Related Concept Videos
02:05Prochirality
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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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02:33Stereoisomerism of Cyclic Compounds
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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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02:52Stereoisomerism
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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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01:17Thermal Electrocyclic Reactions: Stereochemistry
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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02:30Racemic Mixtures and the Resolution of Enantiomers
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A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit...
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01:19Complexation Equilibria: The Chelate Effect
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In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
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Cyclodextrin-Mediated Enantiomeric Separation of Idelalisib: A Validated Capillary Electrophoresis and NMR Study.
International journal of molecular sciences·2026
Cyclodextrin-Enabled Enantioselective Complexation Study of Cathinone Analogs.
András Dohárszky1, Eszter Kalydi1,2, Gergely Völgyi3
1Department of Pharmacognosy, Semmelweis University, Üllői út 26, H-1085 Budapest, Hungary.
Molecules (Basel, Switzerland)
|February 24, 2024
Summary
Researchers investigated cyclodextrin (CD) complex stability with cathinone analogs, identifying specific CD derivatives like succinylated-β-CD for enhanced complexation. This study aids in developing chiral separation methods and potential antidotes for these recreational drugs.
Area of Science:
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
Background:
- Cathinone and its synthetic analogs are characteristic alkaloids from *Catha edulis*, widely used as recreational drugs.
- These cathinone derivatives are chiral compounds, necessitating enantioselective analytical and therapeutic strategies.
- Previous research utilized cyclodextrins (CDs) for chiral separation of cathinone analogs, but their complex stability was not comprehensively studied.
Purpose of the Study:
- To systematically investigate and characterize the enantioselective complex formation and stability of various cyclodextrin derivatives with cathinone analogs.
- To identify specific functional groups and CD properties that contribute to favorable interactions and stable complex formation.
- To provide a foundation for developing advanced chiral separation methods and potential cyclodextrin-based antidotes for cathinone analogs.
Main Methods:
- Screening of 40 neutral, positively, and negatively charged cyclodextrin derivatives using affinity capillary electrophoresis.
- Systematic experimental design to compare CDs based on cavity size, substituent type, and location.
- Job's plot method for determining complex stoichiometry and ROESY NMR for structural elucidation.
Main Results:
- Identification of functional groups responsible for favorable interactions in para-substituted cathinone analogs (mephedrone, flephedrone, 4-MEC) and 3,4-methylenedioxy derivatives (butylone, MDPV).
- Succinylated-β-CD and subetadex demonstrated the highest complex stabilities among the tested cathinone analogs.
- Successful determination of complex stoichiometry and structural insights through NMR measurements.
Conclusions:
- The study provides a comprehensive analysis of cyclodextrin-CD complex stability with cathinone analogs.
- Identified optimal CD derivatives and interaction mechanisms can significantly advance chiral method development for cathinone analysis.
- Findings may pave the way for developing novel cyclodextrin-based therapeutic strategies, including potential antidotes for cathinone analog intoxication.