Synonym
Mesulergine hydrochloride, Mesulergine HCl
IUPAC/Chemical Name
Sulfamide, N'-((8-alpha)-1,6-dimethylergolin-8-yl)-N,N-dimethyl-, monohydrochloride
InChi Key
HANSYUJEPWNHIM-IVMONYBCSA-N
InChi Code
InChI=1S/C18H26N4O2S.ClH/c1-20(2)25(23,24)19-13-9-15-14-6-5-7-16-18(14)12(10-21(16)3)8-17(15)22(4)11-13;/h5-7,10,13,15,17,19H,8-9,11H2,1-4H3;1H/t13-,15+,17+;/m0./s1
SMILES Code
O=S(N[C@@H](C[C@@]12[H])CN(C)[C@]1([H])CC3=CN(C)C4=C3C2=CC=C4)(N(C)C)=O.[H]Cl
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
2934.99.9001
Biological target:
Mesulergine hydrochloride is a 5-HT2A and 2C receptor antagonist (pA2 values are 9.1 for each receptor) and D2-like dopamine receptor partial agonist (Ki = 8 nM).
In vitro activity:
Mesulergine was found to antagonise D1-receptor responses at micromolar, and D2-receptor responses at nanomolar concentrations. In contrast, the bidemethylated metabolite of mesulergine stimulated both D1- and D2-receptors at micromolar and nanomolar concentrations, respectively.
Reference: Eur J Pharmacol. 1983 Nov 11;95(1-2):101-7. https://pubmed.ncbi.nlm.nih.gov/6230246/
In vivo activity:
Three groups of male Wistar rats were individually caged and ad libitum fed with a standard (SD) and 50% sweet carbohydrate enriched diet (CED). Food intake was measured daily 4 hrs and 24 hrs after i.p. injections of mesulergine (1 and 3 mg/kg) or vehicle. There was a dose dependent increase of SD consumption 4 hrs after mesulergine treatment while the CED remained unchanged with total food intake dose dependently increased as a consequence.
Reference: Prog Neuropsychopharmacol Biol Psychiatry. 1998 Jul;22(5):803-13. https://pubmed.ncbi.nlm.nih.gov/9723121/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
39.9 |
100.01 |
|
| Water |
2.0 |
4.99 |
|
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
398.95
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. Havlik S, Peroutka SJ. Differential radioligand binding properties of [3H]5-hydroxytryptamine and [3H]mesulergine in a clonal 5-hydroxytryptamine1C cell line. Brain Res. 1992 Jul 3;584(1-2):191-6. doi: 10.1016/0006-8993(92)90894-f. PMID: 1515938.
2. Markstein R. Mesulergine and its 1,20-N,N-bidemethylated metabolite interact directly with D1- and D2-receptors. Eur J Pharmacol. 1983 Nov 11;95(1-2):101-7. doi: 10.1016/0014-2999(83)90272-8. PMID: 6230246.
3. Giannakopoulos G, Galanopoulou P, Daifotis Z, Couvaris C. Effects of mesulergine treatment on diet selection, brain serotonin (5-HT) and dopamine (DA) turnover in free feeding rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Jul;22(5):803-13. doi: 10.1016/s0278-5846(98)00041-4. PMID: 9723121.
4. Wang Y, Gu Q, Cynader MS. Blockade of serotonin-2C receptors by mesulergine reduces ocular dominance plasticity in kitten visual cortex. Exp Brain Res. 1997 Apr;114(2):321-8. doi: 10.1007/pl00005640. PMID: 9166921.
In vitro protocol:
1. Havlik S, Peroutka SJ. Differential radioligand binding properties of [3H]5-hydroxytryptamine and [3H]mesulergine in a clonal 5-hydroxytryptamine1C cell line. Brain Res. 1992 Jul 3;584(1-2):191-6. doi: 10.1016/0006-8993(92)90894-f. PMID: 1515938.
