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| Other Sizes |
| Targets |
Imidazoleacetic acid is a full agonist of the GABAA receptor (potent GABA-A agonist). It is structurally distinct from GABA but binds to the same receptor. It also acts as a GABAC antagonist. It is orally active and readily able to cross the blood-brain barrier. It induces centrally mediated effects such as analgesia, sedation, and hypnosis.
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| ln Vitro |
In vitro, imidazoleacetic acid (IAA) has been shown to interact with GABA receptors and produce neurochemical and behavioral effects. It is used to study the non-histaminergic effects of histamine metabolism and the interaction between histamine and the GABAergic system.
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| ln Vivo |
In animal studies, imidazoleacetic acid induces centrally mediated effects such as analgesia, sedation, hypnosis, and hypothermia. It is used to study the role of GABAergic signaling in behavior and to explore the connection between histamine metabolism and the GABAergic system. It is effective after oral administration.
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| Enzyme Assay |
A radioligand binding assay uses membranes from rat cerebral cortex (rich in GABAA receptors) and [3H]-muscimol (a GABAA agonist). Imidazoleacetic acid hydrochloride is added to compete for binding. Bound radioactivity is measured by filtration and scintillation counting. The IC₅0 and Kᵢ values are calculated. Alternatively, a functional assay using Xenopus oocytes expressing GABAA receptors can be performed.
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| Cell Assay |
Primary cortical neurons or HEK293 cells expressing GABAA receptors are treated with imidazoleacetic acid hydrochloride (10 uM-1 mM). Chloride influx is measured using a membrane potential-sensitive fluorescent dye (e.g., MQAE or YFP) or by whole-cell patch-clamp electrophysiology to record GABA-evoked currents. Effects on cell viability are measured by MTT.
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| Animal Protocol |
In animal studies, imidazoleacetic acid hydrochloride is typically dissolved in saline and administered to rodents by intraperitoneal injection (10-100 mg/kg) or by oral gavage (due to its oral activity). Behavioral tests (e.g., open field, rotarod, tail-flick for analgesia, loss of righting reflex for sedation, hypothermia measurement) are conducted. Brain amino acid levels are measured by HPLC.
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| ADME/Pharmacokinetics |
Imidazoleacetic acid is water-soluble. It is orally active and readily crosses the blood-brain barrier. Its plasma half-life is short (approximately 30-60 minutes) due to rapid renal clearance. It is primarily excreted unchanged in urine. It is a major metabolite of histamine in the brain and periphery.
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| Toxicity/Toxicokinetics |
The compound has low toxicity, as it is an endogenous metabolite. The hydrochloride salt may be irritating to the gastrointestinal tract at high doses. High doses can cause CNS depression, respiratory depression, and hypothermia. No significant organ toxicity has been reported at research doses (10-100 mg/kg).
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| References | |
| Additional Infomation |
Imidazoleacetic acid hydrochloride is used as a standard for histamine metabolite analysis by GC-MS and LC-MS in clinical diagnostics and metabolomics. It is also a biochemical tool for studying GABAergic signaling and histamine metabolism in the brain. It is used in research on GABAergic mechanisms, epilepsy, and sedation. It is not an approved drug.
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| Molecular Formula |
C5H7CLN2O2
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|---|---|
| Molecular Weight |
162.57
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| Exact Mass |
162.019
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| CAS # |
3251-69-2
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| Related CAS # |
Imidazoleacetic acid;645-65-8
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| PubChem CID |
145685
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.426g/cm3
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| Boiling Point |
447.3ºC at 760mmHg
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| Melting Point |
218-222 °C(lit.)
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| Flash Point |
224.3ºC
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| LogP |
0.838
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
10
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| Complexity |
116
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(NC=N1)CC(=O)O.Cl
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| InChi Key |
MWHLCFYPFGFBQO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H6N2O2.ClH/c8-5(9)1-4-2-6-3-7-4;/h2-3H,1H2,(H,6,7)(H,8,9);1H
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| Chemical Name |
2-(1H-imidazol-5-yl)acetic acid;hydrochloride
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO :~100 mg/mL (~615.12 mM)
H2O :~50 mg/mL (~307.56 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.38 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 25.0 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: ≥ 2.5 mg/mL (15.38 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 25.0 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. View More
Solubility in Formulation 3: 100 mg/mL (615.12 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.1512 mL | 30.7560 mL | 61.5120 mL | |
| 5 mM | 1.2302 mL | 6.1512 mL | 12.3024 mL | |
| 10 mM | 0.6151 mL | 3.0756 mL | 6.1512 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.
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.
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