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Mu-opioid agonists, Cyclic compounds

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fentanyl (437-38-7)  
Fentanyl Citrate  ·  Sublimaze  ·  Duragesic
Fentanyl, also known as fentanil, is an opioid which is used as a pain medication and together with other medications for anesthesia. It has a rapid onset and effects generally last less than an hour or two. Fentanyl is available in a number of forms including by injection, as a skin patch, and to be absorbed through the tissues inside the mouth.
meperidine (57-42-1)  
Demerol  ·  Dolin  ·  Pethidine
Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1939 as a potential anticholinergic agent by the German chemist Otto Eisleb, its analgesic properties were first recognized by Otto Schaumann while working for IG Farben, Germany. 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.
DIPHENOXYLATE (3810-80-8, 915-30-0)  
Diphenoxylate Hydrochloride  ·  Diphenoxylate Monohydrochloride
Diphenoxylate (INN, BAN) (brand name Diocalm), or diphenoxylate hydrochloride (USAN), is a centrally active opioid drug of the phenylpiperidine series that is used for the treatment of diarrhea. It acts by slowing intestinal contractions and peristalsis allowing the body to consolidate intestinal contents and prolong transit time, thus allowing the intestines to draw moisture out of them at a normal or higher rate and therefore stop the formation of loose and liquid stools. It is the main active ingredient in the anti-peristaltic medication Lomotil, which also contains atropine.
SUFENTANIL (56030-54-7)  
Sufentanil (R30730, brand name Sufenta) is a synthetic opioid analgesic drug approximately 5 to 10 times more potent than its parent drug, fentanyl, and 500 times as potent as morphine. Structurally, sufentanil differs from fentanyl through the addition of a methoxymethyl group on the piperidine ring (which is believed to reduce duration of action), and the replacement of the phenyl ring by thiophene. Sufentanil first was synthesized at Janssen Pharmaceutica in 1974.
ALFENTANIL (71195-58-9)  
Alfentanil (R-39209, trade name Alfenta, Rapifen in Australia) is a potent but short-acting synthetic opioid analgesic drug, used for anaesthesia in surgery. It is an analogue of fentanyl with around 1/4 to 1/10 the potency of fentanyl and around 1/3 of the duration of action, but with an onset of effects 4x faster than fentanyl. Alfentanil has a pKa of approximately 6.5, which leads to a very high proportion of the drug being uncharged at physiologic pH.
ANILERIDINE (144-14-9)  
Anileridine (trade name: Leritine) is a synthetic analgesic drug and is a member of the piperidine class of analgesic agents developed by Merck & Co. in the 1950s. It differs from pethidine (meperidine) in that the N-methyl group of meperidine is replaced by an N-aminophenethyl group, which increases its analgesic activity.
Ketobemidone (469-79-4)  
cetobemidon  ·  1-(4-(m-hydroxyphenyl)-1-methyl-4-piperidyl)-1-propanone  ·  ketobemidone hydrochloride
Ketobemidone, sold under the brand name Ketogan among others, is a powerful opioid painkiller. Its effectiveness against pain is in the same range as morphine, and it also has some NMDA-antagonist properties imparted, in part, by its metabolite norketobemidone. This may make it useful for some types of pain that do not respond well to other opioids.
REMIFENTANIL (132875-61-7)  
Remifentanil is a potent, short-acting synthetic opioid analgesic drug. It is given to patients during surgery to relieve pain and as an adjunct to an anaesthetic. Remifentanil is used for sedation as well as combined with other medications for use in general anesthesia.
Alphaprodin (468-59-7, 77-20-3)  
Alphaprodine  ·  Nisentil  ·  Alphaprodine Hydrochloride
Prodine (trade names Prisilidine and Nisentil) is an opioid analgesic that is an analog of pethidine (meperidine). It was developed in Germany in the late 1940s. Several 1-alkyl-4-phenyl-4-acyloxypiperidines have been prepared and found to possess significant analgesic action.
ALPHAPRODINE (77-20-3)  
Nisentil  ·  Alphaprodine Hydrochloride  ·  Prodine
Prodine (trade names Prisilidine and Nisentil) is an opioid analgesic that is an analog of pethidine (meperidine). It was developed in Germany in the late 1940s. Several 1-alkyl-4-phenyl-4-acyloxypiperidines have been prepared and found to possess significant analgesic action.
