A 5-HT1 receptor agonist and 5-HT2 receptor antagonist
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Methysergide (maleate)

Item No. 27658

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9,10-didehydro-N-[(1S)-1-(hydroxymethyl)propyl]-1,6-dimethyl-ergoline-8β-carboxamide, 2Z-butenedioate
CAS Number
129-49-7
Synonyms
  • Desernil
  • NSC 186061
Molecular Formula
C21H27N3O2 • C4H4O4
Formula Weight
469.5
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    25 mg

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    Product Description

    Methysergide is an agonist of the serotonin (5-HT) receptor subtype 5-HT1 and an antagonist of 5-HT2 receptors.1,2 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).2 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 (Item No. 14332) in isolated postmortem human basilar arterial spiral strips (pA2 = 8.07).3 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 (Item No. 29651).4 It has antinociceptive activity in mouse models of pain induced by intrathecal injection of substance P (Item No. 24035), glutamate, NMDA (Item No. 14581), AMPA (Item No. 14571), or kainic acid.5 Methysergide reduces zymosan-induced paw edema in rats when administered at a dose of 10 mg/kg.6 Formulations containing methysergide were previously used in the prevention and treatment of vascular headaches.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoyer, D., Clarke, D.E., Fozard, J.R., et al. International Union of Pharmacology classification of receptors for 5-hydroxytryptamine (Serotonin). Pharmacol. Rev. 46(2), 157-203 (1994).

    2. Ramírez Rosas, M.B., Labruijere, S., Villalón, C.M., et al. Activation of 5-hydroxytryptamine1B/1D/1F receptors as a mechanism of action of antimigraine drugs. Expert Opin. Pharmacother. 14(12), 1599-1610 (2013).

    3. Müller-Schweinitzer, E. Vascular effects of ergot alkaloids: A study on human basilar arteries. Gen. Pharmacol. 14(1), 95-102 (1983).

    4. Villalón, C.M., De Vries, P., Rabelo, G., et al. Canine external carotid vasoconstriction to methysergide, ergotamine and dihydroergotamine: Role of 5-HT1B/1D receptors and α2-adrenoceptors. Br. J. Pharmacol. 126(3), 585-594 (1999).

    5. Chung, K.M., Choi, S.S., Han, K.J., et al. Antinociceptive effects of methysergide in various pain models. Pharmacology 69(2), 93-101 (2003).

    6. Tarayre, J.P., Delhon, A., Aliaga, M., et al. Pharmacological studies on zymosan inflammation in rats and mice. 1: Zymosan-induced paw oedema in rats and mice. Pharmacol. Res. 21(4), 375-384 (1989).