2. Markstein R. Mesulergine and its 1,20-N,N-bidemethylated metabolite interact directly with D1- and D2-receptors. Eur J Pharmacol. 1983 Nov 11;95(1-2):101-7. doi: 10.1016/0014-2999(83)90272-8. PMID: 6230246.
In vivo protocol:
1. Giannakopoulos G, Galanopoulou P, Daifotis Z, Couvaris C. Effects of mesulergine treatment on diet selection, brain serotonin (5-HT) and dopamine (DA) turnover in free feeding rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Jul;22(5):803-13. doi: 10.1016/s0278-5846(98)00041-4. PMID: 9723121.
2. Wang Y, Gu Q, Cynader MS. Blockade of serotonin-2C receptors by mesulergine reduces ocular dominance plasticity in kitten visual cortex. Exp Brain Res. 1997 Apr;114(2):321-8. doi: 10.1007/pl00005640. PMID: 9166921.
1: Pappert EJ, Goetz CG, Vu TQ, Ling ZD, Leurgans S, Raman R, Carvey PM. Animal model of posthypoxic myoclonus: effects of serotonergic antagonists. Neurology. 1999 Jan 1;52(1):16-21. doi: 10.1212/wnl.52.1.16. PMID: 9921842.
2: Pappert EJ, Goetz CG, Stebbins GT, Belden M, Carvey PM. 5-Hydroxytryptophan- induced myoclonus in guinea pigs: mediation through 5-HT1/2 receptor subtypes. Eur J Pharmacol. 1998 Apr 17;347(1):51-6. doi: 10.1016/s0014-2999(98)00086-7. PMID: 9650847.
3: Brüss M, Kiel S, Bönisch H, Kostanian A, Göthert M. Decreased agonist, but not antagonist, binding to the naturally occurring Thr92Lys variant of the h5-HT7(a) receptor. Neurochem Int. 2005 Aug;47(3):196-203. doi: 10.1016/j.neuint.2005.03.003. PMID: 15896881.
4: Borsini F, Cesana R, Vidi A, Mennini T. Evidence that imipramine activates 5-HT1C receptor function. Eur J Pharmacol. 1991 Oct 22;203(3):359-63. doi: 10.1016/0014-2999(91)90891-s. PMID: 1773822.
5: De Vries P, Sánchez-López A, Centurión D, Heiligers JP, Saxena PR, Villalón CM. The canine external carotid vasoconstrictor 5-HT1 receptor: blockade by 5-HT1B (SB224289), but not by 5-HT1D (BRL15572) receptor antagonists. Eur J Pharmacol. 1998 Nov 27;362(1):69-72. doi: 10.1016/s0014-2999(98)00762-6. PMID: 9865532.
6: Dirami G, Teerds KJ, Cooke BA. Effect of a dopamine agonist on the development of Leydig cell hyperplasia in Sprague-Dawley rats. Toxicol Appl Pharmacol. 1996 Nov;141(1):169-77. doi: 10.1006/taap.1996.0273. PMID: 8917689.
7: Taiwo YO, Levine JD. Serotonin is a directly-acting hyperalgesic agent in the rat. Neuroscience. 1992;48(2):485-90. doi: 10.1016/0306-4522(92)90508-y. PMID: 1534874.
8: Bourson A, Wanner D, Wyler R, Petit N, Zwingelstein C, Rudler A, Sleight AJ. Pharmacologic evaluation of the discriminative stimulus of metachlorophenylpiperazine. Pharmacol Biochem Behav. 1996 Jan;53(1):107-14. doi: 10.1016/0091-3057(95)00207-3. PMID: 8848438.
9: Dirami G, Cooke BA. Effect of a dopamine agonist on luteinizing hormone receptors, cyclic AMP production and steroidogenesis in rat Leydig cells. Toxicol Appl Pharmacol. 1998 Jun;150(2):393-401. doi: 10.1006/taap.1998.8429. PMID: 9653071.
