Dihydroergotamine
Title: Dihydroergotamine
CAS Registry Number: 511-12-6
CAS Name: 9,10-Dihydro-12¢-hydroxy-2¢-methyl-5¢-(phenylmethyl)ergotaman-3¢,6¢,18-trione
Molecular Formula: C33H37N5O5
Molecular Weight: 583.68
Percent Composition: C 67.91%, H 6.39%, N 12.00%, O 13.71%
Literature References: a-Adrenergic blocker with selective venoconstrictor properties. Also binds to serotonin 5HT1-receptors. Prepn from ergotamine: Stoll, Hofmann, Helv. Chim. Acta 26, 2070 (1943). Clinical pharmacology: H. de Marées et al., Eur. J. Clin. Pharmacol. 30, 685 (1986). Neurotransmitter receptor binding study: B. G. McCarthy, S. J. Peroutka, Headache 29, 420 (1989). Clinical trials in migraine: P. Winner et al., ibid. 33, 471 (1993); D. Ziegler et al., Neurology 44, 447 (1994).
Properties: Strongly refractive prisms from dil acetone, contg 2 mols acetone and 2 mols water of crystn. mp 239°. [a]D20 -64°; [a]20546 -79° (c = 0.5 in pyridine). Insol in water. Sparingly sol in methanol, ethanol, chloroform, benzene.
Melting point: mp 239°
Optical Rotation: [a]D20 -64°; [a]20546 -79° (c = 0.5 in pyridine)
 
Derivative Type: Tartrate
Trademarks: Divegal (Waldheim)
Molecular Formula: (C33H37N5O5)2.C4H6O6
Molecular Weight: 1317.44
Percent Composition: C 63.82%, H 6.12%, N 10.63%, O 19.43%
Properties: Six-sided plates from methanol, dec 210-215°.
 
Derivative Type: Methanesulfonate
CAS Registry Number: 6190-39-2
Additional Names: Dihydroergotamine mesylate
Trademarks: Agit (Sanofi Winthrop); Angionorm (Farmasan); Dergotamine (Abbott); DET MS (Rentschler); D.H.E. 45 (Novartis); Diergo (Novartis); Dihydergot (Novartis); Dirgotarl (Horita); Endophleban (Rentschler); Ergomimet (Klinge); Ergont (Desitin); Ergotonin (Streuli); Ikaran (Fabre); Migranal (Novartis); Orstanorm (Novartis); Séglor (Sanofi Winthrop); Tonopres (Boehringer, Ing.); Verladyn (Verla)
Molecular Formula: C33H37N5O5.CH3SO3H
Molecular Weight: 679.78
Percent Composition: C 60.07%, H 6.08%, N 10.30%, O 18.83%, S 4.72%
Properties: Large prisms from 95% alc. mp 230-235°. Moderately sol in water.
Melting point: mp 230-235°
 
Therap-Cat: Antimigraine.
Keywords: Antimigraine; Serotonin Receptor Agonist.

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