The real Gordian knot: Racemic mixtures versus pure enantiomers

Szelenyi, Istvan; Geißlinger, Gerd; Polymeropoulos, Emmanuel E.; Paul, W.; Herbst, M.; Brune, Kay

doi:10.1358/dnp.1998.11.3.863651

Cited by 18 publications

(15 citation statements)

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“…More importantly, natural scents may be more effective due to their chirality. Synthetic (racemic) substances always contain mirror molecules that may have important pharmacokinetic differences (Szelenyi et al, ). Furthermore, the majority of synthetic scents consist of only a few molecules.…”

Section: Aromatherapy: Common Misconceptions and Important Requirementsmentioning

confidence: 99%

Medical aromatherapy revisited—Basic mechanisms, critique, and a new development

Schneider¹,

Singer²,

Singer³

2018

Human Psychopharmacology

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Objective According to a series of recent meta‐analyses and systematic reviews, aromatherapy has shown to be effective in treating patients with different medical conditions. However, many of the clinical studies are of rather low methodological quality. Moreover, there is much conceptual ambiguity with regard to what aromatherapy actually constitutes. Method In this paper, we discuss the conditions under which aromatherapy is most likely to be of medical value by outlining the workings of the olfactory system and the necessary requirements of odors to be therapeutic. We then introduce an aromatherapeutic inhaler that was tested in a series of studies involving 465 participants. Results This inhaler (AromaStick®) produced large to very large effects across a variety of physiological target systems (e.g., cardiovascular, endocrine, blood oxygenation, and pain), both short term and long term. Discussion Inhalation of volatile compounds from essential oils yields almost immediate, large, and clinically relevant effects as long as the scents are delivered highly concentrated from an appropriate device. The changes caused in the body seem side effect‐free and can be sustained when inhalation is repeated.

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Section: Aromatherapy: Common Misconceptions and Important Requirementsmentioning

confidence: 99%

Medical aromatherapy revisited—Basic mechanisms, critique, and a new development

Schneider¹,

Singer²,

Singer³

2018

Human Psychopharmacology

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“…The structural features of this disubstituted chroman (or 3,4-dihydro-2 H -1-benzopyran) besides its chirality are (i) the unsymmetrically substituted tertiary amine functionality in position 3 and (ii) the secondary carboxamide group attached to C-5. As is frequently observed also the stereoisomers in this case exhibited a pronounced difference in pharmacological properties which eventually led to choosing the ( R )-enantiomer as the desired form …”

Section: Introduction: Defining the Targetmentioning

confidence: 69%

Development of a Process for a Chiral Aminochroman Antidepressant: A Case Story

Federsel

2000

Org. Process Res. Dev.

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The authentic development aiming at a full-scale method for the new chemical entity ebalzotan (code name NAE-086), a selective 5HT1A-agonist chosen as an Astra candidate drug primarily for the treatment of depression and anxiety is described. As it turned out, largely due to severe time constraints the original Medicinal Chemistry route of synthesis comprising 13 steps arranged in linear fashion (starting from 3-methoxyphenol) and including a “classical” diastereomer resolution to generate the desired (R)-enantiomer had to be scaled up without sufficiently developed methods at hand. This resulted in an extended batch cycle time of 5 months after which time a very poor overall yield of 0.25% (!) could be isolated, albeit the product showed excellent stereochemical purity of 99.9% (R). Starting from this deploring position a process was designed which proved to operate well in a 400−600 L pilot scale affording ∼27 kg of high quality material.

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“…[15][16][17] Table 1 Comparison of enantiomer potency of some racemic drugs with only one chiral center Currently, the great interest raised in chiral drug research produces discussions on the merits of the development of unichiral agents vs. racemic mixtures as new drugs. 18 A great deal of evidence accumulated in favor of unichiral drugs instead of a racemic mixture facilitates and simplifies the study of the basic pharmacology, therapeutic and toxic effects, and pharmacokinetic properties, providing a better judgment on its own merits. However, with the development of biotechnologies and great needs to elucidate the action of mechanism of drugs and drug biomarkers, it is necessary to investigate proteins associated with drugs treatment.…”

Section: Chiral Drugsmentioning

confidence: 99%

Expanding proteomics into the analysis of chiral drugs

et al. 2009

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The chiralities of chiral drugs have been investigated extensively with the purpose of enlightening the role of chirality in drug action. Proteomics, though in its infancy, has recently emerged as the foremost technology in drug development research, possessing the advantage of providing more useful information about an organism than genomics, as it directly addresses the level of genome products and their interactions. In this review, we will discuss the background of chiral drug investigation from which contemporary drug chirality research has emerged, the techniques involved in proteomics technology, the application of proteomics in this exciting area, and the perspectives in future applications of this field.

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The real Gordian knot: Racemic mixtures versus pure enantiomers

Cited by 18 publications

References 0 publications

Medical aromatherapy revisited—Basic mechanisms, critique, and a new development

Medical aromatherapy revisited—Basic mechanisms, critique, and a new development

Development of a Process for a Chiral Aminochroman Antidepressant: A Case Story

Expanding proteomics into the analysis of chiral drugs

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