JNJ-7925476
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JNJ-7925476
JNJ-7925476 is a triple reuptake inhibitor antidepressant discovered by Johnson & Johnson, but never marketed. These molecules were first prepared by Bruce E. Maryanoff and coworkers during the late 1970s–1980s. The structure is a pyrroloisoquinoline core, with an overlaid benzhydryl motif. Incorporating the pyrrolidino ring onto the tetrahydroisoquinoline scaffolding markedly improves potency, although this only works for one of the available stereoisomers. JNJ-7925476 is a racemic preparation of the more potent diastereomer. Of these enantiomers, the eutomer is the (6''R'',10b''S'') stereoisomer, known as JNJ-39836966, and the distomer, (6''S'',10b''R''), is JNJ-39836732 There is some confusion over the nomenclature and ''cis''/''trans'' isomeric relationship at the piperidine ring. The compounds as depicted have the carbon of the pyrrolidine carbon and the phenyl ''cis'', but Maryanoff and coworkers are of the opinion that the compound is ''trans''. (see abstract) ...
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Benzhydryl
The benzhydryl compounds are a group of organic compounds whose parent structures include diphenylmethane (which is two benzene rings connected by a single methane), with any number of attached substituents, including bridges. This group typically excludes compounds in which either benzene is fused to another ring (bicyclic, tricyclic, polycyclic) or includes a heteroatom, or where the methane connects to three or four benzenes. The benzhydryl ''radical'' can be abbreviated or Bzh. Carboaromatic Alcohols *''Acyclic:'' pridinol *''Pyrolidino:'' diphenylprolinol *''2-Piperidine:'' pipradrol *''4-Piperidine:'' terfenadine, fexofenadine *''Benzilic ester:'' QNB, JB-336, JB-318, benactyzine Alkenes *''Tricycle:'' amitriptyline, melitracen, cyclobenzaprine, tianeptine, amineptine, clopenthixol, chlorprothixene, flupentixol, thiothixene, zuclopenthixol *''Tricyclic and piperidine:'' pimethixene, cyproheptadine *''Acyclic:'' gilutensin Alkyl(amine)s *''Acyclic:'' (3-phenylpropyla ...
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Triple Reuptake Inhibitor
Triple is used in several contexts to mean "threefold" or a "treble": Sports * Triple (baseball), a three-base hit * A basketball three-point field goal * A figure skating jump with three rotations * In bowling terms, three strikes in a row * In cycling, a crankset with three chainrings Places * Triple Islands, an uninhabited island group in Nunavut, Canada * Triple Island, British Columbia, Canada * Triple Falls (other), four waterfalls in the United States & Canada * Triple Glaciers, in Grand Teton National Park, Wyoming * Triple Crossing, Richmond, Virginia, believed to be the only place in North America where three Class I railroads cross * Triple Bridge, a stone arch bridge in Ljubljana, Slovenia Transportation * Kawasaki triple, a Japanese motorcycle produced between 1969 and 1980 * Triumph Triple, a motorcycle engine from Triumph Motorcycles Ltd * A straight-three engine * A semi-truck with three trailers Science and technology * Triple (mathematics) (3-tuple), a ...
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Amfonelic Acid
Amfonelic acid (AFA; WIN 25,978) is a research chemical and dopaminergic stimulant with antibiotic properties. History The stimulant properties of AFA were discovered serendipitously at Sterling-Winthrop in the midst of research on the antibiotic nalidixic acid. In addition to behaving as antibiotics, it was found that many derivatives of nalidixic acid have either stimulant or depressant effects on the central nervous system. Researchers at Sterling-Winthrop found that AFA had a higher potency and therapeutic index than cocaine or amphetamine and so it was singled out for further study. A small number of clinical trials were held in the 1970s, but when it was found that AFA exacerbated psychotic symptoms in schizophrenic patients and produced undesirable stimulant properties in geriatric depressives clinical evaluation of AFA was discontinued. AFA remains a widely used pharmacological tool for study of the brain's reward system, dopamine pathways, and the dopamine transporter. S ...
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Ethynyl Compounds
In organic chemistry, the term ethynyl designates a functional group with a double bond with 2 carbon atoms both with sp hybridisation and a triple bond(1 sigma and 2 pi bond) . It is a species similar to acetylene (or in IUPAC ethyne ) with a less H atom thus joined to root chain. * An ethynyl group (HC≡C–), also designated as acetylenic group (from acetylene), and referred to in IUPAC chemical nomenclature as -yne suffix. Also sometimes designed as ''ethinyl'' in compounds (ethinylestradiol, ethisterone (ethinyltestosterone)). See main page alkynes. * The ethynyl radical (HC≡C·), the compound found in interstellar medium, and transiently on earth during chemical reactions. * The ethynyl carbanion Acetylide (HC≡C−) See also * Ethynylation * Propynyl In organic chemistry, a propynyl group is a propyl In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula for the linear form. This substituent form is obtained by removing one ...
