Synonym
Mepyramine Maleate; Pyrilamine maleate; Anisopyradamine; Minihist; Diaminide maleate; Paraminyl maleate; Kriptin; Maleate, Mepyramine;
IUPAC/Chemical Name
(Z)-but-2-enedioic acid;N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
InChi Key
JXYWFNAQESKDNC-BTJKTKAUSA-N
InChi Code
InChI=1S/C17H23N3O.C4H4O4/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15;5-3(6)1-2-4(7)8/h4-11H,12-14H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
SMILES Code
CN(C)CCN(CC1=CC=C(C=C1)OC)C2=CC=CC=N2.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:
Mepyramine maleate, also known as Pyrilamine maleate, is a histamine H1 antagonist.
In vitro activity:
The KCNQ/M K(+) channel plays a crucial role in controlling neuron excitability. Here, we demonstrate that mepyramine and diphenhydramine, two structurally related first-generation antihistamines, can act as potent KCNQ/M channel blockers. Mepyramine also inhibited the individual homomeric KCNQ1-4 and heteromeric KCNQ3/Q5 currents. Moreover, mepyramine inhibited KCNQ2/Q3 current in an outside-out patch excised from HEK293 cells and the inhibitory effect was neither observed when it was applied intracellularly nor affected by blocking phospholipase C (PLC) activity, indicating an extracellular and direct channel blocking mechanism.
Reference: Neuropharmacology. 2008 Mar;54(4):629-39. https://pubmed.ncbi.nlm.nih.gov/18222495/
In vivo activity:
Locally applied mepyramine had analgesic effects on the scorpion toxin-induced excruciating pain and produced pain relief in acute, inflammatory, and chronic pain mouse models. Collectively, these data provide evidence that mepyramine has the potential to be developed as a topical analgesic agent.
Reference: FASEB J. 2021 Dec;35(12):e22025. https://pubmed.ncbi.nlm.nih.gov/34758144/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
25.0 |
62.27 |
| DMSO |
53.4 |
132.97 |
| Ethanol |
20.0 |
49.82 |
| PBS (pH 7.2) |
10.0 |
24.91 |
| Water |
56.7 |
141.27 |
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
401.46
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. Liu B, Zhang X, Wang C, Zhang G, Zhang H. Antihistamine mepyramine directly inhibits KCNQ/M channel and depolarizes rat superior cervical ganglion neurons. Neuropharmacology. 2008 Mar;54(4):629-39. doi: 10.1016/j.neuropharm.2007.11.012. Epub 2007 Nov 28. PMID: 18222495.
2. Zeng S, Guo ZG. Mepyramine inhibits platelet activating factor-induced rabbit platelet aggregation: role of intracellular histamine. Zhongguo Yao Li Xue Bao. 1997 Mar;18(2):155-8. PMID: 10072970.
3. Hao J, Brosse L, Bonnet C, Ducrocq M, Padilla F, Penalba V, Desplat A, Ruel J, Delmas P. The widely used antihistamine mepyramine causes topical pain relief through direct blockade of nociceptor sodium channels. FASEB J. 2021 Dec;35(12):e22025. doi: 10.1096/fj.202100976RR. PMID: 34758144.
4. Fitzsimons CP, Monczor F, Fernández N, Shayo C, Davio C. Mepyramine, a histamine H1 receptor inverse agonist, binds preferentially to a G protein-coupled form of the receptor and sequesters G protein. J Biol Chem. 2004 Aug 13;279(33):34431-9. doi: 10.1074/jbc.M400738200. Epub 2004 Jun 10. PMID: 15192105.
In vitro protocol:
1. Liu B, Zhang X, Wang C, Zhang G, Zhang H. Antihistamine mepyramine directly inhibits KCNQ/M channel and depolarizes rat superior cervical ganglion neurons. Neuropharmacology. 2008 Mar;54(4):629-39. doi: 10.1016/j.neuropharm.2007.11.012. Epub 2007 Nov 28. PMID: 18222495.
