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Codeine (INN) or 3-methylmorphine (a natural isomer of methylated morphine, the other being the semi-synthetic 6-methylmorphine) is an opiate used for its analgesic, antitussive, and antidiarrheal properties. Codeine is the second-most predominant alkaloid in opium, at up to 3 percent; it is much more prevalent in the Iranian poppy (Papaver bractreatum), and codeine is extracted from this species in some places although the below-mentioned morphine methylation process is still much more common. It is considered the prototype of the weak to midrange opioids.
Codeine is found in concentrations of 0.3 to 3.0 per cent in opium prepared by the latex method from unripe pods of Papaver somniferum. The name codeine is derived from the Greek word kodeia for "poppy head." The relative proportion of codeine to morphine, the most common opium alkaloid at 4 to 23 per cent, tends to be somewhat higher in the poppy straw method of preparing opium alkaloids.
Until the beginning of the 19th century, raw opium was used in diverse preparations known as laudanum (see Thomas de Quincey's "Confessions of an English Opium-Eater", 1821) and paregoric elixirs, a number of which were popular in England since the beginning of the 18th century; the original preparation seems to have been elaborated in Leiden, the Netherlands around 1715 by a chemist named Lemort; in 1721 the London Pharmocopeia mentions an Elixir Asthmaticum, replaced by the term Elixir Paregoricum ("pain soother") in 1746.
The progressive isolation of opium's several active components opened the path to improved selectivity and safety of the opiates-based pharmacopeia.
Morphine had been isolated in the early 19th century. Codeine was first isolated in 1832 in France by Pierre Robiquet, a French chemist and pharmacist already famous for the discovery of alizarin, the most widespread red dye, while working on refined morphine extraction processes. This paved the way for the elaboration of a new generation of safer, codeine-based specific antitussive and antidiarrheal potions.
Codeine is currently the most widely used opiate in the world, and probably the most commonly used drug overall according to numerous reports by organizations including the World Health Organization and its League of Nations predecessor agency. It is one of the most effective orally-administered opioid analgesics and has a wide safety margin. Its strength ranges from 8 to 12 percent of morphine in most people; differences in metabolism can change this figure as can other medications, depending on its route of administration.
While codeine can be directly extracted from opium, its original source, most codeine is synthesized from morphine through the process of O-methylation.
By 1972, the effects of the Nixon War On Drugs 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 growing difficult for the United States. After a large percentage of the opium and morphine in the US National Stockpile of Strategic & Critical Materials was tapped in order to ease severe shortages of medicinal opiates — the codeine-based antitussives in particular — in late 1973, researchers were tasked with finding a way to synthesize codeine and its derivatives. They quickly succeeded using petroleum or coal tar and 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).
A dose of approximately 200 mg (oral) of codeine must be administered to give analgesia approximately equivalent to 30 mg (oral) of morphine (Rossi, 2004). However, codeine is, in general, not used in single doses of greater than 60 mg (and no more than 240 mg in 24 hours). When analgesia beyond this is required, stronger opioids such as hydrocodone or oxycodone are favored.
Codeine is metabolized to C6G by uridine diphosphate glucuronosyl transferase UGT2B7, and, since only about 5% of codeine is metabolized by cytochrome P450 CYP2D6, the current evidence is that C6G is the primary active compound. Claims about the supposed "ceiling effect" of codeine doses seemed to rest on the assumption that high doses of codeine saturated CYP2D6, which prevented further conversion of codeine to morphine, which is simply incorrect. There is also no evidence that CYP2D6 inhibition is useful in treating codeine dependence, though the metabolism of codeine to morphine (and hence further metabolism to glucuronide morphine conjugates) does have an effect on the abuse potential of codeine.
The active metabolites of codeine, notably morphine, exert their effects by binding to and activating the μ-opioid receptor.
Cough, though its efficacy in low dose over the counter formulations has been disputed.
