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Codeine: Difference between revisions

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{{headerpanel|{{DepressantOD|opiates}}}}
{{SummarySheet}}
{{SummarySheet}}
{{SubstanceBox/Codeine}}
{{SubstanceBox/Codeine}}


'''Codeine''' (also known as '''3-Methylmorphine''') is a naturally-occurring [[psychoactive class::opioid]] substance of the [[chemical class::morphinan]] class found in extracts of the poppy, particularly ''Papaver bractreatum''.<ref>Dicpinigaitis, P. V., Morice, A. H., Birring, S. S., McGarvey, L., Smith, J. A., Canning, B. J., & Page, C. P. (2014). Antitussive drugs—past, present, and future. Pharmacological Reviews, 66(2), 468-512.</ref> Members of this group produce effects such as [[sedation]], [[cough suppression]], and [[euphoria]] when [[administered]].   
'''Codeine''' (also known as '''3-Methylmorphine''') is a naturally-occurring [[psychoactive class::opioid]] substance of the [[chemical class::morphinan]] class found in extracts of the poppy, particularly ''Papaver bracteatum''.<ref>{{cite journal | vauthors=((Dicpinigaitis, P. V.)), ((Morice, A. H.)), ((Birring, S. S.)), ((McGarvey, L.)), ((Smith, J. A.)), ((Canning, B. J.)), ((Page, C. P.)) | veditors=((Sibley, D. R.)) | journal=Pharmacological Reviews | title=Antitussive Drugs—Past, Present, and Future | volume=66 | issue=2 | pages=468–512 | date= April 2014 | url=http://pharmrev.aspetjournals.org/lookup/doi/10.1124/pr.111.005116 | issn=0031-6997 | doi=10.1124/pr.111.005116}}</ref> Members of this group produce effects such as [[sedation]], [[cough suppression]], and [[euphoria]] when [[administered]].   


Codeine is the second most predominant alkaloid in [[Papaver somniferum (botany)|opium]] (up to three percent).{{citation needed}} Although codeine can be extracted from natural sources, a semi-synthetic process is the primary source of codeine for pharmaceutical use. It is considered the prototype of the weak to midrange [[opioids]] ([[tramadol]], [[dextropropoxyphene]], [[dihydrocodeine]] and [[hydrocodone]].{{citation needed}}
Codeine is the second most predominant [[alkaloid]] in [[Papaver somniferum (botany)|opium]] (up to three percent).{{citation needed}} Although codeine can be extracted from natural sources, a semi-synthetic process is the primary source of codeine for pharmaceutical use. It is considered the prototype of the weak to midrange [[opioids]] ([[tramadol]], [[dextropropoxyphene]], [[dihydrocodeine]] and [[hydrocodone]].{{citation needed}}


Codeine is currently the most widely used opiate in the world,<ref>https://opiates.com/codeine</ref><ref>http://www.sciencedaily.com/releases/2010/03/100314150916.htm</ref> and is one of the most commonly used drugs 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.  
Codeine is currently the most widely used opiate in the world,<ref>{{Citation | title=Codeine General Information | url=https://www.opiates.com/codeine/}}</ref><ref>{{Citation | title=Unlocking the opium poppy’s biggest secret: Genes that make codeine, morphine | url=https://www.sciencedaily.com/releases/2010/03/100314150916.htm}}</ref> and is one of the most commonly used drugs 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.  


Recreationally, it is usually purchased over the counter within painkillers that mix it with other more toxic substances. These can be separated using a [[Extraction of opioids from painkiller products|cold water extraction technique]].
Recreationally, it is usually purchased over the counter within painkillers that mix it with other more toxic substances. These can be separated using a [[Extraction of opioids from painkiller products|cold water extraction technique]].


==Chemistry==
==Chemistry==
Codeine, or 3-methylmorphine, is an opioid of the morphinan class. Codeine 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. Codeine (along with other morphinans) contains an ether bridge between two of its rings, connecting R<sub>4</sub> and R<sub>5</sub> through an oxygen group. It contains a hydroxy group (OH-) bound at R<sub>6</sub> and a methyl group located on the nitrogen atom at R<sub>17</sub>.  
Codeine, or 3-methylmorphine, is an opioid of the morphinan class. Codeine 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. Codeine (along with other morphinans) contains an ether bridge between two of its rings, connecting R<sub>4</sub> and R<sub>5</sub> through an oxygen group. It contains a hydroxy group (OH-) bound at R<sub>6</sub> and a methyl group located on the nitrogen atom at R<sub>17</sub>.  


