Dihydroergotamine Mesylate | CAS#6190-39-2 | serotonin receptor agonist

MedKoo Cat#: 561601 | Name: Dihydroergotamine Mesylate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dihydroergotamine Mesylate, also known as DHE or Migranal, is an ergot alkaloid used to treat migraines. It has similar actions to the triptans, acting as an agonist to the serotonin receptors and causing vasoconstriction of the intracranial blood vessels, but also interacts centrally with dopamine and adrenergic receptors.

Chemical Structure

Dihydroergotamine Mesylate

CAS#6190-39-2 (mesylate)

Theoretical Analysis

MedKoo Cat#: 561601

Name: Dihydroergotamine Mesylate

CAS#: 6190-39-2 (mesylate)

Chemical Formula: C34H41N5O8S

Exact Mass: 0.0000

Molecular Weight: 679.79

Elemental Analysis: C, 60.07; H, 6.08; N, 10.30; O, 18.83; S, 4.72

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
250mg	USD 650.00	2 Weeks
500mg	USD 950.00	2 Weeks
1g	USD 1,450.00	2 Weeks

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Related CAS #

511-12-6 (free base) 6190-39-2 (mesylate)

Synonym

Dihydroergotamine Mesylate; DHE; Migranal; Dihydroergotamine methanesulfonate; Dihydergot; (+)-Dihydroergotamine;

IUPAC/Chemical Name

(2R,4R,7R)-N-[(1S,2S,4R,7S)-7-Benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo-[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene-4-carboxamide mesylate

InChi Key

ADYPXRFPBQGGAH-UMYZUSPBSA-N

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

SMILES Code

O=C([C@@H](CN(C)[C@]1([H])C2)C[C@]1([H])C3=C4C2=CNC4=CC=C3)N[C@](C(N5[C@H]6CC7=CC=CC=C7)=O)(C)O[C@@]5(O)[C@]8([H])CCCN8C6=O.OS(=O)(C)=O

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dihydroergotamine mesylate is an ergot alkaloid used to treat migraines.

In vitro activity:

Knowing that the antimigraine prophylactic effect of DHE (dihydroergotamine) is only observed after long-term treatment, this study chronically exposed the recombinant cells to DHE and 8'-OH-DHE. The number of 5-HT2BR-binding sites was always more affected than 5-HT2CRs. At 5-HT2BRs, 8'-OH-DHE was more effective than DHE, with an uncoupling that persisted for more than 40 h for IP3 or cGMP. Reference: Br J Pharmacol. 2003 Sep;140(2):277-84. https://pubmed.ncbi.nlm.nih.gov/12970106/

In vivo activity:

Administration of DHE (dihydroergotamine) influenced neither the learning processes nor memory in rats. Nevertheless, an increased motor activity of the DHE-administered animals was observed in both the cued and non-cued behavioural tasks. Reference: Ann Agric Environ Med. 2021 Sep 16;28(3):437-445. https://pubmed.ncbi.nlm.nih.gov/34558267/

	Solvent	mg/mL	mM
Solubility
	DMSO	46.0	67.65
	DMSO:PBS (pH 7.2) (1:20)	0.1	0.07
	Ethanol	1.0	1.47

