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ergotamine

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ergotamine Basic information

Product Name:
ergotamine
Synonyms:
  • 12’-hydroxy-2’-methyl-5’alpha-(phenylmethyl)ergotaman-3’,6’,18-trione
  • 18-trione,12’-hydroxy-2’-methyl-5’-(phenylmethyl)-6(5’alpha)-ergotaman-3
  • 6’,18-trione,12’-hydroxy-2’-methyl-5’-(phenylmethyl)-ergotaman-3(5’-alph
  • ergotamin
  • ergotamine
  • Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'α)-
  • Ergotamine (8CI)
  • NSC 95090
CAS:
113-15-5
MF:
C33H35N5O5
MW:
581.66
EINECS:
204-023-9
Product Categories:
  • Organics
Mol File:
113-15-5.mol
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ergotamine Chemical Properties

Melting point:
241-249℃
alpha 
D20 -160° (chloroform)
Boiling point:
651.33°C (rough estimate)
Density 
1.0998 (rough estimate)
refractive index 
1.7500 (estimate)
pka
pKa 6.40±0.09(H2O t=24.0) (Uncertain)
optical activity
-16020 (CHCl3)
CAS DataBase Reference
113-15-5
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Safety Information

RIDADR 
1544
HazardClass 
6.1(b)
PackingGroup 
III
Hazardous Substances Data
113-15-5(Hazardous Substances Data)
Toxicity
LD50 in mice, rats, rabbits (mg/kg): 62, 80, 3 i.v.; in cats: 11 s.c. (Rothlin)
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ergotamine Usage And Synthesis

Uses

Analgesic (specific in migraine).

Uses

Ergotamine, 3′,6′,18′-trione,12′-hydroxy-2′-methyl-5′-benzyl-(5α)-ergotamine (12.2.14), is obtained via microbiological synthesis [52].As an α-adrenoblocker, ergotamine exhibits a direct vasoconstricting effect for which it is used in medicine, particularly for alleviation of severe migraine attacks. It is categorically counterproductive in chronic diseases because of the possibility of side effects such as triggering gangrene.

Definition

ChEBI: A peptide ergot alkaloid that is dihydroergotamine in which a double bond replaces the single bond between positions 9 and 10.

brand name

Ergomar (Harvest);Ergostat (Parke-Davis); Wigrettes (Organon).

Purification Methods

Crystallise it from *benzene, then dry it by prolonged heating in high vacuum. It is very hygroscopic. [Beilstein 25 III/IV 964.]

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