Dihydroergotamine (mesylate)

Dihydroergotamine is a derivative of ergotamine and an agonist of the serotonin (5-HT) receptor subtypes 5-HT1B and 5-HT1D (Kis = 0.3 and 2.5 nM, respectively, for human receptors). It binds to dopamine D2 and D3 as well as 5-HT2A receptors (K0.5s = 5, 16, and 38 nM, respectively) but has lower affinity for D1, 5-HT2C, and 5-HT3 receptors (K0.5s = 2,779, 298, and >10,000 nM, respectively). Dihydroergotamine also binds to alpha-adrenergic receptors. Dihydroergotamine (50 and 100 mg/kg) increases the mechanical pain threshold in a rat model of neuropathic pain following chronic constriction injury to the infraorbital nerve. Formulations containing dihydroergotamine have been used in the treatment of migraine headaches.Formal Name: (5'alpha,10alpha)-9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-ergotaman-3',6',18-trione, methanesulfonate. CAS Number: 6190-39-2. Synonyms: (+)-Dihydroergotamine. Molecular Formula: C33H37N5O5 . CH3SO3H. Formula Weight: 679.8. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 mg/ml, DMSO: 20 mg/ml, DMSO:PBS (pH 7.2) (1:20): 0.05 mg/ml, Ethanol: 1 mg/ml. lambdamax: 284 nm. SMILES: CN1[C@]([C@]2([H])C[C@@H](C(N[C@@]3(C)C(N([C@@H](CC4=CC=CC=C4)C(N5[C@@]6([H])CCC5)=O)[C@@]6(O)O3)=O)=O)C1)([H])CC7=CNC8=C7C2=CC=C8.OS(=O)(C)=O. InChi Code: InChI=1S/C33H37N5O5.CH4O3S/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)43-32,1-5(2,3)4/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39),1H3,(H,2,3,4)/t21-,23-,25-,26+,27+,32-,33+,/m1./s1. InChi Key: ADYPXRFPBQGGAH-UMYZUSPBSA-N.