MiMeDB: Showing metabocard for Trimethylamine (MMDBc0000168)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:22 UTC

Update Date

2024-04-30 19:31:15 UTC

Metabolite ID

MMDBc0000168

Metabolite Identification

Common Name

Trimethylamine

Description

Trimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia like odor in higher concentrations. Trimethylamine has a boiling point of 2.9 degree centigrade and is a gas at room temperature. Trimethylamine usually comes in pressurized gas cylinders or as a 40% solution in water. Trimethylamine is a nitrogenous base and its positively charged cation is called trimethylammonium cation. A common salt of trimethylamine is trimethylammonium chloride, a hygroscopic colorless solid (Wikipedia ). Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the fishy odor often associated with fouling fish, bacterial vagina infections, and bad breath. It is also associated with taking large doses of choline (Wikipedia ). Trimethylaminuria is a genetic disorder in which the body is unable to metabolize trimethylamine from food sources. Patients develop a characteristic fish odour of their sweat, urine, and breath after the consumption of choline-rich foods. Trimethylaminuria is an autosomal recessive disorder involving a trimethylamine oxidase deficiency. Trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell (Wikipedia ). Trimethylamine in the urine is a biomarker for the consumption of legumes. It has also been found to be a product of various types of bacteria, such as Achromobacter, Acinetobacter, Actinobacteria, Aeromonas, Alcaligenes, Alteromonas, Anaerococcus, Bacillus, Bacteroides, Bacteroidetes, Burkholderia, Campylobacter, Citrobacter, Clostridium, Desulfitobacterium, Desulfovibrio, Desulfuromonas, Edwardsiella, Enterobacter, Enterococcus, Escherichia, Eubacterium, Firmicutes, Flavobacterium, Gammaproteobacteria, Haloanaerobacter, Klebsiella, Micrococcus, Mobiluncus, Olsenella, Photobacterium, Proteobacteria, Proteus, Providencia, Pseudomonas, Rhodopseudomonas, Ruminococcus, Salmonella, Sarcina, Serratia, Shewanella, Shigella, Sinorhizobium, Sporomusa, Staphylococcus, Stigmatella, Streptococcus, Vibrio and Yokenella (PMID: 26687352 ; PMID: 25108210 ; PMID: 24909875 ">24909875 ; PMID: 28506279 ; PMID: 27190056 ). Trimethylamine is a marker for urinary tract infection brought on by E. coli. (PMID: 25108210 ; PMID: 24909875 ). It has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
(CH3)3N	ChEBI
N(CH3)3	ChEBI
N,N,N-Trimethylamine	ChEBI
N,N-Dimethylmethanamine	ChEBI
NMe3	ChEBI
TMA	ChEBI
Tridimethylaminomethane	ChEBI
Trimethylamin	ChEBI
Dimethylmethaneamine	HMDB
N,N-Dimethyl-methanamine	HMDB
N-Trimethylamine	HMDB
Trimethylamine anhydrous	HMDB
Trimethylamine aqueous solution	HMDB
HI OF trimethylamine	HMDB
HCL OF Trimethylamine	HMDB
HBR OF Trimethylamine	HMDB

Molecular Formula

C₃H₉N

Average Mass

59.1103

Monoisotopic Mass

59.073499293

IUPAC Name

trimethylamine

Traditional Name

trimethylamine

CAS Registry Number

75-50-3

SMILES

CN(C)C

InChI Identifier

InChI=1S/C3H9N/c1-4(2)3/h1-3H3

InChI Key

GETQZCLCWQTVFV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Trialkylamines

Alternative Parents

Substituents

Tertiary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tertiary amine (CHEBI:18139 )
methylamines (CHEBI:18139 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	654 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	0.19	ChemAxon
logS	1.04	ALOGPS
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	19.99 m³·mol⁻¹	ChemAxon
Polarizability	7.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-55145d7583823742b4d0	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-55145d7583823742b4d0	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9000000000-6aa19094223b203c2a43	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-9000000000-83029e23f5cbd6a60765	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-ed35409515031a3b1b98	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-902429fa0e6ccf9ef725	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0a4i-9000000000-55145d7583823742b4d0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-642dcafdbfe03e03d6d7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-72c88f801535e64a9a23	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-af4658f148c840dcb767	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-d06cd0ed0adb68499d85	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-89bf02c9ad080630c967	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-d9300b7bd734e223bf4d	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-89bb141981944dac6e56	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-89bb141981944dac6e56	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-e49050d0297528d1845c	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-d9608e4725a25c2900a2	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-d9608e4725a25c2900a2	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-166727f86b2d8ddfffc8	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-12b588010b7079d36b5c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-12b588010b7079d36b5c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-668f5a2f2030e01e42df	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-909841d5aea15e062470	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CCl₄, experimental)		2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Saliva
Skeletal Muscle
Urine

