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| [[File:Codeine_structure.jpg|right]] | | '''Codeine''' is an [[opiate]] used in the treatment of pain and to reduce coughing. It occurs naturally in the [[opium]] poppy and as such has a long history of human use. |
| Codeine is an opiate used for its analgesic, antitussive, antidiarrheal, antihypertensive, anxiolytic,antidepressant, sedative and hypnotic properties. It is also used to suppress premature labor contractions, myocardial infarction, and has many other potential and indicated uses. It is often sold as a salt in the form of either codeine sulfate or codeine phosphate in the United States and Canada; codeine hydrochloride is more common worldwide and the citrate, hydroiodide, hydrobromide, tartrate, and other salts are also seen. It occurs naturally in the opium poppy and as such has a long history of human use.
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| == History == | | == Chemical name == |
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| In 1832, codeine was isolated from opium, which has a codeine content of 2 to 30/0 (see Papaver somniferum). Codeine is also biosynthesized in the roots of Papaver somniferum 1. cv. Marianne (Tam et al. 1980). It is possible that trace amounts of codeine can also be found in other Papaver species (Papaver bracteatum, Papaver decaisnei; cf. Papaver spp.) (Theuns et al. 1986). Codeine is also an endogenous neurotransmitter in humans (cf. morphine). A dosage of 20 to 50 mg produces "general mental stimulation, warmth in the head, and an increase in the pulse rate, as also appear after the consumption of alcohol" (Rompp 1950*). Codeine does not appear to be metabolized in the body and is excreted unchanged. Because codeine suppresses the urge to cough, its most important pharmaceutical use is in cough syrups.
| | (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy- |
| | 17-methylmorphinan-6-ol |
| | {{drugbox | |
| | | IUPAC_name = (5α,6α)-7,8-didehydro-4,5-epoxy-<br />3-methoxy-17-methylmorphinan-6-ol |
| | | image = Codeine.png |
| | | <!-- image2 = Codeine_3d_transparent.gif --> |
| | | CAS_number = 76-57-3 |
| | | CASNo_Ref = {{cascite}} |
| | | ChemSpiderID = 4447447 |
| | | ATC_prefix = R05 |
| | | ATC_suffix = DA04 |
| | | ATC_supplemental = {{ATC|N02|AA59}} |
| | | PubChem = 5284371 |
| | | DrugBank = APRD00120 |
| | | C=18 | H=21 | N=1 | O=3 |
| | | molecular_weight = 299.364 g/mol |
| | | bioavailability = ~90% Oral |
| | | elimination_half-life = 2.5–3 hours |
| | | metabolism = [[Liver|Hepatic]], via [[CYP2D6]] (Cytochrome P450 2D6)<ref>Drug Metab Dispos. 2007 Aug;35(8):1292-300</ref> |
| | | legal_AU = S8 |
| | | legal_CA = Schedule I |
| | | legal_NZ = Class C |
| | | legal_SG = Class B |
| | | legal_UK = Class B |
| | | legal_US = Schedule II |
| | | legal_status = |
| | | routes_of_administration = oral, intra-rectally, [[subcutaneous|SC]], [[intramuscular|IM]] |
| | }} |
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| The dosage when codeine is used as a cough suppressant is 50 mg three times a day. A dosage of 100 to 200 mg results in sleep and sedation.
| | == History == |
| Higher dosages elicit effects comparable to those of morphine. The medical literature contains repeated mentions of "codeine addiction." Codeine "addicts" are said to ingest up to 2 g of codeine daily (Rompp 1950, 115*). Today, codeine is gaining increasing medicinal importance as a substitution therapy for heroin addicts (Gerlach and Schneider 1994). The pharmaceutical industry synthesizes codeine primarily from thebaine, the main active constituent in Papaver bracteatum Lindl. (cf. Papaver spp.) (Morton 1977, 125*; Theuns et al. 1986). Codeine has acquired a certain significance in the music scene (jazz, rock, psychedelia), primarily as a substitute for heroin or morphine. Buffy Saint-Marie sang about the anguish of her codeine dependence in the song "Cod'ine" (LP It's My Way! Vanguard Records 1964). Quicksilver Messenger Service later covered the song and made it famous. In the 1990s, the wave band Codeine had several albums out through Sub Pop. Cough syrups496 with a high codeine content were often consumed as inebriants at concerts, festivals, et cetera (usually in combination with alcohol and cannabis) (Bangs 1978, 158).
