This compound belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.
External Descriptors
Not available
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
No vendor-validated biological assay protocols are provided for this item. Typical research uses (general guidance):
IR/Raman spectroscopy: Prepare dry solutions (e.g., in D2O, acetonitrile-d3) at known concentrations; collect spectra to resolve amide I/II′ bands.
2H NMR quantitation: Acquire 2H NMR of neat material or solutions to assess deuterium content; cross-check with 1H NMR for residual protium.
Neutron scattering: Formulate samples in deuterated media to optimize contrast; verify isotopic enrichment and sample homogeneity.
For application-specific conditions, consult primary literature and adapt to instrument and sample constraints.
Biological Roles
General context (literature): N-Methylacetamide (NMA) is widely used as a small-molecule analog of the peptide bond. It reproduces key hydrogen-bonding and dipole characteristics of amide linkages in proteins and peptides.
Neutron scattering: Enhanced contrast relative to protiated matrices allows interrogation of solvation shells and H-bond networks.
Biochemical insights enabled:
Peptide backbone solvation and hydrogen-bond cooperativity in water and mixed solvents
Kinetic isotope effects in enzyme-mimetic or model systems involving amide proton transfer or enolization
Calibration/validation of computational force fields for peptide-like amide interactions
Important caveats:
NMA-d7 is a research tool; it does not have an endogenous biological role.
Isotopic labeling can slightly modify physical properties (diffusivity, vibrational frequencies), which should be accounted for when extrapolating to native systems.
Buffer Applications
This product is not a buffering reagent and is not typically used to prepare defined pH buffer systems. For experiments requiring controlled pH, select standard buffer components (e.g., phosphate, acetate, HEPES) and, if needed, combine with NMA-d7 as a cosolvent or probe. Refer instead to the Solvent Selection and Reaction & Applications sections for relevant use cases.
Green Alternatives
As a strongly hydrogen-bonding amide with high polarity and boiling point, NMA-d7 is selected for specialized isotopic and spectroscopic roles rather than general solvent use. When environmental or process considerations dominate, consider the following (literature-based, application-dependent):
Potential alternatives and trade-offs:
D2O: green, nonflammable, low toxicity; excellent for aqueous spectroscopy and NMR. Lacks strong aprotic H-bond accepting character; may not mimic peptide-bond solvation as well.
Ethanol-d6: bio-derived option with good handling; weaker H-bond accepting than NMA, lower bp (78 °C), flammable.
2-MeTHF-d (where available): bio-based ether, improved safety vs THF; much less polar and not peptide-mimetic.
DMSO-d6: excellent polar aprotic, recyclable; strong acceptor but poor donor; different H-bonding profile vs amides.
Small qualitative comparison (literature):
NMA-d7: very high polarity, strong donor/acceptor, peptide-bond analog, high bp
D2O: greenest option, strong donor/acceptor via water network, low bp, different solvation microstructure
DMSO-d6: polar aprotic, high bp, recyclable; not a donor
MeCN-d3: lower bp and viscosity; reduced environmental burden per cycle but inferior H-bonding
Selection guidance: If the scientific aim is peptide-bond mimicry or amide vibrational isolation, NMA-d7 has no direct “green” substitute. For general deuterated solvent needs, D2O, ethanol-d6, or DMSO-d6 are often greener.
Pharmaceutical Uses
Role category: research reagent. No pharmacopeial grade or excipient designation is provided for this item.
Formulation research (general/literature): N-Methylacetamide is occasionally employed in preformulation or mechanistic studies as a peptide-bond mimetic solvent/cosolvent to interrogate hydrogen bonding, solvatochromism, or excipient–API interactions. The d7 isotopologue allows spectroscopic deconvolution and tracer studies without adding 1H background.
Manufacturing/analytical contexts:
Spectroscopic marker for process analytics (IR/Raman/NMR) in research settings
Isotopic tracer for studying moisture exposure, H/D exchange, or solvent–API interactions in model systems
No therapeutic or clinical use is implied. For regulated applications, verify suitability, impurity profile, and isotopic enrichment on the CoA.
