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Isomer: Difference between revisions
>Dextromethorphan https://en.wikipedia.org/wiki/Methorphan |
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===Enantiomers=== | ===Enantiomers=== | ||
[[File:File_Chirality_with_hands.png|thumb|right|Two enantiomers of a generic amino acid that is chiral.]] | |||
An enantiomer is one of two stereoisomers that are mirror images of each other that are non-superimposable (not identical). The model used to convey the idea of isomers being non-superimposable is a person's hands. One's left and right hands are the same except for opposite orientation. Organic compounds that contain a chiral carbon usually have two non-superimposable structures. A chiral carbon is a carbon attached to four completely different functional groups. The enantiomers will have a "left-hand" and a "right-hand" molecule. This property is used in naming the isomers: the "right-hand" is given the prefix (R), and the "left-hand" is given the prefix (S). Enantiomers rotate in plane-polarized light, and this property is also used in naming the enantiomers as either clockwise (prefix of dextro- or +) or anti-clockwise (prefix of levo or -). | An enantiomer is one of two stereoisomers that are mirror images of each other that are non-superimposable (not identical). The model used to convey the idea of isomers being non-superimposable is a person's hands. One's left and right hands are the same except for opposite orientation. Organic compounds that contain a chiral carbon usually have two non-superimposable structures. A chiral carbon is a carbon attached to four completely different functional groups. The enantiomers will have a "left-hand" and a "right-hand" molecule. This property is used in naming the isomers: the "right-hand" is given the prefix (R), and the "left-hand" is given the prefix (S). Enantiomers rotate in plane-polarized light, and this property is also used in naming the enantiomers as either clockwise (prefix of dextro- or +) or anti-clockwise (prefix of levo or -). | ||
== Chirality == | == Chirality == | ||
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 entirely 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 entirely different functional groups. | ||
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One example of this is with the [[dissociative]] drug [[DXM]]. DXM, or dextromethorphan, is the isomer that rotates clockwise in plane-polarized light. It has antitussive (cough suppressant) and dissociative effects. Levomethorphan is the isomer that rotates anti-clockwise in plane-polarized light. This difference in rotation can radically alter the effects and character of the drug; for example, levomethorphan is an [[opioid]] painkiller. | One example of this is with the [[dissociative]] drug [[DXM]]. DXM, or dextromethorphan, is the isomer that rotates clockwise in plane-polarized light. It has antitussive (cough suppressant) and dissociative effects. Levomethorphan is the isomer that rotates anti-clockwise in plane-polarized light. This difference in rotation can radically alter the effects and character of the drug; for example, levomethorphan is an [[opioid]] painkiller. | ||
[[File:DXM_chirality.png|thumb| | [[File:DXM_chirality.png|thumb|right|Two different chiral forms of methorphan can give rise to radically different effects.]] | ||
=== Racemic mixture === | === Racemic mixture === | ||