Methysergide dimaleate

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

MedKoo CAT#: 577330

CAS#: 120220-03-3

Description: Methysergide dimaleate is a biochemical studied for use in prophylaxis of cluster headaches/migraine headaches. It is no longer recommended due to side effects such as retroperitoneal/retropulmonary fibrosis. It is also used in carcinoid syndrome to treat severe diarrhea. It may also be used in the treatment of serotonin syndrome.

Chemical Structure

img
Methysergide dimaleate
CAS# 120220-03-3
Instruction

Theoretical Analysis

MedKoo Cat#: 577330
Name: Methysergide dimaleate
CAS#: 120220-03-3
Chemical Formula: C29H35N3O10
Exact Mass: 585.23
Molecular Weight: 585.610
Elemental Analysis: C, 59.48; H, 6.02; N, 7.18; O, 27.32

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Methysergide dimaleate

IUPAC/Chemical Name: Ergoline-8-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta(S))-, (Z)-2-butenedioate (1:2) (salt)

InChi Key: FUYUWMZGKBNTIB-VMTAUMJGSA-N

InChi Code: InChI=1S/C21H27N3O2.2C4H4O4/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;2*5-3(6)1-2-4(7)8/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26);2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-/t14-,15+,19-;;/m1../s1

SMILES Code: CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3cn(C)c4cccc(C2=C1)c34.OC(=O)\C=C/C(=O)O.OC(=O)\C=C/C(=O)O

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 585.61 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Valic M, Pecotic R, Pavlinac Dodig I, Valic Z, Stipica I, Dogas Z. Intermittent hypercapnia-induced phrenic long-term depression is revealed after serotonin receptor blockade with methysergide in anaesthetized rats. Exp Physiol. 2016 Feb 1;101(2):319-31. doi: 10.1113/EP085161. Epub 2015 Dec 20. PubMed PMID: 26621042.

2: David RB, Roncari CF, Lauar MR, Vendramini RC, Antunes-Rodrigues J, Menani JV, De Luca LA Jr. Sodium intake, brain c-Fos protein and gastric emptying in cell-dehydrated rats treated with methysergide into the lateral parabrachial nucleus. Physiol Behav. 2015 Nov 1;151:111-20. doi: 10.1016/j.physbeh.2015.07.014. Epub 2015 Jul 11. PubMed PMID: 26171591.

3: Andréjak M, Szymanski C, Maréchaux S, Arnalsteen E, Gras V, Rémadi JP, Tribouilloy C. Valvular heart disease associated with long-term treatment by methysergide: a case report. Therapie. 2014 May-Jun;69(3):255-7. doi: 10.2515/therapie/2014030. Epub 2014 Jun 18. PubMed PMID: 24934823.

4: Matsuta Y, Schwen Z, Mally AD, Shen B, Wang J, Roppolo JR, de Groat WC, Tai C. Effect of methysergide on pudendal inhibition of micturition reflex in cats. Exp Neurol. 2013 Sep;247:250-8. doi: 10.1016/j.expneurol.2013.05.006. Epub 2013 May 18. PubMed PMID: 23688680; PubMed Central PMCID: PMC3742625.

5: Hernekamp JF, Hu S, Schmidt K, Walther A, Lehnhardt M, Kremer T. Methysergide attenuates systemic burn edema in rats. Microvasc Res. 2013 Sep;89:115-21. doi: 10.1016/j.mvr.2013.03.002. Epub 2013 May 11. PubMed PMID: 23669653.

6: 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.

7: Cittadini E, Goadsby PJ. Retraction. Psychiatric side effects during methysergide treatment. J Neurol Neurosurg Psychiatry. 2010 Aug;81(8):942. doi: 10.1136/jnnp.2004.48363.ret2. PubMed PMID: 20682724.

8: Peres e Serra A, Ashmawi HA. Influence of naloxone and methysergide on the analgesic effects of low-level laser in an experimental pain model. Rev Bras Anestesiol. 2010 May-Jun;60(3):302-10. doi: 10.1016/S0034-7094(10)70037-4. PubMed PMID: 20682161.

9: Valic M, Pecotic R, Pavlinac I, Valic Z, Peros K, Dogas Z. Microinjection of methysergide into the raphe nucleus attenuated phrenic long-term facilitation in rats. Exp Brain Res. 2010 May;202(3):583-9. doi: 10.1007/s00221-010-2161-2. Epub 2010 Jan 20. PubMed PMID: 20087578.

10: Lozano-Cuenca J, Muñoz-Islas E, González-Hernández A, Centurión D, Cobos-Puc LE, Sánchez-López A, Pertz HH, Villalón CM. Pharmacological profile of the inhibition by dihydroergotamine and methysergide on the cardioaccelerator sympathetic outflow in pithed rats. Eur J Pharmacol. 2009 Jun 10;612(1-3):80-6. doi: 10.1016/j.ejphar.2009.03.072. Epub 2009 Apr 6. PubMed PMID: 19356724.

11: Cai FZ, Tesar P, Klestov A. Methysergide-induced retroperitoneal fibrosis and pericardial effusion. Intern Med J. 2004 May;34(5):297-8. PubMed PMID: 15151680.

12: Chung KM, Choi SS, Han KJ, Han EJ, Lee HK, Suh HW. Antinociceptive effects of methysergide in various pain models. Pharmacology. 2003 Oct;69(2):93-101. PubMed PMID: 12928583.

13: Fisher AA, Le Couteur DG. Silent myocardial ischaemia following methysergide overdose. Aust N Z J Med. 2000 Dec;30(6):737-8. PubMed PMID: 11198591.

14: Zhang XJ, Irtun O, Zheng Y, Wolfe RR. Methysergide reduces nonnutritive blood flow in normal and scalded skin. Am J Physiol Endocrinol Metab. 2000 Mar;278(3):E452-61. PubMed PMID: 10710499.

15: Liston H, Bennett L, Usher B Jr, Nappi J. The association of the combination of sumatriptan and methysergide in myocardial infarction in a premenopausal woman. Arch Intern Med. 1999 Mar 8;159(5):511-3. PubMed PMID: 10074961.

16: Varanasi S, Chi J, Rogers RC, Stephens RL Jr. Methiothepin but not methysergide antagonizes TRH effects at the dorsal vagal complex. Ann N Y Acad Sci. 1998 Dec 15;861:292-3. PubMed PMID: 9928297.

17: Silberstein SD. Methysergide. Cephalalgia. 1998 Sep;18(7):421-35. Review. PubMed PMID: 9793694.

18: Comer SD, Haney M, Ward AS, Fischman MW, Foltin RW. Effects of methysergide and loratadine on food intake, mood, and performance of humans living in a residential laboratory. Physiol Behav. 1998 May;64(2):159-64. PubMed PMID: 9662080.

19: Hammond DL, Nelson V, Thomas DA. Intrathecal methysergide antagonizes the antinociception, but not the hyperalgesia produced by microinjection of baclofen in the ventromedial medulla of the rat. Neurosci Lett. 1998 Mar 13;244(2):93-6. PubMed PMID: 9572593.

20: Kemp BK, Cocks TM. Effects of U46619 on contractions to 5-HT, sumatriptan and methysergide in canine coronary artery and saphenous vein in vitro. Br J Pharmacol. 1995 Oct;116(4):2183-90. PubMed PMID: 8564247; PubMed Central PMCID: PMC1908960.