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Prindamine
Pirandamine (AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI). It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed. Pirandamine is structurally related to tandamine, which, in contrast, is a selective norepinephrine reuptake inhibitor. Synthesis Condensation of 1-indanone (1) with ethyl bromoacetate and zinc affords Reformatsky reaction product 2; then reduction with LiAlH4 gives diol 3. Dehydration with H2SO4 gives the indene ethanol 4. Acid catalyzed condensation of 4 with ethyl acetoacetate then gives the fused tetrahydropyran derivative 5 (no doubt by a scheme quite analogous to prodolic acid). The ester is then saponified to the corresponding acid, which is then converted to the dimethylamide (6). Reduction with LiAlH4 completes the synthesis of the antidepressant agent pirandamine (7). See also * Tandamine *Prindamine Pirandamine (AY- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pirandamine Synthesis
Pirandamine (AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI). It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed. Pirandamine is structurally related to tandamine, which, in contrast, is a selective norepinephrine reuptake inhibitor. Synthesis Condensation of 1-indanone (1) with ethyl bromoacetate and zinc affords Reformatsky reaction product 2; then reduction with LiAlH4 gives diol 3. Dehydration with H2SO4 gives the indene ethanol 4. Acid catalyzed condensation of 4 with ethyl acetoacetate then gives the fused tetrahydropyran derivative 5 (no doubt by a scheme quite analogous to prodolic acid). The ester is then saponified to the corresponding acid, which is then converted to the dimethylamide (6). Reduction with LiAlH4 completes the synthesis of the antidepressant agent pirandamine (7). See also * Tandamine *Prindamine Pirandamine (AY ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Prindamine
Pirandamine (AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI). It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed. Pirandamine is structurally related to tandamine, which, in contrast, is a selective norepinephrine reuptake inhibitor. Synthesis Condensation of 1-indanone (1) with ethyl bromoacetate and zinc affords Reformatsky reaction product 2; then reduction with LiAlH4 gives diol 3. Dehydration with H2SO4 gives the indene ethanol 4. Acid catalyzed condensation of 4 with ethyl acetoacetate then gives the fused tetrahydropyran derivative 5 (no doubt by a scheme quite analogous to prodolic acid). The ester is then saponified to the corresponding acid, which is then converted to the dimethylamide (6). Reduction with LiAlH4 completes the synthesis of the antidepressant agent pirandamine (7). See also * Tandamine *Prindamine Pirandamine (AY- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tricyclic
Tricyclics are chemical compounds that contain three interconnected rings of atoms. Many compounds have a tricyclic structure, but in pharmacology, the term has traditionally been reserved to describe heterocyclic drugs. Among these are antidepressants, antipsychotics, anticonvulsants, and antihistamines (as antiallergens, anti-motion sickness drugs, antipruritics, and hypnotics/sedatives) of the dibenzazepine, dibenzocycloheptene, dibenzothiazepine, dibenzothiepin, phenothiazine, and thioxanthene chemical classes, and others. History * Promethazine and other first generation antihistamines with a tricyclic structure were discovered in the 1940s. * Chlorpromazine, derived from promethazine originally as a sedative, was found to have neuroleptic properties in the early 1950s, and was the first typical antipsychotic. * Imipramine, originally investigated as an antipsychotic, was discovered in the early 1950s, and was the first tricyclic antidepressant. * Carbamazepine was disco ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemical Derivative
In chemistry, a derivative is a compound that is derived from a similar compound by a chemical reaction. In the past, derivative also meant a compound that ''can be imagined to'' arise from another compound, if one atom or group of atoms is replaced with another atom or group of atoms, but modern chemical language now uses the term structural analog for this meaning, thus eliminating ambiguity. The term "structural analogue" is common in organic chemistry. In biochemistry, the word is used for compounds that at least theoretically can be formed from the precursor compound. Chemical derivatives may be used to facilitate analysis. For example, melting point (MP) analysis can assist in identification of many organic compounds. A crystalline derivative may be prepared, such as a semicarbazone or 2,4-dinitrophenylhydrazone (derived from aldehydes or ketones), as a simple way of verifying the identity of the original compound, assuming that a table of derivative MP values is available ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Selective Serotonin Reuptake Inhibitor
Selective serotonin reuptake inhibitors (SSRIs) are a class of drugs that are typically used as antidepressants in the treatment of major depressive disorder, anxiety disorders, and other psychological conditions. SSRIs increase the extracellular level of the neurotransmitter serotonin by limiting its reabsorption (reuptake) into the presynaptic cell. They have varying degrees of selectivity for the other monoamine transporters, with pure SSRIs having strong affinity for the serotonin transporter and only weak affinity for the norepinephrine and dopamine transporters. SSRIs are the most widely prescribed antidepressants in many countries. The efficacy of SSRIs in mild or moderate cases of depression has been disputed and may or may not be outweighed by side effects, especially in adolescent populations. Medical uses The main indication for SSRIs is major depressive disorder; however, they are frequently prescribed for anxiety disorders, such as social anxiety disorder, ge ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Antidepressant
