Synonym
Lisuride Maleate ; Cuvalit; Lysenyl; Lysenyl bimaleate; Lysenyl hydrogen maleate; Lisuride hydrogen maleate; Mesylate, Lisuride; Methylergol ;Carbamide Revanil;
IUPAC/Chemical Name
1,1-diethyl-3-(7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)urea fumarate
InChi Key
CVQFAMQDTWVJSV-WLHGVMLRSA-N
InChi Code
InChI=1S/C20H26N4O.C4H4O4/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14;5-3(6)1-2-4(7)8/h6-8,10-11,14,18,21H,4-5,9,12H2,1-3H3,(H,22,25);1-2H,(H,5,6)(H,7,8)/b;2-1+
SMILES Code
CCN(CC)C(=O)NC1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C.C(=CC(=O)O)C(=O)O
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, 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
Biological target:
Lisuride (maleate) is a potent agonist of dopamine with a probably direct action on dopaminergic receptors.
In vitro activity:
Glutamate treatment resulted in doubling of NO and superoxide radical formation, increased dopaminergic cell degeneration and extensively altered neuronal appearance. Pretreatment with lisuride significantly lowered the levels of either reactive species and increased the survival of dopaminergic neurons compared to glutamate-treated cultures. Moreover, the beneficial effect of lisuride could be completely inhibited by the D2/D3 receptor antagonist sulpiride when co-treated in cultures.
Reference: J Neural Transm (Vienna). 2006 Sep;113(9):1095-105. https://pubmed.ncbi.nlm.nih.gov/16463121/
In vivo activity:
Both lisuride and (R)-ketamine significantly ameliorated the increased immobility time of forced swimming test, and the decreased dendritic spine density in the prelimbic region of medial prefrontal cortex, CA3 and dentate gyrus of hippocampus of LPS-treated mice. In contrast, DOI did not improve these changes produced after LPS administration. This study suggests that antidepressant-like effect of lisuride in LPS-treated mice is not associated with 5-HT2AR-related psychedelic effects.
Reference: Pharmacol Biochem Behav. 2023 Jan;222:173500. https://pubmed.ncbi.nlm.nih.gov/36476377/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
34.8 |
76.63 |
|
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
454.52
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. Moldzio R, Radad K, Duvigneau JC, Kranner B, Krewenka C, Piskernik C, Rausch WD. Glutamate-induced cell death and formation of radicals can be reduced by lisuride in mesencephalic primary cell culture. J Neural Transm (Vienna). 2006 Sep;113(9):1095-105. doi: 10.1007/s00702-005-0394-1. Epub 2006 Feb 6. PMID: 16463121.
2. Qu Y, Chang L, Ma L, Wan X, Hashimoto K. Rapid antidepressant-like effect of non-hallucinogenic psychedelic analog lisuride, but not hallucinogenic psychedelic DOI, in lipopolysaccharide-treated mice. Pharmacol Biochem Behav. 2023 Jan;222:173500. doi: 10.1016/j.pbb.2022.173500. Epub 2022 Dec 5. PMID: 36476377.
3. Jiang K, Liu X, Su R. Contrasting effects of DOI and lisuride on impulsive decision-making in delay discounting task. Psychopharmacology (Berl). 2022 Nov;239(11):3551-3565. doi: 10.1007/s00213-022-06229-y. Epub 2022 Sep 15. PMID: 36107207.
In vitro protocol:
1. Moldzio R, Radad K, Duvigneau JC, Kranner B, Krewenka C, Piskernik C, Rausch WD. Glutamate-induced cell death and formation of radicals can be reduced by lisuride in mesencephalic primary cell culture. J Neural Transm (Vienna). 2006 Sep;113(9):1095-105. doi: 10.1007/s00702-005-0394-1. Epub 2006 Feb 6. PMID: 16463121.
In vivo protocol:
1. Qu Y, Chang L, Ma L, Wan X, Hashimoto K. Rapid antidepressant-like effect of non-hallucinogenic psychedelic analog lisuride, but not hallucinogenic psychedelic DOI, in lipopolysaccharide-treated mice. Pharmacol Biochem Behav. 2023 Jan;222:173500. doi: 10.1016/j.pbb.2022.173500. Epub 2022 Dec 5. PMID: 36476377.
2. Jiang K, Liu X, Su R. Contrasting effects of DOI and lisuride on impulsive decision-making in delay discounting task. Psychopharmacology (Berl). 2022 Nov;239(11):3551-3565. doi: 10.1007/s00213-022-06229-y. Epub 2022 Sep 15. PMID: 36107207.
1: Zweckberger K, Simunovic F, Kiening KL, Unterberg AW, Sakowitz OW.
Anticonvulsive effects of the dopamine agonist lisuride maleate after
experimental traumatic brain injury. Neurosci Lett. 2010 Feb 12;470(2):150-4.
doi: 10.1016/j.neulet.2009.12.075. Epub 2010 Jan 5. PubMed PMID: 20056133.
2: López-Rosales C, Aguilar-Guerrero JA, García-Moreno L. [Treatment of
premenstrual tension syndrome (PMS) with lisuride maleate]. Ginecol Obstet Mex.
1996 Dec;64:556-60. Spanish. PubMed PMID: 9019440.
3: Kaleli S, Aydin Y, Erel CT, Colgar U. Symptomatic treatment of premenstrual
mastalgia in premenopausal women with lisuride maleate: a double-blind
placebo-controlled randomized study. Fertil Steril. 2001 Apr;75(4):718-23. PubMed
PMID: 11287025.
4: Hougaku H, Matsumoto M, Hata R, Handa N, Imaizumi M, Sugitani Y, Yoneda S,
Etani H, Sueyoshi K, Kusunoki M, et al. [Therapeutic effect of lisuride maleate
on post-stroke depression]. Nihon Ronen Igakkai Zasshi. 1994 Jan;31(1):52-9.
Japanese. PubMed PMID: 8158872.
