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| Targets |
(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol acts as a beta-adrenergic receptor blocker. Beta-adrenergic receptors (β-ARs) are G protein-coupled receptors that mediate the effects of catecholamines such as epinephrine and norepinephrine. By blocking these receptors, the compound reduces sympathetic nervous system activity, leading to decreased heart rate, reduced cardiac output, and lowered blood pressure. The (1S,2R) stereochemistry is critical for its biological activity, as the compound's chirality determines its binding affinity and selectivity for beta-adrenergic receptors. The compound is also used as a chiral intermediate for the synthesis of other pharmaceuticals.
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| ln Vitro |
In vitro, (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol exhibits beta-adrenergic receptor antagonist activity. As a beta-blocker, it competes with endogenous catecholamines for binding to beta-adrenergic receptors, inhibiting receptor activation and downstream signaling. In cell-based assays, the compound would be expected to inhibit isoproterenol-induced cAMP accumulation in cells expressing beta-adrenergic receptors. Typical IC₅₀ values for beta-blockers range from nanomolar to micromolar concentrations, depending on receptor subtype and assay conditions. The compound's chiral purity is critical for its activity, as the enantiomers may have different potencies.
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| ln Vivo |
In vivo, (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol is used in the treatment of hypertension as a beta-adrenergic blocker. Beta-blockers reduce blood pressure by decreasing cardiac output, reducing sympathetic outflow from the central nervous system, and suppressing renin release from the kidneys. The compound would be administered orally or intravenously, with effects on heart rate and blood pressure observed within hours of dosing. The duration of action depends on the formulation and dosage. However, the compound itself is primarily used as an intermediate for other drugs, such as Indinavir, rather than as the final therapeutic agent.
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| Enzyme Assay |
In vitro receptor binding assays for (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol typically involve competition binding studies using radiolabeled ligands such as [³H]-dihydroalprenolol or [¹²⁵I]-iodocyanopindolol. Membranes prepared from cells expressing beta-adrenergic receptors are incubated with the radioligand and varying concentrations of the test compound. Non-specific binding is determined in the presence of excess propranolol. Bound radioligand is separated by filtration and quantified by scintillation counting. IC₅₀ values are calculated from dose-response curves, and Kᵢ values are derived using the Cheng-Prusoff equation. Functional assays measure inhibition of isoproterenol-stimulated cAMP accumulation.
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| Cell Assay |
In vitro cell culture experiments with (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol typically involve cells expressing beta-adrenergic receptors (e.g., HEK-293 cells transfected with β₁-AR or β₂-AR). Cells are cultured in DMEM supplemented with 10% FBS and antibiotics. For activity assays, cells are treated with the compound at concentrations ranging from 1 nM to 100 µM for 30-60 minutes, followed by stimulation with isoproterenol (1 µM). cAMP levels are measured using ELISA or HTRF-based assays. Cytotoxicity is assessed using MTT or CellTiter-Glo assays after 24-72 hours of exposure. The compound's effects on cell viability and signaling are compared to known beta-blockers such as propranolol.
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| Animal Protocol |
In vivo animal studies with (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol typically involve hypertensive rat models (e.g., spontaneously hypertensive rats or DOCA-salt hypertensive rats). The compound is administered orally by gavage or intravenously at doses ranging from 0.1-10 mg/kg. Blood pressure and heart rate are monitored using tail-cuff plethysmography or telemetry. Blood samples are collected at various time points for pharmacokinetic analysis. For efficacy studies, animals are treated daily for 1-4 weeks, and blood pressure is measured at regular intervals. At study termination, tissues are collected for histopathological examination and biomarker analysis.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol are not fully characterized as it is primarily used as an intermediate. Based on its physicochemical properties (molecular weight 149.19, moderate water solubility, logP approximately 0.5-1.0), the compound is expected to have good oral bioavailability. It would likely be metabolized via cytochrome P450-mediated oxidation and conjugation reactions (glucuronidation, sulfation). The compound may undergo extensive first-pass metabolism. The elimination half-life is expected to be 2-6 hours, typical of small molecule beta-blockers. The compound is primarily excreted in urine as metabolites.
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| Toxicity/Toxicokinetics |
Toxicological data for (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol are limited as it is a research reagent and pharmaceutical intermediate. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves, safety glasses, and working in a fume hood. The compound should be stored at 2-8°C in a refrigerator. No acute toxicity data are available. The compound is not intended for drug use without further formulation and testing. It should be stored in a cool, dry place away from light and moisture.
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| Additional Infomation |
(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol is a chiral amino alcohol that serves as a key intermediate in the synthesis of the HIV protease inhibitor Indinavir (Crixivan). It is also known as cis-aminoindanol and (1S,2R)-1-Aminoindan-2-ol (USP). The compound's chirality is critical for its use in asymmetric synthesis and pharmaceutical applications. It has applications in the synthesis of various bioactive compounds and as a chiral resolving agent. The compound has not undergone clinical trials as a standalone drug but is an important intermediate in pharmaceutical manufacturing. Its mechanism of action as a beta-blocker involves competitive antagonism of beta-adrenergic receptors.
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| Molecular Formula |
C9H11NO
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| Molecular Weight |
149.19
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| Exact Mass |
149.084
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| CAS # |
126456-43-7
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| Related CAS # |
(1R,2R)-1-Aminoindan-2-ol;163061-73-2
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| PubChem CID |
9866743
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| Appearance |
White to light yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
290.0±40.0 °C at 760 mmHg
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| Melting Point |
118-121 °C(lit.)
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| Flash Point |
129.2±27.3 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.626
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| LogP |
0.43
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
149
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| Defined Atom Stereocenter Count |
2
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| SMILES |
O([H])[C@]1([H])C([H])([H])C2=C([H])C([H])=C([H])C([H])=C2[C@]1([H])N([H])[H]
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| InChi Key |
LOPKSXMQWBYUOI-BDAKNGLRSA-N
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| InChi Code |
InChI=1S/C9H11NO/c10-9-7-4-2-1-3-6(7)5-8(9)11/h1-4,8-9,11H,5,10H2/t8-,9+/m1/s1
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| Chemical Name |
(1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol
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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: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 6.7029 mL | 33.5143 mL | 67.0286 mL | |
| 5 mM | 1.3406 mL | 6.7029 mL | 13.4057 mL | |
| 10 mM | 0.6703 mL | 3.3514 mL | 6.7029 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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