Page last updated: 2024-11-04

trimethyloxamine

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

Description

trimethyloxamine: used in manufacture of quaternary ammonium cpds; insect attractant; warming agent for gas; oxidant; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

trimethylamine N-oxide : A tertiary amine oxide resulting from the oxidation of the amino group of trimethylamine. [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 CID1145
CHEBI ID15724
MeSH IDM0047672

Synonyms (62)

Synonym
n,n-dimethylmethanamine oxide
CHEBI:15724
trimethyloxamine
trimethylaminoxid
me3n(o)
me3n(+)o(-)
n(ch3)3o
methanamine, n,n-dimethyl-, n-oxide
nsc-408426
tmao
nsc408426
trimethylamine, n-oxide
methanamine,n-dimethyl-, n-oxide
triox
trimethylamine oxide
(ch3)3no
C01104
trimethylamine n-oxide
1184-78-7
n,n-dimethylmethanamine oxide (iupac)
einecs 214-675-6
n,n-dimethylmethanamine n-oxide
ai3-60110
nsc 408426
uypyrkyukchhib-uhfffaoysa-
inchi=1/c3h9no/c1-4(2,3)5/h1-3h3
trimethyl-oxido-ammonium
trimethylamine, n-oxide (8ci)
BMSE000426
trimethylamine-n-oxide
tmano
trimenthlamine-n-o
T0466
T1362
A803941
unii-fld0k1sj1a
fld0k1sj1a ,
AKOS015917746
tmae
trimethylamine oxide [fhfi]
trimethylamine oxide [inci]
trimethylamine n-oxide [mi]
fema no. 4245
trimethylamineoxide
trimethlamine-n-oxide
n,n-dimethyl-methanamine-n-oxide
DTXSID8049678
mfcd00002048
trimethylamine n-oxide anhydrous
FT-0697390
J-003759
AS-62713
tma-oxide
FT-0675602
Q419802
trimethylamine n-oxide hcl
trimethylamine n-oxide hydrochloride
trimethylaminoxide
CS-0063748
HY-116084
EN300-396337
SY112165

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Levocarnitine treatment is usually well tolerated, with essentially dose-dependent diarrhea as the main induced adverse effect."( [L-carnitine treatment and fish odor syndrome: an unwaited adverse effect].
Broly, F; Caruba, C; Lebrun, C; Rocher, F,
)
0.13
"This adverse effect seems to be correlated with excedent carnitine intake and might be expressed when the elimination pathway becomes saturated or in a situation of deficiency enzymatic metabolism."( [L-carnitine treatment and fish odor syndrome: an unwaited adverse effect].
Broly, F; Caruba, C; Lebrun, C; Rocher, F,
)
0.13

Pharmacokinetics

ExcerptReferenceRelevance
" The resulting modeled plasma and urinary concentration curves by simple physiologically based pharmacokinetic models (or semi-physiological pharmacokinetic models) were consistent with reported concentrations."( Human plasma and urinary metabolic profiles of trimethylamine and trimethylamine N-oxide extrapolated using a simple physiologically based pharmacokinetic model.
Shimizu, M; Yamazaki, H, 2017
)
0.46
" We previously reported a human physiologically based pharmacokinetic (PBPK) model for trimethylamine and its primary metabolite, trimethylamine N-oxide, based on reported rat trimethylamine pharmacokinetics."( Human plasma concentrations of trimethylamine N-oxide extrapolated using pharmacokinetic modeling based on metabolic profiles of deuterium-labeled trimethylamine in humanized-liver mice.
Kusama, T; Miura, T; Mizuno, S; Shimizu, M; Suemizu, H; Uehara, S; Yamazaki, H, 2018
)
0.48