On the same ring containing the hydroxy group, codeine contains a double bond which [[dihydrocodeine]] lacks. Codeine is closely related to morphine as both contain an oxygen group at R<sub>3</sub>, but this oxygen group in codeine is substituted by a methyl group (making a methoxy group). Codeine is analogous to the other morphinans including [[dihydrocodeine]], [[heroin]], [[ethylmorphine]], [[hydrocodone]], and [[oxycodone]].
On the same ring containing the hydroxy group, codeine contains a double bond which [[dihydrocodeine]] lacks. Codeine is closely related to morphine as both contain an oxygen group at R<sub>3</sub>, but this oxygen group in codeine is substituted by a methyl group (making a methoxy group). Codeine is analogous to the other morphinans including [[dihydrocodeine]], [[heroin]], [[ethylmorphine]], [[hydrocodone]], and [[oxycodone]].


==Pharmacology==
==Pharmacology==
Codeine is not itself centrally active, and must first be converted via first pass metabolism into [[morphine]] by the cytochrome P450 enzyme CYP2D6 (as such, it is a [[prodrug]] for morphine). Codeine is also metabolised into the inactive norcodeine via the CYP3A4 enzyme system. Both resultant forms are conjugated by UGT2B7 into their corresponding 3-glucuronide.{{citation needed}}  
Codeine is not itself centrally active, and must first be converted via first-pass metabolism into [[morphine]] by the cytochrome P450 enzyme CYP2D6 (as such, it is a [[prodrug]] for morphine). Codeine is also metabolized into the inactive norcodeine via the CYP3A4 enzyme system. Both resultant forms are conjugated by UGT2B7 into their corresponding 3-glucuronide.{{citation needed}}  


Some percentage of the population produce less CYP2D6 enzymes and so experience a significant reduction of effects from codeine in comparison to that of the average person. However, others produce CYP2D6 enzymes in higher quantities which can result in a hypersensitivity to the drug. Some methods of potentiating [[opioids]], such as using grapefruit juice throughout the day before consumption, inhibits the CYP3A4 enzyme.<ref>https://www.ncbi.nlm.nih.gov/pubmed/17995595</ref> This results in less codeine being converted into norcodeine which leaves more to be metabolised into morphine. This also indicates a lacking capability in metabolism of codeine into morphine when a user consumes antihistamines such as [[diphenhydramine]] prior to ingestion of codeine. <ref>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2148980/</ref>  
Some percentage of the population produces less CYP2D6 enzymes and so experience a significant reduction of effects from codeine in comparison to that of the average person. However, others produce CYP2D6 enzymes in higher quantities which can result in hypersensitivity to the drug. Some methods of potentiating [[opioids]], such as using grapefruit juice throughout the day before consumption, inhibits the CYP3A4 enzyme.<ref>{{cite journal | vauthors=((Girennavar, B.)), ((Jayaprakasha, G. K.)), ((Patil, B. S.)) | journal=Journal of Food Science | title=Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins | volume=72 | issue=8 | pages=C417-421 | date= October 2007 | issn=1750-3841 | doi=10.1111/j.1750-3841.2007.00483.x}}</ref> This results in less codeine being converted into norcodeine which leaves more to be metabolized into morphine{{Citation needed|reason=The claim is not backed up by any provided source, the claim here goes beyond the content of the previous source.}}. This also indicates a lacking capability in the metabolism of codeine into morphine when a user consumes antihistamines such as [[diphenhydramine]] prior to the ingestion of codeine. <ref>{{cite journal | vauthors=((Lurcott, G.)) | journal=Anesthesia Progress | title=The effects of the genetic absence and inhibition of CYP2D6 on the metabolism of codeine and its derivatives, hydrocodone and oxycodone. | volume=45 | issue=4 | pages=154–156 | date= 1998 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2148980/ | issn=0003-3006}}</ref>  


There is an upper limit to the amount of codeine which can be converted by enzymatic metabolism into morphine throughout an individual session. This limit is commonly referred to as the "ceiling dose", which is commonly believed to be around 400mg. Consuming higher doses will lead to greater side effects such as [[itchiness]] and [[nausea]], but will not increase [[euphoria]].  
There is an upper limit to the amount of codeine which can be converted by enzymatic metabolism into morphine throughout an individual session. This limit is commonly referred to as the "ceiling dose", which is commonly believed to be around 400mg. Consuming higher doses will lead to greater side effects such as [[itchiness]] and [[nausea]], but will not increase [[euphoria]].  


