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| 100mg |
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| Targets |
3-Aminopropylphosphonic acid primarily targets GABA receptors, specifically acting as a partial agonist at the GABAB receptor and as an antagonist at the GABA(C) receptor. The GABAB receptor is a metabotropic G protein-coupled receptor that mediates slow inhibitory neurotransmission in the central nervous system through activation of G proteins and modulation of potassium and calcium channels. GABA(C) receptors are ionotropic receptors (now classified as a subtype of GABAA receptors containing ρ subunits) that mediate fast inhibitory neurotransmission, particularly in the retina. The compound exhibits an IC50 of 1.5 μM for GABAB receptor binding, indicating moderate affinity. Additionally, it functions as an antagonist of basal prolactin secretion, suggesting potential effects on neuroendocrine regulation. This receptor profile makes the compound useful for distinguishing GABAB-mediated effects from GABA(C)-mediated effects in pharmacological studies.
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| ln Vitro |
In vitro, 3-Aminopropylphosphonic acid demonstrates activity as a GABAB receptor partial agonist with an IC50 of 1.5 μM in receptor binding assays. In functional assays, the compound has been shown to inhibit baclofen binding to rat cerebellar membranes, confirming its interaction with GABAB receptors. It also acts as a selective antagonist of GABA(C) receptors, making it a useful tool for distinguishing between GABAB and GABA(C) receptor-mediated effects. The compound's partial agonist activity at GABAB receptors means it can activate the receptor but with lower efficacy than full agonists like baclofen, potentially acting as a functional antagonist in the presence of endogenous GABA. In studies of prolactin secretion, the compound antagonizes basal prolactin secretion, indicating a role in neuroendocrine regulation. However, specific quantitative data beyond the IC50 for binding have not been extensively reported.
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| ln Vivo |
In vivo activity of 3-Aminopropylphosphonic acid has been studied primarily in the context of its effects on GABA receptor-mediated functions. As a GABAB receptor agonist and GABA(C) receptor antagonist, the compound would be expected to modulate GABAergic neurotransmission in vivo. However, specific in vivo efficacy data, including detailed animal model studies, dosing regimens, and quantitative outcomes, are not extensively reported in the available literature. The compound has been used as a research tool to study the roles of GABAB and GABA(C) receptors in various physiological and behavioral processes. Its effects on basal prolactin secretion suggest potential neuroendocrine effects. Given its polar nature and water solubility, the compound could be administered systemically, but detailed in vivo pharmacokinetic and pharmacodynamic studies are lacking.
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| Enzyme Assay |
In vitro enzyme or receptor binding assay protocols for 3-Aminopropylphosphonic acid typically involve radioligand binding competition assays using membrane preparations from rat cerebellum or other brain regions rich in GABA receptors. A standard protocol involves incubating varying concentrations of 3-aminopropylphosphonic acid (typically 0.1 μM to 1 mM) with radiolabeled baclofen (e.g., 3H-baclofen) and cerebellar membrane preparations in binding buffer (e.g., Tris-HCl, pH 7.4) for a defined period (e.g., 30-60 minutes at room temperature or 4°C). Non-specific binding is determined in the presence of excess unlabeled baclofen or GABA. Bound radioactivity is separated by filtration through glass fiber filters and quantified by liquid scintillation counting. IC50 values are calculated from competition curves, and Ki values are derived using the Cheng-Prusoff equation. For GABA(C) receptor studies, similar protocols using membranes from cells expressing recombinant GABA(C) receptors or from retinal tissue can be employed.
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| Cell Assay |
In vitro cell-based assay protocols for 3-Aminopropylphosphonic acid typically involve measuring its effects on GABA receptor-mediated signaling in cultured cells expressing recombinant GABAB or GABA(C) receptors. A standard protocol for studying GABAB receptor activity involves using cells (e.g., CHO or HEK293 cells) co-transfected with GABAB1 and GABAB2 receptor subunits and a G protein-coupled inwardly rectifying potassium (GIRK) channel or a calcium-sensitive reporter system. Cells are loaded with a calcium indicator dye (e.g., Fluo-4) or a membrane potential-sensitive dye, and responses to GABA or baclofen are measured in the presence or absence of 3-aminopropylphosphonic acid. For GABA(C) receptor studies, cells expressing ρ subunits are used, and receptor activity is assessed by measuring chloride influx using patch-clamp electrophysiology or fluorescent chloride indicators. The compound's partial agonist activity at GABAB receptors and antagonist activity at GABA(C) receptors can be characterized by comparing responses to full agonists in the presence of the compound.