Compound-Compound Interactions

ExcerptReferenceRelevance
"We investigated the effect of compatible and non-compatible osmolytes in combination with macromolecular crowding on the kinetics of yeast hexokinase."( Effects of osmolytes on hexokinase kinetics combined with macromolecular crowding: test of the osmolyte compatibility hypothesis towards crowded systems.
Olsen, SN; Ramløv, H; Westh, P, 2007
)
0.34
"To evaluate the effect of L-carnitine (LC) in combination with leucine supplementation on muscle strength and muscle hypertrophy in aged women participating in a resistance exercise training (RET) program."( L-Carnitine Combined with Leucine Supplementation Does Not Improve the Effectiveness of Progressive Resistance Training in Healthy Aged Women.
Brzeska, B; Jaworska, J; Olek, RA; Radkiewicz, M; Sabisz, A; Samborowska, E; Sawicka, AK; Szarmach, A; Szurowska, E; Winklewski, PJ, 2022
)
0.72
" One of the supplemented groups received 1 g of L-carnitine-L-tartrate in combination with 3 g of L-leucine per day (LC+L group; n = 12), and the second supplemented group received 4 g of L-leucine per day (L group; n = 13)."( L-Carnitine Combined with Leucine Supplementation Does Not Improve the Effectiveness of Progressive Resistance Training in Healthy Aged Women.
Brzeska, B; Jaworska, J; Olek, RA; Radkiewicz, M; Sabisz, A; Samborowska, E; Sawicka, AK; Szarmach, A; Szurowska, E; Winklewski, PJ, 2022
)
0.72
"LC combined with leucine or leucine alone does not appear to improve the effectiveness of RET."( L-Carnitine Combined with Leucine Supplementation Does Not Improve the Effectiveness of Progressive Resistance Training in Healthy Aged Women.
Brzeska, B; Jaworska, J; Olek, RA; Radkiewicz, M; Sabisz, A; Samborowska, E; Sawicka, AK; Szarmach, A; Szurowska, E; Winklewski, PJ, 2022
)
0.72