Difenoxin (28782-42-5, 35607-36-4)  
diphenoxylic acid  ·  difenoxin hydrochloride  ·  difenoxin hydrochloride, 14C-labeled
Difenoxin (Motofen, R-15403) is an opioid drug used, often in combination with atropine, to treat diarrhea. It is the principal metabolite of diphenoxylate. Difenoxin crosses the blood brain barrier and induces some euphoria; it is often sold with or administered with atropine to reduce the potential for abuse and overdose.
Mefentanyl (42045-86-3)  
3-Methylfentanyl (3-MF, mefentanyl) is an opioid analgesic that is an analog of fentanyl. 3-Methylfentanyl is one of the most potent drugs that has been widely sold on the black market, estimated to be between 400 and 6000 times stronger than morphine, depending on which isomer is used (with the cis isomers being the more potent ones). 3-Methylfentanyl was first discovered in 1974 and subsequently appeared on the street as an alternative to the clandestinely produced fentanyl analog α-methylfentanyl.
CARFENTANIL (59708-52-0)  
Carfentanil or carfentanyl is an analog of the synthetic opioid analgesic fentanyl. A unit of carfentanil is 100 times as potent as the same amount of fentanyl, 5,000 times as potent as a unit of heroin and 10,000 times as potent as a unit of morphine. The toxicity of carfentanil in humans and its ready commercial availability has aroused concerns over its potential use as a weapon of mass destruction by rogue nations and terrorist groups.
Piritramide (302-41-0)  
Dipydolor  ·  Piritramid  ·  Pirinitramide
Piritramide (R-3365, trade names Dipidolor, Piridolan, Pirium and others) is a synthetic opioid analgesic (narcotic painkiller) that is marketed in certain European countries including: Austria, Belgium, Czech Republic, Germany and the Netherlands. It comes in free form, is about 0.75x times as potent as morphine and is given parenterally (by injection) for the treatment of severe pain. Nausea, vomiting, respiratory depression and constipation are believed to be less frequent with piritramide than with morphine (the gold standard opioid against which other opioids are compared and contrasted), and it produces more rapid-onset analgesia (pain relief) when compared to morphine and pethidine.
3-Methylthiofentanyl (86052-04-2)  
3-Methyl-thiofentanyl is an opioid analgesic and analogue of fentanyl. 3-Methyl-thiofentanyl was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared. 3-Methyl-thiofentanyl has similar effects to fentanyl.
CHEBI:77817 (38690-93-6, 17243-69-5, 51931-66-9, 20380-56-7)  
Tilidine  ·  Valerone  ·  Tilidine Hydrochloride, (+-)-211Trans
BEZITRAMIDE (15301-48-1)  
bezitramide monohydrochloride  ·  Burgodin
Bezitramide is an opioid analgesic. Bezitramide itself is a prodrug which is readily hydrolyzed in the gastrointestinal tract to its main metabolite, despropionyl-bezitramide. Bezitramide was discovered at Janssen Pharmaceutica in 1961.
Dimethylthiambutene (524-84-5)  
Dimethylthiambutene (N,N-Dimethyl-1-methyl-3,3-di-2-thienylallylamine, DMTB, trade names Ohton, Aminobutene, Dimethibutin, Kobaton, Takaton, Dimethibutin) is an opioid analgesic drug, most often used in veterinary medicine in Japan and to a lesser extent in other countries in the region and around the world. It is the most prominent and widely used of the thiambutenes, a series of open-chain opioids structurally related to methadone which are also called the thienyl derivative opioids which also includes diethylthiambutene and ethylmethylthiambutene, as well as the non-opioid cough suppressant tipepidine. Dimethylthiambutene was developed in the United Kingdom in the late 1940s and introduced to the market by Burroughs-Wellcome in 1951.
TILIDINE (51931-66-9, 32447-90-8, 20380-58-9)  
Valerone  ·  Tilidine Hydrochloride, (+-)-211Trans  ·  Tilidine Hydrochloride
Tilidine, or tilidate (brand names: Tilidin, Valoron and Valtran) is a synthetic opioid painkiller, used mainly in Germany, Switzerland, South Africa and Belgium for treatment of moderate to severe pain, both acute and chronic. Its onset of pain relief after oral administration is about 10–15 minutes and peak relief from pain occurs about 25–50 minutes after oral administration.
Pyrrolamidolum (357-56-2)  
Dextromoramide  ·  Palfium  ·  Faulding Brand of Dextromoramide Tartrate
Dextromoramide (Palfium, Palphium, Jetrium, Dimorlin) is a powerful opioid analgesic approximately three times more potent than morphine but shorter acting. It is subject to drug prohibition regimes, both internationally through UN treaties and by the criminal law of individual states. It is still marketed solely in the Netherlands.
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