Quinazolinone
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Quinazolinone
Quinazolinone is a heterocyclic chemical compound, a quinazoline with a carbonyl group in the C4N2 ring. Two isomers are possible: 2-quinazolinone and 4-quinazolinone, with the 4-isomer being the more common. These compounds are of interest in medicinal chemistry. File:2-Quinazolinone.png, 2-Quinazolinone File:4-Quinazolinone.png, 4-Quinazolinone Synthesis Common routes to quinazolines involve condensation of amides to anilines with ortho nitrile, carboxylic acids and amides. Quinazolinone drugs that function as hypnotic/sedatives usually contain a 4-quinazolinone core with a 2-substituted phenyl group at nitrogen atom 3. See also * Idelalisib (Zydelig) * Methaqualone (Quaalude) * Cloroqualone * SL-164 (Dicloqualone) * Diproqualone * Etaqualone * Mebroqualone * Mecloqualone * Methylmethaqualone * Nitromethaqualone Nitromethaqualone is an analogue of methaqualone Methaqualone is a hypnotic sedative. It was sold under the brand names Quaalude ( ) and Sopor among others, wh ...
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Hypnotic
Hypnotic (from Greek ''Hypnos'', sleep), or soporific drugs, commonly known as sleeping pills, are a class of (and umbrella term for) psychoactive drugs whose primary function is to induce sleep (or surgical anesthesiaWhen used in anesthesia to produce and maintain unconsciousness, "sleep" is metaphorical as there are no regular sleep stages or cyclical natural states; patients rarely recover from anesthesia feeling refreshed and with renewed energy. The word is also used in art.) and to treat insomnia (sleeplessness). This group of drugs is related to sedatives''. ''Whereas the term sedative describes drugs that serve to calm or relieve anxiety, the term hypnotic generally describes drugs whose main purpose is to initiate, sustain, or lengthen sleep. Because these two functions frequently overlap, and because drugs in this class generally produce dose-dependent effects (ranging from anxiolysis to loss of consciousness), they are often referred to collectively as sedative-h ...
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Methylmethaqualone
Methylmethaqualone (MMQ) is a quinazolinone and an analogue of methaqualone that has similar sedative and hypnotic properties to its parent compound (resulting from its agonist activity at the β subtype of the GABAA receptor), and is much more potent. Methylmethaqualone differs from methaqualone by 4-methylation on the phenyl ring. It was made illegal in Germany in 1999 and listed by the DEA as a "drug of forensic interest" at about the same time, but little other information is available. It would appear that this compound was sold on the black market in Germany as a designer drug analogue of methaqualone. Animal studies of methylmethaqualone have shown it to produce convulsions A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is sometimes used as a s ... at only slightly above the effective sedative do ...
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Mecloqualone
Mecloqualone (Nubarene, Casfen) is a Quinazolinone-class GABAergic and is an analogue of methaqualone that was first made in 1960 and marketed mainly in France and some other European countries. It has sedative, hypnotic, and anxiolytic properties caused by its agonist activity at the β subtype of the GABAa receptor, and was used for the treatment of insomnia. Mecloqualone is faster-acting but shorter-lasting than methaqualone and so was used only as a sleeping pill, in contrast to methaqualone, which was used as a general-purpose anxiolytic as well. Mecloqualone was never as widely used as methaqualone and is no longer prescribed because of concerns about its potential for abuse and overdose. In the United States it is a Schedule I non-narcotic (depressant) controlled substance with an ACSCN of 2572 and 30 g annual aggregate manufacturing quota. See also * Methaqualone * Afloqualone * Etaqualone * Methylmethaqualone * Mebroqualone * Cloroqualone * Diproqualone Diproqual ...
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Etaqualone
Etaqualone (Aolan, Athinazone, Ethinazone) is a quinazolinone-class GABAergic and is an analogue of methaqualone that was developed in the 1960s and marketed mainly in France and some other European countries. It has sedative, hypnotic, muscle relaxant and central nervous system depressant properties resulting from its agonist activity at the β-subtype of the GABAA receptor, and was used for the treatment of insomnia. The dosage and effects are reported to be similar to those of methaqualone, but shorter acting and slightly weaker. Typical reports use between 50 and 500 mg of etaqualone, depending on desired effects. Old pharmaceutical formulations of Ethinazone were 350 mg tablets. Etaqualone is thought to act in a similar way to barbiturates and benzodiazepines by increasing the sensitivity of GABAA receptors . Recreational effects include euphoria, relaxation, increased sociability and sexuality, reduction of short-term memory, and loss of coordination. Combinat ...
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SL-164
SL-164, also known as dicloqualone or DCQ is an analogue of methaqualone Methaqualone is a hypnotic sedative. It was sold under the brand names Quaalude ( ) and Sopor among others, which contained 300 mg of methaqualone, and sold as a combination drug under the brand name Mandrax, which contained 250 mg me ... developed in the late 1960s by a team at Sumitomo. SL-164 has similar sedative, hypnotic and anticonvulsant properties to the parent compound, but was never marketed for clinical use. References Sedatives Quinazolinones GABAA receptor positive allosteric modulators {{sedative-stub ...
