Mepyramine
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MedKoo CAT#: 591314

CAS#: 91-84-9 (free base)

Description: Mepyramine, a histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.

Chemical Structure

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Mepyramine
CAS# 91-84-9 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 591314
Name: Mepyramine
CAS#: 91-84-9 (free base)
Chemical Formula: C17H23N3O
Exact Mass: 285.18
Molecular Weight: 285.391
Elemental Analysis: C, 71.55; H, 8.12; N, 14.72; O, 5.61

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250mg USD 450 2 weeks
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Related CAS #: 59-33-6 (maleate)   91-84-9 (free base)   6036-95-9 (HCl)    

Synonym: Mepyramine; NSC 13136; NSC-13136; NSC13136

IUPAC/Chemical Name: 1,2-Ethanediamine, N-((4-methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-

InChi Key: YECBIJXISLIIDS-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3

SMILES Code: CN(C)CCN(CC1=CC=C(OC)C=C1)C2=NC=CC=C2

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: Soluble in DMSO

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

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Product Data:
Product Data
Instruction:
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Biological target: Mepyramine, 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/

Preparing Stock Solutions

The following data is based on the product molecular weight 285.39 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. 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.

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1: Jain S, Panyutin A, Liu N, Xiao C, Piñol RA, Pundir P, Girardet C, Butler AA, Dong X, Gavrilova O, Reitman ML. Melanotan II causes hypothermia in mice by activation of mast cells and stimulation of histamine 1 receptors. Am J Physiol Endocrinol Metab. 2018 May 29. doi: 10.1152/ajpendo.00024.2018. [Epub ahead of print] PubMed PMID: 29812984.

2: Alachkar A, Latacz G, Siwek A, Lubelska A, Honkisz E, Gryboś A, Łażewska D, Handzlik J, Stark H, Kiec-Kononowicz K, Sadek B. Anticonvulsant evaluation of novel non-imidazole histamine H3R antagonists in different convulsion models in rats. Pharmacol Biochem Behav. 2018 May 3;170:14-24. doi: 10.1016/j.pbb.2018.04.010. [Epub ahead of print] PubMed PMID: 29729290.

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4: Popiolek-Barczyk K, Łażewska D, Latacz G, Olejarz A, Makuch W, Stark H, Kieć-Kononowicz K, Mika J. Antinociceptive effects of novel histamine H(3) R and H(4) R receptor antagonists and their influence on morphine analgesia of neuropathic pain in the mouse. Br J Pharmacol. 2018 Feb 27. doi: 10.1111/bph.14185. [Epub ahead of print] PubMed PMID: 29486058.

5: Suzuki Y, Ogasawara T, Tanaka Y, Takeda H, Sawasaki T, Mogi M, Liu S, Maeyama K. Functional G-Protein-Coupled Receptor (GPCR) Synthesis: The Pharmacological Analysis of Human Histamine H1 Receptor (HRH1) Synthesized by a Wheat Germ Cell-Free Protein Synthesis System Combined with Asolectin Glycerosomes. Front Pharmacol. 2018 Feb 6;9:38. doi: 10.3389/fphar.2018.00038. eCollection 2018. PubMed PMID: 29467651; PubMed Central PMCID: PMC5808195.

6: Stoddart LA, Vernall AJ, Bouzo-Lorenzo M, Bosma R, Kooistra AJ, de Graaf C, Vischer HF, Leurs R, Briddon SJ, Kellam B, Hill SJ. Development of novel fluorescent histamine H(1)-receptor antagonists to study ligand-binding kinetics in living cells. Sci Rep. 2018 Jan 25;8(1):1572. doi: 10.1038/s41598-018-19714-2. PubMed PMID: 29371669; PubMed Central PMCID: PMC5785503.

7: Akanuma SI, Yamazaki Y, Kubo Y, Hosoya KI. Role of cationic drug-sensitive transport systems at the blood-cerebrospinal fluid barrier in para-tyramine elimination from rat brain. Fluids Barriers CNS. 2018 Jan 8;15(1):1. doi: 10.1186/s12987-017-0087-9. PubMed PMID: 29307307; PubMed Central PMCID: PMC5757291.

8: Lin JG, Lee YC, Tu CH, MacDonald I, Chung HY, Luo ST, Hung SY, Chen YH. Histamine H(1) Receptor Antagonists Facilitate Electroacupuncture Analgesia. Am J Chin Med. 2018;46(1):55-68. doi: 10.1142/S0192415X18500039. Epub 2018 Jan 3. PubMed PMID: 29298517.

