This compound belongs to the class of organic compounds known as n-acetyl-2-arylethylamines. These are compounds containing an acetamide group that is N-linked to an arylethylamine.
External Descriptors
imidazoles - acetamides
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
Item-specific tested application protocols are not provided for this product. For general laboratory use as a reference standard or assay analyte:
LC–MS sample preparation (general):
Dissolve in water or 50:50 water:methanol to prepare a 1–10 mM stock. Filter (0.22 µm). Store aliquots at −20°C.
Spike into matrix, precipitate proteins with cold acetonitrile or methanol (3:1, v/v), centrifuge, and analyze supernatant.
HPLC–UV:
Mobile phase: water (0.1% formic acid) / acetonitrile gradient; detect at 210–220 nm.
Use an imidazole-friendly column (C18 or polar-embedded) to improve peak shape.
Enzymatic assays (HNMT/HAT research):
Prepare fresh aqueous working solutions; maintain assay pH 6–7.4 and include appropriate controls and internal standards.
These are literature-style, non-validated suggestions. Optimize for your specific instrumentation and matrix. No diagnostic or clinical use is implied.
Biological Roles
Literature context (non-clinical):
Metabolic role: Nω-acetylhistamine is the N-acetylated metabolite of histamine formed by histamine N-acetyltransferase (HNMT/HAT depending on organism). It participates in histamine catabolism in diverse tissues.
Chemical features influencing biology:
Amide formation neutralizes the primary amine of histamine, reducing basicity and modifying transporter/receptor interactions relative to histamine.
The imidazole ring remains capable of protonation near physiological pH, affecting binding and solubility.
Research utilities:
Serves as a standard or spike-in control for quantifying histamine turnover in biochemical assays and metabolomics.
Useful for studying enzyme specificity of N-acetyltransferases and for mapping histamine metabolic flux.
Notes and boundaries:
No medical or therapeutic claims are made. Use is restricted to research and laboratory investigations.
Detailed biological pathway placement, enzyme kinetics, and organism-specific data should be sourced from primary literature pertinent to the experimental model.
Buffer Applications
This compound is not typically used as a buffering agent. While its imidazole ring exhibits acid–base behavior near neutral pH, dedicated buffers (e.g., phosphate, HEPES, MOPS, imidazole itself) are preferred for reproducible pH control.
Practical guidance:
If included in assays, account for its minor buffering capacity around pH ~6–7 (literature) when modeling ionic strength, but do not rely on it to set pH.
Select buffers compatible with imidazole-containing analytes and your detection method (e.g., volatile ammonium formate/acetate for LC–MS).
For robust buffer recipes and pH ranges, consult standard buffer tables; Nω-acetylhistamine is best treated as an analyte, not a buffer component.
Green Alternatives
Because Nω-acetylhistamine is a polar, water-compatible metabolite standard, greener choices focus on solvent systems and workup rather than replacing the compound itself.
Prefer aqueous systems:
Use water or aqueous buffers as primary media for dissolution and chromatography where feasible (e.g., HILIC or RP with high aqueous content).
Greener organic cosolvents:
Favor ethanol over acetonitrile or methanol when assay constraints allow (recognizing impacts on UV cutoff and viscosity).
Isopropanol can substitute for acetonitrile in some LC gradients to reduce toxicity, at the cost of higher backpressure.
Avoid problematic solvents:
Minimize DMF/DMAC; choose DMSO or water when high polarity is required.
Solid-phase extraction (SPE):
Use water-wettable sorbents to avoid large volumes of chlorinated solvents during cleanup of biological matrices.
Example comparison (general):
Acetonitrile + 0.1% formic acid (common) vs Ethanol + 0.1% formic acid (greener): ethanol may yield broader peaks and higher pressure; validate resolution and sensitivity.
Waste minimization:
Prepare concentrated stocks and aliquot to reduce discarded, degraded solutions.
Adopt microflow LC-MS where possible to decrease solvent consumption.
