Ergotamine

Ergoline is a chemical compound whose structure serves as the skeleton for a diverse range of alkaloids and synthetic drugs. Substances derived from ergoline are used clinically as oxytocics and in the treatment of migraine and Parkinson's disease, and are implicated in the disease ergotism and in the action of psychedelic drugs such as ololiuhqui and LSD. Ergometrine and ergotamine are listed as Table I precursors under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances. more...

Chemistry

There are three main classes of ergoline derivatives, the water-soluble amides of lysergic acid, the water-insoluble ergopeptide alkaloids, and the clavine group.

Lysergic acid amides

The prototype of this class is

• Ergine (d-lysergic acid amide, LSA, LAA, LA-111)
  • IUPAC name: 9,10-didehydro-6-methylergoline-8beta-carboxamide
  • CAS number: 478-94-4

Other important members include:

• Ergonovine (ergobasine)
  • INN: ergometrine
  • IUPAC name: (8beta(S))-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methyl-ergoline-8-carboxamide
  • CAS number: 60-79-7
• Methergine (ME-277)
  • INN: methylergometrine
  • IUPAC name: (8beta(S))-9,10-didehydro-N-(1-(hydroxymethyl)propyl)-6-methyl-ergoline-8-carboxamide
  • CAS number: 113-42-8
• Methysergide (UML-491)
  • INN: methysergide
  • IUPAC name: (8beta)-9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-ergoline-8-carboxamide
  • CAS number: 361-37-5
• LSD (d-lysergic acid diethylamide; LSD-25)
  • INN: lysergamide
  • IUPAC name: (8beta)-9,10-didehydro-N,N-diethyl-6-methyl-ergoline-8-carboxamide
  • CAS number: 50-37-3

The relationship between these compounds is summarized in the following structural formula and table of substitutions.

Peptide alkaloids

These compounds have a tripeptide structure attached to the basic ergoline ring, in the same location as the amide group of the lysergic acid derivatives. Some of the important ergopeptides are summarized below. In addition to the following ergopeptides, a commonly encountered term is ergotoxine, which refers to a mixture of equal proportions of ergocristine, ergocornine and ergocryptine.

• Ergotamine
  • IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)- (9CI)
  • CAS number: 113-15-5
• Ergocristine
  • IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'-alpha)-
  • CAS number: 511-08-0
• Ergocornine
  • IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2',5'-bis(1-methylethyl)-, (5'-alpha)-
  • CAS number: 564-36-3
• Ergocryptine
  • IUPAC name:Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)- (9CI)
  • CAS number: 511-09-1
• Bromocriptine (INN)
  • IUPAC name: Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)-
  • CAS number: 25614-03-3
• Ergovaline
  • IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylethyl)-, (5'alpha)-
  • CAS number: 2873-38-3

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