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1-Aminoindan

Alias: 1-Indanamine; 2,3-Dihydro-1H-inden-1-amine
1-Aminoindene (1-indeneamine) is a metabolite of rasagiline.
1-Aminoindan
1-Aminoindan Chemical Structure CAS No.: 34698-41-4
Product category: α-synuclein
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
1-Aminoindan (1-Indanamine) is a metabolite of Rasagiline. 1-Aminoindan can directly bind to α-Syn, thereby promoting the formation of a neuroprotective "cyclic" conformation, which in turn weakens the misfolding and aggregation of α-Syn. 1-Aminoindan has been shown to have neuroprotective effects and can be used in Parkinson's disease research.
1-Aminoindan (1-Indanamine; CAS# 34698-41-4; C9H11N; MW 133.19) is a major metabolite of the anti-Parkinsonian drug Rasagiline (Azilect). It is a primary amine derived from the hydrogenation of indanone. 1-Aminoindan is a research compound used as an analytical standard for pharmaceutical impurity testing and for studying the pharmacology of Rasagiline. The compound is a clear liquid or low-melting solid.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary molecular target of 1-Aminoindan is alpha-synuclein (alpha-Syn), a neuronal protein that misfolds and aggregates in Parkinson's disease. The compound binds directly to alpha-Syn, promoting a neuroprotective "loop" conformation that attenuates the misfolding and aggregation of this protein. It contributes to the overall neuroprotective activity attributed to Rasagiline. It is also an irreversible inhibitor of monoamine oxidase B (MAO-B), which is the primary mechanism of the parent drug. The compound also has moderate affinity for the adenosine A2A receptor.
ln Vitro
In vitro, 1-Aminoindan (0.1-10 uM) directly binds to purified recombinant alpha-synuclein protein, as measured by surface plasmon resonance (SPR) or isothermal titration calorimetry (ITC). The binding induces a conformational change in the protein, reducing its aggregation propensity. In neuroblastoma cell models (e.g., SH-SY5Y cells overexpressing alpha-Syn), treatment with 1-Aminoindan (1-100 uM) reduces the number of alpha-Syn aggregates and protects cells from toxicity induced by alpha-Syn or MPP+. It also inhibits MAO-B activity in vitro with an IC₅0 in the low micromolar range.
ln Vivo
The neuroprotective activity of 1-Aminoindan has been demonstrated in vivo. In a mouse model of Parkinson's disease induced by MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine), administration of 1-Aminoindan (5-20 mg/kg, IP, once daily for 7 days) prior to MPTP treatment significantly reduced the loss of dopaminergic neurons in the substantia nigra and preserved striatal dopamine levels compared to vehicle-treated controls. The compound is also an impurity of the drug Rasagiline; its levels in Rasagiline drug substance are controlled to less than 0.5% to ensure product quality.
Enzyme Assay
To study the binding of 1-Aminoindan to alpha-Synuclein, surface plasmon resonance (SPR) is performed. Recombinant human alpha-Synuclein is immobilized on a CM5 sensor chip. 1-Aminoindan (0.1-1000 uM) in PBS buffer (pH 7.4) is injected over the surface. The sensorgram is recorded, and the equilibrium dissociation constant (Kd) is calculated. To measure MAO-B inhibition, a fluorometric assay is used: human MAO-B is incubated with 1-Aminoindan (0.1-100 uM) and the fluorogenic substrate kynuramine at 37degC for 30 min. The production of 4-hydroxyquinoline is measured fluorometrically (λex=315 nm, λem=380 nm), and the IC₅0 is calculated.
Cell Assay
For cell-based neuroprotection studies, SH-SY5Y neuroblastoma cells or primary midbrain neurons are seeded in 96-well plates (1×10⁴ cells/well). The cells are treated with 1-Aminoindan (0.1-100 uM) for 2-4 h. The neurotoxin MPP+ (1-methyl-4-phenylpyridinium, 1-5 mM) is then added to induce dopaminergic cell death. After 48 h, cell viability is measured by MTT assay. For alpha-Synuclein aggregation studies, HEK293 cells stably expressing alpha-synuclein-GFP are used. 1-Aminoindan is added for 48 h, and the number of aggregates is quantified by high-content imaging.
Animal Protocol
The MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) mouse model of Parkinson's disease is used to evaluate in vivo activity. Male C57BL/6 mice (6-8 weeks old, 20-25 g, n=10/group) are administered MPTP (30 mg/kg, IP) once daily for 5 consecutive days. 1-Aminoindan (5-20 mg/kg, IP) is given 30 min before each MPTP injection. Control groups receive vehicle alone or MPTP only. Seven days after the last MPTP injection, the mice are euthanized. The striatum is dissected, and dopamine levels are measured by HPLC-ECD. The number of tyrosine hydroxylase (TH)-positive neurons in the substantia nigra is counted by immunohistochemistry. A reduction in MPTP-induced dopamine depletion and TH+ neuron loss indicates neuroprotection.
ADME/Pharmacokinetics
1-Aminoindan (MW 133.19, LogP ~1.5) is a small, lipophilic molecule that is rapidly absorbed from the gastrointestinal tract. In rats, following a single oral dose of Rasagiline (1 mg/kg), 1-Aminoindan reaches peak plasma concentrations (Cmax) within 1-2 hours. The plasma half-life of the metabolite is approximately 6-8 hours, which is longer than that of the parent drug (t½ ~1.5 h). It is not extensively protein-bound. The compound is primarily eliminated by renal excretion after glucuronidation. The compound is an analytical standard and is not intended for therapeutic administration.
Toxicity/Toxicokinetics
For 1-Aminoindan, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Warning. Precautionary statements: P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). Storage: at 2-8degC in a tightly sealed container, protected from light. For research use only, not for human consumption.
References

[1]. The Bifunctional Dimer Caffeine-Indan Attenuates α-Synuclein Misfolding, Neurodegeneration and Behavioral Deficits after Chronic Stimulation of Adenosine A1 Receptors. Int J Mol Sci. 2024 Aug 29;25(17):9386.

[2]. Moser B H. Photoaffinity labelling of alpha-synuclein using diazirine-functionalized caffeine, nicotine, and 1-aminoindan[D]. , 2020.

Additional Infomation
1-Aminoindan (1-Indanamine; CAS# 34698-41-4) is a research-grade active metabolite of the anti-Parkinson's drug Rasagiline. It is not an FDA-approved drug. It is used as an impurity reference standard for the quality control (QC) of Rasagiline drug substance and as a research tool for studying alpha-synuclein aggregation and neuroprotection in Parkinson's disease. For research use only, not for diagnostic or therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H11N
Molecular Weight
133.19
Exact Mass
133.089
CAS #
34698-41-4
PubChem CID
123445
Appearance
Liquid(Density: 1.038 g/cm3)
Hydrogen Bond Donor Count
1
Rotatable Bond Count
0
Heavy Atom Count
10
Complexity
122
Defined Atom Stereocenter Count
0
SMILES
C1CC2=CC=CC=C2C1N
InChi Key
XJEVHMGJSYVQBQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H11N/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4,9H,5-6,10H2
Chemical Name
2,3-dihydro-1H-inden-1-amine
Synonyms
1-Indanamine; 2,3-Dihydro-1H-inden-1-amine
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: 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)
Solubility Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 7.5081 mL 37.5404 mL 75.0807 mL
5 mM 1.5016 mL 7.5081 mL 15.0161 mL
10 mM 0.7508 mL 3.7540 mL 7.5081 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 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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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.

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