Codeine: Difference between revisions

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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.


<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0">
== History ==


<tr>
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.
<td valign="top" width="50%"><strong>Other Names</strong>


Codein, codeina, codeine, codeinum, 4,5u-epoxy3-
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).


methoxy-17-methyl-7-morphinen-6u-ol, kodein
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])


Substance type: opium alkaloid
== Dosage ==


In 1832, codeine was isolated from opium, which
{| class="wikitable"
|+ Oral
|-
| Light || 50-100mg
|-
| Common || 100-150mg
|-
| Strong || 150-200mg
|-
| Ceiling || 400-600mg
|}


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


somniferum). Codeine is also biosynthesized in the
{| class="wikitable"
|+ Oral
|-
| Onset || 30-45 minutes
|-
| Duration || 3-6 hours
|}


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


et al. 1980). It is possible that trace amounts of
=== Positive ===


codeine can also be found in other Papaver species
* Euphoria


(Papaver bracteatum, Papaver decaisnei; cf. Papaver
* Pain relief


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


neurotransmitter in humans (cf. morphine).
* Overall feeling of contentedness


A dosage of 20 to 50 mg produces "general
=== Neutral ===


mental stimulation, warmth in the head, and an
* Itching


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


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


does not appear to be metabolized in the body and
* Constipation


is excreted unchanged.
* CNS depression


Because codeine suppresses the urge to cough,
* Drowsiness


its most important pharmaceutical use is in cough
* Hot/cold flashes


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


cough suppressant is 50 mg three times a day. A
* Vomiting


dosage of 100 to 200 mg results in sleep and
* Urinary retention (difficulty urinating)


sedation. Higher dosages elicit effects comparable
== Harm Reduction ==


to those of morphine. The medical literature
* 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.


contains repeated mentions of "codeine addiction."
* Avoid driving and operating heavy machinery


Codeine "addicts" are said to ingest up to 2 g
* Recommended time (pauses) between using the substance


of codeine daily (Rompp 1950, 115*). Today,
* Addictive


codeine is gaining increasing medicinal importance
=== Interactions ===


as a substitution therapy for heroin addicts
* Do not mix with alcohol, benzodiazepines, opioids, or other CNS depressants


(Gerlach and Schneider 1994). The pharmaceutical
* Avoid combining with stimulants


industry synthesizes codeine primarily
== Chemistry and Pharmacology ==


from thebaine, the main active constituent in Papaver bracteatum Lindl. (cf. Papaver spp.)
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.


(Morton 1977, 125*; Theuns et al. 1986).
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.


Codeine has acquired a certain significance in
The active metabolites of codeine, notably morphine, exert their effects by binding to and activating the μ-opioid receptor.


the music scene (jazz, rock, psychedelia), primarily
== Legal Status ==


as a substitute for heroin or morphine. Buffy
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.


Saint-Marie sang about the anguish of her codeine
== Links ==


dependence in the song "Cod'ine" (LP It's My Way!
[http://en.wikipedia.org/wiki/Codeine Wikipedia]


Vanguard Records 1964). Quicksilver Messenger
[http://www.erowid.org/pharms/codeine/codeine.shtml Erowid]


Service later covered the song and made it famous.
[[Category:Drugs]]


In the 1990s, the wave band Codeine had several
[[Category:Opioid]]
 
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).</td>
<td valign="top" width="53%"><strong>Commercial Forms and Regulations</strong>
 
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.
 
<strong>Literature</strong>
 
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.</td>
[[Category:Depressant]]
</tr>
 
</table>
 
[[Category:Opioid]]
[[Category:Drugs]]

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