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Pethidine: Difference between revisions
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==Chemistry== | ==Chemistry== | ||
{{chemistry}} | {{chemistry}} | ||
Pethidine is | Pethidine is a synthetic opioid of the phenylpiperidine class. Pethidine is the prototype of a large family of analgesics including the pethidine 4-phenylpiperidines (piminodine, anileridine and others), the prodines (alphaprodine, MPPP, ''etc.''), bemidones (ketobemidone, etc.) and others more distant, including diphenoxylate and analogues.<ref>{{cite journal | journal=Journal of the American Pharmaceutical Association (Scientific ed.) | title=Morphine & Allied Drugs | volume=46 | issue=11 | pages=704 | date= November 1957 | url=https://linkinghub.elsevier.com/retrieve/pii/S0095955315343857 | issn=00959553 | doi=10.1002/jps.3030461119}}</ref> The most coomon hydrochloride form is a white crystalline substance with a melting point of 186 C to 189 C. It is readily soluble in water and has a neutral reaction and a slightly bitter taste.<ref name=":0">{{Citation | title=(+-)-Pethidine hydrochloride, Drug Information, Uses, Side Effects, Chemistry | url=https://www.pharmacompass.com/chemistry-chemical-name/pethidine-hydrochloride}}</ref> | ||
Toxic pethidine blood concentration: 500 ug/dL and lethal pethidine blood concentration: 1-3 mg/dL.<ref name=":0" /> | |||
Pethidine can be produced in a two-step synthesis. The first step is reaction of benzyl cyanide and chlormethine in the presence of sodium amide to form a piperidine ring. The nitrile is then converted to an ester.<ref>Patent Appl. DE 679 281 IG Farben 1937.</ref> | |||
==Pharmacology== | ==Pharmacology== | ||
[[Opioid]]s exert their effects by binding to and activating the [[Opioid#Mu_.28.CE.BC.29|μ-opioid]] [[receptor]]. 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]] 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 bioavailability of orally administered pethidine can vary from 50% to around 60%. | [[Opioid]]s exert their effects by binding to and activating the [[Opioid#Mu_.28.CE.BC.29|μ-opioid]] [[receptor]]. 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]] 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 bioavailability of orally administered pethidine can vary from 50% to around 60%. | ||
Compared to traditional opioids, pethidine has a very unique pharmacological profile. In addition to being an opioid, pethidine is also a muscarinic [[acetylcholine]] [[receptor]] [[antagonist]]. Pethidine is also a [[dopamine]] [[reuptake inhibitor]] and [[norepinephrine]] reuptake inhibitor. Pethidine is a κ-opioid agonist and its metabolite norpethidine is also an extremely powerful [[serotonin]] reuptake inhibitor.<ref> Meperidine: A Critical Review | | Compared to traditional opioids, pethidine has a very unique pharmacological profile. In addition to being an opioid, pethidine is also a muscarinic [[acetylcholine]] [[receptor]] [[antagonist]]. Pethidine is also a [[dopamine]] [[reuptake inhibitor]] and [[norepinephrine]] reuptake inhibitor. Pethidine is a κ-opioid agonist and its metabolite norpethidine is also an extremely powerful [[serotonin]] reuptake inhibitor.<ref>{{cite journal | vauthors=((Latta, K. S.)), ((Ginsberg, B.)), ((Barkin, R. L.)) | journal=American Journal of Therapeutics | title=Meperidine: A Critical Review: | volume=9 | issue=1 | pages=53–68 | date= January 2002 | url=http://journals.lww.com/00045391-200201000-00010 | issn=1075-2765 | doi=10.1097/00045391-200201000-00010}}</ref> | ||
==Subjective effects== | ==Subjective effects== | ||
{{Preamble/SubjectiveEffects}} Many users note that they find pethidine just as, or more euphoric than [[oxycodone]].<ref> Subjective, Psychomotor, and Physiological Effects of Cumulative Doses of Opioid μ Agonists in Healthy Volunteers | | {{Preamble/SubjectiveEffects}} Many users note that they find pethidine just as, or more euphoric than [[oxycodone]].<ref>{{cite journal | vauthors=((Walker, D. J.)), ((Zacny, J. P.)) | journal=Journal of Pharmacology and Experimental Therapeutics | title=Subjective, Psychomotor, and Physiological Effects of Cumulative Doses of Opioid μ Agonists in Healthy Volunteers | volume=289 | issue=3 | pages=1454–1464 | date=1 June 1999 | url=https://jpet.aspetjournals.org/content/289/3/1454 | issn=0022-3565}}</ref> | ||
{{effects/base | {{effects/base | ||