Antidepressants are a class of medication used to treat major depressive disorder, anxiety disorders, chronic pain conditions, and to help manage addictions. Common side-effects of antidepressants include dry mouth, weight gain, dizziness, headaches, sexual dysfunction, and emotional blunting. There is a slight increased risk of suicidal thinking and behavior when taken by children, adolescents, and young adults. Discontinuation syndrome may occur after stopping any antidepressant which resembles recurrent depression. Some research regarding the effectiveness of antidepressants for depression in adults has found benefits, whilst other research has not. Evidence of benefit in children and adolescents is unclear. The twenty-one most commonly prescribed antidepressant medications are more effective than placebo for the short-term (acute) treatments of adults with major depressive disorder. There is debate in the medical community about how much of the observed effects of antidep ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemical Structure
A chemical structure determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target molecule or other solid. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together, and can be represented using structural formulae and by molecular models; complete electronic structure descriptions include specifying the occupation of a molecule's molecular orbitals. Structure determination can be applied to a range of targets from very simple molecules (e.g., diatomic oxygen or nitrogen), to very complex ones (e.g., such as protein or DNA). Background Theories of chemical structure were first developed by August Kekulé, Archibald Scott Couper, and Aleksandr Butlerov, among others, from about 1858. These theories were first to state that chemical compounds are not a random cluster of atoms and functional groups, but rather had a definite order ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tandamine
Tandamine is a selective norepinephrine reuptake inhibitor with a tricyclic structure. It was developed in the 1970s as an antidepressant but was never commercialized. Tandamine is analogous to pirandamine, which, instead, acts as a selective serotonin reuptake inhibitor (SSRI). The exact identical same structure, although this time changing the thioether to a methylene group revealed a strongest compound of the series called AY 24614. See also * Pirandamine Pirandamine (AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI). It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed. ... References Norepinephrine reuptake inhibitors {{nervous-system-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Norepinephrine Reuptake Inhibitor
A norepinephrine reuptake inhibitor (NRI, NERI) or noradrenaline reuptake inhibitor or adrenergic reuptake inhibitor (ARI), is a type of drug that acts as a reuptake inhibitor for the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline) by blocking the action of the norepinephrine transporter (NET). This in turn leads to increased extracellular concentrations of norepinephrine and epinephrine and therefore can increase adrenergic neurotransmission. Medical use NRIs are commonly used in the treatment of conditions like ADHD and narcolepsy due to their psychostimulant effects and in obesity due to their appetite suppressant effects. They are also frequently used as antidepressants for the treatment of major depressive disorder, anxiety and panic disorder. Additionally, many addictive substances such as cocaine and methylphenidate possess NRI activity, though NRIs without combined dopamine reuptake inhibitor (DRI) properties are not significantly reward ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1-Indanone
1-Indanone is the organic compound with the formula C6H4(CH2)2CO. It is one of two isomeric benzocyclopentanones, the other being 2-indanone. It is a colorless solid. 1-Indanone is a substrate for the enzyme indanol dehydrogenase. Preparation It is prepared by oxidation of indane or indene. It can also be prepared by cyclization of phenylpropionic acid. :300px 3 (three) is a number, numeral and digit. It is the natural number following 2 and preceding 4, and is the smallest odd prime number and the only prime preceding a square number. It has religious or cultural significance in many societie ... References {{DEFAULTSORT:Indanone, 1- Aromatic ketones ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ethyl Bromoacetate
Ethyl bromoacetate is the chemical compound with the formula CH2BrCO2C2H5. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid. It is a lachrymator and has a fruity, pungent odor. It is also a highly toxic alkylating agent and may be fatal if inhaled. Applications Ethyl bromoacetate is listed by the World Health Organization as a riot control agent, and was first employed for that purpose by French police in 1912. The French army used rifle grenades 'grenades lacrymogènes' filled with this gas against the Germans beginning in August 1914, but the weapons were largely ineffective, even though ethyl bromoacetate is twice as toxic as chlorine. In the early months of the war the British also used the weaponized use of tear gas agents and more toxic gasses including sulfur dioxide. The German army then used these attacks to justify their subsequent employment of it as odorant or warning agent in odorless, toxic gases and chemical weapons in 1915 und ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Reformatsky Reaction
The Reformatsky reaction (sometimes misspelled Reformatskii reaction) is an organic reaction which condenses aldehydes or ketones with α-halo esters using metallic zinc to form β-hydroxy-esters: The organozinc reagent, also called a 'Reformatsky enolate', is prepared by treating an alpha-halo ester with zinc dust. Reformatsky enolates are less reactive than lithium enolates or Grignard reagents and hence nucleophilic addition to the ester group does not occur. The reaction was discovered by Sergey Nikolaevich Reformatsky. Some reviews have been published. In addition to aldehydes and ketones, it has also been shown that the Reformatsky enolate is able to react with acid chlorides, imines, nitriles (see Blaise reaction), and nitrones. Moreover, metals other than zinc have also been used, including magnesium, iron, cobalt, nickel, germanium, cadmium, indium, barium, and cerium. Additionally, metal salts are also applicable in place of metals, notably samarium(II) iodide, chr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
