Codeine: Difference between revisions

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(Created page with "Other Names Codein, codeina, codeine, codeinum, 4,5u-epoxy3- methoxy-17-methyl-7-morphinen-6u-ol, kodein Substance type: opium alkaloid In 1832, codeine was isolated from ...")
 
(Edited Harm Reduction section, added "interactions" subsection, added minor details)
 
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Other Names
[[File:Codeine_structure.jpg|right]]
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.


Codein, codeina, codeine, codeinum, 4,5u-epoxy3-
== History ==


methoxy-17-methyl-7-morphinen-6u-ol, kodein
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.


Substance type: opium alkaloid
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.
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).


In 1832, codeine was isolated from opium, which
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])


has a codeine content of 2 to 30/0 (see Papaver
== Dosage ==


somniferum). Codeine is also biosynthesized in the
{| class="wikitable"
|+ Oral
|-
| Light || 50-100mg
|-
| Common || 100-150mg
|-
| Strong || 150-200mg
|-
| Ceiling || 400-600mg
|}


roots of Papaver somniferum 1. cv. Marianne (Tam
== Duration ==


et al. 1980). It is possible that trace amounts of
{| class="wikitable"
|+ Oral
|-
| Onset || 30-45 minutes
|-
| Duration || 3-6 hours
|}


codeine can also be found in other Papaver species
== Effects ==


(Papaver bracteatum, Papaver decaisnei; cf. Papaver
=== Positive ===


spp.) (Theuns et al. 1986). Codeine is also an endogenous
* Euphoria


neurotransmitter in humans (cf. morphine).
* Pain relief


A dosage of 20 to 50 mg produces "general
* Elevated mood


mental stimulation, warmth in the head, and an
* Overall feeling of contentedness


increase in the pulse rate, as also appear after the
=== Neutral ===


consumption of alcohol" (Rompp 1950*). Codeine
* Itching


does not appear to be metabolized in the body and
=== Negative ===


is excreted unchanged.
* Nausea


Because codeine suppresses the urge to cough,
* Constipation


its most important pharmaceutical use is in cough
* CNS depression


syrups. The dosage when codeine is used as a
* Drowsiness


cough suppressant is 50 mg three times a day. A
* Hot/cold flashes


dosage of 100 to 200 mg results in sleep and
* Dizziness


sedation. Higher dosages elicit effects comparable
* Vomiting


to those of morphine. The medical literature
* Urinary retention (difficulty urinating)


contains repeated mentions of "codeine addiction."
== Harm Reduction ==


Codeine "addicts" are said to ingest up to 2 g
* 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.


of codeine daily (Rompp 1950, 115*). Today,
* Avoid driving and operating heavy machinery


codeine is gaining increasing medicinal importance
* Recommended time (pauses) between using the substance


as a substitution therapy for heroin addicts
* Addictive


(Gerlach and Schneider 1994). The pharmaceutical
=== Interactions ===


industry synthesizes codeine primarily
* Do not mix with alcohol, benzodiazepines, opioids, or other CNS depressants


from thebaine, the main active constituent in Papaver bracteatum Lindl. (cf. Papaver spp.)
* Avoid combining with stimulants


(Morton 1977, 125*; Theuns et al. 1986).
== Chemistry and Pharmacology ==


Codeine has acquired a certain significance in
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.


the music scene (jazz, rock, psychedelia), primarily
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.


as a substitute for heroin or morphine. Buffy
The active metabolites of codeine, notably morphine, exert their effects by binding to and activating the μ-opioid receptor.


Saint-Marie sang about the anguish of her codeine
== Legal Status ==


dependence in the song "Cod'ine" (LP It's My Way!
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.


Vanguard Records 1964). Quicksilver Messenger
== Links ==


Service later covered the song and made it famous.
[http://en.wikipedia.org/wiki/Codeine Wikipedia]


In the 1990s, the wave band Codeine had several
[http://www.erowid.org/pharms/codeine/codeine.shtml Erowid]


albums out through Sub Pop. Cough syrups496
[[Category:Drugs]]


with a high codeine content were often consumed
[[Category:Opioid]]


as inebriants at concerts, festivals, et cetera
[[Category:Depressant]]
 
(usually in combination with alcohol and
 
cannabis) (Bangs 1978, 158).
 
 
 
Commercial Forms and Regulations
 
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.
 
Literature
 
See also the entries for Papaver somniferum,
 
morphine, and opium alkaloids.
 
Bangs, Lester. 1978. Ich sah Gott und/oder Tangerine
 
Dream. Rocksession 2:155-58. Reinbek: Rowohlt.
 
Esser, Barbara. 1998. Vom Regen in die Traufe: Das
 
Verbot des Ersatzstoffs Codein ... Focus 26 (6):
 
58-60.
 
Gerlach, Ralf, and Wolfgang Schneider. 1994.
 
Methadon- und Codeinensubstitution:
 
Erfahrungen, Forschungsergebnisse,
 
Praxiskonsequenzen. Berlin: VWB.
 
Tam, W. H. John, Friedrich Constabel, and Wolfgang
 
G. W. Kurz. 1980. Codeine from cell suspension cultures of Papaver somniferum. Phytochemistry
 
19:486-87.
 
Theuns, Hubert G., H. Leo Theuns, and Robert J. J.
 
Ch. Lousberg. 1986. Search for new natural
 
sources of morphinians. Economic Botany 40 (4):
 
485-97.

Latest revision as of 20:54, 4 August 2015

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.

History

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.

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. 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).

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 purple drank and several artists have released songs about it. (Hart, Agnich, Stogner, Miller 2013)

Dosage

Oral
Light 50-100mg
Common 100-150mg
Strong 150-200mg
Ceiling 400-600mg

Duration

Oral
Onset 30-45 minutes
Duration 3-6 hours

Effects

Positive

  • Euphoria
  • Pain relief
  • Elevated mood
  • Overall feeling of contentedness

Neutral

  • Itching

Negative

  • Nausea
  • Constipation
  • CNS depression
  • Drowsiness
  • Hot/cold flashes
  • Dizziness
  • Vomiting
  • Urinary retention (difficulty urinating)

Harm Reduction

  • 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 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.
  • Avoid driving and operating heavy machinery
  • Recommended time (pauses) between using the substance
  • Addictive

Interactions

  • Do not mix with alcohol, benzodiazepines, opioids, or other CNS depressants
  • Avoid combining with stimulants

Chemistry and Pharmacology

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.

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.

The active metabolites of codeine, notably morphine, exert their effects by binding to and activating the μ-opioid receptor.

Legal Status

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.

Links

Wikipedia

Erowid