Bioavailability

ExcerptReferenceRelevance
"Trimethylamine N-oxide (TMAO), which is naturally occurring in dietary marine fish, is well absorbed and excreted apparently unchanged as judged by end-product analysis."( Disclosure of the metabolic retroversion of trimethylamine N-oxide in humans: a pharmacogenetic approach.
Al-Waiz, M; Ayesh, R; Idle, JR; Mitchell, SC; Smith, RL, 1987
)
0.27
", genotype) and diet affect TMA production and colonization of these microbes, and the effects TMA-producing microbes have on the bioavailability of dietary choline remain largely unknown."( Intestinal microbiota composition modulates choline bioavailability from diet and accumulation of the proatherogenic metabolite trimethylamine-N-oxide.
Amador-Noguez, D; Rey, FE; Romano, KA; Vivas, EI, 2015
)
0.42
" This work identifies members of the human gut microbiota responsible for both the accumulation of trimethylamine (TMA), the precursor of the proatherogenic compound TMAO, and subsequent decreased choline bioavailability to the host."( Intestinal microbiota composition modulates choline bioavailability from diet and accumulation of the proatherogenic metabolite trimethylamine-N-oxide.
Amador-Noguez, D; Rey, FE; Romano, KA; Vivas, EI, 2015
)
0.42
" A growing body of evidence supports the hypothesis that phenolic phytochemicals with poor bioavailability are possibly acting primarily through remodeling of the gut microbiota."( Resveratrol Attenuates Trimethylamine-N-Oxide (TMAO)-Induced Atherosclerosis by Regulating TMAO Synthesis and Bile Acid Metabolism via Remodeling of the Gut Microbiota.
Chen, ML; Mi, MT; Ran, L; Yang, J; Yi, L; Zhang, QY; Zhang, Y; Zhou, X; Zhu, JD, 2016
)
0.43
" Carnitine supplementation of AA-MFs shows reduced bioavailability due, in part, to bacterial degradation to TMAO, whereas the bioavailability of carnitine is greater with prebiotic GMP-MFs."( Metabolomic Markers of Essential Fatty Acids, Carnitine, and Cholesterol Metabolism in Adults and Adolescents with Phenylketonuria.
Broniowska, K; Levy, HL; Murali, SG; Nair, N; Ney, DM; Rohr, F; Stroup, BM, 2018
)
0.48
" Given the poor oral bioavailability of BBR, the mechanisms through which BBR mediates metabolic disorders are not well understood."( Berberine treatment reduces atherosclerosis by mediating gut microbiota in apoE-/- mice.
Geng, J; Hu, J; Hu, T; Jiang, Y; Li, J; Liu, S; Shi, Y; Wang, B; Yan, W, 2018
)
0.48
" Here, we demonstrated a personalized TMAO formation and carnitine bioavailability from carnitine supplements by differentiating individual TMAO productivities with a recently developed oral carnitine challenge test (OCCT)."( Characterization of TMAO productivity from carnitine challenge facilitates personalized nutrition and microbiome signatures discovery.
Chen, CC; Chen, YH; Chiu, THT; Chuang, HL; Chung, CH; Hsu, CC; Kao, HL; Kuo, CH; Kuo, HC; Lee, YC; Liao, BY; Lin, AY; Liu, PY; Orekhov, AN; Panyod, S; Sheen, LY; Tang, SL; Wang, JT; Wu, MS; Wu, WK; Wu, YW; Zou, HB, 2020
)
0.56
"Vascular dysfunction: develops progressively with ageing; increases the risk of cardiovascular diseases (CVD); and is characterized by endothelial dysfunction and arterial stiffening, which are primarily mediated by superoxide-driven oxidative stress and consequently reduced nitric oxide (NO) bioavailability and arterial structural changes."( Initiation of 3,3-dimethyl-1-butanol at midlife prevents endothelial dysfunction and attenuates in vivo aortic stiffening with ageing in mice.
Brunt, VE; Casso, AG; Clayton, ZS; Davy, KP; Gioscia-Ryan, RA; Greenberg, NT; Hutton, DA; Neilson, AP; Seals, DR; VanDongen, NS; Ziemba, BP, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" The contributions of the metabolites to the separation of control from dosed liver tissues varied depending on the type of spectral editing method used."( Spectral editing and pattern recognition methods applied to high-resolution magic-angle spinning 1H nuclear magnetic resonance spectroscopy of liver tissues.
Antti, H; Beckonert, O; Bollard, ME; Ebbels, TM; Holmes, E; Keun, H; Lindon, JC; Nicholson, JK; Tang, H; Wang, Y, 2003
)
0.32
" However, concerns about the possible deleterious consequences of such a dosage regimen still remain given that plasma concentrations of trimethylamine-N-oxide were continually rising and approximately doubled in a two-week period."( Oral L-carnitine: metabolite formation and hemodialysis.
Bain, MA; Evans, AM; Faull, R; Milne, RW, 2006
)
0.33
" Treatment of transfected cells with TMAO improved the solubility of the D384N mutant, which was corrected for secretion in a dose-response manner."( Correction of the disease phenotype of myocilin-causing glaucoma by a natural osmolyte.
Gong, B; Huang, Y; Jia, LY; Lam, DS; Pang, CP; Wang, N; Yam, GH, 2009
)
0.35
" In this study, we delivered a single dose of mequindox to mice with dosage levels of 15, 75, and 350 mg/kg body weight and collected urine samples over a 7 day period, as well as plasma and liver tissues at 7 days postdose."( Dynamic metabolic response of mice to acute mequindox exposure.
Huang, C; Lei, H; Nie, X; Tang, H; Wang, Y; Zhao, XJ, 2011
)
0.37
" We aimed to synthesize the evidence on the relation between TMAO levels and the risk of diabetes mellitus (DM) and to investigate the association further in a dose-response meta-analysis."( Gut microbe-generated metabolite trimethylamine N-oxide and the risk of diabetes: A systematic review and dose-response meta-analysis.
Fan, H; Ge, X; Gong, X; Han, L; Liu, Z; Meng, Q; Yu, P; Zhang, Y; Zheng, L; Zhou, X; Zhuang, R, 2019
)
0.51
" Further, its potential was demonstrated in a side-by-side comparison to RapidFire-MS in a primary screen and subsequent dose-response experiments."( Chemical Derivatization Enables MALDI-TOF-Based High-Throughput Screening for Microbial Trimethylamine (TMA)-Lyase Inhibitors.
Bartlett, C; Binetti, R; Bischoff, D; Bretschneider, T; Broadwater, J; Büttner, FH; Chandler, S; Fowler, D; Grabowski, D; Kleiner, C; Kley, JT; Luippold, AH; Ries, R; Thamm, S; Winter, M, 2019
)
0.51
"0001) according to the dose-response meta-analysis."( The Gut Microbial Metabolite Trimethylamine N-Oxide and Hypertension Risk: A Systematic Review and Dose-Response Meta-analysis.