Physical Properties
Item-specific specs are not provided in the Product Data. The following values are literature/typical for N‑methylacetamide (parent) or the d7 isotopologue where noted; do not treat as this item’s specifications.
Phase/appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point (literature, parent N-methylacetamide): ~28–30 °C
Boiling point (literature, parent): ~199–204 °C at 1 atm
Density (literature, parent): ~1.01–1.03 g/mL at 20–25 °C (liquid state above mp)
Refractive index (literature, parent): n20 D ~1.43 (reported values vary)
Solubility (literature): miscible with water and many polar organics (alcohols, DMF, DMSO); limited in nonpolar solvents (hexanes, toluene)
Hydrogen-bonding: strong H-bond donor (N–D) and acceptor (C=O)
LogP (literature, parent): approximately −1 to −1.2 (highly hydrophilic)
Dielectric constant (literature, parent): ~170 at 25 °C (very high, reflective of strong polarity)
Notes:
Isotopic substitution (H→D) minimally affects phase transitions and polarity but slightly shifts vibrational frequencies and can subtly change density/boiling point; treat above values as guidance only for the d7 analog.
Quality & Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Isotopic enrichment: For deuterated materials, enrichment level (%D at each site or overall) is a critical quality attribute that affects spectroscopic background and tracer fidelity.
Enrichment for this product is not specified in the Product Data; consult the CoA for percent deuteration at N–D and both methyl groups.
Typical analytical controls for deuterated amides (general guidance):
1H/2H NMR to quantify residual protium and site-specific enrichment
GC/LC and Karl Fischer (if applicable) for organic purity and water
IR (amide I/II band positions) and MS (exact mass shift for d7)
Implications for applications:
High D-enrichment minimizes background in 1H NMR and maximizes contrast in neutron scattering and IR band assignment.
Trace water/protic solvents accelerate H/D back-exchange at N–D and the acetyl methyl (via acid/base catalysis); moisture control is recommended.
Stabilizers/additives: None stated for this item. If present, they would be declared on the CoA; verify absence/presence before sensitive spectroscopic or kinetic studies.
Isotopic tracer in mechanistic studies of hydrogen bonding, peptide-bond mimetics, and solvation dynamics
Spectroscopic assignments: shifts amide I/II bands in IR/Raman; reduces 1H background in NMR; enhances contrast in neutron scattering
Reference compound for calibrating 2H NMR and for H/D exchange kinetics at amide positions
Representative applications:
H/D exchange and kinetic isotope effect (KIE) studies at the amide N–D and the acetyl methyl C–D3 (enolization-mediated exchange)
Solvation and denaturation studies for peptides/proteins using NMA as a peptide bond analog
Benchmarking computational methods (DFT, MD) against experimental vibrational and thermodynamic data of a deuterated amide
Practical tips:
Minimize contact with protic media and acid/base catalysts to avoid loss of deuterium (especially N–D and acetyl methyl C–D’s).
For IR: record spectra in dry cells/solvents; deuteration cleanly separates amide II/II′ bands, aiding assignments.
For NMR: 2H NMR provides quantitative enrichment; residual 1H can be integrated to assess back-exchange.
For kinetic studies: maintain constant ionic strength and temperature; note that isotope substitution can subtly affect viscosity and diffusion.
Limitations:
High boiling point and strong H-bonding can slow mass transfer; consider cosolvents (e.g., D2O, acetonitrile-d3) to tune viscosity/polarity as compatible with study goals.
Reaction Conditions
The following are general literature-style guidelines for amide chemistry and isotopic preservation; they are not item-specific specifications.
Drying/handling: Work under dry nitrogen/argon when isotopic integrity is critical. Use pre-dried glassware and anhydrous cosolvents (e.g., acetonitrile-d3, DMSO-d6).
