Ethylmorphine
Encyclopedia
Ethylmorphine is an opiate
narcotic
analgesic
(pain killer).
Ethylmorphine was invented in Germany at Merck
in 1884 and was used as a weaker alternative to heroin for all indications. Chemically, ethylmorphine is a morphine
molecule
with a -25 group substituted for the aromatic 3- group. Therefore the closest chemical relative of ethylmorphine is codeine
, also known as methylmorphine. Ethylmorphine also has a hydromorphone
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.
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, dihydrocodeine
and similar weak opioid
drugs, ethylmorphine is listed under the international Single Convention on Narcotic Drugs
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 Controlled Substances Act
, Schedule II as a pure compound and Schedule III when combined with non-opioid analgesics such as paracetamol
(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 Schedule V, 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.
, similarly to codeine
. Morphine
is a powerful analgesic
and the main active compound found in naturally occurring opium
. Ethylmorphine's metabolism is hindered by ethanol
, which, being a central nervous system
depressant
, 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.
. It is most widely used in ophthalmology for removing inflammation products from the eyes, inducing miosis
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.
" by a small percentage. Medical oral dosages vary from 5 to 30, even 50 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 parenteral
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 codeine
, dihydrocodeine
, ethylmorphine, dihydroethylmorphine, benzylmorphine
(Peronine), acetyldihydrocodeine
, nicocodeine
, nicodicodeine
, hydrocodone
, thebacon, oxycodone
, acetylcodone, methyldihydromorphine
and others.
The lethal dose is unknown. One source (in Finnish), however, suggests it to be as low as 500 mg.
and constipation
. Also, some people are hypersensitive or allergic 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 physical dependence
, in addition to psychological addiction
. This type of addiction is hard to treat.
Taking ethylmorphine in combination with alcohol
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 respiratory arrest
.
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 indometacin
(e.g. Indalgin), which is toxic in high doses.
Antidepressants such as fluoxetine (Prozac) 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 phenobarbitone 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.
Opiate
In medicine, the term opiate describes any of the narcotic opioid alkaloids found as natural products in the opium poppy plant.-Overview:Opiates are so named because they are constituents or derivatives of constituents found in opium, which is processed from the latex sap of the opium poppy,...
narcotic
Narcotic
The term narcotic originally referred medically to any psychoactive compound with any sleep-inducing properties. In the United States of America it has since become associated with opioids, commonly morphine and heroin and their derivatives, such as hydrocodone. The term is, today, imprecisely...
analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
(pain killer).
Ethylmorphine was invented in Germany at Merck
Merck Serono
Merck Serono is a pharmaceutical company headquartered in Geneva, Switzerland. In September 2006, Merck KGaA announced its intent to purchase the majority of Serono shares from Ernesto Bertarelli and the Bertarelli family. The Merck-Serono merger was announced on September 21, 2006...
in 1884 and was used as a weaker alternative to heroin for all indications. Chemically, ethylmorphine is a morphine
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
molecule
Molecule
A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...
with a -25 group substituted for the aromatic 3- group. Therefore the closest chemical relative of ethylmorphine is codeine
Codeine
Codeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
, also known as methylmorphine. Ethylmorphine also has a hydromorphone
Hydromorphone
Hydromorphone, a more common synonym for dihydromorphinone, commonly a hydrochloride is a very potent centrally-acting analgesic drug of the opioid class. It is a derivative of morphine, to be specific, a hydrogenated ketone thereof and, therefore, a semi-synthetic drug...
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.
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, dihydrocodeine
Dihydrocodeine
Dihydrocodeine, also called DHC, Drocode, Paracodeine and Parzone and known by the brand names of Synalgos DC, Panlor DC, Panlor SS, Contugesic, New Bron Solution-ACE, Huscode, Drocode, Paracodin, Codidol, Didor Continus, Dicogesic, Codhydrine, Dekacodin, DH-Codeine,...
and similar weak opioid
Opioid
An opioid is a psychoactive chemical that works by binding to opioid receptors, which are found principally in the central and peripheral nervous system and the gastrointestinal tract...
drugs, ethylmorphine is listed under the international Single Convention on Narcotic Drugs
Single Convention on Narcotic Drugs
The Single Convention on Narcotic Drugs of 1961 is an international treaty to prohibit production and supply of specific drugs and of drugs with similar effects except under licence for specific purposes, such as medical treatment and research...
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 Controlled Substances Act
Controlled Substances Act
The Controlled Substances Act was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. The CSA is the federal U.S. drug policy under which the manufacture, importation, possession, use and distribution of certain...
, Schedule II as a pure compound and Schedule III when combined with non-opioid analgesics such as paracetamol
Paracetamol
Paracetamol INN , or acetaminophen USAN , is a widely used over-the-counter analgesic and antipyretic . It is commonly used for the relief of headaches and other minor aches and pains and is a major ingredient in numerous cold and flu remedies...
(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 Schedule V, 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.
Metabolism
After ingestion, ethylmorphine is converted to morphine in the human liver by the CYP450-isozyme CYP2D6CYP2D6
Cytochrome P450 2D6 , a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body. Also, many substances are bioactivated by CYP2D6 to form their active compounds...
