today, it is most commonly used as an [[antitussive]] which is available in cough syrup preparations like Cocillana, Cosylan, Solvipect comp. (in combination with guaifenesin) and Lepheton (in combination with [[ephedrine]]), or in tablet form sold as Tussipax (in combination with [[codeine]]). Cough syrup preparations commonly include a mild laxative to counter the [[constipation]] which is a common side effect of opioids. | ||
Ethylmorphine is also used in ophthalmic preparations as dionine to treat inflammations of the eye. In 1904, an ethylmorphine preparation was described as "a new ocular analgesic."<ref> | Ethylmorphine is also used in ophthalmic preparations as dionine to treat inflammations of the eye. In 1904, an ethylmorphine preparation was described as "a new ocular analgesic."<ref>{{cite journal | vauthors=((Hinshelwood, J.)) | journal=Br Med J | title=Dionine: A New Ocular Analgesic | volume=1 | issue=2261 | pages=1009–1010 | date=30 April 1904 | url=https://www.bmj.com/content/1/2261/1009.2 | issn=0007-1447 | doi=10.1136/bmj.1.2261.1009-a}}</ref> | ||
==Chemistry== | ==Chemistry== | ||
Ethylmorphine, or 3-ethylmorphine, is an opioid of the morphinan class. Ethylmorphine and other molecules of this class contain a polycyclic core of three benzene rings fused in a zig-zag pattern called phenanthrene. A fourth nitrogen containing ring is fused to the phenanthrene at R<sub>9</sub> and R<sub>13</sub> with the nitrogen member looking at R<sub>17</sub> of the combined structure. This structure is called morphinan. | Ethylmorphine, or 3-ethylmorphine, is an opioid of the morphinan class. Ethylmorphine and other molecules of this class contain a polycyclic core of three benzene rings fused in a zig-zag pattern called phenanthrene. A fourth nitrogen containing ring is fused to the phenanthrene at R<sub>9</sub> and R<sub>13</sub> with the nitrogen member looking at R<sub>17</sub> of the combined structure. This structure is called morphinan. | ||
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The active metabolites of ethylmorphine, notably [[morphine]], exert their effects by binding to and activating the [[Opioid#Mu_.28.CE.BC.29|μ-opioid]] [[receptor]]. This occurs because opioids structurally mimic endogenous endorphins which are naturally found within the body and also work upon the μ-opioid receptor set. The way in which opioids structurally mimic these natural endorphins results in their [[physical euphoria|euphoria]], [[pain relief]] and [[anxiolytic]] effects. This is because endorphins are responsible for reducing pain, causing sleepiness, and feelings of pleasure. They can be released in response to pain, strenuous exercise, orgasm, or general excitement. | The active metabolites of ethylmorphine, notably [[morphine]], exert their effects by binding to and activating the [[Opioid#Mu_.28.CE.BC.29|μ-opioid]] [[receptor]]. This occurs because opioids structurally mimic endogenous endorphins which are naturally found within the body and also work upon the μ-opioid receptor set. The way in which opioids structurally mimic these natural endorphins results in their [[physical euphoria|euphoria]], [[pain relief]] and [[anxiolytic]] effects. This is because endorphins are responsible for reducing pain, causing sleepiness, and feelings of pleasure. They can be released in response to pain, strenuous exercise, orgasm, or general excitement. | ||
Ethylmorphine has been described as less potent than morphine but slightly more potent than codeine.<ref name="lookchem"> | Ethylmorphine has been described as less potent than morphine but slightly more potent than codeine.<ref name="lookchem">{{Citation | title=Ethylmorphine , CasNO.76-58-4 | url=https://www.lookchem.com/Ethylmorphine/}}</ref> | ||
==Subjective effects== | ==Subjective effects== | ||
{{Preamble/SubjectiveEffects}} | |||
{{effects/base | |||
|{{effects/physical| | |||
The general head space of ethylmorphine is described by many as one of intense euphoria, relaxation, anxiety suppression and pain relief. | The general head space of ethylmorphine is described by many as one of intense euphoria, relaxation, anxiety suppression and pain relief. | ||
*'''[[Effect::Pain relief]]''' | *'''[[Effect::Pain relief]]''' | ||
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*'''[[Effect::Decreased libido]]''' | *'''[[Effect::Decreased libido]]''' | ||
*'''[[Effect::Appetite suppression]]''' | *'''[[Effect::Appetite suppression]]''' | ||
*'''[[Effect::Orgasm suppression]]''' | |||
}} | |||
|{{effects/cognitive| | |||
