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MedKoo Cat#: 598703 | Name: Dihydroergotamine

Description:

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

Dihydroergotamine is a 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.

Chemical Structure

Dihydroergotamine
CAS#511-12-6 (free base)

Theoretical Analysis

MedKoo Cat#: 598703

Name: Dihydroergotamine

CAS#: 511-12-6 (free base)

Chemical Formula: C33H37N5O5

Exact Mass: 583.2795

Molecular Weight: 583.68

Elemental Analysis: C, 67.91; H, 6.39; N, 12.00; O, 13.71

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
511-12-6 (free base) 6190-39-2 (mesylate)
Synonym
Dihydroergotamine; MAP0004; DHE; MAP 0004; MAP-0004; 9,10-Dihydroergotamine; Levadex; Dihidroergotamina; Dehydroergotamine; Dihydroergotaminum; Neomigran; Diidroergotamina;
IUPAC/Chemical Name
(6aR,9R,10aR)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
InChi Key
LUZRJRNZXALNLM-JGRZULCMSA-N
InChi Code
InChI=1S/C33H37N5O5/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/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1
SMILES Code
[H][C@@]12CC3=CNC4=C3C([C@@]1([H])C[C@@H](C(N[C@@]5(C)C(N6[C@@H](CC7=CC=CC=C7)C(N8CCC[C@]8([C@]6(O)O5)[H])=O)=O)=O)CN2C)=CC=C4
Appearance
Solid powder
Purity
>98% (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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 583.68 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.

