Über Oxy-Ephedrine

Schaumann, O.

doi:10.1007/bf01863747

Cited by 69 publications

(5 citation statements)

References 30 publications

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“…Since it was first synthesized in the early 1930s, oxilofrine has been studied in animals and humans. Dozens of studies in a variety of animal models including dogs, cats, rabbits, rats and guinea pigs have been consistent in demonstrating sympathomimetic properties of oxilofrine similar to ephedrine. The US Food and Drug Administration (FDA) banned ephedrine from supplements in 2004 due to serious side effects .…”

Section: Resultsmentioning

confidence: 92%

Pharmaceutical doses of the banned stimulant oxilofrine found in dietary supplements sold in the USA

Cohen

Avula

Venhuis

et al. 2016

Drug Testing and Analysis

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Oxilofrine (4-[1-hydroxy-2-(methylamino)propyl]phenol) is a pharmaceutical stimulant prescribed in dosages of 16 to 40 mg to stimulate the heart and increase blood pressure. It has never been approved for use in the USA as a prescription drug or as a dietary supplement. Several athletes, however, have been banned from sport for testing positive for oxilofrine and have claimed that they inadvertently consumed oxilofrine in sports supplements. Consumption of supplements containing oxilofrine may also pose serious health risks. For example, one brand of supplements containing oxilofrine has been linked to serious adverse events including vomiting, agitation, and cardiac arrest. We designed our study to determine the presence and quantity of oxilofrine in dietary supplements sold in the USA. A validated ultra-high performance liquid chromatography-quadrupole time of flight-mass spectrometry method was developed for the identification and quantification of oxilofrine. The separation was achieved using a reversed phase column, mass spectrometry detection, and a water/acetonitrile gradient as the mobile phase. The presence of oxilofrine was confirmed using a reference standard. We analyzed 27 brands of supplements labelled as containing a synonym of oxilofrine ('methylsynephrine') and found that oxilofrine was present in 14 different brands (52%) at dosages ranging from 0.0003 to 75 mg per individual serving. Of the supplements containing oxilofrine, 43% (6/14) contained pharmaceutical or greater dosages of oxilofrine. Following instructions on the label, consumers could ingest as much as 250 mg of oxilofrine per day. The drug oxilofrine was found in pharmacological and greater dosages in supplements labelled as containing methylsynephrine.

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Section: Resultsmentioning

confidence: 92%

Pharmaceutical doses of the banned stimulant oxilofrine found in dietary supplements sold in the USA

Cohen

Avula

Venhuis

et al. 2016

Drug Testing and Analysis

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“…There is EO qualitative difference that must not be overlooked. Pharmacodynamically the p-hydroxy compounds are qualitatively little different, if any, from the unsubstituted parent; they are essentially musculotropic (53, 64,66,87) The m-hydroxy derivatives, on the other hand, are more sympathicotropic-that is, show to a much greater extent the mechanism of action which is associated with the catechol nucleus (80,96,99). In other words, the unsubstituted phenyl compound, as in ephedrine, mimics the action of epinephrine on the sympathetic system; the introduction of a p-hydroxyl group docs not change appreciably the mechanism of action ; but the presence of the m-hydroxyl group cautm the molecule to evoke a greater degree of sympathetic response.…”

Section: P-nitrophenyl Derivatives Have Been Prepared But the Only Imentioning

confidence: 97%

“…That this'is probably no isolated instance is suggested from a comparison of the available pharmacological data of other pairs of isosteres: C6H6-CH-CH(NH2)-ch, OH MLD (min. lethal dose) 80 mg./kg. of hydrochloride intravenous to rabbits (43) C6H5-CH-CH(NH2)-C H3 CH3 LD6o (dose which is lethal to 50%) 290 mg./kg.…”

Section: Industrial and Engineering Chemistrymentioning

confidence: 99%

Beta-Phenethylamine Derivatives

Hartung¹

1945

Ind. Eng. Chem.

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8 -the compounds derived structurally from p-phenethylamine form an attractive series for the pharmacologist and the pharmaceutical chemist. The structure may be modified within wide limits without destroying the characteristic ability eo raise the blood pressure of an experimental animal. It is now possible to ascribe, with considerable reliance, a constant qualitative or quantitative pharmacodynamic modification to the presence of certain substituents i n given positions of the parent skeleton. The effect of two or more substituents, appropriately placed, may prove additive. The chemical structure, including the phenomena of isosterism and optical isomerism, may be correlated with pharmacological properties, especially pressor effects. The therapeutic usefulness of some members of this series is based o n properties other than their ability to cause an elevation in blood pressure. In the light of information now available, the riddle of Abel's "benzoylepinephrine", which showed to a high degree the quantitative potency of pure epinephrine, becomes all the more enigmatic.

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“…Schaumann (14) and Tainter (15) attribute to the m-hydroxyl group on a pressor molecule a "sympathicotropic" effect, in contrast to the p-hydroxyl group which exhibits more of a "musculotropic" effect. It occurred to us that it would be of interest to learn what the physiological responses would be if both available meta positions were occupied by hydroxyl groups.…”

mentioning

confidence: 99%