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Removed category Category:Thiophene as unnecessary

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{{headerpanel|{{Warning/Sufentanil}}}}
{{SummarySheet}}
{{SubstanceBox/Sufentanil}}

'''Sufentanil''', also known as '''sufentanyl''' and by the brand name '''Sufenta''', is an extremely potent synthetic [[chemical class::anilidopiperidine]] [[psychoactive class::opioid]] [[pain relief |analgesic]]. Sufentanil has a rapid onset and short mechanism and is used medically as an analgesic in surgical procedures or for the management of post-operative pain. Sufentanil is roughly 500 to 1,000 times more potent than pharmaceutical grade [[morphine]] and is approximately 10 times more potent than pharmaceutical grade [[fentanyl]]. The subjective effects of sufentanil are similar to those of [[heroin]], with the exception that many users report a significantly less [[physical euphoria|euphoric]] "high" associated with the drug and stronger [[respiratory depression]], [[sedation]] and [[pain relief]]. Sufentanil is the most potent opioid analgesic currently used in human medicine.

==Chemistry==
Sufentanil is synthetic anilidopiperidine that is similar in structure to both [[fentanyl]] and [[acetylfentanyl]]. One of the key differences is that one of the phenyl groups in sufentanil has been replaced with a thiophene or thiofuran group. Thiophene groups can typically replace phenyl groups without a significant drop in potency. The empirical formula of sufentanil is C22H30N2O2S and has a molar mass of 386.552 grams per mole.

Sufentanil Citrate Injection, is an opioid agonist, available as a solution containing 50 mcg/mL eq. of Sufentanil base, adjusted to pH 3.5 to 6.0. The chemical name is N-[4-(methyoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-N-phenylpropanamide: 2-hydroxy-1,2,3-propanetricarboxylate (1:1). The molecular weight is 578.68. Sufentanil Citrate Injection, is a sterile, non-pyrogenic, preservative free aqueous solution for intravenous or epidural injection.<ref>https://www.drugs.com/pro/sufentanil.html#moreResources</ref>

==Pharmacology==
The recreational effects of sufentanil occur 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. Like endorphins, sufentanil is an extremely potent μ-[[opioid]] agonist. Sufentanil has an extremely short biological half life of only 162 minutes.

Because of its extremely high potency, it is often used in surgery and post-operative pain management for patients that are heavily opioid dependent/opioid tolerant because of long term opiate use for chronic pain or illicit opiate use. Currently sufentanil is the most potent opioid painkiller available for use in humans. Although more potent narcotic pain medications do exist, all medications stronger than sufentanil are approved for veterinary use only. It is also used in surgery and postoperative pain control in patients that are taking high dose buprenorphine for chronic pain because it is the only opioid that has a potency and binding affinity strong enough to displace buprenorphine from the opioid receptors in the central nervous system and provide analgesia.<ref>{{Citation | title=Fentanyl Citrate (fentanyl citrate) dose, indications, adverse effects, interactions... from PDR.net | url=https://www.pdr.net/drug-summary/fentanyl-citrate?druglabelid=2474}}/ref>

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

{{effects/base
|{{effects/physical|
*'''[[Effect::Pain relief]]''' - In comparison to other opiates, sufentanil can be described as a strong analgesic, providing relief even at non-recreational doses.
*'''[[Effect::Physical euphoria]]''' - This particular substance can be considered as less intense in its physical euphoria when compared with that of [[morphine]] or [[fentanyl]]. The sensation itself can be described as strong feelings of physical comfort, warmth and bliss which spread throughout the body.
*'''[[Effect::Itchiness]]''' - Unlike most other [[opioids]], this compound produces very little itchiness due to the lack of histamine activity.{{citation needed}}
*'''[[Effect::Respiratory depression]]''' - In comparison to other opiates, sufentanil displays this effect at lower doses relative to euphoria then other opiates, and even at low doses results in the sensation that the breath is slowed down mildly to moderately, but does not cause noticeable impairment. At high doses and overdoses, opioid-induced respiratory depression can result in a shortness of breath, abnormal breathing patterns, semi-consciousness, or unconsciousness. Severe overdoses can result in a coma or death without immediate medical attention. In the hospital setting, patients that are administered sufentanil are constantly monitored to ensure their breathing is not significantly depressed.
*'''[[Effect::Sedation]]''' - Sufentanil can be described as much more sedating then other opioids. Even at moderate dosages, this compound can result in overwhelming feelings of sedation and tiredness that is considerably more sedating than that of [[heroin]] and [[oxycodone]].
*'''[[Effect::Constipation]]'''
*'''[[Effect::Cough suppression]]'''
*'''[[Effect::Decreased libido]]'''
*'''[[Effect::Difficulty urinating]]'''
*'''[[Effect::Pupil constriction]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Low blood pressure]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Orgasm suppression]]'''