9: Naganuma F, Nakamura T, Yoshikawa T, Iida T, Miura Y, Kárpáti A, Matsuzawa T, Yanai A, Mogi A, Mochizuki T, Okamura N, Yanai K. Histamine N-methyltransferase regulates aggression and the sleep-wake cycle. Sci Rep. 2017 Nov 21;7(1):15899. doi: 10.1038/s41598-017-16019-8. PubMed PMID: 29162912; PubMed Central PMCID: PMC5698467.

10: Sharma HS, Patnaik R, Muresanu DF, Lafuente JV, Ozkizilcik A, Tian ZR, Nozari A, Sharma A. Histaminergic Receptors Modulate Spinal Cord Injury-Induced Neuronal Nitric Oxide Synthase Upregulation and Cord Pathology: New Roles of Nanowired Drug Delivery for Neuroprotection. Int Rev Neurobiol. 2017;137:65-98. doi: 10.1016/bs.irn.2017.09.001. Epub 2017 Nov 3. PubMed PMID: 29132544.

11: Alachkar A, Łażewska D, Kieć-Kononowicz K, Sadek B. The Histamine H3 Receptor Antagonist E159 Reverses Memory Deficits Induced by Dizocilpine in Passive Avoidance and Novel Object Recognition Paradigm in Rats. Front Pharmacol. 2017 Oct 12;8:709. doi: 10.3389/fphar.2017.00709. eCollection 2017. PubMed PMID: 29075190; PubMed Central PMCID: PMC5643952.

12: Hishinuma S, Komazaki H, Tsukamoto H, Hatahara H, Fukui H, Shoji M. Ca(2+) -dependent down-regulation of human histamine H(1) receptors in Chinese hamster ovary cells. J Neurochem. 2018 Jan;144(1):68-80. doi: 10.1111/jnc.14245. Epub 2017 Nov 21. PubMed PMID: 29063596.

13: Lilli NL, Quénéhervé L, Haddara S, Brochard C, Aubert P, Rolli-Derkinderen M, Durand T, Naveilhan P, Hardouin JB, De Giorgio R, Barbara G, Bruley des Varannes S, Coron E, Neunlist M. Glioplasticity in irritable bowel syndrome. Neurogastroenterol Motil. 2018 Apr;30(4):e13232. doi: 10.1111/nmo.13232. Epub 2017 Oct 13. PubMed PMID: 29027719.

14: Wang B, An N, Shaikh AS, Wang H, Xiao L, Liu H, Li J, Zhao D. Hyperosmolarity evokes histamine release from ileum mucosa by stimulating a cholinergic pathway. Biochem Biophys Res Commun. 2017 Nov 18;493(2):1037-1042. doi: 10.1016/j.bbrc.2017.09.093. Epub 2017 Sep 19. PubMed PMID: 28939039.

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17: Tu L, Lu Z, Dieser K, Schmitt C, Chan SW, Ngan MP, Andrews PLR, Nalivaiko E, Rudd JA. Brain Activation by H(1) Antihistamines Challenges Conventional View of Their Mechanism of Action in Motion Sickness: A Behavioral, c-Fos and Physiological Study in Suncus murinus (House Musk Shrew). Front Physiol. 2017 Jun 14;8:412. doi: 10.3389/fphys.2017.00412. eCollection 2017. PubMed PMID: 28659825; PubMed Central PMCID: PMC5470052.

18: Yusof SR, Abbott NJ, Avdeef A. Impact of capillary flow hydrodynamics on carrier-mediated transport of opioid derivatives at the blood-brain barrier, based on pH-dependent Michaelis-Menten and Crone-Renkin analyses. Eur J Pharm Sci. 2017 Aug 30;106:274-286. doi: 10.1016/j.ejps.2017.06.016. Epub 2017 Jun 11. PubMed PMID: 28614733.

19: Tun T, Kang YS. Imperatorin is Transported through Blood-Brain Barrier by Carrier-Mediated Transporters. Biomol Ther (Seoul). 2017 Jul 1;25(4):441-451. doi: 10.4062/biomolther.2017.082. PubMed PMID: 28554202; PubMed Central PMCID: PMC5499624.

20: Köchling H, Schaper K, Wilzopolski J, Gutzmer R, Werfel T, Bäumer W, Kietzmann M, Rossbach K. Combined treatment with H1 and H4 receptor antagonists reduces inflammation in a mouse model of atopic dermatitis. J Dermatol Sci. 2017 Aug;87(2):130-137. doi: 10.1016/j.jdermsci.2017.04.004. Epub 2017 Apr 21. PubMed PMID: 28495120.