Tissue Locations

Epidermis
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191814	Dimethylaniline monooxygenase [N-oxide-forming] 5	Unknown	P49326	Homo sapiens
MMDBp0191826	Dimethylaniline monooxygenase [N-oxide-forming] 2	Unknown	Q99518	Homo sapiens
MMDBp0191836	Dimethylaniline monooxygenase [N-oxide-forming] 4	Unknown	P31512	Homo sapiens
MMDBp0191842	Dimethylaniline monooxygenase [N-oxide-forming] 3	Unknown	P31513	Homo sapiens
MMDBp0191856	Dimethylaniline monooxygenase [N-oxide-forming] 1	Unknown	Q01740	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007976	Hydrogen Ion	Water	Not Available	Trimethylamine N-oxide reductase (menaquinol 8)	VMH	30371894
MMDBr0007977	Hydrogen Ion	Water	Not Available	Trimethylamine N-oxide reductase menaquinol 8 (extracellular)	VMH	30371894
MMDBr0007978	2-Demethylmenaquinol 8	2-Demethylmenaquinone 8	Not Available	Trimethylamine N-oxide reductase (demethylmenaquinol 8)	VMH	30371894
MMDBr0007979	2-Demethylmenaquinol 8	2-Demethylmenaquinone 8	Not Available	Trimethylamine N-oxide reductase demethylmenaquinol 8 (extracellular)	VMH	30371894
MMDBr0008216	Hydrogen Ion	Hydrogen Ion	Not Available	Trimethylamine transport via proton symport, reversible	VMH	30371894
MMDBr0008229	Betaine	Acetyl phosphate	Not Available	Betaine reductase	VMH	30371894
MMDBr0008293	Choline	Acetaldehyde	Not Available	Choline-TMA lyase	VMH	30371894
MMDBr0010690	Trimethylamine	Water	Flavin containing monooxygenase 1	Flavin-Containing Monooxygenase	VMH; KEGG	30371894
MMDBr0010993	2-Demethylmenaquinol 8	2-Demethylmenaquinone 8	Not Available	Trimethylamine-N-oxide reductase (2-demethylmenaquinone)	VMH	30371894
MMDBr0011005	Hydrogen Ion	Water	Not Available	Trimethylamine-N-oxide reductase (Menaquinol)	VMH	30371894
MMDBr0013057	Hydrogen Ion	Dimethylamine	Trimethylamine dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0014428	Iron(3+)	Fe2+	Dimethyl sulfoxide/trimethylamine N-oxide reductase	Reduction	RHEA	34755880
MMDBr0014429	Fe2+	Iron(3+)	Trimethylamine-N-oxide reductase 2	Reduction	RHEA	34755880
MMDBr0015392	Choline	Acetaldehyde	Choline trimethylamine-lyase	Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880
MMDBr0015695	cobalt(+)	Dimethylamine	Trimethylamine methyltransferase MttB	Methylation	RHEA	34755880
MMDBr0016797	(R)-Carnitine	(3R)-3-hydroxy-4-oxobutanoic acid	Carnitine monooxygenase oxygenase subunit	Oxygenation; Reduction	RHEA	34755880
MMDBr0016798	(R)-Carnitine	(3R)-3-hydroxy-4-oxobutanoic acid	Carnitine monooxygenase oxygenase subunit	Oxygenation; Reduction	RHEA	34755880
MMDBr0019157	Trimethylamine N-oxide	Trimethylamine	Trimethylamine-N-oxide reductase 1	Reduction	PathBank	31602464
MMDBr0024397	Water	Hydrogen Ion	Glycine/sarcosine/betaine reductase complex component A	Reduction	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Dimethylglycine dehydrogenase deficiency		Association	Human Urine	HMDB	10102904
Kidney disease		Association	Human Blood	HMDB	17073580
Trimethylaminuria	Increased	Association	Human Urine	HMDB	9246418
Trimethylaminuria		Association	Human Urine	HMDB	16601883
Trimethylaminuria	Increased	Association	Human Urine	HMDB	7474897
Uremia		Association	Human Blood	HMDB	22626821
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	58	Human ; Human mucosa; Human supragingival plaque; Human saliva; Human feces; Human subgingival plaque; Human stool; Human sputum; Human pleural fluid plaque; Cattle	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	114	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human subgingival plaque; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Chicken	Microbial culture; Metabolic reconstruction
Archaea	Euryarchaeota	2		Microbial culture
Bacteria	Bacteroidetes	1	Human feces; Human stool; Human saliva	Microbial culture
Bacteria	Actinobacteria	17	Human feces; Human ; Human nasopharyngeal swab; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	1		Metabolic reconstruction
Bacteria/NULL	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human subgingival plaque; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Chicken	Microbial culture; Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	4		Microbial culture
Archaea/Archaea	nah	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Food			FooDB	31437929
Food	Coffee	Coffea canephora	FooDB	31437929
Food			FooDB	31437929
Food	Coffee	Coffea arabica	FooDB	31437929
Plant		Theobroma cacao	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified			87.2	322.7	umol/mmol creatinine	Adult (>18 years old)	Both	Trimethylaminuria	HMDB	7474897