|{{effects/physical| | |{{effects/physical| | ||
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===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://erowid.org/experiences/subs/exp_Pharms_Meperidine.shtml Erowid Experience Vaults: Pethidine] | |||
*[https://erowid.org/experiences/subs/exp_Pharms_Meperidine.shtml Erowid Experience Vaults: Pethidine] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
Pethidine has a [[Toxicity::high toxicity]] relative to dose. As with all opioids, long-term effects can vary but can include diminished libido, apathy and memory loss. It is also [[Toxicity::potentially [[respiratory depression|lethal]] when mixed with [[depressants]] like [[alcohol]] or [[benzodiazepines]]]] and generally has a wider range of substances which it is [[pethidine#Dangerous interactions|dangerous to combine with]] in comparison to other opioids. | Pethidine has a [[Toxicity::high toxicity]] relative to dose. As with all opioids, long-term effects can vary but can include diminished libido, apathy and memory loss. It is also [[Toxicity::potentially [[respiratory depression|lethal]] when mixed with [[depressants]] like [[alcohol]] or [[benzodiazepines]]]] and generally has a wider range of substances which it is [[pethidine#Dangerous interactions|dangerous to combine with]] in comparison to other opioids. | ||
One of pethdine's metabolites, norpethidine has little to no opioid action, but is known to cause seizures. Pethidine should not be taken during [[Benzodiazepine#Discontinuation|benzodiazepine withdrawals]] as this can potentially cause [[seizure]]s. In 1984, Libby Zion, a teenager was brought to the emergency room due to a "flu-like" ailment. She was previously prescribed and taking phenelzine, a [[MAOI |monoamine oxidase inhibitor]], which in combination caused fatal serotonin syndrome.<ref> Serotonin Syndrome and the Libby Zion Affair | | One of pethdine's metabolites, norpethidine has little to no opioid action, but is known to cause seizures. Pethidine should not be taken during [[Benzodiazepine#Discontinuation|benzodiazepine withdrawals]] as this can potentially cause [[seizure]]s. In 1984, Libby Zion, a teenager was brought to the emergency room due to a "flu-like" ailment. She was previously prescribed and taking phenelzine, a [[MAOI |monoamine oxidase inhibitor]], which in combination caused fatal serotonin syndrome.<ref>{{Citation | year=2011 | title=Serotonin Syndrome and the Libby Zion Affair |publisher=Emergency Physicians Monthly | url=https://epmonthly.com/article/serotonin-syndrome-and-the-libby-zion-affair/}}</ref> | ||
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug. | It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug. | ||
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Tolerance to many of the effects of pethidine [[Time to full tolerance::develops with prolonged and repeated use]]. 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. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Pethidine presents cross-tolerance with [[Cross-tolerance::all other [[opioids]]]], meaning that after the consumption of pethidine all [[opioid]]s will have a reduced effect. | Tolerance to many of the effects of pethidine [[Time to full tolerance::develops with prolonged and repeated use]]. 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. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Pethidine presents cross-tolerance with [[Cross-tolerance::all other [[opioids]]]], meaning that after the consumption of pethidine all [[opioid]]s will have a reduced effect. | ||
The risk of fatal opioid overdoses rise sharply after a period of cessation and [[relapse]], largely because of reduced tolerance.<ref>Why Heroin Relapse Often Ends In Death - Lauren F Friedman (Business Insider) | http://www.businessinsider.com.au/philip-seymour-hoffman-overdose-2014-2</ref> To account for this lack of tolerance, it is safer to only dose a fraction of one's usual [[dosage]] if relapsing. It has also been found that the environment one is in can play a role in opioid tolerance. In one scientific study, rats with the same history of heroin administration were significantly more likely to die after receiving their dose in an environment not associated with the drug in contrast to a familiar environment.<ref>Siegel, S., Hinson, R., Krank, M., | The risk of fatal opioid overdoses rise sharply after a period of cessation and [[relapse]], largely because of reduced tolerance.