Codeine is marketed as both a single-ingredient drug and in combination preparations with the analgesic acetaminophen (paracetamol), as co-codamol, paracod, panadeine, or the Tylenol With Codeine series (e.g., Tylenol 3 and 4 tablets and elixir); with the analgesic acetylsalicylic acid (aspirin), as co-codaprin; or with the NSAID (non-steroidal anti-inflammatory drug) ibuprofen, as Nurofen Plus. These combinations provide greater pain relief than either agent alone (drug synergy). Codeine is also commonly marketed in products containing codeine with other pain killers or muscle relaxers such as Fioricet with Codeine, Soma Compound/Codeine, as well as codeine mixed with phenacetin (Emprazil With Codeine No. 1, 2, 3, and 4), naproxen, indomethacin, diclofenac and others as well as more complex mixtures including such mixtures as aspirin + paracetamol + codeine ± caffeine ± antihistamines and other agents such as mentioned above.
Codeine-only products can be obtained with a prescription as a time release tablet (e.g., Codeine Contin 100 mg and Perduretas 50 mg). Codeine is also marketed in cough syrups with zero to a half-dozen other active ingredients, and a linctus (e.g., Paveral) for all of the uses for which codeine is indicated.
Injectable codeine is available for subcutaneous or intramuscular injection; intravenous injection can cause a serious reaction that can progress to anaphylaxis. Codeine suppositories are also marketed in some countries.
In certain jurisdictions, codeine is available over-the-counter in combination with guaifenesin or promethazine to be sold at the pharmacist's discretion, though many pharmacists decline to do so .
Codeine and morphine as well as opium were used for control of diabetes until relatively recently, and still in rare cases in some countries, and the hypoglycaemic effect of codeine, although usually weaker than that of morphine, diamorphine, or hydromorphone, can lead to cravings for sugar.
Tolerance to many of the effects of codeine develops with prolonged use, including therapeutic effects. 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.
A potentially serious adverse drug reaction, as with other opioids, is respiratory depression. This depression is dose-related and is the mechanism for the potentially fatal consequences of overdose. As codeine is metabolized to morphine, morphine can be passed through breast milk in potentially lethal amounts, fatally depressing the respiration of a breastfed baby.
In some countries, cough syrups and tablets containing codeine are available without prescription; some potential recreational users are reported to buy codeine from multiple pharmacies so as not to arouse suspicion. A heroin addict may use codeine to ward off the effects of a withdrawal.
Codeine is also available in conjunction with the anti-nausea medication promethazine in the form of a syrup. Brand named as Phenergan with Codeine or in generic form as promethazine with codeine. Called 'syrup', this medication is quickly becoming one of the most highly abused codeine preparations.
Codeine is also demethylated by reaction with pyridine to illicitly synthesize morphine. Pyridine is toxic and possibly carcinogenic, so morphine illicitly produced in this manner (and potentially contaminated with pyridine) may be particularly harmful. Codeine can also be turned into α-chlorocodide, which is used in the clandestine synthesis of desomorphine (Permonid).
Equivalent scales for labeling stronger opioids such as diacetylmorphine (heroin), morphine, opium salts mixtures, and others were in common use in the past, and on occasion one can find past references to brand names for hydrocodone (invented 1920, introduced in US 1943), hydromorphone (invented 1924), oxycodone (invented 1916), paregoric and similar drugs containing narcotic content numbers. For example. from circa 1900 to 1925, the most common cough medicine was terpin hydrate With Heroin Elixir No. 2.
Contrary to the advertising matter of some pharmacies, 60 mg is No. 4, not No. 6, and tablets with 45 mg of codeine are not No. 4 and would in all likelihood be classified as No. 3½ under that system. Whether the scale goes to No. 5 and higher is moot at this point, as in the United States and Canada single-dose-unit concentrations of more than 64 mg are not manufactured. The United States Controlled Substances Act of 1970 does place dosage unit strengths of 90 mg of codeine and higher in Schedule II, even if mixed with another active ingredient. Oral tablets, hypodermic tablets, liquid forms, and capsules of less common doses such as 5, 10, 12, 20, 25, 40, 45, 50, 75, 80, 90, 96, 100, 105, 120 and 128 mg and others and in some cases the equivalent dihydrocodeine, dionine, benzylmorphine, and opium dosages were previously available in North America (and in most cases still are in other countries, particularly the 45 mg paracetamol/codeine and 50 and 100 mg single-ingredient codeine tablets).
