![]() Subsequently, amphetamine was used in the treatment of narcolepsy, obesity, hay fever, orthostatic hypotension, epilepsy, Parkinson's disease, alcoholism and migraine.Adderall XR (amphetamine / dextroamphetamine) for ADHD "I have ADD and chronic fatigue. Over-the-counter use of substituted amphetamines was initiated in the early 1930s by the pharmaceutical company Smith, Kline & French (now part of GlaxoSmithKline), as a medicine ( Benzedrine) for colds and nasal congestion. This synthesis was a by-product of a search for ephedrine, a bronchodilator used to treat asthma extracted exclusively from natural sources. In the 1920s, both methamphetamine and the dextrorotatory optical isomer of amphetamine, dextroamphetamine, were synthesized. However, this synthesis also went largely unnoticed. MDMA was produced in 1912 (in 1914, according to other sources ) as an intermediate product. Īmphetamine was first synthesized in 1887 by Romanian chemist Lazăr Edeleanu, although its pharmacological effects remained unknown until the 1930s. The active substances of khat are cathinone and, to a lesser extent, cathine. Natives of Yemen and Ethiopia have a long tradition of chewing khat leaves to achieve a stimulating effect. Main article: History and culture of substituted amphetaminesĮphedra was used 5000 years ago in China as a medicinal plant its active ingredients are alkaloids ephedrine, pseudoephedrine, norephedrine ( phenylpropanolamine) and norpseudoephedrine ( cathine). MBDB ( N-methyl-1,3-benzodioxolylbutanamine)ģ,4,5-Trimethoxyamphetamine (α-methylmescaline) MDEA (3,4-methylenedioxy- N-ethylamphetamine)ĮDMA (3,4-ethylenedioxy-N-methylamphetamine) Typical reaction is substitution by methyl and sometimes ethyl groups at the amine and phenyl sites: Substance Substitution of hydrogen atoms results in a large class of compounds. The wavy line between α carbon and CH 3 group indicates isomerism the CH 3 group may either be towards or away from the viewer.Īmphetamines are a subgroup of the substituted phenethylamine class of compounds. This shows amphetamine with its substitution points marked, excluding the N-position at the NH 2 group which is unmarked. Amphetamine and its substituted derivatives contain a CH 3 group at the alpha-position (R α). This shows phenethylamine in blue with its substitution points marked. ![]() This section needs expansion with: substituents and structures for phenelzine, phenylephrine, phenylpropanolamine, selegiline, fenfluramine, mescaline, diethylpropion, desmethylselegiline, and benzphetamine from this table. Prodrugs of amphetamine/methamphetamine Ī variety of prodrugs of amphetamine and/or methamphetamine exist, and include amfecloral, amphetaminil, benzphetamine, clobenzorex, D-deprenyl, dimethylamphetamine, ethylamphetamine, fencamine, fenethylline, fenproporex, furfenorex, lisdexamfetamine, mefenorex, prenylamine, and selegiline. ![]() Β-Keto-3-chloro- N- tert-butylamphetamine Β-Hydroxy- N-methylamphetamine, (1 S,2 S)-ģ-Trifluoromethyl- N-ethylamphetamine, ( S)-ĭimethoxytrifluoromethylamphetamine (DOTFM)Ģ,5-Dimethoxy-4-trifluoromethylamphetamine Β-Hydroxy- N-methylamphetamine, (1 R,2 S). ![]() N-(2-chlorobenzyl)-1-phenylpropan-2-amine Para-Fluoroamphetamine (PFA, 4-FA, 4-FMP) Partial list of substituted amphetamines Generic or Trivial Name Various substituted amphetamines may cause these actions either separately or in combination. Their effects on the central nervous system are diverse, but can be summarized by three overlapping types of activity: psychoanaleptic, hallucinogenic and empathogenic. By the 1930s, amphetamine and some of its derivative compounds found use as decongestants in the symptomatic treatment of colds and also occasionally as psychoactive agents. Amphetamine was first produced at the end of the 19th century. Some of amphetamine's substituted derivatives occur in nature, for example in the leaves of Ephedra and khat plants. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP). The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Substituted amphetamines are a class of compounds based upon the amphetamine structure it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents.
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