The active metabolites of codeine, notably [[morphine]], exert their effects by binding to and activating [[opioid]] receptors, mainly the [[Opioid#Receptor_types|μ-opioid]] [[receptor]].<ref>http://jpet.aspetjournals.org/content/308/2/547</ref> 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]], [[muscle relaxation|muscle relaxing]] 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 codeine, notably [[morphine]], exert their effects by binding to and activating [[opioid]] receptors, mainly the [[Opioid#Receptor_types|μ-opioid]] [[receptor]].<ref>{{cite journal | vauthors=((Thompson, C. M.)), ((Wojno, H.)), ((Greiner, E.)), ((May, E. L.)), ((Rice, K. C.)), ((Selley, D. E.)) | journal=Journal of Pharmacology and Experimental Therapeutics | title=Activation of G-Proteins by Morphine and Codeine Congeners: Insights to the Relevance of O- and N-Demethylated Metabolites at μ- and δ-Opioid Receptors | volume=308 | issue=2 | pages=547–554 | date=1 February 2004 | url=https://jpet.aspetjournals.org/content/308/2/547 | issn=0022-3565 | doi=10.1124/jpet.103.058602}}</ref> 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]], [[muscle relaxation|muscle relaxing]] 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.


Codeine itself is a weak ligand for the opioid receptors. However, its main active metabolite, [[morphine]], shows [[Morphine#Binding_affinities_.28Ki.29.5B12.5D|much stronger agonistic effects]].
Codeine itself is a weak ligand for the opioid receptors. However, its main active metabolite, [[morphine]], shows [[Morphine#Binding_affinities_.28Ki.29.5B12.5D|much stronger agonistic effects]].


===Binding affinities (K<sub>i</sub>)<ref>Affinities of Dihydrocodeine and its Metabolites to Opioid Receptors - Helmut Schmidt et al. (August 2002) | http://onlinelibrary.wiley.com/doi/10.1034/j.1600-0773.2002.910203.x/full</ref>===
===Binding affinities (K<sub>i</sub>)<ref>{{cite journal | vauthors=((Schmidt, H.)), ((Vormfelde, S. V.)), ((Klinder, K.)), ((Gundert-Remy, U.)), ((Gleiter, C. H.)), ((Skopp, G.)), ((Aderjan, R.)), ((Fuhr, U.)) | journal=Pharmacology & Toxicology | title=Affinities of Dihydrocodeine and its Metabolites to Opioid Receptors: DIHYDROCODEINE BINDING TO OPIOID RECEPTORS | volume=91 | issue=2 | pages=57–63 | date= August 2002 | url=http://doi.wiley.com/10.1034/j.1600-0773.2002.910203.x | issn=09019928 | doi=10.1034/j.1600-0773.2002.910203.x}}</ref>===


* Mu opioid agonist - 589 nM
*Mu opioid agonist - 589 nM
* Kappa opioid agonist - 18061 nM
*Kappa opioid agonist - 18061 nM
* Delta opioid agonist - 11442 nM
*Delta opioid agonist - 11442 nM


==Subjective effects==
==Subjective effects==
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
{{effects/base
{{effects/base


|{{effects/physical|
|{{effects/physical|


The general head space of codeine is described by many as one of euphoria, relaxation, anxiety suppression and pain relief.  
The general head space of codeine is described by many as one of euphoria, relaxation, anxiety suppression, and pain relief.  


*'''[[Effect::Pain relief]]'''
*'''[[Effect::Pain relief]]'''
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|{{effects/cognitive|
|{{effects/cognitive|


*'''[[Effect::Cognitive euphoria]]''' - 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]]''' - 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 a powerful and overwhelming feeling of emotional bliss, contentment, and happiness.
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Compulsive redosing]]''' - It is worth noting that redosing codeine will not amplify the intensity of its effects.  
*'''[[Effect::Compulsive redosing]]''' - It is worth noting that redosing codeine will not amplify the intensity of its effects.  
*'''[[Effect::Dream potentiation]]'''
*'''[[Effect::Dream potentiation]]'''
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*'''[[Effect::Double vision]]''' - At high doses, the eyes un-focus and re-focus uncontrollably. This creates a blurred effect and double vision that is present no matter where one focuses their eyes. This can be so intense it becomes impossible to read or drive.
*'''[[Effect::Double vision]]''' - At high doses, the eyes un-focus and re-focus uncontrollably. This creates a blurred effect and double vision that is present no matter where one focuses their eyes. This can be so intense it becomes impossible to read or drive.


====Hallucinatory States====
*'''[[Effect::Internal Hallucination]]''' -One may experience a state of semi-consciousness and hypnagogia during heavy dosage nodding which results in dream-like states and up to level 3 imagery. This is often accompanied by ill-defined geometry.
}}
}}
}}
}}
===Experience reports===
===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:
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_Codeine.shtml Erowid Experience Vaults: Codeine]
 
*[https://www.erowid.org/experiences/subs/exp_Codeine.shtml Erowid Experience Vaults: Codeine]


