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ergotamine

CAS No.
113-15-5
Chemical Name:
ergotamine
Synonyms
ergotamin;NSC 95090;ergotamine;Ergotamine (8CI);ergotamine USP/EP/BP;XCGSFFUVFURLIX-VFGNJEKYSA-N;12'-Hydroxy-2'-methyl-5'α-benzylergotaman-3',6',18-trione;12’-hydroxy-2’-methyl-5’alpha-(phenylmethyl)ergotaman-3’,6’,18-trione;6’,18-trione,12’-hydroxy-2’-methyl-5’-(phenylmethyl)-ergotaman-3(5’-alph;18-trione,12’-hydroxy-2’-methyl-5’-(phenylmethyl)-6(5’alpha)-ergotaman-3
CBNumber:
CB2865180
Molecular Formula:
C33H35N5O5
Molecular Weight:
581.66
MDL Number:
MOL File:
113-15-5.mol
Last updated:2023-05-04 15:15:06

ergotamine 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)
CAS DataBase Reference 113-15-5
EWG's Food Scores 1
FDA UNII PR834Q503T
ATC code N02CA02

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H330-H311-H361-H301
Precautionary statements  P280-P302+P352-P312-P322-P361-P363-P405-P501-P201-P202-P281-P308+P313-P405-P501-P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501
RIDADR  1544
HazardClass  6.1(b)
PackingGroup  III
Toxicity LD50 in mice, rats, rabbits (mg/kg): 62, 80, 3 i.v.; in cats: 11 s.c. (Rothlin)

ergotamine Chemical Properties,Uses,Production

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.]

ergotamine Preparation Products And Raw materials

Raw materials

Preparation Products

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 ergotamine Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'α)- Ergotamine (8CI) NSC 95090 12'-Hydroxy-2'-methyl-5'α-benzylergotaman-3',6',18-trione (5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione XCGSFFUVFURLIX-VFGNJEKYSA-N Ergotaman-3',6',18-trione,12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'a)- ergotamine USP/EP/BP ergotamin (6aR,9R)-N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (ergotamine), 113-15-5 Organics