| Size | Price | Stock | Qty |
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| 5g |
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| 25g |
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| Targets |
4-Iodobenzylamine hydrochloride serves as a PROTAC linker, connecting an E3 ubiquitin ligase ligand and a target protein ligand via amide bond formation at the primary amine. The iodine atom can be used for further functionalization via cross-coupling reactions (e.g., Suzuki, Sonogashira) or for radiolabeling with isotopes such as ¹2⁵I or ¹3¹I for imaging studies. The compound itself does not have intrinsic biological activity but is a versatile synthetic building block.
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| ln Vitro |
In vitro, 4-iodobenzylamine hydrochloride is used as an intermediate to synthesize various biologically active compounds, including radioligands for serotonin transporters and dopamine receptors. It is also used as a substrate for the enzyme tyrosinase in model studies. The compound has low cytotoxicity; its IC50 in HepG2 cells is >500 uM. It is not intended for direct use in cell-based assays as an active drug. Its main utility is in medicinal chemistry and radiopharmaceutical research.
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| ln Vivo |
In vivo, 4-iodobenzylamine hydrochloride is not used as a therapeutic agent. However, radiolabeled derivatives (e.g., ¹23I-iodobenzylamine) have been studied as potential imaging probes for the norepinephrine transporter (NET) in the heart and brain. These radiotracers can assess sympathetic innervation. The parent compound itself is not administered to animals due to lack of inherent biological activity. It is purely a chemical intermediate.
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| Enzyme Assay |
For PROTAC synthesis, 4-iodobenzylamine hydrochloride is dissolved in DMF or DMSO (10-100 mM). The hydrochloride salt is neutralized with DIPEA or triethylamine (1.1 eq). The free amine is then reacted with an activated carboxylic acid derivative (NHS ester or HATU-mediated) of an E3 ligase ligand or a target protein ligand at 25degC for 2-4 hours. The product is purified by HPLC. For radiolabeling, the compound can be iodinated with radioactive iodine using oxidative methods (e.g., chloramine-T). For stability studies, the compound is incubated in PBS (pH 7.4) at 37degC and monitored by LC-MS.
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| Cell Assay |
For cell-based assays, the final PROTAC molecule containing the 4-iodobenzylamine-derived linker is tested in target cells. Target cells are cultured in appropriate medium (e.g., DMEM with 10% FBS) at 37degC, 5% CO2. The PROTAC is added at concentrations of 1 nM-10 uM for 6-48 hours. Target protein degradation is assessed by Western blotting. Cell viability is measured by MTT. The linker itself is not directly tested. For radiotracer studies, cells expressing the NET are incubated with ¹23I-labeled 4-iodobenzylamine, and uptake is measured. The non-labeled compound is used to determine non-specific binding.
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| Animal Protocol |
For in vivo imaging studies, rodents (e.g., rats or mice) are injected intravenously with a ¹23I-labeled 4-iodobenzylamine derivative (e.g., ¹23I-IBZ). Animals are imaged using SPECT/CT at various time points. Tissue distribution is measured by gamma counting of harvested organs. Blocking studies with non-radioactive compound are performed to assess specificity. The parent 4-iodobenzylamine hydrochloride is used as a precursor for synthesis and is not directly administered. For PROTAC efficacy studies, the PROTAC molecule is used as described previously.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 4-iodobenzylamine hydrochloride itself are not studied. For radiolabeled derivatives, the elimination half-life depends on the overall molecule. Small iodinated benzylamines are rapidly cleared from the blood (t1/2 <30 min) and are taken up by the liver and kidneys. They are metabolized by deamination and glucuronidation. The iodine label can be dehalogenated in vivo, leading to free iodide accumulation in the thyroid. Thyroid blocking (with potassium iodide) is typically performed in imaging studies.
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| Toxicity/Toxicokinetics |
4-Iodobenzylamine hydrochloride has moderate acute toxicity. The oral LD50 in rats is estimated to be 500-1000 mg/kg. It is a skin and eye irritant (category 2). It may cause respiratory irritation if inhaled. It is harmful if swallowed. The compound is not classified as a carcinogen. It should be handled in a well-ventilated fume hood with appropriate PPE (gloves, goggles, lab coat). It should be stored in a sealed container at room temperature, protected from light. Disposal should follow local regulations.
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| References | |
| Additional Infomation |
4-Iodobenzylamine hydrochloride is a versatile building block in medicinal chemistry and chemical biology. It is commonly used as a PROTAC linker for targeted protein degradation. It is also a precursor for the synthesis of radioligands for molecular imaging of the norepinephrine transporter (NET). NET imaging agents have applications in cardiology (e.g., assessment of cardiac sympathetic innervation in heart failure) and neurology (e.g., Parkinson's disease). The compound is not an approved drug. It is for research use only.
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| Molecular Formula |
C7H9CLIN
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|---|---|
| Molecular Weight |
269.51
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| Exact Mass |
268.947
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| CAS # |
59528-27-7
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| Related CAS # |
4-Iodobenzylamine
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| PubChem CID |
16217505
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| Appearance |
White to off-white Powder
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| Hydrogen Bond Donor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
10
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| Complexity |
77
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=CC=C1CN)I.Cl
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| InChi Key |
GBJMURRFWZREHE-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H8IN.ClH/c8-7-3-1-6(5-9)2-4-7;/h1-4H,5,9H2;1H
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| Chemical Name |
(4-iodophenyl)methanamine;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: 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) |
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 | 3.7104 mL | 18.5522 mL | 37.1044 mL | |
| 5 mM | 0.7421 mL | 3.7104 mL | 7.4209 mL | |
| 10 mM | 0.3710 mL | 1.8552 mL | 3.7104 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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