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Journal ArticleDOI

Über die absolute Konfiguration des Morphins und verwandter Alkaloide

01 Jan 1955-Helvetica Chimica Acta (WILEY‐VCH Verlag GmbH)-Vol. 38, Iss: 7, pp 1847-1856
TL;DR: Thebaine (VII) has been degraded to (−)-cis-[2-methyl-2-carboxy-cyclohexyl-(1)]-acetic acid (III), thus providing experimental proof of the absolute configuration of morphine, thebaine and related alkaloids as discussed by the authors.
Abstract: Thebaine (VII) has been degraded to (−)-cis-[2-methyl-2-carboxy-cyclohexyl-(1)]-acetic acid (III), thus providing experimental proof of the absolute configuration of morphine, thebaine and related alkaloids.
Citations
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Journal ArticleDOI
TL;DR: This study contrasts the cumulative scientific discoveries that have led to the current chemical knowledge of morphine with the centuries-old natural method of morphine production that still dominates the opioid market today.
Abstract: Evidence of human use of opium dates back as far as the sixth millennium BCE. Ancient societies through the Renaissance period created a variety of opium products, proliferating its common use and subsequent addiction. Because the active moiety was not known at this time, the potency of these opium concoctions could neither be predicted nor controlled. The first step in identifying opium's active ingredient, morphine, was its chemical isolation in the early 1800s by Wilhelm Serturner. The subsequent elucidation of morphine's chemical formula and Sir Robert Robinson's derivation of morphine's structural formula, which won him the 1947 Nobel Prize in Chemistry, round out 150 years of the incremental advances in our chemical understanding of morphine. Nevertheless, our attempts to synthesize morphine, despite our advanced knowledge in synthetic chemistry, are still no match for the plant-based extraction of morphine from the poppy plant. The status quo remains problematic socially, economically, and politically; the relationships between the countries laboriously growing poppy plants to extract morphine and those countries importing these painkillers are unstable at best. In this study, we contrast the cumulative scientific discoveries that have led to our current chemical knowledge of morphine with the centuries-old natural method of morphine production that still dominates the opioid market today.

57 citations


Cites methods from "Über die absolute Konfiguration des..."

  • ...By using chemical synthesis and X-ray crystallography, the relative spatial arrangements of the molecules in morphine were found to be arranged in five chiral centers, notated as 5R,6S,9R,13S,14R.[37-41] A chiral center is a carbon atom in a molecule that is surrounded by four atoms; each of a different element....

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Book ChapterDOI
TL;DR: This review surveys classes of structures for which putative dopaminergic agonism has been reported, and cites structure-activity correlations, and some aspects of metabolism of the agents are addressed, which seem to have relevance to structure- activity considerations and to strategy of drug design.
Abstract: In the several years since Blaschko [1] first suggested that dopamine might be a neurotransmitter substance, many chemical compounds have been found to possess dopamine-like actions. This review surveys classes of structures for which putative dopaminergic agonism has been reported, and cites structure-activity correlations. Some aspects of metabolism of the agents are addressed, which seem to have relevance to structure-activity considerations and to strategy of drug design.

51 citations

References
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Journal ArticleDOI
TL;DR: In this article, the erwahnten Triterpene and Steroide mit 30 Kohlenstoffatomen die gleiche Konfiguration und Konstellation im Ringe A besitzen, wie die Abkommlinge des Cholestanols-(3β), dessen absolute Konfigureuration mit Hilfe der asymmetrischen Synthese indirekt bestimmt wurde.
Abstract: Phenylglyoxylsaure-ester von α-Amyrin, Dihydro-lanosterin, Euphol, Cholestanol-(3β), Androstanol-(17β), Cholestanol-(7α) und Cholestanol-(7β) wurden mit Methylmagnesiumjodid umgesetzt, die erhaltenen Ester quantitativ verseift und das Drehungsvermogen der dabei entstandenen Atrolactinsaure gemessen. Anhand der Uberlegungen uber den sterischen Verlauf solcher asymmetrischer Synthesen1) wurden fur die angefuhrten Triterpene und Steroide die Konfigurationen I–III und XII–XV abgeleitet. Daraus folgt, dass die erwahnten Triterpene und Steroide mit 30 Kohlenstoffatomen die gleiche Konfiguration und Konstellation im Ringe A besitzen, wie die Abkommlinge des Cholestanols-(3β), dessen absolute Konfiguration mit Hilfe der asymmetrischen Synthese indirekt bestimmt wurde.

39 citations