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| Since the 1990's codeine has gained popularity in the rap music scene where a mixture containing codeine promethazine cough syrup is consumed under the name [https://en.wikipedia.org/wiki/Purple_drank purple drank] and several artists have released songs about it. ([http://link.springer.com/article/10.1007%2Fs12103-013-9213-7 Hart, Agnich, Stogner, Miller 2013])
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| == Dosage == | |
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| {| class="wikitable"
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| |+ Oral
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| | Light || 50-100mg
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| |-
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| | Common || 100-150mg
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| |-
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| | Strong || 150-200mg
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| |-
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| | Ceiling || 400-600mg
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| |}
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| == Duration ==
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| {| class="wikitable"
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| |+ Oral
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| |-
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| | Onset || 30-45 minutes
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| |-
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| | Duration || 3-6 hours
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| |}
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| == Effects ==
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| === Positive ===
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| * Euphoria
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| * Pain relief
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| * Elevated mood
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| * Overall feeling of contentedness
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| === Neutral ===
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| * Itching
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| === Negative ===
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| * Nausea
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| * Constipation
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| * CNS depression
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| * Drowsiness
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| * Hot/cold flashes
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| * Dizziness
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| * Vomiting
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| * Urinary retention (difficulty urinating)
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| == Harm Reduction ==
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| * People seeking Codeine experiences from medications that contain Acetaminophen (Paracetamol) may be putting themselves at risk for Acetaminophen-related complications such as liver damage. Generally do not consume more than 4g Acetaminophen per day. It is a good idea to conduct a [https://wiki.tripsit.me/wiki/Cold_Water_Extraction cold water extraction] with codeine that contains acetaminophen, which removes most of the acetaminophen. It is an easy and quick procedure. See our wiki for a quick tutorial.
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| * Avoid driving and operating heavy machinery
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| * Recommended time (pauses) between using the substance
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| * Addictive
| | '''Codeine''' is an [[alkaloid]] found in [[opium]] and other poppy saps like Papaver bracteatum, the Iranian poppy, in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. It was first isolated in 1830 in France by Jean-Pierre Robiquet. |
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| === Interactions ===
| | The effects of the Nixon War On Drugs by 1972 or so had caused across-the-board shortages of illicit and licit opiates because of a scarcity of natural opium, poppy straw and other sources of opium alkaloids, and the geopolitical situation was getting less helpful for the United States. After a large percentage of the opium and morphine in the US National Stockpile of Strategic & Critical Materials had to be tapped in order to ease severe shortages of medicinal opiates -- the codeine-based antitussives in particular -- in late 1973, researchers were tasked with and quickly succeeded in finding a way to synthesize codeine and its derivatives and precursors from scratch from petroleum or coal tar using a process developed at the United States' National Institutes of Health. |
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| * Do not mix with alcohol, benzodiazepines, opioids, or other CNS depressants
| | Numerous codeine salts have been prepared since the drug was discovered. The most commonly used are the hydrochloride (freebase conversion ratio 0.805), phosphate (0.736), sulphate (0.859) and citrate (0.842). Others include a salicylate NSAID, codeine salicylate (0.686), and at least four codeine-based barbiturates, the cyclohexenylethylbarbiturate (0.559), cyclopentenylallylbarbiturate (0.561), diallylbarbiturate (0.561), and diethylbarbiturate (0.619). |
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| * Avoid combining with stimulants
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| == Chemistry and Pharmacology == | | == Other names == |
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| The conversion of codeine to morphine occurs in the liver and is catalysed by the cytochrome P450 enzyme CYP2D6. CYP3A4 produces norcodeine and UGT2B7 conjugates codeine, norcodeine, and morphine to the corresponding 3- and 6- glucuronides.
| | *Tylenol with Codeine |
| | *Codate |
| | *Codephos |
| | *Codamol |
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| Some medications are CYP2D6 inhibitors and reduce or even completely block the conversion of codeine to morphine. The most well-known of these are two of the selective serotonin reuptake inhibitors, paroxetine(Paxil) and fluoxetine (Prozac) as well as the antihistamine diphenhydramine (Benadryl) and the antidepressant, bupropion (Wellbutrin, also known as Zyban). Other drugs, such as rifampicin and dexamethasone, induce CYP450 isozymes and thus increase the conversion rate.
| | {{Analgesics}} |
| | | {{Opioids}} |
| The active metabolites of codeine, notably morphine, exert their effects by binding to and activating the μ-opioid receptor.
