Page last updated: 2024-11-04

formamide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Formamide is a colorless liquid with a pungent odor. It is miscible with water and many organic solvents. Formamide is a versatile compound used in various applications. It is synthesized by reacting carbon monoxide with ammonia. It is a highly polar solvent and is often used as a reaction medium in organic chemistry. It is also a precursor to other chemicals, such as formamide resins and dimethylformamide (DMF). Formamide is used as a plasticizer, a solvent for polymers, and a component in antifreeze mixtures. In biology, formamide is a potential source of carbon and nitrogen for microorganisms. It is also a component of the genetic code, as it is the simplest amide that can be incorporated into DNA and RNA. Formamide is studied for its potential applications in diverse fields, including organic synthesis, materials science, and biomedicine. Its unique properties, including its high polarity, hydrogen bonding capabilities, and ability to act as a solvent and reactant, make it a promising candidate for various applications. '

formimidic acid : A carboximidic acid that is formic acid in which the carbonyl oxygen is replaced by an imino group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

primary carboxamide : A carboxamide resulting from the formal condensation of a carboxylic acid with ammonia; formula RC(=O)NH2. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID713
CHEMBL ID266160
CHEBI ID16397
CHEBI ID48431
CHEBI ID140324
MeSH IDM0097888

Synonyms (95)

Synonym
AKOS009031608
ameisensaeureamid
CHEBI:16397 ,
methanamid
formamid
formimidic acid
inchi=1/ch3no/c2-1-3/h1h,(h2,2,3
NCGC00091516-01
hsdb 88
einecs 200-842-0
ai3-15357
methanoic acid, amide
formic acid, amide
ccris 6240
amid kyseliny mravenci [czech]
nsc 748
wln: zvh
formamide ,
C00488
nsc748
75-12-7
methanamide
nsc-748
carbamaldehyde
formamide, bioxtra, >=99% (gc)
formamide, >=99.5% (gc), bioreagent, for molecular biology
formamide, acs reagent, >=99.5%
imidoformic acid
CHEBI:48431
formamide, bioultra, for molecular biology, >=99.5% (t)
primary carboxamide
primary carboxamides
CHEBI:140324
BMSE000267
CHEMBL266160
F0045
A838330
NCGC00091516-02
cas-75-12-7
tox21_302824
NCGC00256321-01
dtxsid8025337 ,
dtxcid805337
NCGC00259491-01
tox21_201942
methanimidic acid
60100-09-6
unii-4781t907zs
4781t907zs ,
amid kyseliny mravenci
ec 200-842-0
FT-0637321
FT-0631311
MB8 ,
formic amide
formamide [usp-rs]
formamide [hsdb]
formamide [mi]
gtpl4739
amide c1
formamide, acs reagent
n-formyl amine
amino-formaldehyde
nh2cho
hconh2
mfcd00007941
J-521386
F0001-1892
formamide, spectrophotometric grade
formamide, >=99.5%
formamide, puriss. p.a., acs reagent, >=99.5% (gc/t)
formamide, jis special grade, >=98.5%
formamide, saj first grade, >=98.5%
formamide, spectrophotometric grade, >=99%
formamide, reagent grade, 98%
formamide, >=99.0%
formamide, for molecular biology, >=99.5% (gc), liquid
formamide, reagentplus(r), >=99.0% (gc)
formamide, p.a., 99.5%
formamide, vetec(tm) reagent grade, 98%
formamide, p.a., acs reagent, 99.5%
imino-methylalkohol
HY-Y0842
CS-0015817
Q283917
residual solvent class 2 - formamide
formamide-1-d1
Q27110288
methanamide;formimidic acid
STL197469
AMY3583
formamide; carbamaldehyde; formimidic acid; methanamide; nsc 748
EN300-19895
formamide-13c-15n (9ci)
formamide (usp-rs)

Research Excerpts

Overview

Formamide is a simple C1 building block hypothesized to be a precursor to many protometabolic compounds. It is a slow-onset inhibitor of mitochondrial cytochrome c oxidase.

ExcerptReferenceRelevance
"Formamide is a key biomonomer and contains the simplest peptide [-(C═O)-NH-] linkage."( Pathways for the Formation of Formamide, a Prebiotic Biomonomer: Metal-Ions in Interstellar Gas-Phase Chemistry.
Ramabhadran, RO; Thripati, S, 2021
)
1.63
"Formamide is a simple C1 building block hypothesized to be a precursor to many protometabolic compounds."( From formamide to adenine: a self-catalytic mechanism for an abiotic approach.
Gu, J; Leszczynski, J; Nguyen, MT; Springsteen, G; Wang, J, 2013
)
1.63
"Formamide is a slow-onset inhibitor of mitochondrial cytochrome c oxidase that is proposed to act by blocking water movement through the protein. "( Formamide probes a role for water in the catalytic cycle of cytochrome c oxidase.
Hill, BC; Liu, Y, 2007
)
3.23
"Formamide is a substrate of xanthine oxidase. "( Formamide as a substrate of xanthine oxidase.
Bray, RC; George, GN; Morpeth, FF, 1984
)
3.15

Effects

Formamide has a higher dielectric constant than water and can solubilize many supporting electrolytes. Formamide has been proposed as a single-carbon, prebiotic source of nucleobases and nucleic acids.

