113-15-5

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 NO: 113-15-5
• Molecular Formula: C₃₃H₃₅N₅O₅
• Molecular Weight: 581.6615
• EINECS: 204-023-9
• Product Categories: Organics
• Mol File: 113-15-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 241-249℃
• Boiling Point: 651.33°C (rough estimate)
• Flash Point: 506.9 °C
• Appearance: /
• Density: 1.0998 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.7500 (estimate)
• PKA: pKa 6.40±0.09(H2O t=24.0) (Uncertain)
• CAS DataBase Reference: ergotamine(CAS DataBase Reference)
• NIST Chemistry Reference: ergotamine(113-15-5)
• EPA Substance Registry System: ergotamine(113-15-5)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 113-15-5(Hazardous Substances Data)

Usage

Description

Ergotamine is a peptide ergot alkaloid, specifically dihydroergotamine, where a double bond replaces the single bond between positions 9 and 10. It is derived from the ergot fungus and has been used for various medical applications due to its potent effects on blood vessels and neurotransmitters.

Uses

Used in Pharmaceutical Industry:
Ergotamine is used as an analgesic for the treatment of migraine headaches. It works by constricting blood vessels in the brain and mitigating the release of certain neurotransmitters, which are responsible for the pain and other symptoms associated with migraines.
Brand names for ergotamine include Ergomar (Harvest), Ergostat (Parke-Davis), and Wigrettes (Organon). These products are available in various forms, such as tablets, injections, and nasal sprays, to cater to the different preferences and needs of patients.

Purification Methods

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

InChI:InChI=1/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1

Upstream product

• 113-15-5 ergotamine 

Downstream Products

• 561-93-3 5'α-benzyl-10,12'-dihydroxy-2'-methyl-(10β)-9,10-dihydro-ergotamane-18,3',6'-trione 
• 468-88-2 5'α-benzyl-10,12'-dihydroxy-2'-methyl-(10α)-9,10-dihydro-ergotamane-18,3',6'-trione 
• 511-12-6 5'α-benzyl-12'-hydroxy-2'-methyl-(8βH,10β)-9,10-dihydro-ergotamane-18,3',6'-trione 
• 83541-18-8 5'α-benzyl-12'-hydroxy-2'-methyl-(8βH,10α)-9,10-dihydro-ergotamane-18,3',6'-trione 
• 596-86-1 5'α-benzyl-10,12'-dihydroxy-2'-methyl-(8βH,10β)-9,10-dihydro-ergotamane-18,3',6'-trione 
• 561-92-2 5'α-benzyl-10,12'-dihydroxy-2'-methyl-(8βH,10α)-9,10-dihydro-ergotamane-18,3',6'-trione 
• 113-15-5 ergotaminine 
• 511-12-6 9,10-dihydroergotamine 
• 639-81-6 ergotaminine 
• 52897-74-2 5'α-benzyl-3,12'-dihydroxy-2'-methyl-(3β)-3H-ergotamane-2,18,3',6'-tetraone 

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Relevant articles and documents

Conformational analysis of the ergot alkaloids ergotamine and ergotaminine

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