Recalculate based on batch purity %
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
1: 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. 2: Nagy AJ, Gandhi S, Bhola R, Goadsby PJ. Intravenous dihydroergotamine for inpatient management of refractory primary headaches. Neurology. 2011 Nov 15;77(20):1827-32. doi: 10.1212/WNL.0b013e3182377dbb. Epub 2011 Nov 2. PubMed PMID: 22049203. 3: Silberstein SD, Kori SH. Dihydroergotamine: a review of formulation approaches for the acute treatment of migraine. CNS Drugs. 2013 May;27(5):385-94. doi: 10.1007/s40263-013-0061-2. Review. PubMed PMID: 23620146. 4: Tfelt-Hansen P. Is orally inhaled dihydroergotamine (DHE) equivalent in efficacy in migraine to intravenous DHE? Headache. 2014 Feb;54(2):383. doi: 10.1111/head.12269. PubMed PMID: 24512579. 5: Tepper SJ. Orally inhaled dihydroergotamine: a review. Headache. 2013 Sep;53 Suppl 2:43-53. doi: 10.1111/head.12184. Review. PubMed PMID: 24024602. 6: Kellerman DJ, Forst A, Combs DL, Borland S, Kori S. Assessment of the consistency of absorption of dihydroergotamine following oral inhalation: pooled results from four clinical studies. J Aerosol Med Pulm Drug Deliv. 2013 Oct;26(5):297-306. doi: 10.1089/jamp.2012.0999. Epub 2012 Dec 28. PubMed PMID: 23273242. 7: Lambru G, Shanahan P, Matharu M. Exacerbation of SUNCT and SUNA syndromes during intravenous dihydroergotamine treatment: A case series. Cephalalgia. 2015 Oct;35(12):1115-24. doi: 10.1177/0333102415570495. Epub 2015 Feb 9. PubMed PMID: 25667300. 8: Tfelt-Hansen PC. Relatively slow and long-lasting antimigraine effect of dihydroergotamine is most likely due to basic pharmacological attributes of the drug: a review. Cephalalgia. 2013 Oct;33(13):1122-31. doi: 10.1177/0333102413483372. Epub 2013 Apr 15. Review. PubMed PMID: 23588793. 9: Noveck RJ, Douglas PS, Chow SC, Mangum B, Kori S, Kellerman DJ. Assessing acute systemic effects of an inhaled drug with serial echocardiography: a placebo-controlled comparison of inhaled and intravenous dihydroergotamine. Drug Des Devel Ther. 2013 Jul 24;7:619-25. doi: 10.2147/DDDT.S44093. Print 2013. PubMed PMID: 23926420; PubMed Central PMCID: PMC3728267. 10: Eller M, Gelfand AA, Riggins NY, Shiboski S, Schankin C, Goadsby PJ. Exacerbation of headache during dihydroergotamine for chronic migraine does not alter outcome. Neurology. 2016 Mar 1;86(9):856-9. doi: 10.1212/WNL.0000000000002406. Epub 2016 Feb 3. PubMed PMID: 26843569; PubMed Central PMCID: PMC4793780. 11: Marichal-Cancino BA, González-Hernández A, Manrique-Maldonado G, Ruiz-Salinas II, Altamirano-Espinoza AH, MaassenVanDenBrink A, Villalón CM. Intrathecal dihydroergotamine inhibits capsaicin-induced vasodilatation in the canine external carotid circulation via GR127935- and rauwolscine-sensitive receptors. Eur J Pharmacol. 2012 Oct 5;692(1-3):69-77. doi: 10.1016/j.ejphar.2012.07.033. Epub 2012 Jul 27. PubMed PMID: 22841658. 12: Bauermeister A, Aguiar FA, Marques LM, Malta JD Jr, Barros F, Callejon DR, de Oliveira AR, Lopes NP. In Vitro Metabolism Evaluation of the Ergot Alkaloid Dihydroergotamine: Application of Microsomal and Biomimetic Oxidative Model. Planta Med. 2016 Oct;82(15):1368-1373. Epub 2016 Aug 2. PubMed PMID: 27485816. 13: Chou DE, Tso AR, Goadsby PJ. Aprepitant for the management of nausea with inpatient IV dihydroergotamine. Neurology. 2016 Oct 11;87(15):1613-1616. Epub 2016 Sep 14. PubMed PMID: 27629088; PubMed Central PMCID: PMC5067541. 14: Dahlöf C, Maassen Van Den Brink A. Dihydroergotamine, ergotamine, methysergide and sumatriptan - basic science in relation to migraine treatment. Headache. 2012 Apr;52(4):707-14. doi: 10.1111/j.1526-4610.2012.02124.x. Epub 2012 Mar 22. Review. PubMed PMID: 22444161. 15: Charles A. Comment: Outcomes of migraine therapy with IV dihydroergotamine. Neurology. 2016 Mar 1;86(9):859. doi: 10.1212/WNL.0000000000002408. Epub 2016 Feb 3. PubMed PMID: 26843565. 16: Robbins NM, Ito H, Scheinman MM, Goadsby PJ. Safety of domperidone in treating nausea associated with dihydroergotamine infusion and headache. Neurology. 2016 Dec 13;87(24):2522-2526. Epub 2016 Nov 11. PubMed PMID: 27837002; PubMed Central PMCID: PMC5206996. 17: 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. 18: Silberstein S. MAP0004: dihydroergotamine mesylate inhalation aerosol for acute treatment of migraine. Expert Opin Pharmacother. 2012 Sep;13(13):1961-8. doi: 10.1517/14656566.2012.711319. Epub 2012 Aug 4. Review. PubMed PMID: 22860628. 19: Schenkat DH, Schulz LT, Johnson BD. Dihydroergotamine-induced vasospastic angina in a patient taking a calcium channel blocker. Ann Pharmacother. 2011 Jul;45(7-8):e41. doi: 10.1345/aph.1P776. Epub 2011 Jun 21. PubMed PMID: 21693700. 20: Bérard A, Kori S. Dihydroergotamine (DHE) use during gestation and the risk of adverse pregnancy outcomes. Headache. 2012 Jul-Aug;52(7):1085-93. doi: 10.1111/j.1526-4610.2012.02172.x. Epub 2012 May 21. PubMed PMID: 22612391.

View History

MLS-0390969

MLS-0390969