Talk:Doxpicomine

Latest comment: 24 days ago by 2A0A:EF40:E7B:F301:276F:2B6D:3CAD:2922 in topic Enantiomers of (R)-1-(1,3-dioxan-5-yl)-N,N-dimethyl-1-(pyridin-3-yl)methanamine

Enantiomers of (R)-1-(1,3-dioxan-5-yl)-N,N-dimethyl-1-(pyridin-3-yl)methanamine

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I was interested to understand if Doxpicomine was a racemic or chiral product. Pubchem lists:

(R)-1-(1,3-dioxan-5-yl)-N,N-dimethyl-1-(pyridin-3-yl)methanamine AS Doxpicomine while no proprietary name is assigned to the (S) enantiomer.

While I appreciate it may have no bearing, I decided to look at the optical activity of other opioids with a chiral amine linked to the benzylic carbon i.e. ciramadol, lefetamine (and derivatives) & trimebutine. In all those cases it was the (R) enantiomer that appeared to be the active.

All searches were carried out using PubChem. 2A0A:EF40:E7B:F301:6D2B:7F37:B8ED:ECEB (talk) 13:08, 4 September 2024 (UTC)Reply

Column 10 lines 33-43 read:
In a preferred embodiment of the present invention, dl-N,N-dimethyl-o-phenyl-m-dioxane-5-methylamine is resolved to provide the analgesically active l-N,N-dimethyl-α-phenyl-m-dioxane-5-methylamine by the use of dibenzoyl-l-tartaric acid monohydrate. The re solved solid l-amine is taken up in ether and treated with gaseous hydrogen chloride to provide pure l-N,N- dimethyl-O-phenyl-m-dioxane-5-methylamine hydro chloride after recrystallization from methanol-ethyl acetate. 2A0A:EF40:E7B:F301:276F:2B6D:3CAD:2922 (talk) 08:53, 5 September 2024 (UTC)Reply