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Amide
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid () with the hydroxyl group () replaced by an amine group (); or, equivalently, an acyl (alkanoyl) group () joined to an amine group. Common examples of amides are acetamide (), benzamide (), and dimethylformamide (). Amides are qualified as primary, secondary, and tertiary according to whether the amine subgroup has the form , , or , where R and R' are groups other than hydrogen. The core of amides is called the amide group (specifically, carboxamide group). Amides are pervasive in nature and technology. Proteins and important plastics l ...
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Styrene Oxide
Styrene oxide is an epoxide derived from styrene. It can be prepared by epoxidation of styrene with peroxybenzoic acid, in the Prilezhaev reaction: Styrene oxide is slightly soluble in water. A trace amount of acid in water causes hydrolysis to racemic phenylethyleneglycol via a benzylic cation. If the amount of water is not sufficient, acid-catalyzed isomerization for phenylacetaldehyde will occur. Styrene oxide in the body is metabolized to mandelic acid, phenylglyoxylic acid, benzoic acid and hippuric acid. Hydrogenation of styrene oxide affords phenethyl alcohol. Stereospecific reactions Since styrene oxide has a chiral center at the benzylic carbon atom, there are (''R'')-styrene oxide and (''S'')-styrene oxide. If optically pure reagent is used, only one optically pure compound will be obtained. Toxicology Styrene oxide is a main metabolite of styrene in humans or animals, resulting from oxidation by cytochrome P450. It is considered possibly carcinogenic from ...
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Mandelic Acid
Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is a useful precursor to various drugs. The molecule is chiral. The racemic mixture is known as ''paramandelic acid''. Isolation, synthesis, occurrence Mandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler (1801–1868) while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. The name is derived from the German "Mandel" for "almond". Mandelic acid is usually prepared by the acid-catalysed hydrolysis of mandelonitrile, which is the cyanohydrin of benzaldehyde. Mandelonitrile can also be prepared by reacting benzaldehyde with sodium bisulfite to give the corresponding adduct, forming mandelonitrile with sodium cyanide, which is hydrolyzed: : Alternatively, it can be prepared by base hydrolysis of phenylchloroacetic acid as well as dibromac ...
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Impotent
Erectile dysfunction (ED), also called impotence, is the type of sexual dysfunction in which the penis fails to become or stay erect during sexual activity. It is the most common sexual problem in men.Cunningham GR, Rosen RC. Overview of male sexual dysfunction. In: UpToDate, Martin KA (Ed), UpToDate, Waltham, MA, 2018. Through its connection to self-image and to problems in sexual relationships, erectile dysfunction can cause psychological harm. In about 80% of cases, physical causes can be identified. These include cardiovascular disease; diabetes mellitus; neurological problems, such as those following prostatectomy; hypogonadism; and drug side effects. About 10% of cases are psychological impotence, caused by thoughts or feelings; here, there is a strong response to placebo treatment. The term ''erectile dysfunction'' is not used for other disorders of erection, such as priapism. Treatment involves addressing the underlying causes, lifestyle modifications, and addres ...
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Piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, and typical of amines. The name comes from the genus name ''Piper (genus), Piper'', which is the Latin word for Black pepper, pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring Solenopsin, solenopsins. Production Piperidine was first reported in 1850 by the Scottish chemist Thomas Anderson (chemist), Thomas Anderson and again, independently, in 1852 by the French chemist Auguste André Thomas Cahours, Auguste Cahours, who named it. Both of them obtained piperidine by reacting piperine with nitric acid. Industrially, piperidine is produced by the hydrogenation o ...
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Citalopram
Citalopram, sold under the brand name Celexa among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used to treat major depressive disorder, obsessive compulsive disorder, panic disorder, and social phobia. The antidepressant effects may take one to four weeks to occur. It is taken by mouth. Common side effects include nausea, trouble sleeping, sexual problems, shakiness, feeling tired, and sweating. Serious side effects include an increased risk of suicide in those under the age of 25, serotonin syndrome, glaucoma, and QT prolongation. It should not be used in persons who take or have recently taken a MAO inhibitor. Antidepressant discontinuation syndrome may occur when stopped. There are concerns that use during pregnancy may harm the fetus. Citalopram was approved for medical use in the United States in 1998. It is on the WHO Model List of Essential Medicines, World Health Organization's List of Essential Medicines. It is avai ...
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