ExcerptReferenceRelevance
"Formamide has a higher dielectric constant than water and can solubilize many supporting electrolytes."( Nonaqueous capillary electrophoresis.
Khaledi, MG; Sahota, RS, 1994
)
1.01
"Formamide has been recognized in the literature as a key species in the formation of the complex molecules of life, such as nucleobases. "( Monitoring the Reactivity of Formamide on Amorphous SiO
Balucani, N; Bonino, F; Martra, G; Pantaleone, S; Signorile, M; Ugliengo, P, 2020
)
2.29
"Formamide (NH2CHO, FM) has been considered an active key precursor in prebiotic chemistry on early Earth. "( Theoretical study of the decomposition of formamide in the presence of water molecules.
Leszczynski, J; Nguyen, MT; Nguyen, VS; Orlando, TM, 2013
)
2.1
"Formamide has recently been proposed as a single-carbon, prebiotic source of nucleobases and nucleic acids."( Observations of interstellar formamide: availability of a prebiotic precursor in the galactic habitable zone.
Adande, GR; Woolf, NJ; Ziurys, LM, 2013
)
1.4
"Formamide has long been one of the most widely used reagents in the study of nucleic acids. "( New use for an old reagent: Cell cycle analysis of DNA content using flow cytometry in formamide treated cells.
Carbonari, M, 2016
)
2.1
"Formamide has been deposited on the olivine substrate at 20 K."( Cryogenic synthesis of molecules of astrobiological interest: catalytic role of cosmic dust analogues.
Baratta, GA; Brucato, JR; Colangeli, L; Rotundi, A; Strazzulla, G, 2006
)
1.06
"Formamide has a higher dielectric constant than water and can solubilize many supporting electrolytes."( Nonaqueous capillary electrophoresis.
Khaledi, MG; Sahota, RS, 1994
)
1.01

Treatment

Formamide treatment of normal embryos was used to produce a phenocopy of the unresponsive condition. Pretreatment with formamide abolished contractile Ca2+ transients, but did not affect non-contractile ones.

ExcerptReferenceRelevance
"With formamide treatment the doublets are practically absent, sample recovery is efficient, as well as the preservation of physical parameters, and the stained cells can be stored for at least 10 days at room temperature before acquisition."( New use for an old reagent: Cell cycle analysis of DNA content using flow cytometry in formamide treated cells.
Carbonari, M, 2016
)
1.11
"Formamide treatment decreased cell capacitance by 20%, did not significantly change the density of I(TO), I(K) or I(K1) but decreased the density of I(SS) and L-type Ca current ( I(Ca))."( K(+) current distribution in rat sub-epicardial ventricular myocytes.
Brette, F; Komukai, K; Orchard, CH; Yamanushi, TT, 2002
)
1.04
"Formamide treatment of normal embryos was used to produce a phenocopy of the unresponsive condition, permitting direct comparisons between mutant and normal embryos."( Unresponsive, a behavioral mutant in Xenopus laevis: electrophysiological studies of the neuromuscular system.
Dudek, FE; Ide, CF; Tompkins, R, 1987
)
0.99
"Pretreatment with formamide (2 M for 30 min) abolished contractile Ca2+ transients, but did not affect non-contractile ones."( Reversed effect of caffeine on non-contractile and contractile Ca2+ mobilization operated by acetylcholine receptor in mouse diaphragm muscle.
Kimura, I; Kimura, M; Kondoh, T; Tsuneki, H, 1991
)
0.6