Preserving deuteration:
Avoid prolonged exposure to protic solvents (H2O, alcohols) and Bronsted acids/bases.
For IR/NMR studies, keep water <0.1% when feasible; store/measure at neutral conditions to minimize exchange.
Representative transformations (general):
N-alkylation: NaH (1.1–1.5 equiv), dry DMF-d7 or THF-d8, 0–25 °C, 1–6 h; quench carefully with D2O to limit back-exchange to protium.
Acyl activation (for derivatization): carbodiimides (e.g., DIC/EDC) or SOCl2-type activators at 0–25 °C; monitor for isotope scrambling.
Enolization studies: LDA in THF-d8 at −78 to −20 °C to probe acetyl C–D exchange kinetics; quench with D2O to maintain labeling.
Expected observations:
Amide vibrational bands shift upon deuteration (amide II→II′); monitor by IR (1600–1500 cm−1 region) and compare to protiated controls.
Workup tips:
Use deuterated quench (D2O, CD3OD) when possible.
Remove high-boiling NMA-d7 under high vacuum at gentle warming, if used as a solvent/cosolvent; avoid elevated temperatures that could promote exchange or decomposition.
Safety & Handling
Authoritative safety classification is not provided in the Product Data. Always consult the SDS for this specific lot/isotopologue.
GHS/CLP classification: Not specified for this item; refer to SDS.
Signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.
General hazards (amide class, general knowledge): Low volatility; may cause irritation to skin, eyes, and respiratory tract upon contact or aerosol exposure. Not a peroxide-forming solvent.
Work in a fume hood if heating, aerosolizing, or weighing powders to minimize inhalation.
Handling/storage cautions:
Keep container tightly closed; amides are hygroscopic to varying degrees and can absorb moisture.
Avoid strong oxidizers and strong bases/acids that can catalyze exchange or hydrolysis.
For isotopically labeled material, minimize exposure to protic media and acidic/basic catalysts to limit H/D back-exchange.
First aid (overview; defer to SDS):
Skin/eye contact: Rinse with copious water for ≥15 minutes; remove contaminated clothing; seek medical advice if irritation persists.
Inhalation: Move to fresh air; provide oxygen/medical attention if symptoms occur.
Ingestion: Rinse mouth; seek medical attention; do not induce vomiting unless directed.
Fire response: Use water spray, CO2, dry chemical, or foam as appropriate to surroundings; combustion may produce CO/CO2 and nitrogen oxides.
Solvent Selection
N-Methylacetamide (NMA) is a highly polar, strongly hydrogen-bonding amide. The d7 isotopologue is used less as a bulk solvent and more as an isotopic probe or cosolvent.
Polarity and miscibility (literature):
Very high dielectric constant; excellent hydrogen-bond donor and acceptor
Miscible with water, alcohols, DMSO, DMF, acetonitrile; poor solubility in nonpolar hydrocarbons
When to choose NMA-d7 vs alternatives:
Choose NMA-d7 as a model solvent for peptide-bond environments, H-bond networks, or as a spectroscopically silent (in 1H) cosolvent.
Prefer DMSO-d6, DMF-d7, or acetonitrile-d3 when lower viscosity or weaker H-bonding is required, or when high boiling point is undesirable.
Practical notes:
Above its melting point (~28–30 °C, literature for parent), it is a mobile liquid; mild warming can aid handling if solid at room temperature.
Water content strongly influences hydrogen bonding and IR/NMR signatures; dry if needed (e.g., molecular sieves 3Å/4Å) and minimize exposure to humid air to preserve isotopic integrity.
Small comparison (literature, qualitative):
NMA-d7: very polar, strong H-bond donor/acceptor, bp ~200 °C, excellent for peptide-mimetic environments
DMSO-d6: very polar aprotic, strong acceptor/poor donor, bp 189 °C, good general deuterated solvent
DMF-d7: polar aprotic, lower H-bonding, bp 153 °C, good for polar substrates
MeCN-d3: polar aprotic, low viscosity, bp 82 °C, easy removal
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Container: Store in a tightly sealed, chemically compatible container to limit moisture ingress and H/D back-exchange.
