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N-Acetylputrescine hydrochloride

Cat No.:V32170 Purity: ≥98%
N-Acetylputrescine HCl is a putrescine analogue.
N-Acetylputrescine hydrochloride
N-Acetylputrescine hydrochloride Chemical Structure CAS No.: 18233-70-0
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
500mg

Other Forms of N-Acetylputrescine hydrochloride:

  • N-Acetylputrescine (NAP)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
N-Acetylputrescine HCl is a putrescine analogue.
N-Acetylputrescine hydrochloride (CAS 18233-70-0) is the N-acetylated derivative of putrescine, a naturally occurring polyamine. It is a polyamine metabolite commonly found in normal human urine and serves as a key research tool for investigating polyamine metabolism, catabolism, and transport. The compound regulates cell proliferation and signal transduction mainly by participating in polyamine acetylation modification. N-Acetylation of polyamines, mediated by the enzyme diamine N-acetyltransferase, reduces the positive charge of polyamines, affects protein-nucleic acid interactions, and facilitates polyamine excretion. The hydrochloride salt form improves the compound's solubility and stability for research applications. Its molecular formula is C₆H₁₄N₂O·HCl with a molecular weight of 166.65.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary molecular target of N-acetylputrescine is the polyamine metabolic pathway, specifically the enzyme diamine N-acetyltransferase (also known as spermidine/spermine N¹-acetyltransferase, SSAT). This enzyme catalyzes the N-acetylation of polyamines, including putrescine, spermidine, and spermine, as the first and rate-limiting step in polyamine catabolism. N-Acetylputrescine is the product of putrescine acetylation by SSAT. The compound also serves as a substrate for polyamine oxidase, which further degrades N-acetylated polyamines. By participating in polyamine acetylation modification, N-acetylputrescine regulates cell proliferation and signal transduction. The acetylation of polyamines reduces their positive charge, affecting their interactions with nucleic acids and proteins.
ln Vitro
In vitro studies of N-acetylputrescine hydrochloride focus on its role as a polyamine metabolite and its use in studying polyamine metabolism. The compound is used as a substrate or inhibitor in enzyme assays for diamine N-acetyltransferase and polyamine oxidase. In biochemical assays, N-acetylputrescine is used to study the regulation of polyamine acetylation and its effects on cellular processes. The compound's stability in biological samples and its behavior under various analytical conditions have been characterized. It is also used as a standard in analytical chemistry for the identification and quantification of polyamine metabolites in biological samples. The compound's acetylation modification reduces the positive charge of polyamines, which affects protein-nucleic acid interactions and may influence gene expression and cellular signaling. In cellular studies, N-acetylputrescine hydrochloride is used to investigate polyamine metabolism and its role in cell proliferation, differentiation, and apoptosis. The compound may help in disease diagnosis, such as early screening and efficacy evaluation of lung cancer. In cell culture models, N-acetylputrescine can be used to modulate polyamine metabolism and to study the effects of polyamine acetylation on cellular function. The compound's ability to reduce the positive charge of polyamines may affect protein-nucleic acid interactions and influence cellular processes such as gene expression, DNA replication, and signal transduction. N-Acetylputrescine is also used in studies of polyamine transport and excretion, as N-acetylated polyamines are more readily excreted from cells.
ln Vivo
In vivo studies of N-acetylputrescine hydrochloride focus on its role as a metabolic marker in clinical research. The compound is commonly found in normal human urine and serves as a biomarker of polyamine metabolism. Its levels in urine reflect the activity of polyamine metabolism and can be altered in various disease states, including cancer. In animal models, N-acetylputrescine levels may be measured to assess polyamine metabolism and to evaluate the effects of pharmacological interventions targeting polyamine pathways. The compound is typically measured in urine, blood, or tissue samples by analytical methods such as LC-MS or HPLC. No specific pharmacological or toxicological in vivo studies have been reported for this compound.
Enzyme Assay
For enzyme assays, diamine N-acetyltransferase (SSAT) activity is measured using putrescine or spermidine as substrate and acetyl-CoA as acetyl donor. The reaction mixture contains enzyme source (cell lysate or purified enzyme), substrate (1-10 mM putrescine), acetyl-CoA (0.1-1 mM), and assay buffer (50 mM Tris-HCl, pH 7.8, containing 1 mM DTT) at 37°C for 10-30 minutes. The reaction is terminated by heating or acidification. Product formation (N-acetylputrescine) is measured by HPLC with fluorescence detection (after derivatization with dansyl chloride or o-phthalaldehyde) or by radiometric assay using [¹⁴C]-acetyl-CoA. For polyamine oxidase assays, N-acetylputrescine is used as substrate, and the reaction product (putrescine and acetaldehyde) is measured by HPLC or by following the production of H₂O₂ using peroxidase-coupled assays. For inhibition studies, varying concentrations of test compounds are added to the reaction mixture, and IC50 values are calculated.
Cell Assay
For cellular studies, cells (e.g., cancer cell lines, primary cells) are cultured in appropriate medium (RPMI-1640 or DMEM) with 10% FBS and antibiotics at 37°C in 5% CO₂. Cells are seeded in 6-well or 12-well plates and grown to 70-80% confluence. N-Acetylputrescine hydrochloride is dissolved in water or PBS and added to the culture medium at final concentrations (typically 0.1-100 µM). Cells are treated for 24-72 hours. Cell proliferation is assessed by cell counting, MTT, or BrdU incorporation assays. For polyamine metabolism studies, cells are harvested, and intracellular polyamines (putrescine, spermidine, spermine) and N-acetylputrescine are extracted with perchloric acid or trichloroacetic acid and analyzed by HPLC with fluorescence detection after derivatization. For gene expression studies, RNA is extracted, and SSAT and other polyamine metabolism genes are analyzed by qRT-PCR. Protein expression is assessed by Western blot. For apoptosis assays, cells are stained with Annexin V/PI and analyzed by flow cytometry.
Animal Protocol
For in vivo studies in animal models, N-acetylputrescine hydrochloride is typically not administered as a test compound. However, in metabolomics studies, animals (e.g., mice or rats) are used as models for metabolic and disease research. Urine, blood, and tissue samples are collected, and N-acetylputrescine levels are measured by LC-MS or GC-MS. For studies of cancer, animals may be implanted with tumor cells, and N-acetylputrescine levels in urine are monitored as a biomarker of tumor progression and response to therapy. Body weight, tumor volume, and other clinical parameters are monitored. No specific dosing or administration protocols are reported in the literature for this compound.
ADME/Pharmacokinetics
Pharmacokinetic data for N-acetylputrescine hydrochloride are not applicable, as the compound is an endogenous metabolite rather than a drug. As a naturally occurring compound, N-acetylputrescine is continuously produced and metabolized in the body as part of normal polyamine metabolism. Its levels in urine reflect its production and clearance rates. The compound is excreted in urine, and its urinary excretion is a marker of polyamine metabolism. No specific pharmacokinetic parameters (absorption, distribution, metabolism, excretion) are reported, as these are inherent to its role as an endogenous metabolite.
Toxicity/Toxicokinetics
N-Acetylputrescine is a normal constituent of human urine and is considered a non-toxic metabolite at physiological concentrations. No acute toxicity, organ-specific toxicity, or mutagenicity data have been reported for this compound. As a research chemical, N-acetylputrescine hydrochloride should be handled according to standard laboratory safety protocols, including the use of personal protective equipment (gloves, lab coat, safety glasses) and work in a well-ventilated area. The compound is typically used at low concentrations (micromolar range) in research applications, which are considered safe.
References