*'''[[Effect::Cognitive euphoria|Euphoria]]''' - Like codeine, this particular substance can be considered as less intense in its cognitive euphoria when compared with that of [[morphine]] or [[diacetylmorphine]] (heroin) due to the upper limit of how much can be converted into its active form through metabolism. It is still, however, capable of extreme intensity and overwhelming bliss at heavier dosages with a low tolerance. The sensation itself can be described as powerful and overwhelming feeling of emotional bliss, contentment, and happiness. | *'''[[Effect::Cognitive euphoria|Euphoria]]''' - Like codeine, this particular substance can be considered as less intense in its cognitive euphoria when compared with that of [[morphine]] or [[diacetylmorphine]] (heroin) due to the upper limit of how much can be converted into its active form through metabolism. It is still, however, capable of extreme intensity and overwhelming bliss at heavier dosages with a low tolerance. The sensation itself can be described as powerful and overwhelming feeling of emotional bliss, contentment, and happiness. | ||
*'''[[Effect::Anxiety suppression]]''' | *'''[[Effect::Anxiety suppression]]''' | ||
*'''[[Effect::Compulsive redosing]]''' | *'''[[Effect::Compulsive redosing]]''' | ||
*'''[[Effect::Dream potentiation]]''' | *'''[[Effect::Dream potentiation]]''' | ||
}} | |||
}} | |||
===Experience reports=== | |||
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here: | |||
*[https://www.erowid.org/experiences/subs/exp_Pharms_Ethylmorphine.shtml Erowid Experience Vaults: Ethylmorphine] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
Ethylmorphine has a [[Toxicity::low toxicity]] relative to dose. However, despite its relatively low toxicity for an opioid, at least one death has been attributed to oral consumption of ethylmorphine alone, without the presence of other depressants.<ref> | Ethylmorphine has a [[Toxicity::low toxicity]] relative to dose. However, despite its relatively low toxicity for an opioid, at least one death has been attributed to oral consumption of ethylmorphine alone, without the presence of other depressants.<ref>{{cite journal | vauthors=((Kintz, P.)), ((Jamey, C.)), ((Mangin, P.)) | journal=Archives of Toxicology | title=Ethylmorphine concentrations in human samples in an overdose case | volume=68 | issue=3 | pages=210–211 | date=1 March 1994 | url=https://doi.org/10.1007/s002040050057 | issn=1432-0738 | doi=10.1007/s002040050057}}</ref> As with all opioids, long-term effects can vary but can include diminished libido, apathy and memory loss. It is also [[Toxicity::potentially [[respiratory depression|lethal]] when mixed with [[depressants]] like [[alcohol]] or [[benzodiazepines]]]]. | ||
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug. | It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug. | ||
===Tolerance and addiction potential=== | ===Tolerance and addiction potential=== | ||
As with other [[opioids]], the chronic use of ethylmorphine can be | As with other [[opioids]], the chronic use of ethylmorphine can be [[Addiction potential::very addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[Opioids#Discontinuation|withdrawal symptoms]] may occur if a person suddenly stops their usage. | ||
Tolerance to many of the effects of ethylmorphine [[Time to full tolerance::develops with prolonged and repeated use]]. The rate at which this occurs develops at different rates for different effects, with tolerance to the constipation-inducing effects developing particularly slowly for instance. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Ethylmorphine presents cross-tolerance with [[Cross-tolerance::all other [[opioids]]]], meaning that after the consumption of ethylmorphine all [[opioid]]s will have a reduced effect. | Tolerance to many of the effects of ethylmorphine [[Time to full tolerance::develops with prolonged and repeated use]]. The rate at which this occurs develops at different rates for different effects, with tolerance to the constipation-inducing effects developing particularly slowly for instance. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Ethylmorphine presents cross-tolerance with [[Cross-tolerance::all other [[opioids]]]], meaning that after the consumption of ethylmorphine all [[opioid]]s will have a reduced effect. | ||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
{{DangerousInteractions/Intro}} | |||
{{DangerousInteractions/Opioids}} | |||
==Legal | ==Legal status== | ||
Internationally, Ethylmorphine is listed in the Single Convention on Narcotic Drugs in Schedule III.<ref>{{Citation | year=2022 | title=Single Convention on Narcotic Drugs | url=https://en.wikipedia.org/w/index.php?title=Single_Convention_on_Narcotic_Drugs&oldid=1096299093}}</ref> | |||
* '''France:''' Tussipax tablets containing 10 mg of ethylmorphine and 10 mg of codeine are sold over the counter. | |||
* '''Norway:''' Cosylan and Solvipect comp. cough syrups containing ethylmorphine hydrochloride 1.7mg/mL and 2.5mg/mL, respectively, are regulated in prescription Class B.<ref>http://www.felleskatalogen.no/medisin/cosylan-recip-547676</ref><ref>http://www.felleskatalogen.no/medisin/solvipect-comp-takeda-nycomed-564022</ref> They are commonly prescribed for dry cough. | *'''France:''' Tussipax tablets containing 10 mg of ethylmorphine and 10 mg of codeine are sold over the counter.{{citation needed}} | ||
