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Profadol
Profadol (CI-572) is an opioid analgesic which was developed in the 1960s by Parke-Davis. It acts as a mixed agonist-antagonist of the μ-opioid receptor. The analgetic potency is about the same as of pethidine (meperidine), the antagonistic effect is 1/50 of nalorphine. Synthesis The Knoevenagel condensation between 3'-Methoxybutyrophenone 1550-06-1and Ethyl cyanoacetate gives (1). Conjugate addition of cyanide gives (2). Hydrolysis of both nitrile groups, saponification of the ester and decarboxylation gives the diacidCID:164137621(3). Imide formation occurs upon treatment with methylamine giving 3-(3-Methoxyphenyl)-1-methyl-3-propylpyrrolidine-2,5-dioneCID:163444474(4). Reduction of the imide by lithium aluminium hydride gave 505-32-429369-01-5] (5). Demethylation completed the synthesis of Profadol (6). See also * BDPC, Bromadol * C-8813 * Ciramadol * Faxeladol * Prodilidine * Tapentadol * Tramadol Tramadol, sold under the brand name Ultram among others, is a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Profadol Synthesis
Profadol (CI-572) is an opioid analgesic which was developed in the 1960s by Parke-Davis. It acts as a mixed agonist-antagonist of the μ-opioid receptor. The analgetic potency is about the same as of pethidine (meperidine), the antagonistic effect is 1/50 of nalorphine. Synthesis The Knoevenagel condensation between 3'-Methoxybutyrophenone 1550-06-1and Ethyl cyanoacetate gives (1). Conjugate addition of cyanide gives (2). Hydrolysis of both nitrile groups, saponification of the ester and decarboxylation gives the diacidCID:164137621(3). Imide formation occurs upon treatment with methylamine giving 3-(3-Methoxyphenyl)-1-methyl-3-propylpyrrolidine-2,5-dioneCID:163444474(4). Reduction of the imide by lithium aluminium hydride gave 505-32-429369-01-5] (5). Demethylation completed the synthesis of Profadol (6). See also * BDPC, Bromadol * C-8813 * Ciramadol * Faxeladol * Prodilidine * Tapentadol * Tramadol Tramadol, sold under the brand name Ultram among others, is an ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Opioid
Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioid use disorder, reversing opioid overdose, and suppressing cough. Extremely potent opioids such as carfentanil are approved only for veterinary use. Opioids are also frequently used non-medically for their euphoric effects or to prevent withdrawal. Opioids can cause death and have been used for executions in the United States. Side effects of opioids may include itchiness, sedation, nausea, respiratory depression, constipation, and euphoria. Long-term use can cause tolerance, meaning that increased doses are required to achieve the same effect, and physical dependence, meaning that abruptly discontinuing the drug leads to unpleasant withdrawal symptoms. The euphoria attracts recreational use, and frequent, escalating recreational use of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Prodilidine
Prodilidine is an opioid analgesic which is a ring-contracted analogue of prodine. It has around the same analgesic efficacy as codeine, but is only around 1/3 the potency (100mg prodilidine is equivalent to 3mg oral morphine). It has little abuse potential. See also * Profadol Profadol (CI-572) is an opioid analgesic which was developed in the 1960s by Parke-Davis. It acts as a mixed agonist-antagonist of the μ-opioid receptor. The analgetic potency is about the same as of pethidine (meperidine), the antagonistic eff ... References Opioids Propionate esters Pyrrolidines Mu-opioid receptor agonists {{analgesic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Faxeladol
Faxeladol (INN, USAN) (code names GRTA-9906, GRTA-0009906, EM-906, GCR-9905, GRT-TA300) is an opioid analgesic which was developed by Grünenthal GmbH but was never marketed for medical use anywhere in the world. It is related to tramadol and ciramadol, and was developed shortly after tramadol in the late 1970s. Similarly to tramadol, it was believed faxeladol would have analgesic, as well as antidepressant effects, due to its action on serotonin and norepinephrine reuptake. In various studies in the 1970s alongside tramadol, faxeladol was seen to be slightly more potent than tramadol, but with a higher rate of sudden seizures than tramadol, which is known to cause seizures without warning in some users. See also * Bromadol * Profadol * Tapentadol Tapentadol, brand names Nucynta among others, is a centrally acting opioid analgesic of the benzenoid class with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Analg ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ciramadol
Ciramadol (WY-15,705) is an opioid analgesic that was developed in the late 1970s and is related to phencyclidine, tramadol, tapentadol and venlafaxine. It is a mixed agonist-antagonist for the μ-opioid receptor with relatively low abuse potential and a ceiling on respiratory depression which makes it a relatively safe drug. It has a slightly higher potency and effectiveness as an analgesic than codeine, but is weaker than morphine. Other side effects include sedation and nausea but these are generally less severe than with other similar drugs. Synthesis The Claisen-Schmidt reaction between 3-(methoxymethoxy)benzaldehyde 3709-05-2(1) and cyclohexanone (2) affordeCID:54364197(3). Michael addition of dimethylamine Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to aroun ... leads the am ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
C-8813
C-8813 (thiobromadol) is a potent μ-opioid receptor agonist with a distinctive chemical structure which is not closely related to other established families of opioid drugs. The ''trans''-isomer was found to be around 591 times more potent than morphine in animal studies. The same study assigned a potency of 504 times that of morphine to the related compound BDPC. C-8813 is claimed to be similarly potent at the δ-opioid receptor, which antagonizes the mu depression of breathing, presumably making the drug safer. C-8813 has never been used in humans. See also * BDPC * Ciramadol * Faxeladol * Profadol * Tapentadol * Tramadol Tramadol, sold under the brand name Ultram among others, is an opioid pain medication used to treat moderate to moderately severe pain. When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an h ... References Arylcyclohexylamines Synthetic opioids Thiophenes Tertiary alcohols Organobrom ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