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 679.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Schaerlinger B, Hickel P, Etienne N, Guesnier L, Maroteaux L. Agonist actions of dihydroergotamine at 5-HT2B and 5-HT2C receptors and their possible relevance to antimigraine efficacy. Br J Pharmacol. 2003 Sep;140(2):277-84. doi: 10.1038/sj.bjp.0705437. Epub 2003 Aug 11. PMID: 12970106; PMCID: PMC1574033. 2. Lesage AS, Wouters R, Van Gompel P, Heylen L, Vanhoenacker P, Haegeman G, Luyten WH, Leysen JE. Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines. Br J Pharmacol. 1998 Apr;123(8):1655-65. doi: 10.1038/sj.bjp.0701766. PMID: 9605573; PMCID: PMC1565323. 3. Piechal A, Blecharz-Klin K, Joniec-Maciejak I, Pyrzanowska J, Krzysztoforska K, Mirowska-Guzel D, Widy-Tyszkiewicz E. Dihydroergotamine affects spatial behavior and neurotransmission in the central nervous system of Wistar rats. Ann Agric Environ Med. 2021 Sep 16;28(3):437-445. doi: 10.26444/aaem/126020. Epub 2020 Oct 20. PMID: 34558267. 4. González-Hernández A, Lozano-Cuenca J, Marichal-Cancino BA, MaassenVanDenBrink A, Villalón CM. Dihydroergotamine inhibits the vasodepressor sensory CGRPergic outflow by prejunctional activation of α2-adrenoceptors and 5-HT1 receptors. J Headache Pain. 2018 May 25;19(1):40. doi: 10.1186/s10194-018-0869-8. PMID: 29802544; PMCID: PMC5970131.

In vitro protocol:

In vivo protocol:

1. Piechal A, Blecharz-Klin K, Joniec-Maciejak I, Pyrzanowska J, Krzysztoforska K, Mirowska-Guzel D, Widy-Tyszkiewicz E. Dihydroergotamine affects spatial behavior and neurotransmission in the central nervous system of Wistar rats. Ann Agric Environ Med. 2021 Sep 16;28(3):437-445. doi: 10.26444/aaem/126020. Epub 2020 Oct 20. PMID: 34558267. 2. González-Hernández A, Lozano-Cuenca J, Marichal-Cancino BA, MaassenVanDenBrink A, Villalón CM. Dihydroergotamine inhibits the vasodepressor sensory CGRPergic outflow by prejunctional activation of α2-adrenoceptors and 5-HT1 receptors. J Headache Pain. 2018 May 25;19(1):40. doi: 10.1186/s10194-018-0869-8. PMID: 29802544; PMCID: PMC5970131.

