3174. Dihydroergotamine

Nomenclature

CAS number: 511-12-6
9,10-Dihydro-12′-hydroxy-2′-methyl-5′-(phenylmethyl)ergotaman-3′,6′,18-trione.
C33H37N5O5; mol wt 583.68.
C 67.91%, H 6.39%, N 12.00%, O 13.71%.

Description and references

α-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°. [α]D20 -64°; [α]20546 -79° (c = 0.5 in pyridine). Insol in water. Sparingly sol in methanol, ethanol, chloroform, benzene.

Derivative

Tartrate.

Nomenclature

Divegal (Waldheim).
(C33H37N5O5)2.C4H6O6; mol wt 1317.44.
C 63.82%, H 6.12%, N 10.63%, O 19.43%.

Properties

Six-sided plates from methanol, dec 210-215°.

Derivative

Methanesulfonate.

Nomenclature

CAS number: 6190-39-2
Dihydroergotamine mesylate; 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).
C33H37N5O5.CH3SO3H; mol wt 679.78.
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.

Therapeutic Category

Antimigraine.

Keywords

Antimigraine; Serotonin Receptor Agonist