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R(-)-alpha-Methylhistamine 2HCl

Cat No.:V13552 Purity: ≥98%
(R)-(-)-α-Methylhistamine diHCl is a potent, selective and BBB (blood-brain barrier) permeable/penetrable H3 histamine receptor agonist (activator) with Kd of 50.3 nM.
R(-)-alpha-Methylhistamine 2HCl
R(-)-alpha-Methylhistamine 2HCl Chemical Structure CAS No.: 75614-89-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes
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Product Description
(R)-(-)-α-Methylhistamine diHCl is a potent, selective and BBB (blood-brain barrier) permeable/penetrable H3 histamine receptor agonist (activator) with Kd of 50.3 nM. (R)-(-)-α-Methylhistamine diHCl enhances memory and alleviates memory impairment in rats.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
(R)-(-)-α-Methylhistamine dihydrochloride is more than ten times more efficient as an H3 agonist than histamine (HA). It is more than 1,000 times more selective for H3 receptors than HA is. (R) -(-)-α-Methylhistamine dihydrochloride has a pKi of 4.8 and less than 3.5 for H1 and H2 receptors, respectively, indicating a very low affinity. The dihydrochloride of (R)-(-)-α-methylhistamine binds to the H4 receptor more than 200 times [1][2][3].
ln Vivo
Restoration with (R)-(-)-α-methylhistamine dihydrochloride (RAMH; 10 mg/kg; i.p.; 60 minutes before training) reversed propofol-induced (25 mg/kg; i.p. injection; 30 min before training) (R)-(-)-α-methylhistamine dihydrochloride (6.3 mg/kg; ip) significantly reduced t-MH levels in the mouse brain, and these compounds No significant changes in HA levels
Animal Protocol
Animal/Disease Models: Male SD (SD (Sprague-Dawley)) rats (10-12 weeks) [3]
Doses: 10 mg/kg
Route of Administration: IP; [3]. Results 60 minutes before training: Reversal of propofol-induced memory retention.
References

[1]. Highly potent and selective ligands for histamine H3-receptors. Nature. 1987 May 14-20;327(6118):117-23.

[2]. Histamine, Histamine Receptors, and their Role in Immunomodulation: An Updated Systematic Review. The Open Immunology Journal, 2009, 2, 9-41.

[3]. Effects of the histamine H3-agonist (R)-alpha-methylhistamine and the antagonist thioperamideon histamine metabolism in the mouse and rat brain. J Neurochem. 1989 May;52(5):1388-92.

[4]. The disposition of (R)-alpha-methylhistamine, a histamine H3-receptor agonist, in rats. J Pharm Pharmacol. 1994 May;46(5):371-4.

[5]. (R)-alpha-methylhistamine suppresses inhibitory neurotransmission in hippocampal CA1 pyramidal neurons counteracting propofol-induced amnesia in rats. CNS Neurosci Ther. 2014 Sep;20(9):851-9.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H11N3.2[HCL]
Molecular Weight
198.09352
Exact Mass
197.049
CAS #
75614-89-0
PubChem CID
11957567
Appearance
White to off-white ointment
LogP
2.776
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Heavy Atom Count
11
Complexity
84.4
Defined Atom Stereocenter Count
1
SMILES
C[C@H](CC1=CN=CN1)N.Cl.Cl
InChi Key
IZHCNQFUWDFPCW-ZJIMSODOSA-N
InChi Code
InChI=1S/C6H11N3.2ClH/c1-5(7)2-6-3-8-4-9-6;;/h3-5H,2,7H2,1H3,(H,8,9);2*1H/t5-;;/m1../s1
Chemical Name
(2R)-1-(1H-imidazol-5-yl)propan-2-amine;dihydrochloride
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~1262.05 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (10.50 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (10.50 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (10.50 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.0482 mL 25.2411 mL 50.4821 mL
5 mM 1.0096 mL 5.0482 mL 10.0964 mL
10 mM 0.5048 mL 2.5241 mL 5.0482 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • (R)‐alpha‐methylhistamine prevented propofol‐induced LTP deficit in rat hippocampal CA1. (A, B) The above insets are the raw evoked field potential data traces taken at time points 5 min before (black line, 1 and 2) and 30 min after (gray line, 1′ and 2′) theta‐burst stimulation. Perfusion of RAMH (30 μM, 30 min) alone had no effect on TBS‐induced LTP (B) but significantly reversed propofol‐induced suppression of TBS‐induced LTP (A) in hippocampal CA1 neurons. (C, D) Bar histogram showing group data for the effect of RAMH alone (D) or with propofol (C) on TBS‐induced hippocampal CA1 LTP. (E) Perfusion of RAMH (30 μM, 30 min) had no effect on the slope of the fEPSPs. Each data point represents the mean ± SEM. ***P < 0.001, **P < 0.01 compared with the baseline by one‐way ANOVA; # P < 0.05 compared with the propofol group by Student's t‐test.[1].[5]. (R)-alpha-methylhistamine suppresses inhibitory neurotransmission in hippocampal CA1 pyramidal neurons counteracting propofol-induced amnesia in rats. CNS Neurosci Ther. 2014 Sep;20(9):851-9.
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