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Latest comment: 9 years ago3 comments3 people in discussion
"Levo-Alphamethadol"
"Levo-Betamethadol"
"Dextro-Alphamethadol"
"Dextro-Betamethadol"
Ball-and-stick models that I made. Designed to match the above image before I realised it might be wrong.
"Alphamethadol" (actually the same as the bottom-right) Pubchem seems to agree with this definition for alphamethadol.
"Betamethadol" (actually the same as the bottom-left) Pubchem seems to agree with this definition for betamethadol.
Can anyone get a primary source for the stereochemistry of this compound? I built these four ball-and-stick models to match the four isomers shown in this image that appears in the article (above). But it's since occurred to me that the image might be wrong, since it contradicts two images used in the individual articles, alphamethadol and betamethadol. The "betamethadol" structure appears to be an isomer of alphamethadol and vice versa. In both cases, the image used in the corresponding article is the same one as the Pubchem structure for that compound, which makes it more likely to be correct. However, each article shows only one of the two stereoisomers, and it is impossible to infer from this information what the other one would be.
The image above would suggest that they are diastereomers, (one chiral centre different, but otherwise identical), but it has already been shown to be inaccurate in other ways. However, the nomenclature of "dextro" and "levo" would suggest that they are optical isomers (both chiral centres different, mirror images). So which one is it? I cannot risk a guess. The Pubchem pages are similarly unhelpful. And how do I know which one is the dextro isomer and which one is levo? Until then, I cannot properly label my images of this compound.
I've made you a new image using a mix of ChemDraw (to ensure accurate chiral assignment) and SciFinder to ensure (accurate name assignment). Hope it's of some use. --Project Osprey (talk) 10:12, 4 November 2016 (UTC)Reply
