Ephedrine compounds

Flurer CL, Lin LA, et al. Determination of ephedrine compounds in nutritional supplements by cyclodextrin-modified capillary electrophoresis. J Chromatogr B Biomed Appl 1995 669 133-9. 

Addition of a hydroxyl group to the aromatic ring of ephedrine as well as changing the substitution on nitrogen leads to a compound whose main activity is to raise blood pressure. Thus, lormation of the Shiff base of the m-hydroxy analog of 30 with bcnzylamine (34), followed by catalytic reduction, yields metar- uiiinol (35). When optically active hydroxyketone is employed in... 

Omission of the side chain hydroxyl group from molecules based on epinephrine or ephedrine does not abolish the sympathomimetic activity of the resulting compounds. Many of these agents exert a considerable stimulant action on the central nervous system. As such, drugs in this class have been widely used—and... 

Oxidation of the methyl substituent in compounds 4 to the corresponding aldehydes and subsequent reaction with ephedrine leads to (V.O-acetals, which can be separated by crystallization into the two diastereomers. Treatment with silica gel then gives the enantiomerically pure aldehydes.17... 

It has been proposed that aziridines may be more widespread in biological systems than is generally realized [190]. Many drugs such as ephedrine (124 Scheme 11.18) and pronethalol (125) and endogenous metabolites such as adrenaline (126) contain a P-aminoalcohol moiety, which may act as a precursor to an aziridine metabolite that may explain the known carcinogenicity of some of these compounds such as pronethalol. 

Diuretic teas such as juniper berries and shave grass or horsetail are contraindicated. Juniper berries have been associated with renal damage, and horsetail contains severely toxic compounds Teas with ephedrine should be avoided, especially by individuals with hypertension. 

Aromatics and compounds with aromatic substituents e.g. ephedrine [1, 2]... 

Amino alcohols, which have a broad spectrum of biological activities, can be categorized as adrenahne-like with one chiral center at C-1 or as ephedrine-like with two chiral centers at C-1 and C-2 (Scheme 7). Although a variety of methods have been developed for the stereoselective preparation of 1,2-amino alcohols, " in most cases it is easier and more efficient to prepare these important compounds stereoselectively starting from chiral cyanohydrins (Scheme... 

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 3 presents the mean levels of self-infusion for the 14 phenylethyl-amines shown in figure 1. Of all the drugs tested, injection rates were... 

In a summary of the human abuse literature on anorectic phenylethylamines, Griffiths et al. (1979) found there was a good correlation between the results of self-administration studies in animals and information about the subjective effects and abuse in man. Specifically, amphetamine, diethyl-propion, and phenmetrazine have been associated with numerous clinical case reports involving abuse, and these three compounds as well as benz-phetamine and /-ephedrine have shown similar subjective effects in drug abuser populations (Griffiths et al. 1979). In addition, fenfluramine was associated with low incidence of abuse in humans and did not maintain self-injection responding in animals. Chlorphentermine was similarly associated with low incidence of abuse in man, but did not maintain selfinjection uniformly in animals (Griffiths et al. 1979). 

New modifiers have traditionally been discovered by the trial-and-error method. Many naturally occurring chiral compounds (the chiral pool38) have been screened as possible modifiers. Thus, the hydrogenation product of the synthetic drug vinpocetine was discovered to be a moderately effective modifier of Pt and Pd for the enantioselective hydrogenation of ethyl pyruvate and isophorone.39 Likewise, ephedrine, emetine, strychnine, brucine, sparteine, various amino acids and hydroxy acids, have been identified as chiral modifiers of heterogeneous catalysts.38... 

Metal alkoxides undergo alkoxide exchange with alcoholic compounds such as alcohols, hydro-xamic acids, and alkyl hydroperoxides. Alkyl hydroperoxides themselves do not epoxidize olefins. However, hydroperoxides coordinated to a metal ion are activated by coordination of the distal oxygen (O2) and undergo epoxidation (Scheme 1). When the olefin is an allylic alcohol, both hydroperoxide and olefin are coordinated to the metal ion and the epoxidation occurs swiftly in an intramolecular manner.22 Thus, the epoxidation of an allylic alcohol proceeds selectively in the presence of an isolated olefin.23,24 In this metal-mediated epoxidation of allylic alcohols, some alkoxide(s) (—OR) do not participate in the epoxidation. Therefore, if such bystander alkoxide(s) are replaced with optically active ones, the epoxidation is expected to be enantioselective. Indeed, Yamada et al.25 and Sharp less et al.26 independently reported the epoxidation of allylic alcohols using Mo02(acac)2 modified with V-methyl-ephedrine and VO (acac)2 modified with an optically active hydroxamic acid as the catalyst, respectively, albeit with modest enantioselectivity. 