<ref>Why Heroin Relapse Often Ends In Death - Lauren F Friedman (Business Insider) | http://www.businessinsider.com.au/philip-seymour-hoffman-overdose-2014-2</ref> To account for this lack of tolerance, it is safer to only dose a fraction of one's usual [[dosage]] if relapsing. It has also been found that the environment one is in can play a role in opioid tolerance. In one scientific study, rats with the same history of heroin administration were significantly more likely to die after receiving their dose in an environment not associated with the drug in contrast to a familiar environment.<ref>{{cite journal | vauthors=((Siegel, S.)), ((Hinson, R. E.)), ((Krank, M. D.)), ((McCully, J.)) | journal=Science | title=Heroin “Overdose” Death: Contribution of Drug-Associated Environmental Cues | volume=216 | issue=4544 | pages=436–437 | date=23 April 1982 | url=https://www.science.org/doi/10.1126/science.7200260 | issn=0036-8075 | doi=10.1126/science.7200260}}</ref> | ||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
{{DangerousInteractions/Intro}} | {{DangerousInteractions/Intro}} | ||
{{DangerousInteractions/ | {{DangerousInteractions/Opioids}} | ||
====[[Serotonin syndrome]] risk==== | ====[[Serotonin syndrome]] risk==== | ||
Pethidine is known to have a significantly increased chance of causing serotonin syndrome than other serotonergic opioids such as [[tramadol]].{{citation needed}} | Pethidine is known to have a significantly increased chance of causing serotonin syndrome than other serotonergic opioids such as [[tramadol]].{{citation needed}} | ||
{{DangerousInteractions/SerotoninSyndrome}} | {{DangerousInteractions/SerotoninSyndrome}} | ||
==Legal | ==Legal status== | ||
{{LegalStub}} | {{LegalStub}} | ||
*'''Germany:''' Pethidine is a controlled substance under Anlage III of the BtMG. It can only be prescribed on a narcotic prescription form.<ref>{{Citation | title=Anlage III BtMG - Einzelnorm | url=http://www.gesetze-im-internet.de/btmg_1981/anlage_iii.html}}</ref> | |||
*'''Russia:''' Pethidine is a Schedule I controlled substance.<ref>{{Citation | title=Постановление Правительства РФ от 01.10.2012 N 1002 (ред. от 09.08.2019) | url=https://www.consultant.ru/cons/cgi/online.cgi?req=doc&base=LAW&n=331879&dst=100187&date=03.12.2019}}</ref> | |||
*'''Switzerland''': Pethidine is a controlled substance specifically named under Verzeichnis A. Medicinal use is permitted.<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''': Pethidine 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 Kingdom:''' Pethidine is a Class A, Schedule 2 drug in the United Kingdom.<ref>{{Citation | title=List of most commonly encountered drugs currently controlled under the misuse of drugs legislation | url=https://www.gov.uk/government/publications/controlled-drugs-list--2/list-of-most-commonly-encountered-drugs-currently-controlled-under-the-misuse-of-drugs-legislation}}</ref> | |||
*'''United States:''' Pethidine is a Schedule II Controlled Substance.<ref>DEA Controlled Substances | https://www.deadiversion.usdoj.gov/schedules/orangebook/e_cs_sched.pdf</ref> | *'''United States:''' Pethidine is a Schedule II Controlled Substance.<ref>DEA Controlled Substances | https://www.deadiversion.usdoj.gov/schedules/orangebook/e_cs_sched.pdf</ref> | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Opioid]] | *[[Opioid]] | ||
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==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/Pethidine Pethidine (Wikipedia)] | *[https://en.wikipedia.org/wiki/Pethidine Pethidine (Wikipedia)] | ||
*[https://erowid.org/pharms/meperidine/ Pethidine (Erowid Vault)] | *[https://erowid.org/pharms/meperidine/ Pethidine (Erowid Vault)] | ||
*[https://isomerdesign.com/PiHKAL/explore.php?id=5450 Pethidine (Isomer Design)] | *[https://isomerdesign.com/PiHKAL/explore.php?id=5450 Pethidine (Isomer Design)] | ||
*[https://go.drugbank.com/drugs/DB00454 Pethidine (DrugBank)] | |||
*[https://www.drugs.com/demerol.html Pethidine (Drugs.com)] | |||
==References== | ==References== | ||
<references /> | <references /> | ||
[[Category:Substance]][[Category:Psychoactive substance]][[Category:Depressant]][[Category:Opioid]] | |||
[[Category:Substance]] | |||
[[Category:Psychoactive substance]] | |||
[[Category:Depressant]] | |||
[[Category:Opioid]] | |||
[[Category:Phenylpiperidine]] | |||
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