[1]. N-acetylputrescine as a characteristic constituent of cyanelle peptidoglycan in glaucocystophyte algae. J Bacteriol. 1996 Dec;178(23):6994-7.

[2]. Formulation of N-acetylputrescine and N1-acetylspermidine in cultured human lymphocytes. Biochem J. 1980 Apr 15;188(1):263-7.

[3]. Plasma N-acetylputrescine, cadaverine and 1,3-diaminopropane: potential biomarkers of lung cancer used to evaluate the efficacy of anticancer drugs. Oncotarget. 2017 Jul 17;8(51):88575-88585.

[4]. Identification and Validation of N-Acetylputrescine in Combination With Non-Canonical Clinical Features As a Parkinson's Disease Biomarker Panel[J]. bioRxiv, 2021: 2021.07. 23.453542.

Additional Infomation
See also: N-acetylputrescine (note moved to).
N-Acetylputrescine hydrochloride (CAS 18233-70-0) is the N-acetylated derivative of putrescine, a naturally occurring polyamine. It is a polyamine metabolite commonly found in normal human urine. The compound regulates cell proliferation and signal transduction by participating in polyamine acetylation modification. Its acetylation is mediated by the enzyme diamine N-acetyltransferase (SSAT), and it serves as a substrate for polyamine oxidase in polyamine catabolism. N-Acetylputrescine hydrochloride is used as a research tool for investigating polyamine metabolism, catabolism, and transport. It may also help in disease diagnosis, such as early screening and efficacy evaluation of lung cancer. The compound's molecular formula is C₆H₁₄N₂O·HCl with a molecular weight of 166.65. It is strictly for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H14N2O.HCL
Molecular Weight
166.6491
Exact Mass
166.087
CAS #
18233-70-0
Related CAS #
N-Acetylputrescine; 5699-41-2; N-Acetylputrescine hydrochloride; 18233-70-0
PubChem CID
12471560
Appearance
White to off-white solid powder
Density
0.948g/cm3
Boiling Point
301ºC at 760mmHg
Flash Point
135.8ºC
Vapour Pressure
0.000119mmHg at 25°C
Source
Endogenously produced metabolite
LogP
1.754
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
4
Heavy Atom Count
10
Complexity
83.1
Defined Atom Stereocenter Count
0
SMILES
CC(NCCCCN)=O.Cl
InChi Key
XBECFEJUQZXMFE-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H14N2O.ClH/c1-6(9)8-5-3-2-4-7;/h2-5,7H2,1H3,(H,8,9);1H
Chemical Name
N-(4-aminobutyl)acetamide;hydrochloride
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: 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)
Solubility Data
Solubility (In Vitro)
H2O : ~200 mg/mL (~1200.12 mM)
DMSO : ≥ 125 mg/mL (~750.08 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (12.48 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 20.8 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: ≥ 2.08 mg/mL (12.48 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 20.8 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.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (12.48 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 100 mg/mL (600.06 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.0006 mL 30.0030 mL 60.0060 mL
5 mM 1.2001 mL 6.0006 mL 12.0012 mL
10 mM 0.6001 mL 3.0003 mL 6.0006 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.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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