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MedKoo Cat#: 318254 | Name: Methysergide maleate
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Description:

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

Methysergide is a prescription drug formerly used for prophylaxis of cluster headaches/migraine headaches, but is no longer recommended due to 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

Methysergide maleate
Methysergide maleate
CAS#129-49-7 (maleate)

Theoretical Analysis

MedKoo Cat#: 318254

Name: Methysergide maleate

CAS#: 129-49-7 (maleate)

Chemical Formula: C25H31N3O6

Exact Mass: 353.2103

Molecular Weight: 469.54

Elemental Analysis: C, 63.95; H, 6.66; N, 8.95; O, 20.44

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 weeks
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Related CAS #
129-49-7 (maleate) 361-37-5 (free base) 120220-03-3 (dimlaeate)
Synonym
Methysergide; UML-491; UML 491; UML491; Deseril, Sansert; NSC 186061; NSC186061; NSC-186061
IUPAC/Chemical Name
(6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide; maleate (1:1)
InChi Key
LWYXFDXUMVEZKS-ZVFOLQIPSA-N
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
SMILES Code
O=C([C@H](C=C12)CN(C)[C@]2([H])CC3=CN(C)C4=C3C1=CC=C4)N[C@@H](CC)CO.O=C(O)/C=C\C(O)=O
Appearance
Solid powder
Purity
>95% (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, not in water
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
Certificate of Analysis
View CoA: current batch, Lot#C24M10C09
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Methysergide maleate is a mixed 5-HT1/5-HT2 receptor antagonist.
In vitro activity:
TBD
In vivo activity:
Phrenic nerve long-term depression was revealed in rats pretreated with the serotonin broad-spectrum antagonist, methysergide. Intravenous injection of methysergide before exposure to acute intermittent hypercapnia induced development of amplitude pLTD at T60 (decreased by 46.1 ± 6.9%, P = 0.003). Reference: Exp Physiol. 2016 Feb;101(2):319-31. https://pubmed.ncbi.nlm.nih.gov/26621042/
Solvent mg/mL mM comments
Solubility
Water 4.7 10.00
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 469.54 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:
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;101(2):319-31. doi: 10.1113/EP085161. Epub 2015 Dec 20. 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. PMID: 26171591.
In vitro protocol:
TBD
In vivo protocol:
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;101(2):319-31. doi: 10.1113/EP085161. Epub 2015 Dec 20. 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. PMID: 26171591.
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.