Light/moisture sensitivity: Protect from ambient moisture; isotopic integrity is best preserved under dry conditions. Normal laboratory light is typically acceptable.
Freezing/thawing: Not generally required. If solid at room temperature (mp ~28–30 °C for parent, literature), gentle warming (30–35 °C) may liquefy for easier handling; avoid overheating.
Reconstitution: Not applicable; use neat or dissolve in appropriate deuterated/aprotic solvents (e.g., D2O, acetonitrile-d3, DMSO-d6) as dictated by the application.
Stability: Amides are generally stable at ambient conditions. Avoid strong acids/bases and prolonged contact with protic media to prevent H/D back-exchange.
Always refer to the product’s SDS and CoA for lot-specific handling and storage guidance.
Structure & Identity
Brief description: N-Methylacetamide-d7 is the fully deuterated isotopologue of N-methylacetamide, a simple secondary amide that structurally models a peptide bond. It is commonly used as an isotopic tracer and spectroscopic standard.
Item-specific identifiers (from Product Data)
SKU: N472004
CAS: 3669-74-7
CID: 16213788
InChIKey: 258111 (as provided)
Storage conditions: Room temperature
Research use note: For research use only
Structure and functional groups (general/literature)
Core motifs: secondary amide (–CONH–) with an N-methyl group and an acetyl group; in the d7 isotopologue, all exchangeable/non-exchangeable hydrogens are deuterium (N–D, CD3–CO–, –N–CD3)
Functional groups: amide carbonyl (C=O), N–D (formerly N–H), two deuterated methyl groups (on carbonyl carbon and nitrogen)
2D description: carbonyl carbon double-bonded to oxygen and single-bonded to a methyl (CD3–CO–), and single-bonded to nitrogen; nitrogen is single-bonded to a deuteron (N–D) and to a deuterated methyl (–N–CD3)
Molecular formula (literature/computed for d7): C3D7NO
Canonical SMILES (literature, unlabeled parent for reference): CC(=O)NC
Note: Isotopically labeled SMILES for the d7 form can be represented with [2H] atoms, but item-specific SMILES is Not specified for this item; refer to CoA/Spec Sheet.
Stereochemistry: none (achiral)
Isotopic labeling: 7 deuterons incorporated (one on nitrogen and six across the two methyl groups)
Synthetic Utility
Functional handles (general chemistry):
Secondary amide: nucleophilic at oxygen under strong activation; very weakly nucleophilic at nitrogen unless deprotonated.
N–D bond: can participate in H/D exchange; under strong base (e.g., NaH) the amide can be deprotonated (here deuterated), enabling N-alkylation or acyl transfer reactions while tracking isotopic fate.
Acetyl methyl (CD3–CO–): acidic via enolization; susceptible to isotope exchange and labeling studies under acid/base catalysis.
Use-cases specific to the d7 label:
Synthesis of isotopically labeled derivatives (e.g., N,N-dimethylacetamide-d6/dx) via N-alkylation or acyl substitution while preserving or tracing deuterium distribution.
Mechanistic probes for amide activation (e.g., Vilsmeier-type, carbodiimide couplings) to quantify secondary isotope effects.
Retrosynthetic value:
As a labeled building block, NMA-d7 can be transformed to other labeled amide motifs or serve as a control substrate in catalytic amidation, transamidation, and enolization studies.
Cautions:
Strong acids/bases or metal catalysts can promote H/D scrambling at both N and the acetyl methyl; employ low-temperature, non-protic, and time-controlled conditions to preserve labels.
Target Specificity
Not applicable. This product is a small-molecule deuterated amide, not a biomolecular affinity reagent. No antigen/epitope, species reactivity, clone, or isotype data are relevant.
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