CH₃CH₃

Bromocriptine

Chemistry

83 atoms · Conformer computed and published by PubChem.
Formula
C32H40BrN5O5
Molar mass
654.6 g/mol
IUPAC name
(6aR,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
InChIKey
OZVBMTJYIDMWIL-AYFBDAFISA-N

Chemistry from PubChem CID 31101.

Also known as

  • 25614-03-3
  • Bromoergocryptine
  • Bromocriptin
  • Bromoergocriptine
  • Bromergocryptine
  • 2-Bromo-alpha-ergocryptine
  • Bromocriptina
  • 2-Bromo-alpha-ergokryptin

Stereoisomers

21 distinct stereoisomers are registered for this structure.

  • Bromocriptine this area CID 31101
  • Tocris-0427 CID 5351252
  • (6aS,9S)-5-bromo-N-[(1R,2S,4S,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 6321219
  • (6aR,9S)-5-bromo-N-[(1R,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 6604061
  • Bromocriptine EP Impurity F CID 13187195
  • Bromocriptine Impurity 15 CID 13187196
  • Isobromocriptine CID 13187203
  • (6aR,9S)-5-bromo-N-[(1S,2R,4S,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 13187204
  • (6aS,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 18609907
  • (6aR,9S)-5-bromo-N-[(1R,2S,4S,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 24867280
  • (6aS,9R)-5-bromo-N-[(1R,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 73707474
  • (6aS,9S)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 73896860
  • Bromocriptine Impurity 14 CID 92402735
  • (6aR,9S)-5-bromo-N-[(1R,2R,4S,7R)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 94843986
  • (6aR,9S)-5-bromo-N-[(1R,2R,4S,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 94843987
  • (6aR,9S)-5-bromo-N-[(1S,2R,4S,7R)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 94843988
  • (6aR,9R)-5-bromo-N-[(1R,2S,4R,7R)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 124518263
  • (6aR,9S)-5-bromo-N-[(1R,2S,4R,7R)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 124647989
  • (6aS,9S)-5-bromo-N-[(1R,2S,4R,7R)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 124862844
  • (6aS,9R)-5-bromo-N-[(1R,2S,4R,7R)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 124862845
  • (6aS,9R)-5-bromo-N-[(1R,2R,4S,7R)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide CID 133687734
  • Bromocriptine EP Impurity C mixture CID 2443

Attribution

  • Portrait of Albert Hofmann
    Albert Hofmann — first synthesis, 1968

    2-Bromo-alpha-ergocryptine, from Hofmann's Sandoz department; he is a named inventor with Eduard Flueckiger and Franz Troxler on the patents (US 3,752,814, priority 31 May 1968; DE 1926045A1). Secondary sources date the discovery to 1965 with first publication in 1968. Credit is shared - this was a team result, not a solo synthesis, and the pharmacology (prolactin inhibition) was Flueckiger's side.

    source

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