==Common forms==
==Common forms==
Codeine is available within pharmacies across the world in a variety of forms which combine it with other products which are dangerous or even fatal to consume at higher dosages. This is done to act as a deterrent to prevent their recreational use but can easily be circumvented with the use of a [[Extraction of opioids from painkiller products|cold water extraction]].
Codeine is available within pharmacies across the world in a variety of forms that combine it with other products that are dangerous or even fatal to consume at higher dosages. This is done to act as a deterrent to prevent their recreational use but can easily be circumvented with the use of a [[Extraction of opioids from painkiller products|cold water extraction]].
<gallery>
<gallery>
File:03-44-391291803279-co-codamol.jpg|Co-codamol pills contain 500mg of paracetemol per 8mg of codeine in each pill. It is available behind the counter within any British pharmacy.
File:03-44-391291803279-co-codamol.jpg|Co-codamol contain 500mg of paracetamol per 8mg of codeine. It is available behind the counter in any British pharmacy.
File:Nurofen plus.jpg|Nurofen plus pills contain 12.8mg alongside of ibuprofen. It is available behind the counter within any British pharmacy.
File:Nurofen plus.jpg|Nurofen plus contain 12.8mg of codeine alongside ibuprofen. It is available behind the counter in any British pharmacy. Due to the higher codeine content than co-codamol, they are better for [[Extraction of opioids from painkiller products|cold water extraction]].
File:50383-805-16_full.jpg|Many prescription-strength cough syrups contain codeine and promethazine - an antihistamine. When used recreationally they are commonly known as lean or ''[https://en.wikipedia.org/wiki/Purple_drank purple drank]''.
File:50383-805-16 full.jpg|Many prescription-strength cough syrups contain codeine and promethazine - an antihistamine. When used recreationally they are commonly known as lean or ''[https://en.wikipedia.org/wiki/Purple_drank purple drank]''.
</gallery>
</gallery>


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===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Depressants}}
{{DangerousInteractions/Opioids}}


==Legal status==
==Legal status==
*'''Australia:''' In Australia, codeine preparations are S4 (schedule 4, or Prescription Only) medications. Preparations containing pure codeine (e.g., codeine phosphate tablets or codeine phosphate linctus) are available on prescription and are considered S8 (schedule 8, or Controlled Drug (Possession without authority illegal)). Schedule 8 preparations are subject to the strictest regulation of all medications available to consumers.
 