Fan, H; Ge, X; Liu, G; Xi, X; Xu, Z; Yu, P; Zheng, L; Zhou, X; Zhuang, R, 2020
)
0.56
" Trimethylamine-N-oxide (TMAO), dimethylamine, and dimethyl sulfone are identified and display significant dose-response with intake (p < 0."( The Relationship between Fish Intake and Urinary Trimethylamine-N-Oxide.
Brennan, L; Flynn, A; Frost, G; Gibbons, H; McNulty, BA; Nugent, AP; Rundle, M; Walton, J; Yin, X, 2020
)
0.56
"Urinary TMAO displays a strong dose-response relationship with fish intake; however, use of TMAO alone is insufficient to determine fish intake in a free-living population."( The Relationship between Fish Intake and Urinary Trimethylamine-N-Oxide.
Brennan, L; Flynn, A; Frost, G; Gibbons, H; McNulty, BA; Nugent, AP; Rundle, M; Walton, J; Yin, X, 2020
)
0.56
"Meta-analysis and dose-response analysis of hazard ratio data from prospective observational studies reporting on the association between TMAO plasma concentrations and the incidence of MACE in patients with CHD were conducted."( Trimethylamine-N-oxide has prognostic value in coronary heart disease: a meta-analysis and dose-response analysis.
Liao, PD; Wang, L; Yao, ME; Zhao, XJ, 2020
)
0.56
" The dose-response analysis revealed a 'J' shaped association between TMAO concentration and the incidence of MACE (P = 0."( Trimethylamine-N-oxide has prognostic value in coronary heart disease: a meta-analysis and dose-response analysis.
Liao, PD; Wang, L; Yao, ME; Zhao, XJ, 2020
)
0.56
" In the current study, we summarized the evidence related to the association of circulating TMAO with the risk of obesity measurements, including body mass index (BMI), waist circumference (WC), and waist-to-hip ratio (WHR) in a two-class and dose-response meta-analysis of observational studies."( Gut microbiota-derived metabolite trimethylamine N-oxide (TMAO) potentially increases the risk of obesity in adults: An exploratory systematic review and dose-response meta- analysis.
Asghari-Jafarabadi, M; Dehghan, P; Farhangi, MA; Nikniaz, L; Nikniaz, Z, 2020
)
0.56
" In the current dose-response meta-analysis, we revealed a positive association between TMAO and mortality risk among an adult population."( Gut microbiota-dependent trimethylamine N-oxide and all-cause mortality: Findings from an updated systematic review and meta-analysis.
Farhangi, MA, 2020
)
0.56
" Dose-response analysis revealed a linear association between the TMAO concentration and the OR for frailty."( Trimethylamine N-Oxide, a Gut Microbiota-Dependent Metabolite, is Associated with Frailty in Older Adults with Cardiovascular Disease.
Cui, LL; Guo, D; He, W; Liu, JP; Luo, Y; Sun, N; Wang, H; Yang, JF; Yao, SM; Zheng, PP, 2020
)
0.56
"The aim of this systematic review and meta-analysis was to summarize evidence of the relationship between circulating TMAO levels and risk of hypertension and increased serum lipids in a dose-response and 2-class meta-analysis of discrete and continuous variables."( Gut microbiota-associated trimethylamine N-oxide and increased cardiometabolic risk in adults: a systematic review and dose-response meta-analysis.
Abbasalizad Farhangi, M; Vajdi, M, 2021
)
0.62
" There was a dose-response relationship between circulating TMAO and increased odds of hypertension in cohort studies (P  for nonlinearity = 0."( Gut microbiota-associated trimethylamine N-oxide and increased cardiometabolic risk in adults: a systematic review and dose-response meta-analysis.
Abbasalizad Farhangi, M; Vajdi, M, 2021
)
0.62
" A dose-response meta-analysis was used to investigate the dose-response relationship between TMAO levels and the risk of AF."( A systematic review and meta-analysis of the gut microbiota-dependent metabolite trimethylamine N-oxide with the incidence of atrial fibrillation.
Li, XD; Wang, YT; Yang, R; Yang, WT; Zhao, Q, 2021
)
0.62
" This study aimed to review the available scientific evidence about the relationship between TMAO levels and the risk of stroke in a dose-response meta-analysis."( Plasmatic trimethylamine N-oxide and its relation to stroke: A systematic review and dose-response meta-analysis.
Chen, P; Guo, Z, 2022
)
0.72
"001) in circulating TMAO concentration according to the dose-response meta-analysis."( Plasmatic trimethylamine N-oxide and its relation to stroke: A systematic review and dose-response meta-analysis.
Chen, P; Guo, Z, 2022
)
0.72
"020) for ischemic stroke in an essentially linear dose-response fashion."( Associations of plasma TMAO and its precursors with stroke risk in the general population: A nested case-control study.
Gu, S; Liu, D; Ma, Z; Zhou, Z; Zuo, H, 2023
)
0.91
"There is a dose-response relationship between TMAO levels and NCDs progression."( Trimethylamine N-Oxide as a Potential Risk Factor for Non-communicable Diseases: A Systematic Review.
Ejtahed, HS; Hasani-Ranjbar, S; Hoseini-Tavassol, Z; Larijani, B, 2023
)
0.91
" We aimed to assess the correlation between circulating TMAO concentration and the risk of all-cause and cardiovascular death in CKD patients of different dialysis statuses and different races by dose-response analyses, and the underlying mechanisms were also explored by analyzing the correlations of TMAO with glomerular filtration rate (GFR) and inflammation."( Gut microbiota-derived trimethylamine N-oxide is associated with the risk of all-cause and cardiovascular mortality in patients with chronic kidney disease: a systematic review and dose-response meta-analysis.
Guo, J; Li, Y; Liu, W; Liu, Y; Lu, H; Zhang, M; Zheng, H, 2023
)
0.91
"0 was used to perform the meta-analyses and dose-response analyses with extracted data."( Gut microbiota-derived trimethylamine N-oxide is associated with the risk of all-cause and cardiovascular mortality in patients with chronic kidney disease: a systematic review and dose-response meta-analysis.
Guo, J; Li, Y; Liu, W; Liu, Y; Lu, H; Zhang, M; Zheng, H, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
osmolyteA solute used by a cell under water stress to maintain cell volume.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
[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 (1)