2. Zeng S, Guo ZG. Mepyramine inhibits platelet activating factor-induced rabbit platelet aggregation: role of intracellular histamine. Zhongguo Yao Li Xue Bao. 1997 Mar;18(2):155-8. PMID: 10072970.
In vivo protocol:
1. Hao J, Brosse L, Bonnet C, Ducrocq M, Padilla F, Penalba V, Desplat A, Ruel J, Delmas P. The widely used antihistamine mepyramine causes topical pain relief through direct blockade of nociceptor sodium channels. FASEB J. 2021 Dec;35(12):e22025. doi: 10.1096/fj.202100976RR. PMID: 34758144.
2. Fitzsimons CP, Monczor F, Fernández N, Shayo C, Davio C. Mepyramine, a histamine H1 receptor inverse agonist, binds preferentially to a G protein-coupled form of the receptor and sequesters G protein. J Biol Chem. 2004 Aug 13;279(33):34431-9. doi: 10.1074/jbc.M400738200. Epub 2004 Jun 10. PMID: 15192105.
1: Cingi C, Ural K, Acar A, Uzlu E. Efficacy of mepyramine maleate treatment in
dogs with angioedema. Pol J Vet Sci. 2010;13(3):549-50. PubMed PMID: 21033572.
2: Duke HN. The pulmonary pressor response to hypoxia in isolated perfused lungs
of cats: the influence of mepyramine maleate and semicarbazide. J Physiol. 1969
Feb;200(2):133P+. PubMed PMID: 4388120.
3: [Mepyramine (maleate)]. Ann Pharm Fr. 1961 Jun;19:462-3. French. PubMed PMID:
14447931.
4: GOSWAMI R, DAS PC, PHUKAN D. Local anesthetic action of antihistaminics
(promethazine hydrochloride and mepyramine maleate). Indian J Med Sci. 1958
Feb;12(2):63-71. PubMed PMID: 13524915.
5: HOWAT HT, SCHOFIELD B. The effect of urogastrone, enterogastrone and
mepyramine maleate on gastric and pancreatic secretion. J Physiol. 1954
Jan;123(1):1-15. PubMed PMID: 13131242; PubMed Central PMCID: PMC1366150.
6: BAIN WA, BROADBENT JL, WARIN RP. Comparison of anthisan (mepyramine maleate)
and phenergan as histamine antagonists. Lancet. 1949 Jul 9;2(6567):47-52. PubMed
PMID: 18133887.
7: Pillai AG, Awadhiya RP, Vegad JL. Suppression by mepyramine maleate of the
increased vascular permeability in passive cutaneous anaphylaxis in the chicken.
Vet Res Commun. 1988;12(2-3):161-3. PubMed PMID: 3188384.
8: el-Gizawy SM, Ahmed Ael H. High-performance liquid chromatographic
determination of mepyramine maleate, pheniramine maleate and phenylpropanolamine
hydrochloride in tablets and drops. Analyst. 1987 Jun;112(6):867-9. PubMed PMID:
3619056.
9: Tarayre JP, Aliaga M, Villanova G, Barbara M, Bru M, Caillol V, Lauressergues
H. [Comparative antiallergic and anti-inflammatory action of F1865, mepyramine
maleate, desonide and disodium cromoglycate after cutaneous administration]. J
Pharmacol. 1984 Jan-Mar;15(1):37-51. French. PubMed PMID: 6425568.
10: Al-Haboubi HA, Zeitlin IJ. The actions of cimetidine hydrochloride and
mepyramine maleate in rat adjuvant arthritis. Eur J Pharmacol. 1982 Feb
26;78(2):175-85. PubMed PMID: 7075670.
11: Gopalan S, Nayar CK. A comparative study on the antihistaminic potencies of
promethazine hydrochloride, mepyramine maleate and pheniramine maleate in dogs.
Indian Vet J. 1971 Mar;48(3):295-301. PubMed PMID: 4397014.
12: Vegad JL. Effect of hyaluronidase & nucleosides on vascular permeability in
sheep & its suppression by mepyramine maleate. Indian J Exp Biol. 1970
Apr;8(2):141-2. PubMed PMID: 4097041.
