Immethridine dihydrobromide
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Immethridine dihydrobromide is a selective histamine H3 receptor agonist. Immethridine dihydrobromide inhibits the expression of TLR4/CD14 and the phosphorylation of NF-κB p65. Immethridine dihydrobromide reduces inverse agonist-induced scratching, induces cheek-directed wiping rather than itching, and exerts a protective effect against HCl-induced gastric mucosal injury without affecting gastric acid secretion. Immethridine dihydrobromide attenuates experimental autoimmune encephalomyelitis and reduces inflammatory infiltration/demyelination in the spinal cord. Immethridine dihydrobromide can be used in research on autism spectrum disorders.
For research use only. We do not sell to patients.
- Purity : 99.61%
- CAS No.: 699020-93-4
- Formula: C9H11Br2N3
- Molecular Weight:321.01
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Storage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Protocols
- Purity & Documentation
- References
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Help & FAQs
All Histamine Receptor Isoforms
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Biological Activity
Description
IC50 & Target
[1]|
H3 receptor |
TLR4 |
In Vitro
Immethridine (100 μM) dihydrobromide depolarizes the membrane potential of masseter motor neurons in rat brainstem slices by 6.6 mV without affecting input resistance[3].
Immethridine (0.01 nM-0.1 mM; 60 min) dihydrobromide is a selective rat histamine H3 receptor agonist (pKi 7.97) with 75-fold selectivity for rat H4 in radioligand binding assays using HEK293T membranes[4].
Immethridine dihydrobromide shows high affinity for the histamine H3 receptor in SK-N-MC membrane binding data (pKi 9.07), with 288-fold selectivity over H4[4].
Immethridine dihydrobromide acts as a full agonist at the human histamine H3 receptor in SK-N-MC cells with a pEC50 of 9.74, and has a pEC50 of 6.04 at the human H4 receptor[5].
Immethridine dihydrobromide inhibits electrically induced twitch contractions of the guinea pig ileum myenteric plexus, with a pD2 of 7.45 and an Emax of 38.5%[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Immethridine dihydrobromide (30 mg/kg; intraperitoneal injection; single dose; 30 min before intradermal injection of Pitolisant) reduces Pitolisant (HY-12199)-induced acute itch scratching behavior in female BALB/c mice[8].
Immethridine (20-45 mg/kg; intraperitoneal injection) dihydrobromide reduces spontaneous activity in C57BL/6J mice and, at 45 mg/kg, increases the time spent in stereotyped patterns while decreasing grooming behavior[10].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6 (female, 8-10 weeks old)[1]
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Dosage:15 mg/kg
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Administration:i.p.; every other day; after observable signs of EAE occurred
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Result:Immethridine-administered EAE mice had lower disease scores than control EAE mice.
At day 21, spinal cord sections from Immethridine-administered EAE mice showed fewer inflammatory infiltrates by H&E staining and decreased demyelination by LFB staining.
Splenocytes from Immethridine-administered EAE mice showed lower levels of TNF-α, IFN-γ, and IL-17A.
In splenocytes from Immethridine-administered EAE mice, Th1 cells were 4.6% of CD4+ cells versus 7.0% in vehicle-administered EAE mice, and Th17 cells were 6.7% versus 9.2%, respectively.
MOG35-55-specific T cell proliferation was lower in Immethridine-administered EAE mice.
Expression of CD40 and CD86 on DCs was lower in splenocytes from Immethridine-administered EAE mice.
MHCII expression on DCs in spinal cord was down-regulated in Immethridine-administered EAE mice.
There were fewer Th1 and Th17 cells in spinal cord from Immethridine-administered EAE mice.
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Animal Model:Wistar (male; 180-200 g)[4]
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Dosage:30 mg/kg
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Administration:s.c.; single dose; 30 min before intragastric HCl
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Result:In conscious rats, immethridine and methimepip significantly reduced (66% and 48% inhibition, respectively) the gastric lesions induced by HCl; the effect of immethridine was antagonized by the H3 receptor antagonist A-331440, but not by the H4 receptor antagonist JNJ7777120.
Previous administration of immethridine and methimepip (both at 30 mg/kg) caused a significant inhibition of the mucosal damage induced by concentrated acid.
The inhibitory effect of immethridine was prevented by prior administration of the histamine H3 receptor antagonist A-331440 (30 mg/kg), but not by the selective histamine H4 receptor antagonist JNJ7777120 (10 mg/kg).
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Animal Model:BALB/c (female, 6-8 weeks old)[8]
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Dosage:30 mg/kg
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Administration:i.p.; single administration; 30 min before intradermal pitolisant
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Result:In mice administered immethridine (30 mg/kg i.p.), intradermal pitolisant-induced scratching was 13 bouts/1 h.
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Animal Model:C57BL/6J (male; 11 weeks of age at start; JAX stock #000664)[10]
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Dosage:20 mg/kg and 45 mg/kg
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Administration:i.p.; 30 min before behavioral testing; acute; one-week wash-out periods between assessments
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Result:Decreased distance moved in C57BL/6J mice, with reductions in locomotor activity at 20 mg/kg and 45 mg/kg.
At 45 mg/kg, the reduction in locomotor activity was associated with increased time spent in stereotypic patterns and reduced grooming behavior.
The increased stereotypic patterns at high-dose immethridine occurred in mice with very low activity levels, consistent with general sedative properties.
Chemical Information
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CAS No. 699020-93-4
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Appearance Solid
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Molecular Weight 321.01
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Formula C9H11Br2N3
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Color Off-white to light yellow
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SMILES
[H]Br.[H]Br.C1(CC2=CN=CN2)=CC=NC=C1
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvent & Solubility
In Vitro:
H2O : 15 mg/mL (46.73 mM; Need ultrasonic and warming)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (290 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[1]. Shi Y, et al. Immethridine, histamine H-receptor (HR) agonist, alleviated experimental autoimmune encephalomyelitis via inhibiting the function of dendritic cells. Oncotarget. 2017 Sep 26;8(43):75038-75049. [Content Brief]
[4]. Coruzzi G, et al. Selective histamine H₃ and H₄ receptor agonists exert opposite effects against the gastric lesions induced by HCl in the rat stomach. European journal of pharmacology. 2011 Nov 01;669(1-3):121-7. [Content Brief]
[5]. Kitbunnadaj R, et al. Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist. Journal of medicinal chemistry. 2004 May 06;47(10):2414-7. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| H2O | 1 mM | 3.1152 mL | 15.5758 mL | 31.1517 mL | 77.8792 mL |
| 5 mM | 0.6230 mL | 3.1152 mL | 6.2303 mL | 15.5758 mL | |
| 10 mM | 0.3115 mL | 1.5576 mL | 3.1152 mL | 7.7879 mL | |
| 15 mM | 0.2077 mL | 1.0384 mL | 2.0768 mL | 5.1919 mL | |
| 20 mM | 0.1558 mL | 0.7788 mL | 1.5576 mL | 3.8940 mL | |
| 25 mM | 0.1246 mL | 0.6230 mL | 1.2461 mL | 3.1152 mL | |
| 30 mM | 0.1038 mL | 0.5192 mL | 1.0384 mL | 2.5960 mL | |
| 40 mM | 0.0779 mL | 0.3894 mL | 0.7788 mL | 1.9470 mL |
Immethridine dihydrobromide Related Classifications
HY-108058A Related Classifications
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