Ergometrine

Chemistry

Also known as

• ERGONOVINE
• Ergobasine
• Ergotocine
• Ergostetrine
• Margonovine
• 60-79-7
• Ergoklinine
• Ergometrin

Stereoisomers

6 distinct stereoisomers are registered for this structure.

• Ergometrine this area CID 443884
• (6aR,9R)-N-[(2R)-1-hydroxypropan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 6071
• (6aR,9S)-N-[(2R)-1-hydroxypropan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 114828
• (6aS,9R)-N-[(2R)-1-hydroxypropan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 1268326
• (6aS,9S)-N-[(2R)-1-hydroxypropan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 5393143
• Ergometrinine CID 5486180
• N-(1-Hydroxypropan-2-yl)-6-methyl-9,10-didehydroergoline-8-carboxamide mixture CID 3250

Attribution

• 

  Albert Hofmann — first synthesis, 1938

  Read this one carefully: ergometrine is a natural ergot alkaloid and was isolated in 1935 by other groups (Dudley & Moir; Stoll & Burckhardt; Kharasch & Legault; Thompson). Hofmann did NOT discover it. His contribution, begun in 1935 and published as Stoll & Hofmann, Hoppe-Seyler's Z. physiol. Chem. 251, 155-163 (1938), was the first laboratory (partial) synthesis of a natural ergot alkaloid, joining lysergic acid to propanolamine - the route that later gave methylergometrine, dihydroergotamine and LSD.

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