*'''Austria:''' Codeine is legal for medical use under the AMG (Arzneimittelgesetz Österreich) and illegal when sold or possessed without a prescription under the SMG (Suchtmittelgesetz Österreich).{{citation needed}}
*'''Australia:''' In Australia, codeine preparations are Schedule 4 (Prescription Only) medications when combined with other substances<ref>{{Citation | title=Poisons Standard October 2019 | url=https://www.legislation.gov.au/Details/F2019L01197/Html/Text#_Toc17278861}}</ref>. Preparations containing pure codeine (e.g., codeine phosphate tablets or codeine phosphate linctus) are available on prescription and are considered Schedule 8 (Controlled Drug (Possession without authority illegal))<ref>{{Citation | title=Poisons Standard October 2019 | url=https://www.legislation.gov.au/Details/F2019L01197/Html/Text#_Toc17278865}}</ref>. Schedule 8 drugs are drugs that are available to be prescribed but are heavily restricted to prevent abuse and dependence<ref>{{Citation | title=Poisons Standard October 2019 | url=https://www.legislation.gov.au/Details/F2019L01197/Html/Text#_Toc17278839}}</ref>. Possessing Schedule 8 drugs without authority is a criminal offense and can have varying punishments depending on the state of prosecution.
*'''Canada:''' In Canada, codeine is available over the counter in combination tablets with the following restrictions: no more than 8 mg per dosage unit and it must be combined with at least two other active ingredients. It is kept behind the counter, to be sold on request-- generally to those 18 and over-- after brief consultation and at the pharmacist's discretion. The other active ingredients most commonly consist of another non-opioid analgesic (300 mg acetaminophen, as in Tylenol No. 1; or 325 mg aspirin, as in 222s) and 15 mg caffeine. OTC tablets containing ibuprofen are generally unavailable. Preparations with a codeine content higher than 8 mg per dosage unit, or fewer than two other active ingredients, are available on prescription.{{citation needed}}
*'''Austria:''' Codeine is legal for medical use under the AMG (Arzneimittelgesetz Österreich) and illegal when sold or possessed without a prescription under the SMG (Suchtmittelgesetz Österreich).<ref>{{cite web|url=https://www.ris.bka.gv.at/GeltendeFassung.wxe?Abfrage=Bundesnormen&Gesetzesnummer=10011053|title=Suchtgiftverordnung|publisher=Government of Austria|access-date= February 18, 2022}}</ref>
*'''Denmark:''' In Denmark, codeine is sold over the counter with max 9.6 mg in mixture. The item is given over the counter, no prescriptions. The strongest available over the counter preparation containing codeine has 9.6 mg (with aspirin, brand name Kodimagnyl); anything stronger requires a prescription for legal possession.{{citation needed}}
*'''Canada:''' In Canada, codeine is available over the counter in combination tablets with the following restrictions: no more than 8 mg per dosage unit and it must be combined with at least two other active ingredients. It is kept behind the counter, to be sold on request-- generally to those 18 and over-- after a brief consultation and at the pharmacist's discretion. The other active ingredients most commonly consist of another non-opioid analgesic (300 mg acetaminophen, as in Tylenol No. 1; or 325 mg aspirin, as in 222s) and 15 mg caffeine. OTC tablets containing ibuprofen are generally unavailable. Preparations with a codeine content higher than 8 mg per dosage unit, or fewer than two other active ingredients, are available on prescription.{{citation needed}}
*'''Finland:''' In Finland, codeine cough syrups with a maximum strength of 1mg/ml is sold in pharmacies over the counter. Codeine isn't available in pill form without a prescription. Any stronger cough syrup and combination painkillers (codeine with paracetamol or ibuprofen such as Panacod, Co-codamol and Ardinex) require a prescription.{{citation needed}}
*'''Denmark:''' In Denmark, codeine is sold over the counter with max 9.6 mg in the mixture. The item is given over the counter, with no prescriptions. The strongest available over the counter preparation containing codeine has 9.6 mg (with aspirin, brand name Kodimagnyl); anything stronger requires a prescription for legal possession.{{citation needed}}
*'''France:''' In France, most preparations containing codeine do not require a doctor's prescription. Example products containing codeine include Néocodion (cough pills, and syrup), Codoliprane (codeine with paracetamol), Prontalgine and Migralgine (codeine, paracetamol and caffeine).<ref>http://www.vidal.fr/Substance/codeine-1039.htm</ref>
*'''Finland:''' In Finland, codeine cough syrups with a maximum strength of 1mg/ml is sold in pharmacies over the counter. Codeine isn't available in pill form without a prescription. Any stronger cough syrup and combination painkillers (codeine with paracetamol or ibuprofen such as Panacod, Co-codamol, and Ardinex) require a prescription.{{citation needed}}
*'''France:''' In France, most preparations containing codeine do not require a doctor's prescription. Example products containing codeine include Néocodion (cough pills, and syrup), Codoliprane (codeine with paracetamol), Prontalgine and Migralgine (codeine, paracetamol, and caffeine).<ref>{{Citation | title=Codéine : substance active à effet thérapeutique | url=https://www.vidal.fr/medicaments/substances/codeine-1039.html}}</ref> Codeine is regulated/controlled substance (schedule 2) since 2017 after a decision of the "Minister of Health" Agnès Buzyn, it is therefore now under prescription only and raw pure codeine is not available altogether anymore. The most common prescribed codeine brands are Klipal and Codoliprane, both mixed with paracetamol heavily. Klipal being the strongest ratio, 50mg codeine for 600mg paracetamol.
*'''Germany:''' Codeine is a controlled substance under Anlage III of the BtMG. It can only be prescribed on a narcotic prescription form. There is an exception for preparations, containing up to 2,5% or 100mg codeine per unit, which can be prescribed on a regular prescription if not prescripted to an alcohol or drug dependent person.<ref>{{Citation | title=Anlage III BtMG - Einzelnorm | url=http://www.gesetze-im-internet.de/btmg_1981/anlage_iii.html}}</ref>
