Ephedrine chemical structure

Chemical Structures. Figure 1 shows the chemical structures for 14 phenylethylamine compounds. Nine of these compounds are used clinically as anorectics (ii-amphetamine, phentermine, diethylpropion, phenmetrazine, phendimetrazine, clotermine, chlorphentermine, benzphetamine, and fenfluramine). Four of these compounds are not approved for clinical use and are reported to have hallucinogenic properties (MDA, PMA, DOM, and DOET). The final compound ( /-ephedrine) is used clinically for bronchial muscle relaxation, cardiovascular, and mydriatic effects. Figure 2 shows the chemical structure for MDMA, the methyl analog of MDA. MDMA is not approved for clinical use and has been reported to produce both LSD-like and cocaine-like effects. 

Figure 5.2a The chemical structure of ephedrine. Ephedrine suppresses appetite, but has also been linked to heart failure and stroke and is currently banned in the United States.

This alkaloid was first isolated from Ephedra equisetina, a plant (ma huang) that has been used as medicine by the Chinese since antiquity. Most of the present supply is probably synthetic. Its chemical structure is closely related to epinephrine and tyramine, and differs from epinephrine chiefly by the absence of the two phenolic hydroxyls. Its effects on the circulation, intestines, bronchi, iris, etc., are superficially similar to those of epinephrine. It requires that larger doses be given but they are more lasting, due probably to ephedrine s much greater stability and resistance to oxidation. The effects can be produced by oral administration. Unlike epinephrine, it is not sensitized by cocaine or by denervation. From this, it has been argued that its point of attack is not sympathomimetic but muscular. It also stimulates the CNS. A number of isomers with similar actions are known. Ephedrine is used therapeutically in hay fever and asthma, in which it is less... 

All amphetamines are synthetic, or manufactured, substances derived from alpha-methyl-beta-phenyl-ethyl-amine, a colorless liquid consisting of carbon, hydrogen, and nitrogen. In terms of their chemical structures, amphetamines are related to two natural substances known to boost energy within the human body. Those substances are ephedrine and adrenaline. Ephedrine is a natural stimulant found in plants of the genus Ephedra. It... 

Although the Catha edulis plant contains a number of chemicals, vitamins, and minerals, its main active ingredient is cathinone, an alkaloid with a chemical structure similar to ephedrine and d-amphetamine. Like amphetamine, it increases the levels of dopamine in the brain and acts as a mild stimulant. For this reason, khat is sometimes referred to as a natural amphetamine. 

Look-alikes contain caffeine, ephedrine, or phenylpropanolamine, either singly or in combination. Ephedrine is a natural stimulant with a chemical structure resembling adrenaline that produces more anxiety and less euphoria than amphetamines. It... 

Chemical/Pharmaceutical/Other Class Speed generally contains one or more agents belonging to the drug class of sympathomimetics Chemical Formulas C10H15NO (Ephedrine) C9H13NO (Synephrine) C8H10N4O2 (Caffeine) Chemical Structures ... 

Figure 34-19 Chemical structure of sympathomimetic amines. Ephedrine and pseudoephedrine are diastereoisomers.

The chemical structure of ephedrine is similar to that of mescaline, a hallucinogen, and it was thought initially that this alkaloid also originated from phenylalanine, as in the case of mescaline. However, when [3- C] phenylalanine was fed to E. distachya, it was established that this unit was incorporated into the aromatic ring of the C6-C2-N moiety of (-)-ephedrine [10]. 

Considering the chemical structure of ephedrine, it is interesting to observe the lack of the phenolic group, characteristic of catecholamines. However, ephedrine remains capable to stimulate a- and p-receptor directly and displace norepinephrine (NE) from storage vesicles, releasing these catecholamines at synaptic areas in the brain and in the heart. These released substances act on receptors promoting the adrenergic effect [17, 66]. 

These results indicate that in these new ester mydriatics, the structural factors, which influence the development of this type of pharmacological action are similar to those made evident by the chemical investigations of Jowett and Pyman and the pharmacological work of Marshall, Dale, Laidlaw and Cushny on the tropeines. The nature of the basic component is obviously important since mydriasis is produced by simple bases such as ephedrine. As regards the nature of the esterifying acid, Jowett and Pyman drew the following conclusions — ... 

