Aminoalkanes as Pressor Substances

Rohrmann, Ewald; Shonle, H. A.

doi:10.1021/ja01237a032

Cited by 35 publications

(15 citation statements)

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“…Purified water was obtained from ELGA Purelab Maxima (Vivendi Water Systems, High Wycombe, UK). Methyl-1-testosterone and [19,19, H 3 ]-testosterone (d 3 T) was purchased from LGC Promochem (Teddington, UK). This analysis was performed on a high resolution mass spectrometer (Exactive, Thermo Scientific, Hemel Hempstead, UK) that was coupled to an ultra-performance liquid chromatograph (Acquity UPLC® with 2777C Sample Manager, Waters, Manchester, UK).…”

Section: Methodsmentioning

confidence: 99%

“…Five tablets or the contents of 5 capsules from products containing DHEA (1, 2, 4, and 23), methyl-1-testosterone (3 and 24), androstenedione (6,7,19, and 21), androst-4-ene-3,11,17-trione (13) and the residue from 15 (furazabol) following acid hydrolysis were diluted with methanol, sonicated, allowed to cool and the solution made up to an accurate volume with methanol. Portions of these solutions were taken and analyzed against known amounts of their respective standards using d 3 T as the internal standard by full scan GC-MS as their ether-TMS and/or enol-TMS derivatives.…”

Section: Estimation Of the Amount Of Steroid Using Gc-msmentioning

confidence: 99%

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Anabolic steroids detected in bodybuilding dietary supplements – a significant risk to public health

Abbate

Kicman

Evans-Brown

et al. 2014

Drug Testing and Analysis

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Twenty-four products suspected of containing anabolic steroids and sold in fitness equipment shops in the United Kingdom (UK) were analyzed for their qualitative and semi-quantitative content using full scan gas chromatography-mass spectrometry (GC-MS), accurate mass liquid chromatography-mass spectrometry (LC-MS), high pressure liquid chromatography with diode array detection (HPLC-DAD), UV-Vis, and nuclear magnetic resonance (NMR) spectroscopy. In addition, X-ray crystallography enabled the identification of one of the compounds, where reference standard was not available. Of the 24 products tested, 23 contained steroids including known anabolic agents; 16 of these contained steroids that were different to those indicated on the packaging and one product contained no steroid at all. Overall, 13 different steroids were identified; 12 of these are controlled in the UK under the Misuse of Drugs Act 1971. Several of the products contained steroids that may be considered to have considerable pharmacological activity, based on their chemical structures and the amounts present. This could unwittingly expose users to a significant risk to their health, which is of particular concern for naïve users.

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Section: Methodsmentioning

confidence: 99%

Section: Estimation Of the Amount Of Steroid Using Gc-msmentioning

confidence: 99%

Anabolic steroids detected in bodybuilding dietary supplements – a significant risk to public health

Abbate

Kicman

Evans-Brown

et al. 2014

Drug Testing and Analysis

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“…Further chemical work has been initiated in Hartung's laboratory (126,127,128) and by Rohrmann & Shonle (129). For some time, 2-methylamino-isooctene has been noted for its antispasmodic action on intestines (130).…”

Section: Venommentioning

confidence: 99%

Pharmacology

Chen¹

1945

Annu. Rev. Physiol.

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677Annu. Rev. Physiol. 1945.7:677-706. Downloaded from www.annualreviews.org Access provided by Yale University -Law Library on 02/03/15. For personal use only. Quick links to online content Further ANNUAL REVIEWS Annu. Rev. Physiol. 1945.7:677-706. Downloaded from www.annualreviews.org Access provided by Yale University -Law Library on 02/03/15. For personal use only. PHARMACOLOGY FUNCTIONAL GROUPINGS IN THE MOLECULES OF CARDIAC SUBSTANCES 679 Glycosides, bufagins, and bufotoxins all contain a steroid ring system with an unsaturated lactone ring on Cl7, as, for example, digitoxin (3) and gamabufagin (53, 54) shown in Formula I and Formula II, respectively.

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“…Methyllithium, butyllithium, and phenyllithium were prepared by standard procedures [8] from metallic lithium and methyl iodide, butyl bromide, and phenyl bromide, respectively; benzyllithium was synthesized from benzyl ethyl ether and metallic lithium [8]. The concentration of organolithium reagents was determined by acid-base titration [9]. Compounds IIa [10], IIb [11], IIc [12], IId [13], IIe [14], IIf [13], IIg [15], IIh [16,17], IIi [12], IIIa [18], IIIb [19], IV [20], and V [21] were described previously; they were identified by GC-MS and 1 H and 13 C NMR data.…”

Section: Methodsmentioning

confidence: 99%

Reactions of 2-(α-Haloalkyl)thiiranes with nucleophilic reagents: V. Reactions of 2-(α-Chloroalkyl)thiiranes with organolithium compounds

2010

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2-(α-Haloalkyl)thiiranes reacted with methyl-, butyl-, and phenyllithium to give the corresponding allyl sulfides. The reactions of diastereoisomeric erythro-and threo-2-(1-chloroethyl)thiiranes with phenyllithium were stereospecific, and they afforded (E)-and (Z)-1-phenylsulfanylbut-2-enes, respectively. 3-Chloromethyl-2,2-dimethylthiirane and phenyllithium gave rise to a mixture of 3-methyl-3-phenylsulfanylbut-1-ene and 3-methyl-1-phenylsulfanylbut-2-ene. The reactions of 2-chloromethylthiiranes with phenyllithium and methyllithium in the presence of a catalytic amount of copper(I) iodide (10 mol %) led to the formation of substituted thiiranes as the major products. Mechanisms of the observed transformations are discussed. * For communication IV, see [1]. † Deceased.Unlike oxiranes, reactions of alkylthiiranes with organometallic compounds involve desulfurization or polymerization processes rather than opening of the three-membered ring [2][3][4]. Presumably, desulfurization occurs through intermediate formation of ate complexes and is stereospecific; furthermore, this reaction may be regarded as a method for the preparation of alkenes [2]. On the other hand, there are published data indicating that 2-(chloromethyl)thiirane (Ia) is capable of giving rise to monomeric products of formal chlorine replacement in reactions with organolithium reagents; however, these products have quite specific nature [5, 6] (Scheme 1). Unfortunately, these two examples represent all available information on such reactions which could underlie a convenient procedure for the synthesis of substituted thiiranes. Therefore, in the present work we examined reactions of the simplest organolithium compounds with some 2-(α-haloalkyl)thiiranes in diethyl ether.We found that phenyllithium and butyllithium reacted with 2-(chloromethyl)thiirane (Ia) at a fairly high rate on moderate cooling. Methyllithium was inert up to 0°C, but it did react with compound Ia in the presence of DABCO. Quite surprisingly and contrary to published data, as low-molecular products of these transformations we identified the corresponding allyl sulfides IIa-IIc (Scheme 2). 2-(Bromomethyl)thiirane (Ib) (which is less convenient to handle with) reacted with phenyllithium to give sulfide IIc in a considerably better yield.

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Aminoalkanes as Pressor Substances

Cited by 35 publications

References 2 publications

Anabolic steroids detected in bodybuilding dietary supplements – a significant risk to public health

Anabolic steroids detected in bodybuilding dietary supplements – a significant risk to public health

Pharmacology

Reactions of 2-(α-Haloalkyl)thiiranes with nucleophilic reagents: V. Reactions of 2-(α-Chloroalkyl)thiiranes with organolithium compounds

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