MedKoo Cat#: 413564 | Name: Methysergide Free Base

Description:

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

Methysergide Free Base is an ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.

Chemical Structure

Methysergide Free Base
Methysergide Free Base
CAS# 361-37-5 (free base)

Theoretical Analysis

MedKoo Cat#: 413564

Name: Methysergide Free Base

CAS#: 361-37-5 (free base)

Chemical Formula: C21H27N3O2

Exact Mass: 353.2103

Molecular Weight: 353.47

Elemental Analysis: C, 71.36; H, 7.70; N, 11.89; O, 9.05

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 #
129-49-7 (maleate) 361-37-5 (free base) 120220-03-3 (dimlaeate)
Synonym
Methysergide Free Base; HSDB3237; HSDB-3237; HSDB 3237
IUPAC/Chemical Name
Ergoline-8-beta-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-
InChi Key
KPJZHOPZRAFDTN-NQUBZZJWSA-N
InChi Code
InChI=1S/C21H27N3O2/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/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15?,19-/m1/s1
SMILES Code
[H][C@@]1(N(C)C[C@H](C(NC(CO)CC)=O)C=C12)CC3=CN(C)C4=C3C2=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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 353.47 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: Silberstein SD. Methysergide. Cephalalgia. 1998 Sep;18(7):421-35. doi: 10.1046/j.1468-2982.1998.1807421.x. PMID: 9793694. 2: Koehler PJ, Tfelt-Hansen PC. History of methysergide in migraine. Cephalalgia. 2008 Nov;28(11):1126-35. doi: 10.1111/j.1468-2982.2008.01648.x. Epub 2008 Jul 15. PMID: 18644039. 3: MARSDEN JP. METHYSERGIDE. Br Med J. 1964 Sep 12;2(5410):677. PMID: 14171102; PMCID: PMC1815793. 4: Kerckhoffs HP. Methysergide [Methysergide]. Pharm Weekbl. 1967 May 5;102(18):385-6. Dutch. PMID: 6044088. 5: Graham JR. Methysergide. Practitioner. 1967 Feb;198(184):302-11. PMID: 6038987. 6: METHYSERGIDE FOR MIGRAINE. Br Med J. 1964 May 23;1(5394):1332. PMID: 14132060; PMCID: PMC1814930. 7: 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. PMID: 22444161. 8: Mitchinson MJ. Methysergide and retroperitoneal fibrosis. Lancet. 1987 Apr 11;1(8537):870. doi: 10.1016/s0140-6736(87)91658-8. PMID: 2882279. 9: Kanto J. Clinical pharmacokinetics of ergotamine, dihydroergotamine, ergotoxine, bromocriptine, methysergide, and lergotrile. Int J Clin Pharmacol Ther Toxicol. 1983 Mar;21(3):135-42. PMID: 6133838. 10: Dewhurst WG. Methysergide in mania. Lancet. 1969 Mar 22;1(7595):624-5. doi: 10.1016/s0140-6736(69)91558-x. PMID: 4180147.