Pharmaceutical Uses
No excipient or formulation role is specified for this item; it is supplied for research use only.
Literature/industry context (non-clinical):
Analytical reference: may be used in pharmaceutical R&D and QC laboratories as a reference standard or system suitability control when developing assays that monitor histamine metabolism or related impurities in raw materials and biological samples.
Advantages as a standard: polar, UV-active (200–230 nm) and readily ionizable in positive ESI, enabling dual-mode detection (HPLC–UV and LC–MS).
Compliance note:
This catalog item is not intended for human or veterinary use, not for diagnostic procedures, and is not accompanied by pharmacopeial certification unless explicitly stated on the CoA/label. Always verify suitability and specification requirements for regulated workflows.
Physical Properties
Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.
Literature and general properties (for reference; not product specifications):
Physical state/appearance: typically a solid, polar, water-soluble imidazole amide.
Ionization/acid–base: imidazole pKa (literature) ~6.0–7.0 depending on medium; the acetamide N is nonbasic and the amide carbonyl does not ionize under neutral conditions.
Solubility profile (qualitative, literature):
Water: good solubility expected due to amide + heteroaromatic nitrogens.
Polar organics: soluble in methanol, ethanol, and DMSO; limited in nonpolar solvents (e.g., hexanes, toluene).
Partitioning: low logP/negative logD at neutral pH is typical for histamine derivatives due to polarity and potential charge.
Hygroscopicity: may absorb moisture due to multiple hydrogen-bonding sites (verify per lot).
UV: imidazole ring shows UV absorbance in the 200–230 nm region (literature), enabling HPLC-UV detection; strongest in low-UV solvents.
Practical notes:
For analytical work, prepare fresh aqueous/DMSO stocks and verify pH; the imidazole tautomerism can subtly affect retention in RP-HPLC.
If reporting numerical constants (mp, bp, density, exact solubilities), consult primary literature or the item’s CoA/SDS; they are not specified here.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay, residual solvents, and related-substance limits.
Interpreting typical grades (general guidance):
Research/Biochemical grade: intended for laboratory use; impurity profiles suitable for routine synthesis, enzymology, or standards work.
HPLC/Analytical grade reference: tighter limits on UV-absorbing impurities and residual solvents; validated for chromatographic purity and often provided with chromatograms.
Trace metal specifications: rarely critical for this small-molecule metabolite; if required (e.g., for catalysis-sensitive assays), verify via ICP data on the CoA.
Stabilizers/additives:
None indicated in Product Data. If stabilizers (e.g., anti-caking agents) are present, they will be disclosed on the CoA/SDS.
What to request for method development:
Full CoA with assay method (e.g., HPLC area %), water content (Karl Fischer), related substances, and residual solvents.
For quantitative bioanalytical use (LC–MS), consider obtaining a certified reference material (CRM) or internal standard (isotopically labeled) where appropriate.
Lot-to-lot consistency:
For sensitive quantitative assays, procure a single lot or qualify multiple lots to ensure retention time, response factor, and impurity profile consistency.
Reaction and Applications
This compound is predominantly used as a biochemical/analytical standard and a metabolite probe rather than as a general-purpose reagent.
Applications (general, literature-based):
Biochemical standard: reference material for quantifying histamine N-acetylation products in enzymology (histamine N-acetyltransferase assays) and metabolomics (LC–MS/MS or HPLC–UV).
Ligand/competitor in receptor-binding or transporter studies involving histamine metabolites (non-clinical research only).
Calibration/validation: system suitability standard for chromatographic methods targeting imidazole-containing metabolites.
Chemical reactivity considerations:
Amide stability: resistant to mild acids/bases; hydrolyzes slowly only under forcing conditions (e.g., strong base or acid at elevated temperatures).
Imidazole functionality: can engage in N-alkylation/acylation or coordinate to metals; protonation state modulates reactivity and binding.
Practical tips:
For enzymatic assays, prepare fresh aqueous stocks, maintain pH 5.5–7.4, and minimize freeze–thaw.
