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Other names | Tozalinone, Thozalinon |
Routes of administration | Oral |
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Formula | C11H12N2O2 |
Molar mass | 204.229 g·mol−1 |
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Chirality | Racemic mixture |
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Thozalinone (USAN) (brand name Stimsen; former developmental code name CL-39808) is a psychostimulant that has been used as an antidepressant in Europe. [1] [2] [3] [4] [5] It has also been trialed as an anorectic. [6] Thozalinone is described as a "dopaminergic stimulant", [7] and likely acts via inducing the release of dopamine and to a minimal extent norepinephrine; similar to analogue pemoline, it is reportedly devoid of abuse potential unlike other dopaminergic psychostimulants. [2] [7] [8]
Sodium hydride is used as a strong base to abstract the alcohol proton in ethyl mandelate [774-40-3] (1); addition of the oxyanion to dimethylcyanamide [1467-79-4] gives the intermediate (2). Intramolecular cyclization then occurs giving Thozalinone (3).
Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered as a chemical in 1887 by Lazăr Edeleanu, and then as a drug in the late 1920s. It exists as two enantiomers: levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.
Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation.
Pemoline, sold under the brand name Cylert among others, is a stimulant medication which has been used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy. It has been discontinued in most countries due to rare but serious problems with liver toxicity. The medication was taken by mouth.
Dopaminergic means "related to dopamine" (literally, "working on dopamine"), dopamine being a common neurotransmitter. Dopaminergic substances or actions increase dopamine-related activity in the brain. Dopaminergic brain pathways facilitate dopamine-related activity. For example, certain proteins such as the dopamine transporter (DAT), vesicular monoamine transporter 2 (VMAT2), and dopamine receptors can be classified as dopaminergic, and neurons that synthesize or contain dopamine and synapses with dopamine receptors in them may also be labeled as dopaminergic. Enzymes that regulate the biosynthesis or metabolism of dopamine such as aromatic L-amino acid decarboxylase or DOPA decarboxylase, monoamine oxidase (MAO), and catechol O-methyl transferase (COMT) may be referred to as dopaminergic as well. Also, any endogenous or exogenous chemical substance that acts to affect dopamine receptors or dopamine release through indirect actions (for example, on neurons that synapse onto neurons that release dopamine or express dopamine receptors) can also be said to have dopaminergic effects, two prominent examples being opioids, which enhance dopamine release indirectly in the reward pathways, and some substituted amphetamines, which enhance dopamine release directly by binding to and inhibiting VMAT2.
1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C
10H
6O
2. This yellow solid is prepared by oxidation of 1-amino-2-hydroxynaphthalene with ferric chloride.
An analeptic, in medicine, is a central nervous system stimulant. The term "analeptic" typically refers to respiratory analeptics. Analeptics are central nervous system (CNS) stimulants that include a wide variety of medications used to treat depression, attention deficit hyperactivity disorder (ADHD), and respiratory depression. Analeptics can also be used as convulsants, with low doses causing patients to experience heightened awareness, restlessness, and rapid breathing. The primary medical use of these drugs is as an anesthetic recovery tool or to treat emergency respiratory depression. Other drugs of this category are prethcamide, pentylenetetrazole, and nikethamide. Nikethamide is now withdrawn due to risk of convulsions. Analeptics have recently been used to better understand the treatment of a barbiturate overdose. Through the use of agents, researchers were able to treat obtundation and respiratory depression.
Iprindole, sold under the brand names Prondol, Galatur, and Tertran, is an atypical tricyclic antidepressant (TCA) that has been used in the United Kingdom and Ireland for the treatment of depression but appears to no longer be marketed. It was developed by Wyeth and was marketed in 1967. The drug has been described by some as the first "second-generation" antidepressant to be introduced. However, it was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.
DNQX (6,7-dinitroquinoxaline-2,3-dione) is a competitive antagonist at AMPA and kainate receptors, two ionotropic glutamate receptor (iGluR) subfamilies. It is used in a variety of molecular biology subfields, notably neurophysiology, to assist researchers in determining the properties of various types of ion channels and their potential applications in medicine.
Fenozolone (Ordinator) was developed by Laboratoires Dausse in the 1960s and is a psychostimulant related to pemoline.
Cyclazodone is a centrally acting stimulant drug developed by American Cyanamid Company in the 1960s. The drug is related to other drugs such as pemoline and thozalinone. It displayed a favorable therapeutic index and margin of safety in comparison to Pemoline and other N-lower-alkyl-substituted Pemoline derivatives. The patents concluded that Cyclazodone possessed properties efficacious in reducing fatigue and as a potential anorectic. Structural congeners of Pemoline have been described as "excitants with unique properties distinguishing them from the sympathomimetic amines" whilst displaying less stimulatory activity and toxicity compared to amphetamine.
Bromantane, sold under the brand name Ladasten, is an atypical psychostimulant and anxiolytic drug of the adamantane family related to amantadine and memantine which is used in Russia in the treatment of neurasthenia. Although the effects of the bromantane have been determined to be dependent on the dopaminergic and possibly serotonergic neurotransmitter systems, its exact mechanism of action is unknown, and it is distinct in its properties relative to typical psychostimulants such as amphetamine. Because of its unique aspects, bromantane has sometimes been described instead as an adaptogen and actoprotector.
Amfonelic acid is a research chemical and dopaminergic stimulant with antibiotic properties. Although limited clinical trials have been conducted, it's primarily used in scientific research.
Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.
Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.
Lortalamine (LM-1404) is an antidepressant which was synthesized in the early 1980s. It acts as a potent and highly selective norepinephrine reuptake inhibitor. Lortalamine was under development for clinical use but was shelved, likely due to the finding that it produced ocular toxicity in animals. It has been used to label the norepinephrine transporter in positron emission tomography studies.
Fenmetozole (DH-524) is a drug which was patented as an antidepressant, but was later studied as an antagonist of the effects of ethanol, though results were poor and it even increased its effects in some cases. It acts as an α2-adrenergic receptor antagonist similarly to other imidazoles like idazoxan. It was never marketed.
G-130 is a drug with stimulant and anorectic effects, related to phenmetrazine.
3-Hydroxymorphinan (3-HM), or morphinan-3-ol, is a psychoactive drug of the morphinan family. It is the racemic counterpart to norlevorphanol.
Adapromine is an antiviral drug of the adamantane group related to amantadine (1-aminoadamantane), rimantadine, and memantine (1-amino-3,5-dimethyladamantane) that is marketed in Russia for the treatment and prevention of influenza. It is an alkyl analogue of rimantadine and is similar to rimantadine in its antiviral activity but possesses a broader spectrum of action, being effective against influenza viruses of both type A and B. Strains of type A influenza virus with resistance to adapromine and rimantadine and the related drug deitiforine were encountered in Mongolia and the Soviet Union in the 1980s.