Methysergide (maleate)

Methysergide is an agonist of the serotonin (5-HT) receptor subtype 5-HT1 and an antagonist of 5-HT2 receptors. It binds to recombinant human 5-HT1A (KD = 23.44 nM), 5-HT1E (Ki = 229.09 nM), 5-HT1F (Ki = 33.88 nM), and rodent 5-HT1B receptors (KD = 1,513.56 nM). It also binds to recombinant human 5-HT2A (Ki = 2.69 nM) and 5-HT2C receptors (KD = 1.26 nM) and is an insurmountable antagonist at 5-HT2B receptors. It inhibits vasoconstriction induced by 5-HT (Cay-14332) in isolated postmortem human basilar arterial spiral strips (pA2 = 8.07). Methysergide decreases external carotid blood flow in a dose-dependent manner in vagosympathectomized dogs, an effect that is inhibited by the 5-HT1B/1D receptor antagonist GR127935 (Cay-29651). It has antinociceptive activity in mouse models of pain induced by intrathecal injection of substance P (Cay-24035), glutamate, NMDA (Cay-14581), AMPA (Cay-14571), or kainic acid. Methysergide reduces zymosan-induced paw edema in rats when administered at a dose of 10 mg/kg. Formulations containing methysergide were previously used in the prevention and treatment of vascular headaches.Formal Name: 9,10-didehydro-N-[(1S)-1-(hydroxymethyl)propyl]-1,6-dimethyl-ergoline-8beta-carboxamide, 2Z-butenedioate. CAS Number: 129-49-7. Synonyms: Desernil, NSC 186061. Molecular Formula: C21H27N3O2 . C4H4O4. Formula Weight: 469.5. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMSO: slightly soluble, Methanol: slightly soluble. lambdamax: 213, 321 nm. SMILES: OC(/C=C\C(O)=O)=O.CN1C=C2C3=C1C=CC=C3C4=C[C@@H](C(N[C@H](CO)CC)=O)CN(C)[C@]4([H])C2. InChi Code: InChI=1S/C21H27N3O2.C4H4O4/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14,5-3(6)1-2-4(7)8/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26),1-2H,(H,5,6)(H,7,8)/b,2-1-/t14-,15+,19-,/m1./s1. InChi Key: LWYXFDXUMVEZKS-ZVFOLQIPSA-N.