BDPC
BDPC (systematic name 4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol; also known as bromadol) is a potent narcotic analgesic with a distinctive arylcyclohexylamine chemical structure. It was developed by Daniel Lednicer at Upjohn in the 1970s. Initial studies estimated that it was around 10,000 times the strength of morphine in animal models. However, later studies using more modern techniques assigned a value of 504 times the potency of morphine for the more active ''trans''-isomer. This drug was first seized along with three kilograms of acetylfentanyl in an April 25, 2013 police action in Montreal, Canada, and has reportedly continued to be available on the designer drug black market internationally. Analogues where the ''para''-bromine is replaced by chlorine or a methyl group retain similar activity, as does the ''meta''-hydroxyl derivative. ] ] See also * 3-OH-PCP * 4-Keto-PCP * C-8813 * Cebranopadol * Ciramadol * Dimetamine * Faxeladol * Profadol ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tapentadol
Tapentadol, brand names Nucynta among others, is a centrally acting opioid analgesic of the benzenoid class with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Analgesia occurs within 32 minutes of oral administration, and lasts for 4–6 hours. It is similar to tramadol in its dual mechanism of action; namely, its ability to activate the mu opioid receptor and inhibit the reuptake of norepinephrine. Unlike tramadol, it has only weak effects on the reuptake of serotonin and is a significantly more potent opioid with no known active metabolites. Tapentadol is not a pro-drug and therefore does not rely on metabolism to produce its therapeutic effects; this makes it a useful moderate-potency analgesic option for patients who do not respond adequately to more commonly used opioids due to genetic disposition (poor metabolizers of CYP3A4 and CYP2D6), as well as providing a more consistent dosage-response range among the p ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tramadol
Tramadol, sold under the brand name Ultram among others, is an opioid pain medication used to treat moderate to moderately severe pain. When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an hour. It is also available by injection. It is available in combination with paracetamol (acetaminophen). As is typical of opioids, common side effects include constipation, itchiness, and nausea. Serious side effects may include hallucinations, seizures, increased risk of serotonin syndrome, decreased alertness, and drug addiction. A change in dosage may be recommended in those with kidney or liver problems. It is not recommended in those who are at risk of suicide or in those who are pregnant. While not recommended in women who are breastfeeding, those who take a single dose should not generally stop breastfeeding. Tramadol is converted in the liver to ''O''-desmethyltramadol (desmetramadol), an opioid with a stronger affinity to the μ ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Knoevenagel Condensation
In organic chemistry, the Knoevenagel condensation () reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation. A Knoevenagel condensation is a nucleophilic addition of an active hydrogen compound to a carbonyl group followed by a dehydration reaction in which a molecule of water is eliminated (hence ''condensation''). The product is often an α,β-unsaturated ketone (a conjugated enone). In this reaction the carbonyl group is an aldehyde or a ketone. The catalyst is usually a weakly basic amine. The active hydrogen component has the form * or for instance diethyl malonate, Meldrum's acid, ethyl acetoacetate or malonic acid, or cyanoacetic acid. * , for instance nitromethane. where Z is an electron withdrawing group. Z must be powerful enough to facilitate deprotonation to the enolate ion even with a mild base. Using a strong base in this reaction would induce self-condensation of the aldehyde o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ethyl Cyanoacetate
Ethyl cyanoacetate is an organic compound that contains a carboxylate ester and a nitrile. It is a colourless liquid with a pleasant odor. This material is useful as a starting material for synthesis due to its variety of functional groups and chemical reactivity. Production Ethyl cyanoacetate may be prepared in various ways: *Kolbe nitrile synthesis using ethyl chloroacetate and sodium cyanide. *Fischer esterification of cyanoacetic acid with ethanol in the presence of a strong mineral acids (e.g. concentrated sulfuric acid). The cyanoacetic acid can be prepared via Kolbe nitrile synthesis using sodium chloroacetate and sodium cyanide. *Reaction of the sodium cyanoacetate with ethyl bromide in an aqueous–organic two-phase system in the presence of a phase transfer catalyst. *Oxidation of 3-ethoxypropionitrile, an ether, with oxygen under pressure in the presence of cobalt(II) acetate tetrahydrate as catalyst and ''N''-hydroxyphthalimide as a radical generator. Properties Phys ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nalorphine
Nalorphine () (brand names Lethidrone, Nalline), also known as ''N''-allylnormorphine, is a mixed opioid agonist–antagonist with opioid antagonist and analgesic properties. It was introduced in 1954 and was used as an antidote to reverse opioid overdose and in a challenge test to determine opioid dependence. Nalorphine was the second opioid antagonist to be introduced, preceded by nalodeine (''N''-allylnorcodeine) in 1915 and followed by naloxone in 1960 and naltrexone in 1963. Due to potent activation of the κ-opioid receptor, nalorphine produces side effects such as dysphoria, anxiety, confusion, and hallucinations, and for this reason, is no longer used medically. Pharmacology Pharmacodynamics Nalorphine acts at two opioid receptors — the μ-opioid receptor (MOR) where it has antagonistic effects, and at the κ-opioid receptor (KOR) (Ki = 1.6 nM; EC50 = 483 nM; Emax = 95%) where it exerts high-efficacy partial agonist/near-full agonist characteristics. Chemistry Ana ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