ClassDescription
tertiary amine oxideAn N-oxide where there are three organic groups bonded to the nitrogen atom.
[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 (12)

PathwayProteinsCompounds
Metabolism14961108
Biological oxidations150276
Phase I - Functionalization of compounds69175
FMO oxidises nucleophiles313
N-Oxide Electron Transfer2110
Diet-dependent trimethylamine/trimethylamine N-oxide metabolism112
hydrogen to trimethylamine N-oxide electron transfer916
superpathway of trimethylamine degradation1224
trimethylamine degradation711
formate to trimethylamine N-oxide electron transfer815
NADH to trimethylamine N-oxide electron transfer158
respiration (anaerobic)-- electron acceptors reaction list021
formate to trimethylamine N-oxide electron transfer14

Research

Studies (1,539)

TimeframeStudies, This Drug (%)All Drugs %
pre-199061 (3.96)18.7374
1990's96 (6.24)18.2507
2000's199 (12.93)29.6817
2010's627 (40.74)24.3611
2020's556 (36.13)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 7.86

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index7.86 (24.57)
Research Supply Index7.41 (2.92)
Research Growth Index5.27 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (7.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials75 (4.77%)5.53%
Reviews197 (12.52%)6.00%
Case Studies15 (0.95%)4.05%
Observational27 (1.72%)0.25%
Other1,259 (80.04%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]