N,N-Dimethylacetamide

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H9NO
Molecular Weight	87.1204
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)C(C)=O

InChI

InChIKey=FXHOOIRPVKKKFG-UHFFFAOYSA-N

InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3

HIDE SMILES / InChI

Molecular Formula	C4H9NO
Molecular Weight	87.1204
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28176838 | https://www.alfa.com/en/catalog/A10924/ | https://www.ncbi.nlm.nih.gov/pubmed/30081462 | https://www.accessdata.fda.gov/scripts/cder/iig/index.cfm?event=browseByLetter.page&Letter=N

N,N-Dimethylacetamide (DMA) is a multipurpose reagent which delivers its own H, C, N and O atoms for the synthesis of a variety of compounds under a number of different experimental conditions. N,N-Dimethylacetamide is a water-miscible solvent, FDA approved as excipient and therefore widely used as drug-delivery vehicle. It has been shown that DMA is epigenetically active since it binds bromodomains and inhibits osteoclastogenesis and inflammation. DMA has a potential as an anti-osteoporotic agent via the inhibition of osteoclast mediated bone resorption and enhanced bone regeneration. N,N-Dimethylacetamide is used as a polar solvent in organic synthesis as well as in reactions involving strong bases such as sodium hydroxide. N,N-Dimethylacetamide finds application as a reaction medium in the production of pharmaceuticals, agrochemicals, dyes and plasticizers. It is widely used in polymer industry due to its high solving power for high molecular-weight polymers and synthetic resins. It plays an important role as a catalyst in various reactions viz. cyclization, halogenation, cynidation, alkylation and dehydrogenation and increases the yield of main products. It is also used as an extracting agent for oil and gases, in paint removers, in the production of photo-resist stripping compounds and as booster solvent in coatings.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Excipient 2 Sources: https://www.accessdata.fda.gov/scripts/cder/iig/index.cfm?event=browseByLetter.page&Letter=N	Inactive ingredient		Approved 8583

Doses

Dose	Population	Adverse events
400 mg/kg 1 times / day multiple, oral Highest studied dose Dose: 400 mg/kg, 1 times / day Route: oral Route: multiple Dose: 400 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14005854/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/14005854/	Other AEs: Hallucination... Other AEs: Hallucination Sources: https://pubmed.ncbi.nlm.nih.gov/14005854/

AEs

AE	Significance	Dose	Population
Hallucination		400 mg/kg 1 times / day multiple, oral Highest studied dose Dose: 400 mg/kg, 1 times / day Route: oral Route: multiple Dose: 400 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14005854/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/14005854/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP19A1 429 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/31374#section=Biological-Test-Results Page: 3.0	inconclusive [IC50 81.1373 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/31374#section=Biological-Test-Results Page: 4.0	inconclusive [IC50 91.0376 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/31374#section=Biological-Test-Results Page: 116.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/31374#section=Biological-Test-Results Page: 177.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/31374#section=Biological-Test-Results Page: 177.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/31374#section=Biological-Test-Results Page: 178.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/31374#section=Biological-Test-Results Page: 178.0