1: Maasumi K, Tepper SJ, Kriegler JS. Menstrual Migraine and Treatment Options: Review. Headache. 2017 Feb;57(2):194-208. doi: 10.1111/head.12978. Epub 2016 Dec 2. Review. PubMed PMID: 27910087. 2: Bekan G, Tfelt-Hansen P. Is the Generally Held View That Intravenous Dihydroergotamine Is Effective in Migraine Based on Wrong "General Consensus" of One Trial? A Critical Review of the Trial and Subsequent Quotations. Headache. 2016 Oct;56(9):1482-1491. doi: 10.1111/head.12904. Epub 2016 Sep 6. Review. PubMed PMID: 27595607. 3: Chua AL, Silberstein S. Inhaled drug therapy development for the treatment of migraine. Expert Opin Pharmacother. 2016 Sep;17(13):1733-43. doi: 10.1080/14656566.2016.1203901. Epub 2016 Jul 28. Review. PubMed PMID: 27416108. 4: Richer L, Billinghurst L, Linsdell MA, Russell K, Vandermeer B, Crumley ET, Durec T, Klassen TP, Hartling L. Drugs for the acute treatment of migraine in children and adolescents. Cochrane Database Syst Rev. 2016 Apr 19;4:CD005220. doi: 10.1002/14651858.CD005220.pub2. Review. PubMed PMID: 27091010. 5: Kabbouche M, Khoury CK. Management of Primary Headache in the Emergency Department and Inpatient Headache Unit. Semin Pediatr Neurol. 2016 Feb;23(1):40-3. doi: 10.1016/j.spen.2015.08.004. Epub 2015 Aug 19. Review. PubMed PMID: 27017021. 6: Patniyot IR, Gelfand AA. Acute Treatment Therapies for Pediatric Migraine: A Qualitative Systematic Review. Headache. 2016 Jan;56(1):49-70. doi: 10.1111/head.12746. Review. PubMed PMID: 26790849. 7: Kacperski J, Kabbouche MA, O'Brien HL, Weberding JL. The optimal management of headaches in children and adolescents. Ther Adv Neurol Disord. 2016 Jan;9(1):53-68. doi: 10.1177/1756285615616586. Review. PubMed PMID: 26788131; PubMed Central PMCID: PMC4710107. 8: Kabbouche M. Pediatric Inpatient Headache Therapy: What is Available. Headache. 2015 Nov-Dec;55(10):1426-9. doi: 10.1111/head.12701. Epub 2015 Oct 31. Review. PubMed PMID: 26517974. 9: Becker WJ. Acute Migraine Treatment. Continuum (Minneap Minn). 2015 Aug;21(4 Headache):953-72. doi: 10.1212/CON.0000000000000192. Review. PubMed PMID: 26252584. 10: Schuster NM, Vollbracht S, Rapoport AM. Emerging treatments for the primary headache disorders. Neurol Sci. 2015 May;36 Suppl 1:109-13. doi: 10.1007/s10072-015-2133-1. Review. PubMed PMID: 26017524. 11: Baron EP. Headache, cerebral aneurysms, and the use of triptans and ergot derivatives. Headache. 2015 May;55(5):739-47. doi: 10.1111/head.12562. Epub 2015 Apr 22. Review. PubMed PMID: 25903747. 12: Becker WJ. Acute Migraine Treatment in Adults. Headache. 2015 Jun;55(6):778-93. doi: 10.1111/head.12550. Epub 2015 Apr 15. Review. PubMed PMID: 25877672. 13: Marmura MJ, Goldberg SW. Inpatient management of migraine. Curr Neurol Neurosci Rep. 2015 Apr;15(4):13. doi: 10.1007/s11910-015-0539-z. Review. PubMed PMID: 25704007. 14: Marmura MJ, Silberstein SD, Schwedt TJ. The acute treatment of migraine in adults: the american headache society evidence assessment of migraine pharmacotherapies. Headache. 2015 Jan;55(1):3-20. doi: 10.1111/head.12499. Review. PubMed PMID: 25600718. 15: Gelfand AA, Goadsby PJ. Medication overuse in children and adolescents. Curr Pain Headache Rep. 2014 Jul;18(7):428. doi: 10.1007/s11916-014-0428-1. Review. PubMed PMID: 24898106; PubMed Central PMCID: PMC4086803. 16: Orr SL, Aubé M, Becker WJ, Davenport WJ, Dilli E, Dodick D, Giammarco R, Gladstone J, Leroux E, Pim H, Dickinson G, Christie SN. Canadian Headache Society systematic review and recommendations on the treatment of migraine pain in emergency settings. Cephalalgia. 2015 Mar;35(3):271-84. doi: 10.1177/0333102414535997. Epub 2014 May 29. Review. PubMed PMID: 24875925. 17: Tfelt-Hansen PC, Diener HC. Use of dihydroergotamine (DHE) should be restricted to no more than twice a week. Headache. 2014 Oct;54(9):1523-5. doi: 10.1111/head.12389. Epub 2014 May 26. Review. PubMed PMID: 24862945. 18: Drug-related cardiac valve disease. Prescrire Int. 2013 Dec;22(144):292-5. Review. PubMed PMID: 24600729. 19: Tfelt-Hansen PC, Pihl T, Hougaard A, Mitsikostas DD. Drugs targeting 5-hydroxytryptamine receptors in acute treatments of migraine attacks. A review of new drugs and new administration forms of established drugs. Expert Opin Investig Drugs. 2014 Mar;23(3):375-85. doi: 10.1517/13543784.2014.861817. Epub 2013 Dec 2. Review. PubMed PMID: 24289494. 20: Worthington I, Pringsheim T, Gawel MJ, Gladstone J, Cooper P, Dilli E, Aube M, Leroux E, Becker WJ; Canadian Headache Society Acute Migraine Treatment Guideline Development Group. Canadian Headache Society Guideline: acute drug therapy for migraine headache. Can J Neurol Sci. 2013 Sep;40(5 Suppl 3):S1-S80. Review. PubMed PMID: 23968886.