* '''Sweden:''' Cocillana-Etyfin cough syrup containing ethylmorphine 2.5mg/mL is sold as a prescription drug.<ref> | *'''Germany:''' Ethylmorphine is controlled under BtMG Anlage II, making it illegal to manufacture, import, possess, sell, or transfer it without a license. There is an exception for preparations containing up to 2.5% or up to 100mg ethylmorphine per unit, which can be prescribed on a narcotic prescription form.<ref>{{Citation | title=Anlage II BtMG - Einzelnorm | url=http://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html}}</ref> | ||
* '''United States:''' No preparations containing ethylmorphine are on the market in the US. Pure ethylmorphine is listed in Schedule II and combination products containing no more than ethylmorphine 3mg/mL (or 15 mg per dosage unit together with a non-narcotic active ingredient) are listed in Schedule III. Preparations containing no more than ethylmorphine 1mg/mL or 1mg/g are listed in schedule V.<ref>http://www.deadiversion.usdoj.gov/21cfr/cfr/2108cfrt.htm</ref> This is similar to codeine, but unlike codeine, ethylmorphine is not available for medical purposes in the United States | *'''Norway:''' Cosylan and Solvipect comp. cough syrups containing ethylmorphine hydrochloride 1.7mg/mL and 2.5mg/mL, respectively, are regulated in prescription Class B.<ref>http://www.felleskatalogen.no/medisin/cosylan-recip-547676</ref><ref>http://www.felleskatalogen.no/medisin/solvipect-comp-takeda-nycomed-564022</ref> They are commonly prescribed for dry cough. | ||
*'''Russia:''' Ethylmorphine is a Schedule II controlled substance.<ref>{{Citation | title=Постановление Правительства РФ от 01.10.2012 N 1002 (ред. от 09.08.2019) | url=https://www.consultant.ru/cons/cgi/online.cgi?req=doc&base=LAW&n=331879&dst=100295&date=03.12.2019}}</ref> | |||
*'''Sweden:''' Cocillana-Etyfin cough syrup containing ethylmorphine 2.5mg/mL is sold as a prescription drug.<ref>{{Citation | title=Cocillana-Etyfin - FASS Allmänhet | url=https://www.fass.se/LIF/product?docType=6&userType&nplId=19641222000010}}</ref> The same goes for Lepheton, a combination containing 0.82 mg/mL ethylmorphine hydrochloride and 2.05 mg/mL ephedrine.<ref>{{Citation | title=Lepheton® - FASS Allmänhet | url=https://www.fass.se/LIF/product?userType=2&nplId=19350429000012&docType=6}}</ref> | |||
*'''Switzerland''': Ethylmorphine is a controlled substance specifically named under Verzeichnis A. Medicinal use is permitted. Some preparations containing ethylmorphine are included in Verzechnis C, while certain ones are excluded.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | |||
*'''United Kingdom:''' Ethylmorphine is a Class B controlled substance under the Misuse of Drugs Act.<ref>{{Citation | title=Misuse of Drugs Act 1971 | url=https://www.legislation.gov.uk/ukpga/1971/38/schedule/2}}</ref> This is the same class as codeine, but unlike codeine, there exist no legal preparations of ethylmorphine. | |||
*'''United States:''' No preparations containing ethylmorphine are on the market in the US. Pure ethylmorphine is listed in Schedule II and combination products containing no more than ethylmorphine 3mg/mL (or 15 mg per dosage unit together with a non-narcotic active ingredient) are listed in Schedule III. Preparations containing no more than ethylmorphine 1mg/mL or 1mg/g are listed in schedule V.<ref>http://www.deadiversion.usdoj.gov/21cfr/cfr/2108cfrt.htm</ref> This is similar to codeine, but unlike codeine, ethylmorphine is not available for medical purposes in the United States. | |||
In general, ethylmorphine and codeine, owing to their structural and pharmacological similarity, are treated similarly by law in most countries. | In general, ethylmorphine and codeine, owing to their structural and pharmacological similarity, are treated similarly by law in most countries. | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Codeine]] | *[[Codeine]] | ||
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==External links== | ==External links== | ||
* [http://en.wikipedia.org/wiki/Ethylmorphine Ethylmorphine (Wikipedia | |||
*[http://en.wikipedia.org/wiki/Ethylmorphine Ethylmorphine (Wikipedia)] | |||
*[https:// | *[https://isomerdesign.com/PiHKAL/explore.php?domain=pk&id=7661 Ethylmorphine (Isomer Design)] | ||
*[http://www.drugs.com/international/ethylmorphine.html Ethylmorphine (Drugs.com)] | *[http://www.drugs.com/international/ethylmorphine.html Ethylmorphine (Drugs.com)] | ||
==References== | ==References== | ||
<references /> | <references /> | ||
[[Category: | [[Category:Psychoactive substance]] | ||
[[Category:Benzofuran]] | |||
[[Category:Morphinan]] | [[Category:Morphinan]] | ||
[[Category:Opioid]] | [[Category:Opioid]] | ||
{{#set:featured=true}} | {{#set:featured=true}} | ||