*'''Greece:''' Codeine is classed as an illegal drug in Greece, and individuals possessing it could conceivably be arrested, even if they were legitimately prescribed it in another country. It is sold only with a doctor's prescription.<ref>http://gogreece.about.com/od/planagreattriptogreece/a/greecepharmacy_2.htm</ref>
*'''Greece:''' Codeine is classed as an illegal drug in Greece, and individuals possessing it could conceivably be arrested, even if they were legitimately prescribed it in another country. It is sold only with a doctor's prescription.<ref>http://gogreece.about.com/od/planagreattriptogreece/a/greecepharmacy_2.htm</ref>
*'''Hong Kong:''' In Hong Kong, codeine is regulated under Laws of Hong Kong, Dangerous Drugs Ordinance, Chapter 134, Schedule 1. It can be used legally only by health professionals and for university research purposes. The substance can be given by pharmacists under a prescription. However, codeine is available without prescription from licensed pharmacists in doses up to 0.1%<ref>Laws of Hong Kong, Dangerous Drugs Ordinance, Chapter 134</ref>
*'''Hong Kong:''' In Hong Kong, codeine is regulated under Laws of Hong Kong, Dangerous Drugs Ordinance, Chapter 134, Schedule 1. It can be used legally only by health professionals and for university research purposes. The substance can be given by pharmacists under a prescription. However, codeine is available without prescription from licensed pharmacists in doses up to 0.1%<ref>Laws of Hong Kong, Dangerous Drugs Ordinance, Chapter 134</ref>
*'''Iceland:''' Preparations of paracetamol and codeine require a prescription in Iceland.{{citation needed}}
*'''Iceland:''' Preparations of paracetamol and codeine require a prescription in Iceland.{{citation needed}}
*'''India:''' Codeine preparations require a prescription in India. A preparation of paracetamol and codeine is available in India. Codeine is also present in various cough syrups as codeine phosphate.{{citation needed}}
*'''India:''' Codeine preparations require a prescription in India. Preparation of paracetamol and codeine is available in India. Codeine is also present in various cough syrups as codeine phosphate.{{citation needed}}
*'''Iran:''' Preparations of codeine in Iran normally comes with paracetamol, but can be purchased over-the-counter. Iran's deputy health minister reported that codeine is Iran's best selling OTC medication. The recreational use of codeine has also become widespread throughout Iran but authorities continue to let codeine be purchased without permission from a doctor, although the pharmacist may ask for the identification of the purchaser to verify they are 18 years or older to buy.{{citation needed}}
*'''Iran:''' Preparations of codeine in Iran normally comes with paracetamol, but can be purchased over-the-counter. Iran's deputy health minister reported that codeine is Iran's best selling OTC medication. The recreational use of codeine has also become widespread throughout Iran but authorities continue to let codeine be purchased without permission from a doctor, although the pharmacist may ask for the identification of the purchaser to verify they are 18 years or older to buy.{{citation needed}}
*'''Ireland:''' Codeine remains a semi non-prescriptive, over-the-counter drug up to a limit of 12.8 mg per pill, but codeine products must be out of the view of the public. Products containing more than 12.8 mg codeine are available on prescription only.{{citation needed}}
*'''Ireland:''' Codeine remains a semi non-prescriptive, over-the-counter drug up to a limit of 12.8 mg per pill, but codeine products must be out of the view of the public. Products containing more than 12.8 mg codeine are available on prescription only.{{citation needed}}
*'''Italy:''' Codeine tablets or preparations require a prescription in Italy. Preparations of paracetamol and codeine are available in Italy as Co-Efferalgan and Tachidol.{{citation needed}}
*'''Italy:''' Codeine tablets or preparations require a prescription in Italy. Preparations of paracetamol and codeine are available in Italy as Co-Efferalgan and Tachidol.{{citation needed}}
*'''Japan:''' Codeine and similar mid-level centrally acting agents in combination with non-opioid analgesics, antihistamines, vitamins, inert GI agents like kaolin & pectin, mild laxatives, antacids, and herbal preparations, can be purchased over the counter, with 10 mg being the ceiling for OTC dispensing.{{citation needed}}
*'''Japan:''' Codeine and similar mid-level centrally acting agents in combination with non-opioid analgesics, antihistamines, vitamins, inert GI agents like kaolin & pectin, mild laxatives, antacids, and herbal preparations, can be purchased over the counter, with 10 mg being the ceiling for OTC dispensing.{{citation needed}}
*'''Russia:''' According to ITAR-Tass and Austria Presse-Agentur, OTC availability of codeine products was rescinded nationwide in 2012 because of the discovery of the Krokodil method of underground desomorphine synthesis.
*'''Sri Lanka:''' Codeine preparations are available as over the counter pharmacy medicines in Sri Lanka. The most common preparation is Panadeine, which contains 500 mg of Paracetamol and 8 mg of Codeine.
*'''Maldives:''' The Maldives takes an infamously strict line on medicines, with many common drugs, anything containing codeine is banned unless you have a notarized and authenticated doctor's prescription. Visitors breaking the rules, even inadvertently, have been deported or imprisoned.{{citation needed}}
*'''Maldives:''' The Maldives takes an infamously strict line on medicines, with many common drugs, anything containing codeine is banned unless you have a notarized and authenticated doctor's prescription. Visitors breaking the rules, even inadvertently, have been deported or imprisoned.{{citation needed}}
*'''United States:''' In the United States, codeine is regulated by the Controlled Substances Act. Federal law dictates that codeine be a Schedule II controlled substance when used in products for pain-relief that contain codeine alone or more than 90 mg per dosage unit. Tablets of codeine in combination with aspirin or acetaminophen (paracetamol/Tylenol) made for pain relief are listed as Schedule III; and cough syrups are Schedule III or V, depending on formula.{{citation needed}}