Therapeutic Function Sympathomimetic Bronchodilator Chemical Name Benzenemethanol, a-(l-(methylamino)ethyl)-, (R-(R, S ))-Common Name Efedrin Ephedrine Structural Formula ... 

In order to avoid this unfavourable effect of the functional groups in the dendrimer structure, a rigid hydrocarbon backbone without heteroatoms was synthesized. Dendrimers with poly(phenylethyne) backbones, bearing three and six ephedrine derivatives at the periphery, were studied in the alkylation of aldehydes and N-diphenylphosphinylimines and proved to be highly en-antioselective catalysts. For example, the system containing six catalytic sites catalyzed the addition of diisopropylzinc to aldehydes with enantioselectivi-ties of up to 86% ee. As a third backbone a polycarbosilane dendrimer was used, which is chemically inert and more flexible than the poly(phenylethyne)... 

Chemical/Pharmaceutical/Other Class A synthetic sympathomimetic drug structurally related to ephedrine and amphetamine... 

Juge developed a powerful method (Juge-Stephan method) [1, 51] for the preparation of / -stereogenic phosphines based on the use of ephedrine as a chiral auxiliary. The key reactants in this methodology are 1,3,2-oxazaphospholidine boranes 78, prepared by a one-pot reaction from bis(diethylamino)phenylphosphine and (—)-ephedrine, followed by protection with BH3. The cyclization of the (—)-ephedrine takes place stereoselectively, with preferential formation of the (/ p)-diastereoisomer in 90% de [52, 53]. The absolute configuration at the phosphorus atom has been determined by chemical correlations and NMR analysis, and proved by X-ray analysis [54]. Oxazaphospholidines react readily with electrophiles or nucleophiles to provide various chiral phosphorus compounds. Enantiomeric antipodes of tertiary phosphines (Sp)-79 and (Rp)-81 were obtained from (-1-)- or (-)-ephedrine, as shown in Scheme 25. The configuration at the E-atom is controlled by the configuration at the Ph-substituted Cj of (-i-)-pseudoephedrine or ( )-ephedrine, respectively. This was confirmed by X-ray crystal-structure analyses of two intermediate compounds in the synthetic route to the chiral triarylborane-phosphine adducts [54]. 

Ephedrine is an alkaloid, a sympathomimetic amine with molecular formula Cjo Hi5 NOi, a molecular mass of 165.2, and the stmctural name (IR, 25)-2-methylamino-l-phenylpropan-l-ol. This bitter colorless or white solid-crystal is completely soluble in water, alcohol, chloroform, ether, and glycerol. Ephedrine is also produced by chemical synthesis and there is significant documentation of commercial ephedrine production using microbial biotransformation techniques [42]. Ephedrine has a structure close to methamphetamines, and its stimulant actions are comparable to epinephrine (adrenaline), a hormone produces by the adrenal glands that enhances heart rate and constriction of blood vessels in high-stress situations. Medicinal use of ephedrine began around 3000 B.C with the Chinese from md hudng, but its isolation was first reported in 1855 and its pharmaceutical application started in 1930 [22]. Studies on ephedrine s molecular structure show that two asynunetric carbon atoms are involved in ephedrine s molecular skeleton therefore, four optically active stereoisomers forms naturally occur as follows (IR, 2S)-(—)-ephedrine, (IS, 2R)-(+)-ephedrine, (IR, 2R)-( )-pseudoephedrine, (IS, 2S)-(+)-pseudoephedrine (Fig. 27.2). 

Indeed, PDC catalyzes mainly the reaction of pyruvate with benzaldehyde for the formation of (R)-PAC 27. This C—C bond formation, a two-carbon unit elongation, is coupled to the concomitant decarboxylation of pyruvate 26. This reaction is industrially developed for the synthesis of (—)-ephedrine by adding a second step, a reductive amination. Ephedrine (marketed by Merck especially) is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, and decongestant, and it is used to treat hypotension associated with anesthesia. It is similar in structure to the (semisynthetic) derivatives amphetamine and meth-amphetamine. Chemically, it is an alkaloid derived from various plants in the genus Ephedra (family Ephedra-ceae). It works mainly by increasing the activity of noradrenaline on adrenergic receptors. ... 

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