Toxicity

ExcerptReferenceRelevance
" In summary, the maternal toxicity no-observed-adverse-effect level (NOAEL) was 100 mg/kg/day and the low observed adverse effect level (LOAEL) was 200 mg/kg/day under the conditions of this study."( Evaluation of the developmental toxicity of formamide in Sprague-Dawley (CD) rats.
George, JD; Jahnke, GD; Marr, MC; Myers, CB; Price, CJ, 2000
)
0.57
"Multiple-CPA solutions were significantly less toxic than single-CPA solutions (P<0."( Cryoprotective agent toxicity interactions in human articular chondrocytes.
Almansoori, KA; Elliott, JA; Forbes, JF; Jomha, NM; Law, GK; McGann, LE; Prasad, V, 2012
)
0.38
" PG was the most toxic CPA when used in combinations."( Cryoprotective agent toxicity interactions in human articular chondrocytes.
Almansoori, KA; Elliott, JA; Forbes, JF; Jomha, NM; Law, GK; McGann, LE; Prasad, V, 2012
)
0.38
" elegans are more resistant to the toxic effect of M22 compared to wild-type worms."( Cryoprotectant toxicity in Caenorhabditis elegans.
Johnson, TE; Schumacher, GJ; Tedesco, PM, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Similar dose-response curves were obtained for inactivation by formamide of native and renatured DNA, but the residual-active material was much more resistant."( RESIDUAL ACTIVITY OF THERMALLY DENATURED TRANSFORMING DEOXYRIBONUCLEIC ACID FROM HAEMOPHILUS INFLUENZAE.
BARNHART, BJ, 1965
)
0.48
" It was shown that the dose-response behaviour of the NIPAM/Bis gel dosimeter is comparable to that of normoxic polyacrylamide gel (PAGAT) in terms of high dose-sensitivity and low dependence on dose rate and irradiation temperature, within the ranges considered."( Polymer gel dosimeters with reduced toxicity: a preliminary investigation of the NMR and optical dose-response using different monomers.
De Jean, P; McAuley, KB; Schreiner, LJ; Senden, RJ, 2006
)
0.33
" SWW was intermittently dosed at two points, Sheets 1 and 38, in a 2 to 1 volume ratio respectively."( Nitrogen dynamics and removal in a horizontal flow biofilm reactor for wastewater treatment.
Clifford, E; Nielsen, M; Rodgers, M; Sørensen, K, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
solventA liquid that can dissolve other substances (solutes) without any change in their chemical composition.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
carboximidic acid
one-carbon compoundAn organic molecular entity containing a single carbon atom (C1).
formamidesAmides with the general formula R(1)R(2)NCHO (R(1) and R(2) can be H).
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
one-carbon compoundAn organic molecular entity containing a single carbon atom (C1).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (10)

PathwayProteinsCompounds
succinate to cytochrome bo oxidase electron transfer831
NADH to cytochrome bo oxidase electron transfer II526
D-lactate to cytochrome bo oxidase electron transfer527
glycerol-3-phosphate to cytochrome bo oxidase electron transfer529
proline to cytochrome bo oxidase electron transfer531
NADH to cytochrome bo oxidase electron transfer I1734
pyruvate to cytochrome bo oxidase electron transfer535
cyanide detoxification II15
L-histidine degradation I414
histidine degradation I48

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency68.58960.001022.650876.6163AID1224838
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency60.29450.001530.607315,848.9004AID1224841
pregnane X nuclear receptorHomo sapiens (human)Potency68.58960.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency13.80220.000229.305416,493.5996AID743069
nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_aHomo sapiens (human)Potency21.875119.739145.978464.9432AID1159509
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID116888Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice at dose of 400-100 mg/kg per day1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID110030Antitumor activity was evaluated against the TLX5 lymphoma in mice measured for control as death day at a optimal doses of 800 mg/Kg/day1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID122264Antitumor activity was evaluated against the TLX5 lymphoma in mice measured as treated to control at optimal dose. 800 mg/Kg/day1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID116704Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice at dose of 400-100 mg/kg per day1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID23734Micelle/water partition coefficient (Pmic) of the compound was determined1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Thermodynamic aspects of hydrophobicity and the blood-brain barrier permeability studied with a gel filtration chromatography.
AID122376Antitumor activity was evaluated for the compound against the M5076 reticulum cell sarcoma in mice and the % T/C(treated/control) value was calculated at optimal dose of 200 mg/kg1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID118240Antitumor activity was evaluated against the TLX5 lymphoma measured as mean death day for the treated at a optimal dose of 800 mg/Kg/day1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID118234Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice measured as mean tumor volume for the treated at the optimal dose 200 mg/Kg/day1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID110147Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice measured as Control tumor volume for the treated at the optimal dose 200 mg/Kg/day1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (550)

TimeframeStudies, This Drug (%)All Drugs %
pre-199091 (16.55)18.7374
1990's103 (18.73)18.2507
2000's170 (30.91)29.6817
2010's165 (30.00)24.3611
2020's21 (3.82)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 79.55

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index79.55 (24.57)
Research Supply Index6.34 (2.92)
Research Growth Index4.63 (4.65)
Search Engine Demand Index140.77 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (79.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews13 (2.30%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other551 (97.70%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]