In LC–MS, use volatile buffers (formate/acetate, pH 3–6) to enhance ionization and reduce adduct formation.
Include isotopically labeled internal standards when quantifying in complex matrices.
Manufacturer applications: Not specified in Product Data; above use cases are common literature practices for this metabolite and should be tailored to your assay design.
Reaction Conditions
General, literature-informed conditions for transforming imidazole amides such as Nω-acetylhistamine (for research chemistry; not item specifications):
Imidazole N-alkylation:
Base: K2CO3, Cs2CO3, or NaH in DMF/DMSO or acetonitrile.
Electrophiles: alkyl halides, sulfonates.
Temperature: 0–60°C; hours to overnight. Monitor by LC–MS.
Notes: mixtures of Nτ/Nπ isomers may form; separation by chromatography may be required.
Amide activation/derivatization (side chain):
Reagents: CDI, EDC/HOBt (or Oxyma), or SOCl2 to form acid chloride from acyl variants (for analogs where the acyl group is changed, starting from histamine + acid derivative).
Solvents: DMF, DCM, or mixed aqueous/organic for carbodiimide couplings.
Temperature: 0–25°C for couplings; 40–70°C for chlorination steps with SOCl2.
Hydrolysis (analytical degradation):
Acidic: 1–6 M HCl, 60–100°C; hours to convert to histamine (and acetate).
Basic: 1–6 M NaOH/KOH, reflux; hours. Use only for controlled studies.
Analytical detection:
HPLC: aqueous 0.1% formic acid + ACN/MeOH; UV at ~210 nm and MS (ESI+). Retention sensitive to pH and organic content.
Always validate conditions on small scale; the imidazole can be sensitive to over-alkylation or ring-opening under harsh conditions.
Safety and Handling
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the current SDS for authoritative information.
Expected hazards (general): Low–moderate acute toxicity typical of small polar amides; may cause skin/eye/respiratory irritation. Avoid dust generation and inhalation.
PPE (good laboratory practice):
Lab coat, safety glasses or splash goggles, and appropriate disposable gloves (e.g., nitrile).
Use in a chemical fume hood when handling powders or preparing concentrated solutions.
Incompatibilities (general chemistry):
Strong oxidizers (risk of oxidation of the imidazole ring/side chain).
Strong acids/bases can lead to hydrolysis (amide under strongly basic or strongly acidic, high-temperature conditions) or protonation state changes impacting handling.
First-aid overview (non-exhaustive; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical advice for irritation.
Ingestion: rinse mouth; do not induce vomiting; obtain medical attention.
Fire safety: Organic solid; use water spray, CO2, dry chemical, or foam as appropriate. Combustion may produce nitrogen oxides and carbon oxides.
Spillage: Avoid dust, collect with inert absorbent or sweep gently; wash area with water. Dispose according to institutional and local regulations.
Always consult the SDS before use; the above are general lab-safety considerations for imidazole-containing amides.
Solvent Selection
Nω-Acetylhistamine is a small, polar, imidazole-bearing amide; solvent choice should reflect its high hydrogen-bonding capacity and potential protonation around neutral pH.
Polarity and miscibility (general):
Prefer aqueous media, aqueous buffers (pH ~4–8), methanol, ethanol, or DMSO. Limited solubility in nonpolar solvents.
Typical stock solutions:
Aqueous: 10–100 mM stocks are commonly achievable; adjust pH slightly acidic (pH 5–6) to enhance stability/solubility if needed.
DMSO: suitable for concentrated stocks for spiking into aqueous systems (keep final DMSO ≤1–2% v/v for biochemical assays).
Chromatography solvents:
RP-HPLC: water with 0.1% formic acid (or ammonium formate/acetate) and acetonitrile/methanol. Imidazole’s basic site benefits from volatile acidic modifiers for sharp peaks and positive-ion ESI.
Comparison guidance (general):
Water/buffer: best for biological assays and ionizable analyte stability.
Methanol vs acetonitrile: methanol can increase retention and peak shape for basic heterocycles; acetonitrile provides lower backpressure and stronger elution.
