Chemical structure of ergolineSubstituted ergine (structural formula)Ergopeptides (structural formula)
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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...

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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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Fit for life
From Essence, 11/1/05

Reduce Migraine Pain

We've all probably experienced a headache from time to time--but for nearly 30 million Americans, migraines are an affliction that can be so debilitating as to affect their ability to perform everyday activities. The problem is particularly troublesome for women, who are three times more likely to suffer from migraines than men.

What is a Migraine?

A migraine is more than a really bad headache. Migraines are often characterized by throbbing pain on one side of the head. They may be accompanied by nausea, vomiting and sensitivity to light and/or sound. Migraines can last from several hours to several days if untreated. "If you find that headaches are keeping you from work or social activities, if you find that you're taking over-the-counter medications on a daily or near daily basis, make an appointment to specifically talk to your healthcare provider about these headaches," says Suzanne Simons, Executive Director of the National Headache Foundation.

Find the Right Treatment

There are two kinds of migraine treatment. Acute therapy treats the symptoms of the migraine at the start of an attack to reduce the severity or duration of the headache. Migraine sufferers take a prescribed treatment such as a triptan medication or an ergotamine preparation whenever they feel a headache beginning.

Preventive therapy requires migraine sufferers to take medication daily to stop the headaches from occurring. Preventive medications include propranolol, beta blockers and the most recently approved topiramate. Simons says preventive therapies can decrease the occurrence of migraines by 50 to 80 percent, as well as reduce the duration and severity of the pain. Yet the American Migraine Prevalence and Prevention (AMPP) study, the largest study of migraine sufferers ever conducted, revealed that prevention is being underutilized. "We found that up to 40 percent of the people in the AMPP study would be appropriate candidates for prevention, but only one in five was receiving it," says Simons. "So one of the things we're trying to tell people is that you really should have the discussion with your healthcare provider to see it you are a candidate for migraine prevention."

For more information about headache causes and treatments, visit www.headaches.org or call 1-888-NHE-5552.

COPYRIGHT 2005 Essence Communications, Inc.
COPYRIGHT 2005 Gale Group

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