CAS 113-15-5

Ergotamine

Description:

Ergotamine is a naturally occurring alkaloid derived from the ergot fungus, specifically from the species Claviceps purpurea. It is primarily known for its use in the treatment of migraines and cluster headaches due to its vasoconstrictive properties. The chemical formula of ergotamine is C33H35N5O5, and it has a molecular weight of approximately 585.67 g/mol. Ergotamine is characterized by its complex tetracyclic structure, which includes an indole moiety and a side chain that contributes to its pharmacological activity. It is typically administered in the form of its tartrate salt, ergotamine tartrate, to enhance solubility and bioavailability. The substance exhibits a range of effects on the central nervous system and vascular system, acting as a selective agonist for certain serotonin receptors. However, its use is associated with potential side effects, including nausea, vomiting, and cardiovascular complications, necessitating careful dosage and monitoring. Due to its potent effects, ergotamine is classified as a prescription medication and is subject to regulatory controls in many countries.

Formula: C₃₃H₃₅N₅O₅

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

InChI key: InChIKey=XCGSFFUVFURLIX-VFGNJEKYSA-N

SMILES: O[C@@]12N([C@@H](CC3=CC=CC=C3)C(=O)N4[C@]1(CCC4)[H])C(=O)[C@@](NC(=O)[C@@H]5C=C6C=7C=8C(C[C@]6(N(C)C5)[H])=CNC8C=CC7)(C)O2

Synonyms:

• (5′α)-12′-Hydroxy-2′-methyl-5′-(phenylmethyl)ergotaman-3′,6′,18-trione
• 8H-Oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine, ergotaman-3′,6′,18-trione deriv.
• Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'α)-
• Ergotaman-3′,6′,18-trione, 12′-hydroxy-2′-methyl-5′-(phenylmethyl)-, (5′α)-
• Ergotamin
• Ergotamina
• Indolo[4,3-fg]quinoline, ergotaman-3′,6′,18-trione deriv.
• Nsc 95090
• ergotaman-3',6',18'-trione, 12'-hydroxy-2'-methyl-5'- (phenylmethyl)-,(5α)
• Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-
• 4-25-00-00964 (Beilstein Handbook Reference)
• Ergotamine [INN:BAN]
• (5'alpha)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
• BRN 0078890
• Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)- (9CI)
• HSDB 4076
• Ergotaminum [INN-Latin]
• 5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
• Ergonsvine
• Ergotamine
• Ergotamine
• UNII-PR834Q503T
• Ergotamina [INN-Spanish]
• 12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione
• Ergotaminum
• 12'-Hydroxy-2'-methyl-5'α-benzylergotaman-3',6',18-trione
• (5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione
• 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

Controlled Product

CAS: 113-15-5

Formula: C₃₃H₃₅N₅O₅

Color and Shape: Neat

Molecular weight: 581.66

Ref: 04-C13201600

5'-Hydroxy Dihydro Ergotamine

Controlled Product

CAS: 113-15-5

Formula: C₃₃H₃₇N₅O₆

Color and Shape: Neat

Molecular weight: 599.677

Ref: TR-H121735

Dihydroergotamine EP Impurity A

Controlled Product

CAS: 113-15-5

Formula: C₃₃H₃₅N₅O₅

Molecular weight: 581.67

Ref: ST-EA-CP-D123001