As it can be observed in Fig. 2, three out of the 16 investigated compounds, namely, heroin, lysergic acid diethylamide (LSD), and its metabolite 2-oxo, 3-hydroxy-LSD (O-H-LSD), were not detected in any wastewater sample. Two other target analytes, 6-acetyl morphine (6ACM) and A9-tetrahydrocannabinol (THC), were only present in influent wastewaters and with low detection frequencies. The most ubiquitous compounds, present in all influent and effluent wastewater samples analyzed, were the cocaine metabolite benzoylecgonine, and the amphetamine-like compounds ephedrine (EPH) and 3,4-methylenedioxymethamphetamine (MDMA or ecstasy). Cocaine, cocaethylene (CE, transesterification product of cocaine formed after the joint consumption of cocaine and ethanol), and morphine (MOR) were detected in all influent, but not in all effluent wastewaters (see Fig. 2). 

In agreement with previous works, elimination of amphetamine-like compounds was diverse. Amphetamine and ephedrine are the best removed amphetamine-like compounds in the Ebro River basin. On the other hand, MDMA and methamphet-amine were poorly removed compared to other studies as they were found randomly at higher concentrations in effluents than in influents. Similar to these compounds and in contrast to previous studies, the only lysergic analyte determined in waste-waters, nor-LSD, was poorly or not eliminated during wastewater treatment processes (see Fig. 5). 

The present work reports on the presence of illicit drugs and metabolites in waste and surface waters of the Ebro River basin. In agreement to previous works done in this line in other locations of Spain and in diverse European countries, the most abundant and ubiquitous compounds in waters were cocaine and its major metabolite benzoy-lecgonine, and the amphetamine-like compounds ephedrine and ecstasy. Removal of these compounds during wastewater treatment processes was considered satisfactory for most compounds, but not enough to avoid the presence of these... 

In 1969, Fiaud and Kagan[U1 tested ephedrine boranes but achieved only 3.6-5% enantiomeric excess in the reduction of acetophenone. Itsuno et a/.[121 reported in 1981 an interesting enantioselective reduction of a ketone using an amino alcohol-borane complex as a catalyst. Buono[131 investigated and developed the reactivity of phosphorus compounds as ligands in borane complexes for asymmetric hydrogenation. 

Ephedrine (17) was known to give coloured products on exposure to sunlight. When a 1 % solution was irradiated with UV light from a 30 W tube the solution became coloured and colourless needle-shaped crystals separated. With prolonged exposure, the crystals redissolved as the solution darkened to an intense brown. On analysis, the crystalline compound was identified as the oxazolidine (18). This compound was known to be formed by reaction between ephedrine and benzaldehyde, so it was assumed that the primary photodegradation product of the drug was benzaldehyde [27]. 

Find the quantity of sodium chloride to be used in compounding the following prescription. The sodium chloride equivalent of ephedrine sulfate is 0.23. 

Several examples exist of the application of chiral natural N-compounds in base-catalyzed reactions. Thus, L-proline and cinchona alkaloids have been applied [35] in enantioselective aldol condensations and Michael addition. Techniques are available to heterogenize natural N-bases, such as ephedrine, by covalent binding to mesoporous ordered silica materials [36]. 

The optically active thiones (4), readily obtainable from (—)-ephedrine, undergo P—N bond fission, with inversion of configuration at phosphorus, when treated with ethanolic HC1 this provides a highly recommendable method for the preparation of valuable amounts of optically active acyclic compounds (5), isolable as the 5-methyl esters (6).9... 

A spectrophotometric method for determination of primary and secondary amines requires development for each particular compound, determining the kinetics of reaction of the amine with sodium l,2-naphthoquinone-4-sulfonate (143) and the UVV absorption spectrum of the product, under a set of fixed conditions. The procedure was applied to determination of ephedrine (30) and amphetamine (28) in pharmaceutical samples339. Reagent 143 in a FLA. system was used for the fast determination of lysine (144) in commercial feed samples by multivariate calibration techniques, without need of chromatographic separation340. 

The gas-phase guest-exchange reaction 29 has been employed to probe the enantioselectivity of permethylated /3-CD for pharmacologically important compounds, such as DOPA, amphetamine, ephedrine, and penicillamine (Scheme... 

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