Avoid strong nonpolar solvents (hexanes, toluene): poor solubility and risk of precipitation.
Practical tips:
Filter aqueous stocks (0.22 µm) to remove particulates before analytical injections.
Check pH after dissolution; protonation of the imidazole can change retention and detector response.
Storage and Reconstitution
Storage (Product Data): Store at −20°C. Shipped in ice chest with ice pads to maintain cold chain.
Research use note: For research use only.
General handling guidance:
Upon receipt: allow the sealed container to equilibrate to room temperature before opening to minimize moisture condensation; then promptly reseal or aliquot.
Reconstitution:
Solvents: water, aqueous buffer (pH 5–7), or DMSO for concentrated stocks. Methanol/ethanol are also suitable cosolvents.
Typical concentrations: 1–100 mM, depending on downstream use. Filter through 0.22 µm for analytical applications.
Prepare single-use aliquots to avoid repeated freeze–thaw. Store frozen (−20°C) protected from light and moisture.
Solid-state stability is generally good when kept dry and cold; solution stability varies by solvent/pH—verify by HPLC/LC–MS over time for critical work.
Incompatibilities: Avoid contact with strong oxidizers. Do not store solutions in reactive plastics for long periods; use glass vials when possible.
For definitive shelf-life and retest information, consult the item’s CoA/Spec Sheet.
Structure and Identity
Nω-Acetylhistamine is the N-acylated derivative of histamine, bearing an acetamide on the side-chain primary amine and an unsubstituted imidazole ring.
Item-specific identifiers (Product Data):
CAS: 673-49-4
InChIKey: 419901 (as provided; refer to CoA/SDS for confirmation)
SKU: N340451
Literature identity (for reference only; not item-specific specifications):
Common name: N-Acetylhistamine; 2-(1H-imidazol-4-yl)ethylacetamide
Protonation states: imidazole ring can be protonated/deprotonated near neutral pH; the amide nitrogen is nonbasic.
2D description: an acetamide (CH3–CO–NH–) connected to –CH2–CH2– which is attached at C-4 of an imidazole ring; the ring retains one [N–H] (1H-imidazole).
Notes: Structural strings and formula above are provided as literature references to aid method development and do not supersede the item’s official CoA/Spec Sheet.
Synthetic Utility
Although primarily a metabolite standard, Nω-acetylhistamine has features of interest to synthetic and medicinal chemists.
Functional group handles:
Primary amide (acetamide): generally inert under mild conditions; can be activated (e.g., via CDI, SOCl2) to form more reactive intermediates if derivatization of the side chain is desired.
Imidazole ring: nucleophilic at N and C-2 under appropriate conditions; can undergo N-alkylation/acylation or metal-catalyzed C–H functionalization.
Typical transformations (literature):
N-alkylation on the imidazole with alkyl halides under basic conditions (risk of mixtures; protect/deprotect strategies may be required).
Cross-coupling from pre-functionalized imidazole derivatives (e.g., 4- or 5-halogenated analogs) to elaborate structure–activity series.
Hydrolysis back to histamine under forcing conditions (synthetic degradation control or labeled-compound preparation).
Retrosynthetic value:
Serves as a node in libraries of histamine analogs: varying the acyl group (propionyl, butyryl, aromatic) modulates polarity and receptor interaction for SAR studies in research.
Practical notes:
Control protonation state (slightly basic conditions) to direct N-alkylation on imidazole vs competing O/N-acyl migrations.
For selective Nτ vs Nπ functionalization, consider temporary protection of the alternative imidazole nitrogen.
Target Specificity
Not applicable. This product is a small-molecule metabolite and not an antibody, enzyme, or affinity reagent. No target specificity, clone, isotype, or species reactivity information is provided or relevant for this item.
Perguntas frequentes
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 673-49-4, the molecular formula is C7H11N3O, and the molecular weight is 153.18 g/mol. InChIKey XJWPISBUKWZALE-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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