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Quinazoline
Quinazoline is an organic compound with the formula C8H6N2. It is an aromatic heterocycle with a bicyclic structure consisting of two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring. It is a light yellow crystalline solid that is soluble in water. Also known as 1,3-diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Though the parent quinazoline molecule is rarely mentioned by itself in technical literature, substituted derivatives have been synthesized for medicinal purposes such as antimalarial and anticancer agents. Quinazoline is a planar molecule. It is isomeric with the other diazanaphthalenes of the benzodiazine subgroup: cinnoline, quinoxaline, and phthalazine. Over 200 biologically active quinazoline and quinoline alkaloids are identified. Synthesis : The synthesis of quinazoline was first reported in 1895 by August Bischler and Lang through the decarboxylation of the 2-carboxy derivative (quinazoline-2-car ...
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Nitromethaqualone
Nitromethaqualone is an analogue of methaqualone Methaqualone is a hypnotic sedative. It was sold under the brand names Quaalude ( ) and Sopor among others, which contained 300 mg of methaqualone, and sold as a combination drug under the brand name Mandrax, which contained 250 mg me ... that has similar sedative and hypnotic properties. It is significantly more potent (10x) compared to the parent compound; the typical dose is approximately 25 mg. References Sedatives Quinazolinones GABAA receptor positive allosteric modulators {{sedative-stub ...
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Cloroqualone
Cloroqualone is a quinazolinone-class GABAergic and is an analogue of methaqualone developed in the 1980s and marketed mainly in France and some other European countries. It has sedative and antitussive properties resulting from its agonist activity at the β subtype of the GABAa receptor and sigma-1 receptor, and was sold either alone or in combination with other ingredients as a cough medicine. Cloroqualone has weaker sedative properties than methaqualone and was sold for its useful cough-suppressing effects, but was withdrawn from the French market in 1994 because of concerns about its potential for abuse and overdose. See also * Methaqualone * Afloqualone * Etaqualone * Methylmethaqualone * Mecloqualone * Mebroqualone * Diproqualone Diproqualone is a quinazolinone class GABAergic and is an analogue of methaqualone developed in the late 1950s by a team at Nogentaise de Produits Chimique. It was marketed primarily in France and some other European countries. It has sed ...
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Mebroqualone
Mebroqualone (MBQ) is a quinazolinone-class GABAergic and is an analogue of mecloqualone that has similar sedative and hypnotic properties to its parent compound, resulting from its agonist activity at the β subtype of the GABAa receptor. It was originally synthesized in the 1960s Mebroqualone differs from mecloqualone by having a bromine atom instead of a chlorine on the 3-phenyl ring. It was made illegal in Germany in 1998 but little other information is available. It would appear that this compound was sold on the black market in Germany as a designer drug analogue of mecloqualone. See also * Methaqualone * Afloqualone * Etaqualone * Methylmethaqualone * Mecloqualone * Cloroqualone * Diproqualone Diproqualone is a quinazolinone class GABAergic and is an analogue of methaqualone developed in the late 1950s by a team at Nogentaise de Produits Chimique. It was marketed primarily in France and some other European countries. It has sedative ... * Gamma-Aminobutyric acid ...
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Diproqualone
Diproqualone is a quinazolinone class GABAergic and is an analogue of methaqualone developed in the late 1950s by a team at Nogentaise de Produits Chimique. It was marketed primarily in France and some other European countries. It has sedative, anxiolytic, antihistamine and analgesic properties, resulting from its agonist activity at the β subtype of the GABAa receptor, antagonist activity at all histamine receptors, inhibition of the cyclooxygenase-1 enzyme, and possibly its agonist activity at both the sigma-1 receptor and sigma-2 receptor (the function of these receptors and their clinical relevance has not yet been determined). Diproqualone is used primarily for the treatment of inflammatory pain associated with osteoarthritis and rheumatoid arthritis, and more rarely for treating insomnia, anxiety and neuralgia. Diproqualone is the only analogue of methaqualone that is still in widespread clinical use, due to its useful anti-inflammatory and analgesic effects in addition to ...
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Methaqualone
Methaqualone is a hypnotic sedative. It was sold under the brand names Quaalude ( ) and Sopor among others, which contained 300 mg of methaqualone, and sold as a combination drug under the brand name Mandrax, which contained 250 mg methaqualone and 25 mg diphenhydramine within the same tablet, mostly in Europe. Commercial production of methaqualone was halted in the mid-1980s due to widespread abuse and addictiveness. It is a member of the quinazolinone class. The sedative–hypnotic activity of methaqualone was first noted in 1955. In 1962, methaqualone was patented in the United States by Wallace and Tiernan. Its use peaked in the early 1970s for the treatment of insomnia, and as a sedative and muscle relaxant. Methaqualone became increasingly popular as a recreational drug and club drug in the late 1960s and 1970s, known variously as "ludes" or "disco biscuits" due to its widespread use during the popularity of disco in the 1970s, or "sopers" (also "soaps") ...
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Heterocyclic
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of heterocyclic chemistry focuses especially on unsaturated derivatives, and the preponderance of work and applications involves unstrained 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are quinol ...
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