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| Animal Protocol |
In vivo animal experimental protocols for 3-Aminopropylphosphonic acid are not extensively reported in the literature. However, based on its receptor pharmacology, potential studies might involve administering the compound to rodents to assess its effects on GABAergic neurotransmission, behavior, or neuroendocrine function. A hypothetical protocol for studying its effects on prolactin secretion would involve administering the compound (e.g., intraperitoneally or intracerebroventricularly) to rats, collecting blood samples at various time points, and measuring serum prolactin levels by radioimmunoassay or ELISA. For behavioral studies, the compound could be administered prior to testing in models of anxiety, seizure, or motor function, given the known roles of GABAB receptors in these processes. Doses would need to be determined based on preliminary studies, and appropriate vehicle controls would be included. However, specific published protocols are not available.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 3-Aminopropylphosphonic acid have not been extensively characterized in published studies. The compound is highly water-soluble (≥100 mg/mL in water), indicating good aqueous solubility. Its small molecular weight (139.09) and polar nature suggest that it would have limited ability to cross the blood-brain barrier, which is a consideration for CNS-targeted applications. The compound is stable at 4°C with protection from light. In solvent, it can be stored at -80°C for 6 months or -20°C for 1 month. However, specific PK parameters such as half-life, Cmax, AUC, bioavailability, volume of distribution, and clearance have not been reported. The compound's metabolism, protein binding, and routes of elimination remain uncharacterized. Further pharmacokinetic studies would be required to understand its absorption, distribution, metabolism, and excretion profile.
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| Toxicity/Toxicokinetics |
Toxicological data for 3-Aminopropylphosphonic acid are limited, as the compound is intended for research use only and has not undergone systematic toxicity testing. No acute toxicity (LD50), subchronic toxicity, genotoxicity, or reproductive toxicity studies have been reported specifically for this compound. Based on its structure as a phosphonic acid derivative, the compound may have moderate toxicity, but specific data are lacking. As with all research chemicals, appropriate safety precautions should be taken when handling the compound, including working in a fume hood, wearing appropriate personal protective equipment, and avoiding inhalation, ingestion, or skin contact. The compound is not intended for human use. Researchers should consult the material safety data sheet (MSDS) for specific safety information and handling recommendations. The compound requires protection from light during storage.
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| References | |
| Additional Infomation |
(3-Aminopropyl)phosphonic acid is a phosphonic acid in which the hydrogen atom on the phosphorus atom is replaced by a 3-aminopropyl group. It is a partial agonist of the GABAB receptor and exhibits the function of a GABAB receptor agonist. It is a primary amino compound belonging to the phosphonic acid class. Functionally, it is related to phosphonic acids. It is the zwitterion tautomer of (3-aminopropyl)phosphonic acid.
3-Aminopropylphosphonic acid is a research-grade compound used as a pharmacological tool for studying GABA receptor function. It acts as a partial agonist at GABAB receptors (IC50 = 1.5 μM) and as an antagonist at GABA(C) receptors. The compound has also been shown to antagonize basal prolactin secretion. It is used to differentiate between GABAB and GABA(C) receptor-mediated effects in neuroscience research. 3-Aminopropylphosphonic acid has not entered clinical trials and is not approved for any therapeutic indication. Its mechanism involves binding to GABA receptors with moderate affinity, modulating inhibitory neurotransmission. The compound's dual activity (agonist at GABAB, antagonist at GABA(C)) makes it a valuable tool for receptor pharmacology studies. It is available exclusively for research purposes and is not intended for diagnostic, therapeutic, or human applications. The compound should be stored at 4°C protected from light. |
| Molecular Formula |
C3H10NO3P
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| Molecular Weight |
139.09
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| Exact Mass |
139.039
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| CAS # |
13138-33-5
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| PubChem CID |
97587
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
343.0±44.0 °C at 760 mmHg
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| Melting Point |
290-294ºC
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| Flash Point |
161.2±28.4 °C
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| Vapour Pressure |
0.0±1.6 mmHg at 25°C
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| Index of Refraction |
1.495
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| LogP |
-2.38
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
8
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| Complexity |
98.7
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C([P](O)(O)=O)CCN
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| InChi Key |
GSZQTIFGANBTNF-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C3H10NO3P/c4-2-1-3-8(5,6)7/h1-4H2,(H2,5,6,7)
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| Chemical Name |
3-aminopropylphosphonic acid
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
Typically soluble in DMSO (e.g. 10 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.1896 mL | 35.9479 mL | 71.8959 mL | |
| 5 mM | 1.4379 mL | 7.1896 mL | 14.3792 mL | |
| 10 mM | 0.7190 mL | 3.5948 mL | 7.1896 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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