Preparations for cough or diarrhea containing small amounts of codeine in combination with two or more other active ingredients are Schedule V in the US, and in some states may be dispensed in amounts up to 4 fl. oz. per 48 hours (one or two states set the limit at 4 fl. oz. per 72 hours) without a prescription. Schedule V specifically consigns the product to state and local regulation beyond certain required record-keeping requirements (a dispensary log must be maintained for two years in a ledger from which pages cannot easily be removed and/or are pre-numbered, and the pharmacist must ask for a picture ID such as a driving licence) and also maintain controlled substances in the closed system at the root of the régime intended by the Controlled Substances Act of 1970; the codeine in these products was a Schedule II substance when the company making the Schedule V product acquired it for mixing up the end-product.
In locales where dilute codeine preparations are non-prescription, anywhere from very few to perhaps a moderate percentage of pharmacists will sell these preparations without a prescription. However, many states have their own laws that do require a prescription for Schedule V drugs. The December 2008 issue of The Bulletin of the National Codeine OTC Lobby (Vol. XVIII, No. 4) listed 12 states with some kind of OTC access to codeine, noting that small independent pharmacies are the most likely to have it. This situation is roughly equivalent to that in February 1991, when the aforementioned organisation undertook its first comprehensive study of Schedule V and overall codeine, dihydrocodeine, ethylmorphine, and hydrocodone availability.
Other drugs that are present in Schedule V narcotic preparations like the codeine syrups are ethylmorphine and dihydrocodeine. Paregoric and hydrocodone were transferred to Schedule III from Schedule V even if the preparation contains two or more other active ingredients, and diphenoxylate is usually covered by state prescription laws even though this relative of pethidine is a Schedule V substance when adulterated with atropine to prevent abuse.
Codeine is also available outside the United States as an over-the-counter drug in liquid cough-relief formulations. Around the world, codeine is, contingent on its concentration, a Schedule II and IV drug under the Single Convention on Narcotic Drugs.
Title 76 of the Schengen treaty has made it possible for countries within the signatory states to import and export drugs with various provisos, recording and ordering requirements, and various other rules.
However, codeine is available without prescription from licensed pharmacists in doses up to 0.1% (5 mg/5ml) according to Hong Kong "Dangerous Drugs Ordinance".
Category:French inventions Category:Antitussives Category:Antidiarrhoeals Category:Natural opium alkaloids Category:Prodrugs Category:World Health Organization essential medicines Category:Phenol ethers Category:Morphinans Category:Alkenes
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Name | The Barracudas |
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Background | group_or_band |
Origin | London, England |
Genre | Garage rock revival, Surf rock, Jangle pop |
Years active | 1979-1984, 1989, 2005-present |
Label | EMICloser RecordsFlicknife RecordsNDN Records |
Current members | Jeremy GluckRobin WillsChris WilsonRob CoyneYan Quellien |
Past members | Nick TurnerDavid BuckleyJim DicksonTerry Smith Steve Robinson |
The band's original lineup consisted of: Jeremy Gluck (vocals), Robin Wills (guitar and vocals), David Buckley (bass and vocals) and Nick Turner (drums).
They are notable for their summer 1980 hit single "Summer Fun", which started with an excerpt from a spoof 1960s advertisement for the Plymouth Barracuda, in which one of the announcers has difficulty pronouncing the word barracuda. The single reached number 37 in the UK Singles Chart
Originally perceived as a novelty surf act due to the first album, subsequent recordings showed them to be a fierce garage rock and roll band, in the mold of the 13th Floor Elevators and The Seeds. The band split in 1984, but reformed in 1989 to record "Wait For Everything", and then again in 2005 for the self titled album on NDN. Throughout their career their live performances have been energetic and frenetic.
Category:British New Wave musical groups Category:English rock music groups Category:English pop music groups Category:Musical groups established in 1979 Category:Surf groups Category:Garage punk
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Name | Jon Fratelli |
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Alias | Jon Fratelli, Jon Lawler |
Background | solo_singer |
Birth name | John Paul Lawler |
Born | March 04, 1979 |
Origin | Glasgow, Scotland |
Instrument | Guitar, piano, vocals |
Genre | Alternative rock, Post-punk revival |
Occupation | Musician, songwriter |
Years active | 2005–present |
Associated acts | The Fratellis, Codeine Velvet Club |
Notable instruments | Fender Telecaster Gibson Les Paul Black Beauty |
Current members | Jon FratelliWill FosterRoss MacFarlaneLewis GordonMince Fratelli |
Jon Fratelli (born John Paul Lawler on March 4, 1979 in Glasgow, Scotland) is a Scottish musician and songwriter best known for his work with the band The Fratellis. He has also played with Codeine Velvet Club before moving onto a new solo career.
