An agonist of 5-HT1B and 5-HT1D receptors
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Dihydroergotamine (mesylate)

Item No. 23847

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5'α,10α)-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
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:20): 0.05 mg/mlEthanol: 1 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $41

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    50 mg

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    100 mg

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    250 mg

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    Product Description

    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).1 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).2 Dihydroergotamine also binds to α-adrenergic receptors.3 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.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lesage, A.S., Wouters, R., Gompel, P.V., et al. Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines. Br. J. Pharmacol. 123(8), 1655-1665 (1998).

    2. Toll, L., Berzetei-Gurske, I.P., Polgar, W.E., et al. Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. NIDA Res. Monogr. 178, 440-466 (1998).

    3. U'Prichard, D.C., Greenberg, D.A., and Snyder, S.H. Binding characteristics of a radiolabeled agonist and antagonist at central nervous system alpha noradrenergic receptors. Mol. Pharmacol. 13(3), 454-473 (1977).

    4. Kayser, V., Aubel, B., Hamon, M., et al. The antimigraine 5-HT1B/1D receptor agonists, sumatriptan, zolmitriptan and dihydroergotamine, attenuate pain-related behaviour in a rat model of trigeminal neuropathic pain. Br. J. Pharmacol. 137(8), 1287-1297 (2002).