PubMed

Title	Date	PubMed
The use of acridine orange base (AOB) as molecular probe to characterize nonaqueous AOT reverse micelles.	2006-04-01	16214159
Analysis of amides in the air by sampling with SPME and detection by GC-FID.	2006-02	16544874
Animal genetic resources conservation in the Netherlands and Europe: poultry perspective.	2006-02	16523616
Studies of the condensation of sulfones with ketones and aldehydes.	2006-01-20	16408963
The effect of DMA level on morphology and fertilising ability of Japanese quail (Coturnix japonica) spermatozoa.	2006-01-20	16188306
Dynamic dissolution of persimmon leaves in DMSO and DMAc and the influence of acid-base interactions.	2006-01-15	16406493
Size-exclusion chromatography of technical lignins in dimethyl sulfoxide/water and dimethylacetamide.	2006-01-13	16288767
Convenient and efficient Pd-catalyzed regioselective oxyfunctionalization of terminal olefins by using molecular oxygen as sole reoxidant.	2006-01-09	16323234
The effect of commonly used vehicles on canine hematology and clinical chemistry values.	2006-01	16539331
Dual mesomorphic assemblage of chitin normal acylates and rapid enthalpy relaxation of their side chains.	2006-01	16398515
X-ray structures and homolysis of some alkylcobalt(III) phthalocyanine complexes.	2005-12-26	16363861
One-electron reduction potential for oxygen- and sulfur-centered organic radicals in protic and aprotic solvents.	2005-11-16	16277514
Influence of the supramolecular structure and physicochemical properties of cellulose on its dissolution in a lithium chloride/N,N-dimethylacetamide solvent system.	2005-09-13	16153102
Use of low volatility mobile phases in electroosmotic thin-layer chromatography.	2005-08-19	16114230
Covalent molecular assembly of oligoimide ultrathin films in supercritical and liquid solvent media.	2005-08-16	16089387
The burden borne by urease.	2005-08-10	16076178
Alginate-based in situ gelling suspensions and emulsions comprising N4-alkyloxycarbonyl derivatives of cytosine: zero-order release and effect of physicochemical properties.	2005-08	16207614
Evaluation of sample recovery of malodorous livestock gases from air sampling bags, solid-phase microextraction fibers, Tenax TA sorbent tubes, and sampling canisters.	2005-08	16187584
Mono- and beta,beta-double-Heck reactions of alpha,beta-unsaturated carbonyl compounds in aqueous media.	2005-05-27	15903312
Solvent effects in the interaction of methyl-beta-cyclodextrin with solvatochromic merocyanine dyes.	2005-05-07	15858660
Oral formulation of a novel antiviral agent, PG301029, in a mixture of gelucire 44/14 and DMA (2:1, wt/wt).	2005-04-08	16353952
FTIR analysis of cellulose treated with sodium hydroxide and carbon dioxide.	2005-02-28	15680597
The first nitro-substituted heteroscorpionate ligand.	2005-02-21	15859260
[Headspace GC/MS analysis of residual vinyl chloride and vinylidene chloride in polyvinyl chloride and polyvinylidene chloride products].	2005-02	15881249
Low-temperature (180 K) crystal structures of tetrakis-mu-(niflumato)di(aqua)dicopper(II) N,N-dimethylformamide and N,N-dimethylacetamide solvates, their EPR properties, and anticonvulsant activities of these and other ternary binuclear copper(II)niflumate complexes.	2005-02	15621267
Tailored cellulose esters: synthesis and structure determination.	2005-01-11	15638537
Solvent effects on coupling yields during rapid solid-phase synthesis of CGRP(8-37) employing in situ neutralization.	2005-01	15686538
Matrix media selection for the determination of residual solvents in pharmaceuticals by static headspace gas chromatography.	2004-11-19	15584240
Effect of processing on Celecoxib and its solvates.	2004-11	15581078
Synthesis and spectroscopy of a series of substituted N-confused tetraphenylporphyrins.	2004-10-29	15497965
Inclusion by a fluorenyl host with volatile guests: structures, thermal stability and kinetics.	2004-08-21	15305209
Beta-cyclodextrin as a suitable solubilizing agent for in situ absorption study of poorly water-soluble drugs.	2004-08-06	15265550
Kinetics of degradation and oil solubility of ester prodrugs of a model dipeptide (Gly-Phe).	2004-08	15265509
Two polymorphs of cobalt(II) imidazolate polymers synthesized solvothermally by using one organic template N,N-dimethylacetamide.	2004-07-26	15257592
One-step synthesis and characterization of difunctionalized N-confused tetraphenylporphyrins.	2004-07-09	15230577
Ruthenium- and rhodium-catalyzed direct carbonylation of the ortho C-H bond in the benzene ring of N-arylpyrazoles.	2004-06-25	15202898
A catalytic synthesis of thiosilanes and silthianes: palladium nanoparticle-mediated cross-coupling of silanes with thio phenyl and thio vinyl ethers through selective carbon-sulfur bond activation.	2004-06-16	15186178
Solubilization behavior of poorly soluble drugs with combined use of Gelucire 44/14 and cosolvent.	2004-06	15124205
Preparation, characterization, and solution viscosity of polystyrene-block-polyisoprene nanofiber fractions.	2004-05-25	15969181
Chemical valorization of forest and agricultural by-products. Obtention, chemical characteristics, and mechanical behavior of a novel family of hydrophobic films.	2004-05	15473642
Molar mass distribution of a commercial aliphatic hyperbranched polyester based on 2,2-bis(methylol)propionic acid.	2004-04-23	15116916
Structure-activity relationships of a novel class of endothelin receptor selective antagonists; 6-carboxy-2-isopropylamino-5,7-diarylcyclopenteno[1,2-b]pyridines.	2004-03-22	15006391
Solubilizing excipients in oral and injectable formulations.	2004-02	15032302
Transdermal iontophoresis of insulin: IV. Influence of chemical enhancers.	2004-01-09	14698582
Protein interaction networks by proteome peptide scanning.	2004-01	14737190
Zebrafish sperm cryopreservation.	2004	15602936
Experimental validation of theoretical potassium and sodium cation affinities of amides by mass spectrometric kinetic method measurements.	2004	14755622
Elimination of oxidative degradation during the per-O-methylation of carbohydrates.	2003-12-31	14692762
Zebrafish sperm cryopreservation with N,N-dimethylacetamide.	2003-11	14628669
Characterization of solid-state forms of celecoxib.	2003-11	14592696

Patents

Sample Use Guides

In Vivo Use Guide

Rats: N,N-Dimethylacetamide (DMA) was administered once a week via i.p. injections (92 ul DMA plus 108 ul PBS per 100 gr. rat).

Route of Administration: Intraperitoneal

In Vitro Use Guide

N,N-Dimethylacetamide (DMA) inhibits the binding activity of BRD2 and BRD4 with an IC50 value of 11 mM and 6 mM, respectively. RAW264.7 cells were seeded on a 24-well culture plate and treated with RANKL alone or with different concentrations of DMA (1.25 mM, 2.5 mM, 5mM). After 6 days of incubation, TRAP activity was measured.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:56 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:56 GMT 2025`
Record UNII	JCV5VDB3HY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

N,N-Dimethylacetamide

Systematic Name

English

DIMETHYLACETAMIDE

Preferred Name

English

N,N-DIMETHYLACETAMIDE [HSDB]

Common Name

English

N,N-DIMETHYLACETAMIDE [VANDF]

Common Name

English

NSC-3138

Code

English

DIMETHYLACETAMIDE [EP MONOGRAPH]

Common Name

English

N,N-DIMETHYL ACETAMIDE

Systematic Name

English

N,N-DIMETHYLACETAMIDE [USP-RS]

Common Name

English

DIMETHYLACETAMIDE [MART.]

Common Name

English

ACETAMIDE, N,N-DIMETHYL-

Systematic Name

English

N,N-DIMETHYLACETAMIDE [MI]

Common Name

English

N,N-DIMETHYLACETAMIDE [II]

Common Name

English

ACETIC ACID, DIMETHYLAMIDE

Common Name

English

Code System Code Type Description

MESH

C013959