*'''Poland:''' Codeine is listed in "Wykaz środków odurzających i substancji psychotropowych" group " II-N" which means it's legal to use in scientific and medical pruposes, and  is available over the counter in doses of 15mg in combination with 500mg paracetamol (Antidol) or 300mg sulfogaiacol (Thiocodin), or 10mg in combination with thyme extract (Neoazarina). However a pharmacy worker can refuse to sell it if they believe the client is a minor or wants to use it for drug abuse purposes.<ref>{{Citation | title=Wykaz środków odurzających i substancji psychotropowych | url=https://pl.wikipedia.org/wiki/Wykaz_%C5%9Brodk%C3%B3w_odurzaj%C4%85cych_i_substancji_psychotropowych#Grupa_II-N}}</ref> <ref>{{Citation | title=Kodeina – Narkopedia | url=https://narkopedia.org/Kodeina#Polska}}</ref>
*'''Romania:''' Codeine is sold OTC (when combined with another active ingredient), the limit being 12.8mg of codeine per pill, which is seen in Nurofen Plus. Any amount above 12.8mg/unit requires a prescription, whether it has another ingredient or not.
*'''Russia:''' According to ITAR-Tass and Austria Presse-Agentur, OTC availability of codeine products was rescinded nationwide in 2012 because of the discovery of the Krokodil method of underground desomorphine synthesis.{{citation needed}}
*'''Spain:''' Codeine tablets or preparations require a prescription in Spain, although this is often not enforced and many pharmacies will sell codeine products without the requirement of a prescription.{{citation needed}}
*'''Spain:''' Codeine tablets or preparations require a prescription in Spain, although this is often not enforced and many pharmacies will sell codeine products without the requirement of a prescription.{{citation needed}}
*'''Sri Lanka:''' Codeine preparations are available as over the counter pharmacy medicines in Sri Lanka. The most common preparation is Panadeine, which contains 500 mg of Paracetamol and 8 mg of Codeine.{{citation needed}}
*'''Sweden:''' Codeine is Schedule III under Swedish law, which means it is heavily regulated and sold only to those who have a prescription.{{citation needed}}
*'''Switzerland''': Codeine is a controlled substance specifically named under Verzeichnis A. Medicinal use is permitted. Some preparations containing codeine are included in Verzeichnis 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>
*'''Turkey''': Codeine is a 'red prescription' only substance<ref>KIRMIZI REÇETEYE TABİ İLAÇLAR | https://www.titck.gov.tr/storage/Archive/2019/contentFile/K%C4%B1rm%C4%B1z%C4%B1%20Re%C3%A7eteye%20Tabi%20%C4%B0la%C3%A7lar%2005072019_ebcc7e92-6661-4983-870a-fe8983a9c2b7.pdf</ref> and illegal when sold or possessed without a prescription.{{citation needed}}
*'''United Arabian Emirates:''' The UAE takes an exceptionally strict line on medicines, with many common drugs, notably anything with containing codeine being banned unless you have a notarized and authenticated doctor's prescription. Visitors breaking the rules, even inadvertently, have been deported or imprisoned. The US Embassy to the UAE maintains an [http://abudhabi.usembassy.gov/restricted_medication.html unofficial list] of what may not be imported.{{citation needed}}
*'''United Arabian Emirates:''' The UAE takes an exceptionally strict line on medicines, with many common drugs, notably anything with containing codeine being banned unless you have a notarized and authenticated doctor's prescription. Visitors breaking the rules, even inadvertently, have been deported or imprisoned. The US Embassy to the UAE maintains an [http://abudhabi.usembassy.gov/restricted_medication.html unofficial list] of what may not be imported.{{citation needed}}
*'''Romania:''' Codeine is not allowed without a medical prescription.{{citation needed}}
*'''United Kingdom:''' Under the Misuse of Drugs Act 1971 codeine is a Class B controlled substance or a Class A drug when prepared for injection.<ref>{{Citation |title=Misuse of Drugs Act 1971 | url=https://www.legislation.gov.uk/ukpga/1971/38/schedule/2}}</ref> The possession of controlled substances without a prescription is a criminal offense.<ref>{{Citation | title=Misuse of Drugs Act 1971 | url=https://www.legislation.gov.uk/ukpga/1971/38/contents}}</ref> However, certain preparations of codeine are exempt from this restriction under Schedule 5 of the Misuse of Drugs Regulations 2001. It is thus legal to possess codeine without a prescription, provided that it is compounded with at least one other active or inactive ingredient and that the dosage of each tablet, capsule, etc does not exceed 100 mg or 2.5% concentration in the case of liquid preparations.{{citation needed}}
*'''United Kingdom:''' Under the Misuse of Drugs Act 1971 codeine is a Class B controlled substance or a Class A drug when prepared for injection.<ref>http://www.legislation.gov.uk/ukpga/1971/38/schedule/2</ref> The possession of controlled substances without a prescription is a criminal offence.<ref>http://www.legislation.gov.uk/ukpga/1971/38/contents</ref> However, certain preparations of codeine are exempt from this restriction under Schedule 5 of the Misuse of Drugs Regulations 2001. It is thus legal to possess codeine without a prescription, provided that it is compounded with at least one other active or inactive ingredient and that the dosage of each tablet, capsule, etc does not exceed 100 mg or 2.5% concentration in the case of liquid preparations.{{citation needed}}
*'''United States:''' In the United States, codeine is regulated by the Controlled Substances Act. Federal law dictates that codeine be a Schedule II controlled substance when used in products for pain-relief that contain codeine alone or more than 90 mg per dosage unit. Tablets of codeine in combination with aspirin or acetaminophen (paracetamol/Tylenol) made for pain relief are listed as Schedule III; and cough syrups are Schedule III or V, depending on the formula.{{citation needed}}
*'''Sweden:''' Codeine is Schedule III under Swedish law, which means it is heavily regulated and sold only to those who have a prescription.{{citation needed}}