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| == Legal Status ==
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| Codeine is available as a pure substance and as codeine hydrochloride, codeine phosphate, and codeine phosphate hemihydrate. Codeine is on Schedule III in the United States. Preparations containing codeine (tinctures, cough syrups, et cetera) require a special prescription (i.e., with no refills allowed and/or on special prescription forms). But in other countries, including France, Spain, Nepal, and India, a prescription is still unnecessary and the medicine can be obtained over the counter from any pharmacy.
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| == Links ==
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| [http://en.wikipedia.org/wiki/Codeine Wikipedia]
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| [http://www.erowid.org/pharms/codeine/codeine.shtml Erowid]
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| | [[Category:Opioids]] |
| | [[Category:Analgesics]] |
| [[Category:Drugs]] | | [[Category:Drugs]] |
| | | [[Category:Medicine]] |
| [[Category:Opioid]] | | [[sv:Kodein]] |
| | | [[es:Codeina]] |
| [[Category:Depressant]] | |
Codeine is an opiate used in the treatment of pain and to reduce coughing. It occurs naturally in the opium poppy and as such has a long history of human use.
Chemical name
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-
17-methylmorphinan-6-ol
History
Codeine is an alkaloid found in opium and other poppy saps like Papaver bracteatum, the Iranian poppy, in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. It was first isolated in 1830 in France by Jean-Pierre Robiquet.
The effects of the Nixon War On Drugs by 1972 or so had caused across-the-board shortages of illicit and licit opiates because of a scarcity of natural opium, poppy straw and other sources of opium alkaloids, and the geopolitical situation was getting less helpful for the United States. After a large percentage of the opium and morphine in the US National Stockpile of Strategic & Critical Materials had to be tapped in order to ease severe shortages of medicinal opiates -- the codeine-based antitussives in particular -- in late 1973, researchers were tasked with and quickly succeeded in finding a way to synthesize codeine and its derivatives and precursors from scratch from petroleum or coal tar using a process developed at the United States' National Institutes of Health.
Numerous codeine salts have been prepared since the drug was discovered. The most commonly used are the hydrochloride (freebase conversion ratio 0.805), phosphate (0.736), sulphate (0.859) and citrate (0.842). Others include a salicylate NSAID, codeine salicylate (0.686), and at least four codeine-based barbiturates, the cyclohexenylethylbarbiturate (0.559), cyclopentenylallylbarbiturate (0.561), diallylbarbiturate (0.561), and diethylbarbiturate (0.619).
Other names
- Tylenol with Codeine
- Codate
- Codephos
- Codamol
Opioids (N02A) |
|---|
| Opium
derivatives | Whole Opium
Preparations | | | | Natural Opiates | | | | Semisynthetics | | Morphine Family | | | | 3,6 Diesters of Morphine | | | | Codeine-Dionine Family | | | | Morphinones | | | | Codeinones | | | | Dihydrocodeine Series | | | | Nitrogen Morphine Derivatives | | | | Hydrazones | | | | Others | |
| | Active Opiate
Metabolites | |
| | | Morphinans | | | | Benzomorphans | | | | 4-Phenylpiperidines | | | Open Chain
Opioids | | Amidones | | | | Methadols | | | | Moramides | | | | Thiambutenes | | | | Phenalkoxams | | | | Ampromides | | | | Others | |
| | | Anilidopiperidines | | | Oripavine
derivatives | | | | Phenazepines | | | | Pirinitramides | | | | Benzimidazoles | | | | Indoles | | | | Diphenylmethylpiperazines | | | Opioid peptides
see also: The Opioid Peptides | | | | Others | | | Opioid Antagonists
&
Inverse-Agonists | |
|
- ↑ Drug Metab Dispos. 2007 Aug;35(8):1292-300