}}

|{{effects/cognitive|
*'''[[Effect::Cognitive euphoria]]''' - This particular substance can be considered as significantly less intense in its cognitive euphoria when compared with that of [[morphine]] or [[fentanyl]]. 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::Anxiety suppression]]'''
*'''[[Effect::Compulsive redosing]]'''
}}

}}

==Toxicity and harm potential==
Recreational use of sufentanil by individuals without opioid tolerance is extremely dangerous due to its potency. It is [[Toxicity::potentially fatal at heavy dosages]] and even those with opiate tolerances are at high risk for overdoses. Once the sufentanil is in the user's system, it is extremely difficult to stop its course because of the nature of absorption. Because of the extremely high strength of pure sufentanil powder, it is very difficult to dilute appropriately, and often the resulting mixture may be far too strong and, therefore, very dangerous. It is also [[Toxicity::potentially [[respiratory depression|lethal]] when mixed with [[depressants]] like [[alcohol]] or [[benzodiazepines]]]].

Like most opioids, unadulterated sufentanil at appropriate dosages does not cause many long-term complications other than dependence and [[constipation]]. Outside of the extremely powerful addiction and physical dependence, the harmful or toxic aspects of opioid usage are exclusively associated with not taking the necessary precautions in regards to its administration, overdosing and using impure products.

It is important to consider that particular care must be taken with sufentanil due to its extreme potency and ability to be absorbed through the skin. This means that simply [[Toxicity::unintentionally spilling a very small amount of sufentanil on one's skin could result in a fatal overdose.]]

Heavy dosages of sufentanil can result in [[Respiratory depression|respiratory depression]], leading onto fatal or dangerous levels of anoxia (oxygen deprivation). This occurs because the breathing reflex is suppressed by [[agonists|agonism]] of [[µ-opioid receptors]] proportional to the dosage consumed.

Sufentanil can also cause nausea and vomiting; a significant number of deaths attributed to opioid overdose are caused by aspiration of vomit by an unconscious victim. This is when an unconscious or semi-conscious user who is lying on their back vomits into their mouth and unknowingly suffocates. It can be prevented by ensuring that one is lying on their side with their head tilted downwards so that the airways cannot be blocked in the event of vomiting while unconscious (also known as the [[recovery position]]). In case of overdose, it is advised to administer a dose of [[naloxone]] intravenously or intramuscularly to reverse the effects of opioid agonism. It has been noted that naloxone is not very effective for the management of opioid overdoses in cases where extremely potent opioids like sufentanil have been used. In the case of sufentanil, naltrexone should be used in case of an overdose.

It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.

===Tolerance and addiction potential===
As with other [[opioids]], the chronic use of sufentanil can be considered [[Addiction potential::extremely addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[Opioids#Discontinuation|withdrawal symptoms]] may occur if a person suddenly stops their usage.

Tolerance to many of the effects of sufentanil [[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. It is unknown how long it takes for sufentanil tolerance to decrease to baseline (no distinguishable tolerance). Sufentanil presents cross-tolerance with [[Cross-tolerance::all other [[opioids]]]], meaning that after the consumption of sufentanil 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>{{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===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Opioids}}

====[[Serotonin syndrome]] risk====
{{DangerousInteractions/SerotoninSyndrome}}

==Legal status==
{{LegalStub}}

*'''Germany:''' Sufentanil 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=https://www.gesetze-im-internet.de/btmg_1981/anlage_iii.html}}</ref>
*'''Russia:''' Sufentanil is a Schedule II 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=100282&date=03.12.2019}}</ref>
*'''Switzerland''': Sufentanil 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>
*'''United States:''' Sufentanil is classified as a Schedule II Controlled Substance under the Controlled Substances Act.<ref>Controlled Drugs | https://www.deadiversion.usdoj.gov/schedules/orangebook/e_cs_sched.pdf</ref>

==See also==

*[[Responsible use]]
*[[Opioid]]
*[[Heroin]]
*[[Morphine]]
*[[Fentanyl]]

==External links==

*[https://en.wikipedia.org/wiki/Sufentanil Sufentanil (Wikipedia)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=10716 Sufentanil (Isomer Design)]

==References==
<references />

[[Category:Psychoactive substance]]
[[Category:Opioid]]
[[Category:Anilidopiperidine]]

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Sufentanil - Revision history

Sysop: 1 revision imported

en>Tracer: Removed category Category:Thiophene as unnecessary