Clinical data | |
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Drug class | Antidepressant; Coronary vasodilator |
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Chemical and physical data | |
Formula | C25H27NO |
Molar mass | 357.497 g·mol−1 |
3D model (JSmol) | |
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Cinfenine (INN ) is a drug described as an antidepressant and coronary vasodilator which was never marketed. [1] [2] [3] It was first described in the literature by 1970. [1] [4] The drug is similar in chemical structure to the modafinil derivative and atypical dopamine reuptake inhibitor JJC8-016, as well as to the antihistamine and anticholinergic diphenhydramine and derivatives of diphenhydramine like ebastine. [1] [5]
Corbadrine, sold under the brand name Neo-Cobefrine and also known as levonordefrin and α-methylnorepinephrine, is a catecholamine sympathomimetic used as a topical nasal decongestant and vasoconstrictor in dentistry in the United States. It is usually used in a pre-mixed solution with local anesthetics, such as mepivacaine.
Methoxamine, sold under the brand names Vasoxine, Vasoxyl, and Vasylox among others, is a sympathomimetic medication used as an antihypotensive agent. It has mostly or entirely been discontinued.
Gepefrine, also known as 3-hydroxyamphetamine or α-methyl-meta-tyramine and sold under the brand names Pressionorm and Wintonin, is a sympathomimetic medication used as an antihypotensive agent which has been marketed in Germany.
Prazitone is a barbiturate derivative described as an antidepressant which was developed in the 1960s. Unlike most barbiturates, it has little or no sedative effects, instead acting as a non-sedating anxiolytic and antidepressant. The dosage range in humans is around 200–600 mg, although higher doses have been used in trials for the treatment of depression associated with Parkinson's disease.
Imuracetam is a drug of the racetam group described as a nootropic. It was under development in the 1970s but was never marketed.
Amidephrine, or amidefrine, sold under the brand name Fentrinol among others, is a selective α1-adrenergic receptor agonist which is described as an adrenergic or sympathomimetic, vasoconstrictor, and topical nasal decongestant used to treat allergic rhinitis. It is used as the mesylate salt, which has the generic names amidefrine mesilate and amidephrine mesylate. The drug is a substituted phenethylamine derivative and is also known as 3-methylsulfonamidyl-β-hydroxy-N-methylphenethylamine. As of 2000, it remained marketed only in Austria.
Hydroxystenozole, also known as 17α-methylandrost-4-eno[3,2-c]pyrazol-17β-ol, is an orally active androgen/anabolic steroid (AAS) and a 17α-alkylated derivative of testosterone that was described in the literature in 1967 but was never marketed. It is closely related to stanozolol (17α-methyl-5α-androstano[3,2-c]pyrazol-17β-ol), differing from it only in hydrogenation.
Pholedrine, also known as 4-hydroxy-N-methylamphetamine and sold under the brand names Paredrinol, Pulsotyl, and Veritol among others, is a sympathomimetic drug used in topical eye drops to dilate the pupil. It can be used to diagnose Horner's syndrome.
Ampyzine, also known as dimethylaminopyrazine or as ampyzine sulfate in the case of the sulfate salt, is a drug described as a "central stimulant" or "CNS stimulant" and "euphoriant". It is said to be a monoamine oxidase inhibitor (MAOI). Ampyzine was first described in the scientific literature by 1960.
Alifedrine is a drug described as a sympathomimetic and cardiotonic or positive inotropic agent which was never marketed. It is a β-adrenergic receptor partial agonist and was studied in the treatment of heart failure. The drug is taken by mouth or intravenously. It is a β-hydroxylated substituted amphetamine derivative.
Nilestriol, also known as nylestriol, is a synthetic estrogen which was patented in 1971 and is marketed in China. It is the 3-cyclopentyl ether of ethinylestriol, and is also known as ethinylestriol cyclopentyl ether (EE3CPE). Nilestriol is a prodrug of ethinylestriol, and is a more potent estrogen in comparison. It is described as a slowly-metabolized, long-acting estrogen and derivative of estriol. Nilestriol was assessed in combination with levonorgestrel for the potential treatment of postmenopausal osteoporosis, but this formulation ultimately was not marketed.
Dioxifedrine, or dioxifedrin, also known as α-methylepinephrine or as 3,4-dihydroxyephedrine, is a sympathomimetic medication that was never marketed. It is described as a β-adrenergic receptor agonist and bronchodilator. The drug is a substituted phenethylamine and amphetamine and is the catecholamine (3,4-dihydroxylated) derivative of ephedrine and the amphetamine (α-methylated) analogue of epinephrine (adrenaline). Analogues of dioxifedrine include dioxethedrin (α-methyl-N-ethylnorepinephrine), corbadrine, and α-methyldopamine.
Bufenadrine, also known as 2-tert-butyldiphenhydramine, is a drug described as an antiemetic, antihistamine, anticholinergic, and antiparkinsonian agent which was never marketed. It is the 2-tert-butyl analogue of diphenhydramine. The drug was found to produce stereoselective hepatotoxicity in animals and this led to the discontinuation of its development. Bufenadrine was first described in the literature by 1967. Its INNTooltip International Nonproprietary Name suffix "-drine" is generally for sympathomimetics but bufenadrine itself is not actually a sympathomimetic or related agent.
Tinofedrine, also known as N-(3,3-di-3-thienyl)-2-propenyl)norephedrine, is a sympathomimetic and cerebral vasodilator of the amphetamine family which was never marketed. It is a derivative of norephedrine and an analogue of related agents like oxyfedrine, buphenine (nylidrin), and isoxsuprine. The drug was first described in the literature by 1978.
Clofenetamine, also known as phenoxethamine or as Keithon, is a drug described as a tranquilizer, antihistamine, anticholinergic, and antiparkinsonian agent. It is a derivative of diphenhydramine and is closely structurally related to mephenhydramine, chlorphenoxamine, and embramine, among other drugs. Clofenetamine was discovered by Searle in the 1940s and was first described in the literature by 1956.
Monometacrine, also known as desmethyldimetacrine, is a drug of the tricyclic family described as an antidepressant which was never marketed. It was first described in the literature by 1966. The drug is the N-desmethyl analogue of dimetacrine and is a metabolite of dimetacrine.
Tipindole, also known as typindole, is a drug of the tricyclic family described as a serotonin antagonist and monoamine oxidase inhibitor (MAOI) which was never marketed. The drug was developed by Soviet researchers and was first described by 1962.
Botiacrine is a drug of the tricyclic family described as an antiparkinsonian agent which was either never marketed or was possibly marketed outside of the United States. It was first described in the literature by 1965. The drug is an acridine derivative and is structurally related to the tricyclic antidepressant dimetacrine.
Triampyzine, also known as triampyzine sulfate in the case of the sulfate salt, as (dimethylamino)trimethylpyrazine, or as 3,5,6-trimethylampyzine, is a drug described as an anticholinergic and antisecretory agent which was never marketed. It was first described in the literature by 1966. The drug is the 3,5,6-trimethylated derivative of ampyzine (W-3580B), which is also a drug and is, conversely, described as a "central stimulant".
Benapryzine, or benaprizine, also known as benapryzine hydrochloride (USANTooltip United States Adopted Name in the case of the hydrochloride salt and sold under the brand name Brizin, is an antiparkinsonian agent and anticholinergic which has been used in the treatment of parkinsonism. As an anticholinergic, it is specifically a muscarinic acetylcholine receptor antagonist. Structurally, benapryzine is a benzilate, and is closely related to other antimuscarinic benzilate derivatives like benactyzine. The drug was first described in the literature by 1973.