Isomer: Difference between revisions
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A chiral molecule is a type of molecule that has a non-superimposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom, where the carbon is attached to four completely different functional groups. | A chiral molecule is a type of molecule that has a non-superimposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom, where the carbon is attached to four completely different functional groups. | ||
Most biological molecules (proteins, sugars, etc.) are present in only one of many chiral forms, so different enantiomers of a chiral | Most biological molecules (proteins, sugars, etc.) are present in only one of many chiral forms, so different enantiomers of a chiral drug molecule bind differently (or not at all) to target receptors. One enantiomer of a drug may have a desired beneficial effect while the other may cause serious and undesired side effects, or sometimes even beneficial but entirely different effects. | ||
One example of this is with the [[dissociative]] | One example of this is with the [[dissociative]] drug [[DXM]]. DXM, or dextromethorphan, is the isomer that rotates clockwise in plane-polarised light. It has antitussive (cough suppressant) and dissociative effects. Levomethorphan is the isomer that rotates anti-clockwise in plane-polarised light. This difference in rotation can radically alter the effects and character of the drug; for example, levomethorphan is an [[opioid]] painkiller. | ||