, similarly to codeine
Codeine
Codeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
. Morphine
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
is a powerful analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
and the main active compound found in naturally occurring opium
Opium
Opium is the dried latex obtained from the opium poppy . Opium contains up to 12% morphine, an alkaloid, which is frequently processed chemically to produce heroin for the illegal drug trade. The latex also includes codeine and non-narcotic alkaloids such as papaverine, thebaine and noscapine...
. Ethylmorphine's metabolism is hindered by ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
, which, being a central nervous system
Central nervous system
The central nervous system is the part of the nervous system that integrates the information that it receives from, and coordinates the activity of, all parts of the bodies of bilaterian animals—that is, all multicellular animals except sponges and radially symmetric animals such as jellyfish...
depressant
Depressant
A depressant, or central depressant, is a drug or endogenous compound that depresses the function or activity of a specific part of the brain...
, 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 antitussive to treat dry cough. It is also a moderately strong analgesicAnalgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
. It is most widely used in ophthalmology for removing inflammation products from the eyes, inducing miosis
Miosis
Miosis is the constriction of the pupil of the eye to two millimeters or less...
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
Ethylmorphine is "less potent than morphine" but "more potent than codeineCodeine
Codeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
" by a small percentage. Medical oral dosages vary from 5 to 30, even 50 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 parenteral
Parenteral
Parenteral is a route of administration that involves piercing the skin or mucous membrane. Parenteral nutrition refers to providing nutrition via the veins.-Etymology:...
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 codeine
Codeine
Codeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
, dihydrocodeine
Dihydrocodeine
Dihydrocodeine, also called DHC, Drocode, Paracodeine and Parzone and known by the brand names of Synalgos DC, Panlor DC, Panlor SS, Contugesic, New Bron Solution-ACE, Huscode, Drocode, Paracodin, Codidol, Didor Continus, Dicogesic, Codhydrine, Dekacodin, DH-Codeine,...
, ethylmorphine, dihydroethylmorphine, benzylmorphine
Benzylmorphine
Benzylmorphine is a semi-synthetic opiate narcotic introduced to the international market in 1896 and that of the United States very shortly thereafter...
(Peronine), acetyldihydrocodeine
Acetyldihydrocodeine
Acetyldihydrocodeine is an opiate derivative discovered in Germany in 1914 and was used as as a cough suppressant and analgesic. It is not commonly used, but has activity similar to other opiates...
, nicocodeine
Nicocodeine
Nicocodeine is an opiate derivative, closely related to dihydrocodeine and the codeine analogue of nicomorphine developed as a cough suppressant and analgesic. It is not commonly used in most countries, but has activity similar to other opiates. Nicocodeine and nicomorphine were introduced in the...
, nicodicodeine
Nicodicodeine
Nicodicodeine is an opiate derivative developed as a cough suppressant and analgesic. Synthesized in 1904, it is not commonly used, but has activity similar to other opiates. Nicodicodeine is metabolised in the liver by demethylation to produce 6-nicotinoyldihydromorphine, and subsequently further...
, hydrocodone
Hydrocodone
Hydrocodone or dihydrocodeinone is a semi-synthetic opioid derived from either of two naturally occurring opiates: codeine and thebaine. It is an orally active narcotic analgesic and antitussive...
, thebacon, oxycodone
Oxycodone
Oxycodone is an opioid analgesic medication synthesized from opium-derived thebaine. It was developed in 1916 in Germany, as one of several new semi-synthetic opioids in an attempt to improve on the existing opioids: morphine, diacetylmorphine , and codeine.Oxycodone oral medications are generally...
, acetylcodone, methyldihydromorphine
Methyldihydromorphine
Methyldihydromorphine is a semi-synthetic opioid drug developed in Germany in 1936, controlled under both domestic law and UN conventions because of its possible potential for abuse...
and others.
The lethal dose is unknown. One source (in Finnish), however, suggests it to be as low as 500 mg.
Problems
Tolerance 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, miosisMiosis
Miosis is the constriction of the pupil of the eye to two millimeters or less...
and constipation
Constipation
Constipation refers to bowel movements that are infrequent or hard to pass. Constipation is a common cause of painful defecation...
. Also, some people are hypersensitive or allergic 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 physical dependence
Physical dependence
Physical dependence refers to a state resulting from chronic use of a drug that has produced tolerance and where negative physical symptoms of withdrawal result from abrupt discontinuation or dosage reduction...
, in addition to psychological addiction
Substance dependence
The section about substance dependence in the Diagnostic and Statistical Manual of Mental Disorders does not use the word addiction at all. It explains:...
. This type of addiction is hard to treat.
Taking ethylmorphine in combination with alcohol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
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 respiratory arrest
Respiratory arrest
Respiratory arrest is the cessation of breathing. It is a medical emergency and it usually is related to or coincides with a cardiac arrest. Causes include opiate overdose, head injury, anaesthesia, tetanus, or drowning...
.
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 indometacin
Indometacin
Indometacin or indomethacin is a non-steroidal anti-inflammatory drug commonly used to reduce fever, pain, stiffness, and swelling. It works by inhibiting the production of prostaglandins, molecules known to cause these symptoms...
(e.g. Indalgin), which is toxic in high doses.
Antidepressants such as fluoxetine (Prozac) 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 phenobarbitone 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.