Jon's role in the band is songwriter, lead vocalist and lead guitarist. He was initially accompanied on guitar by the man now called Mince Fratelli (Gordon McRory), but Mince switched to drums after the initial drummer didn't work out. Writing credits for the first album are for The Fratellis, however, for the second album, they are solely credited to him.
After playing the Coachella festival in California in 2007, during promotion of Fratellis' debut album Costello Music, Jon decided to flee from the US tour and return to Glasgow, stating that he was too tired to continue the rest of the tour. He later saw this as a mistake, but it allowed him to be even more grateful for the success of the band. The band are currently on hiatus while the band members pursue other projects.
For The Fratellis' debut album, Costello Music, Jon mainly used a Fender Telecaster, with the exception of a few songs in which he used a Gibson Les Paul and a Gibson ES-335.
For the second album, Here We Stand, he used a Fender Telecaster, Fender Stratocaster, Gibson Firebird, Rickenbacker 12 string, Gibson Les Paul, and an ES-335 for his electrics. For the acoustic performances, he used a Gibson SJ-200, a Gibson Hummingbird, and a Gibson J-45. During promotional performances of the album, Jon was mainly using a Gibson Les Paul Black Beauty with Bareknuckle Mississippi Queen pickups (humbucker sized P-90's)
It emerged in an NME article that the band was set to be called Codeine Breakfast Club, however, on August 23, 2009, it was confirmed that the band had changed its name to Codeine Velvet Club and their debut album was to be released on November 16, 2009 (however, this was later pushed back to December 28, 2009). This album sees Jon sharing songwriting duties with Lou for about half the tracks on the album, penning the other half by himself (one track, "Nevada" was composed by Will Foster).
Jon and Lou took their band (consisting of Ross MacFarlane on drums, Will Foster on keys and guitar, Lewis Gordon on bass and various horn players known as 'The Velvet Horns') for a tour of the UK in 2009 and the US in 2010. However, Jon decided that he couldn't commit to the band anymore and called an end to the band, finishing off what live dates they had and announcing his solo career.
He has recorded his debut solo album in LA with Tony Hoffer, who produced the Fratellis' first album. During this time, he kept people up to date on the progres of the album via his Twitter page. During the end of 2010, Jon played a handful of solo shows both before and after recording the album, mixing new tracks in with his back catalogue of Fratellis' and Codeine Velvet Club songs. The album is expected to be released in the first half of 2011 by Island Records in the UK and Dangerbird Records in the US. Jon recently announced that his Fratellis' bandmate Mince would be joining him during live shows in 2011, sharing drumming duties with Ross MacFarlane.
Category:Scottish rock musicians Category:1979 births Category:Living people Category:People from Cumbernauld
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Name | Jason Isbell |
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Background | solo_singer |
Origin | Greenhill, Alabama |
Instrument | GuitarElectronic KeyboardVocals |
Genre | RockProgressive countryAlternative country |
Occupation | Singer-songwriterGuitarist |
Years active | 2001 – present |
Label | New West Records, Lightning Rod Records |
Associated acts | Drive-By TruckersJason Isbell and the 400 Unit |
Url | http://www.jasonisbell.com/ |
Jason Isbell (born February 1, 1979 ) is a singer, songwriter, and guitarist from Greenhill, Alabama, near Muscle Shoals.
On April 5, 2007 Isbell announced that he was no longer a member of Drive-By Truckers. The following day, Patterson Hood confirmed the break on the band's official site. In his letter to the fans, Hood described the parting of ways as "amicable" and expressed the hope that fans would continue to support Drive-By Truckers as well as Jason's solo efforts.
Jason Isbell released his first solo album, Sirens of the Ditch, on July 10, 2007.
Jason Isbell and The 400 Unit's eponymous album was released on February 17, 2009 on Lightning Rod Records. Jason Isbell and The 400 Unit is Isbell's second solo release and his first release with his band The 400 Unit. Matt Pence of Centro-Matic serves as co-producer, drummer and engineer.
Isbell's current band, Jason Isbell and the 400 Unit, is primarily made up of other Alabama musicians. The lineup is:
This text is licensed under the Creative Commons CC-BY-SA License. This text was originally published on Wikipedia and was developed by the Wikipedia community.