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Extraction of opioids from painkiller products]]
*[[Extraction of opioids from painkiller products]]
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*[[Oxycodone]]
*[[Oxycodone]]
*[[Kratom]]
*[[Kratom]]
==External links==
==External links==
*[https://en.wikipedia.org/wiki/Codeine Codeine (Wikipedia)]
*[https://en.wikipedia.org/wiki/Codeine Codeine (Wikipedia)]
*[https://erowid.org/pharms/codeine/codeine.shtml Codeine (Erowid Vault)]
*[https://erowid.org/pharms/codeine/codeine.shtml Codeine (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=9293 Codeine (TiHKAL / Isomer Design)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=9293 Codeine (Isomer Design)]
*[https://go.drugbank.com/drugs/DB00318 Codeine (DrugBank)]
*[https://www.drugs.com/codeine.html Codeine (Drugs.com)]
*[https://drugs-forum.com/wiki/Codeine Codeine (Drugs-Forum)]


==Literature==
==Literature==
* Friswell J, Phillips C, Holding J, Morgan CJ, Brandner B, Curran HV. (2008). Acute effects of opioids on memory functions of healthy men and women. Psychopharmacology (Berl.). 198 (2): 243–50. https://doi.org/10.1007/s00213-008-1123-x.
 
* Schmidt, H., Vormfelde, S. V., Klinder, K., Gundert-Remy, U., Gleiter, C. H., Skopp, G., Aderjan, R. and Fuhr, U. (2002), Affinities of Dihydrocodeine and its Metabolites to Opioid Receptors. Pharmacology & Toxicology, 91: 57–63.  https://doi.org/10.1034/j.1600-0773.2002.910203.x
*Friswell J, Phillips C, Holding J, Morgan CJ, Brandner B, Curran HV. (2008). Acute effects of opioids on memory functions of healthy men and women. Psychopharmacology (Berl.). 198 (2): 243–50. https://doi.org/10.1007/s00213-008-1123-x.
* Koch T, Höllt V. (2008). Role of receptor internalization in opioid tolerance and dependence. Pharmacol. Ther. 117 (2): 199–206. https://doi.org/10.1016/j.pharmthera.2007.10.003
*Schmidt, H., Vormfelde, S. V., Klinder, K., Gundert-Remy, U., Gleiter, C. H., Skopp, G., Aderjan, R. and Fuhr, U. (2002), Affinities of Dihydrocodeine and its Metabolites to Opioid Receptors. Pharmacology & Toxicology, 91: 57–63.  https://doi.org/10.1034/j.1600-0773.2002.910203.x
* Pert, C. B., Pasternak, G., & Snyder, S. H. (1973). Opiate Agonists and Antagonists Discriminated by Receptor Binding in Brain. Science, 182 (4119), 1359-1361. https://doi.org/10.1126/science.182.4119.1359
*Koch T, Höllt V. (2008). Role of receptor internalization in opioid tolerance and dependence. Pharmacol. Ther. 117 (2): 199–206. https://doi.org/10.1016/j.pharmthera.2007.10.003
* Stefano GB, Ptáček R, Kuželová H, Kream RM. (2012). Endogenous morphine: up-to-date review (2011). Folia Biol. (Praha). 58 (2): 49–56. PMID 22578954.
*Pert, C. B., Pasternak, G., & Snyder, S. H. (1973). Opiate Agonists and Antagonists Discriminated by Receptor Binding in Brain. Science, 182 (4119), 1359-1361. https://doi.org/10.1126/science.182.4119.1359
*Stefano GB, Ptáček R, Kuželová H, Kream RM. (2012). Endogenous morphine: up-to-date review (2011). Folia Biol. (Praha). 58 (2): 49–56. PMID 22578954.


=References=
=References=
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[[Category:Psychoactive substance]]
 
[[Category:Naturally-occuring]]
[[Category:Alkaloid]]
[[Category:Depressant]]
[[Category:Morphinan]]
[[Category:Benzofuran]]
[[Category:Opioid]]
[[Category:Opioid]]
[[Category:Prodrug]]
[[Category:Prodrug]]
[[Category:Morphinan]]
 
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