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0679		0.0492	0.0866	uM	Adult (>18 years old)	Both	Normal	HMDB	8257730
Human Urine	Detected and Quantified	7.7	7.4			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9246418
Human Urine	Detected and Quantified	22.2				umol/mmol creatinine	Adult (>18 years old)	Both	Trimethylaminuria	HMDB	9246418
Human Urine	Detected and Quantified	<2				umol/mmol creatinine	Adult (>18 years old)	Male	Dimethylglycinuria	HMDB	10102904
Human Urine	Detected and Quantified	<2				umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	10102904
Human Saliva	Detected and Quantified	159		9	309	uM	Adult (>18 years old)	Both	Normal	HMDB	12097436
Human Blood	Detected and Quantified	0.42	0.12			uM	Adult (>18 years old)	Both	Normal	HMDB	16401621
Human Urine	Detected and Quantified	<10				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	16601883
Human Urine	Detected and Quantified			5	160	umol/mmol creatinine	Children (1-13 years old)	Both	Trimethylaminuria	HMDB	16601883
Human Blood	Detected and Quantified	1.5	0.5			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	17073580
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Crohn's Disease	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ulcerative Colitis	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Crohn's disease	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ulcerative colitis	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Campylobacter jejuni infection	HMDB	17314143
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	18052033
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	18085514
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Periodontal diseases	HMDB	20300169
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Pancreatic cancer	HMDB	20300169
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Female	Breast cancer	HMDB	20300169
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Both	Oral cancer	HMDB	20300169
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20300169
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Irritable bowel syndrome	HMDB	21761941
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21761941
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ulcerative colitis	HMDB	21761941
Human Blood	Detected and Quantified	13.3 (2.0)				uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Blood	Detected and Quantified	11.2 (3.1)				uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Blood	Detected and Quantified	1.38	0.48			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified	6.03 (2.0)				uM	Adult (>18 years old)	Female	Late-onset preeclampsia	HMDB	23159745
Human Blood	Detected and Quantified	7.6 (3.3)				uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23159745
Human Urine	Detected and Quantified	2.5		0.3	19.4	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	40		20	60	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	25012580
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25670064
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	25985090
Human Blood	Detected and Quantified	32.36(6.19)				uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	HMDB	26010610
Human Blood	Detected and Quantified	34.06(8.59)				uM	Adult (>18 years old)	Both	Heart failure with reduced ejection fraction	HMDB	26010610
Human Blood	Detected and Quantified	26.55(7.07)				uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	asymptomatic diverticulosis	HMDB	27622378
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	symptomatic uncomplicated diverticular disease	HMDB	27622378
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	27622378
Human Urine	Detected and Quantified			2	6	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Saliva	Detected and Quantified	20.72	17.19			uM	Adult (>18 years old)	Both	Normal	HMDB	Zerihun T. Dame, Farid Aziat, Rupasri Mandal, Ram Krishnamurthy, Souhaila Bouatra, Shima Borzouie, An Chi Guo, Tanvir Sajed, Lu Deng, Hong Lin, Philip Liu, Edison Dong, David S. Wishart "The human saliva metabolome" Metabolomics (2015) DOI 10.1007/s11306-015-0840-5
Human Urine	Detected and Quantified	3.366	1.991			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	3.659	2.462			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			0.24	2.33	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Lee SK, Kim D-H, Jin C, Yoo HH. Determination of urinary trimethylamine and trimethylamine-N-oxide by liquid chromatography-tandem mass spectrometry using mixed-mode stationary phases. Bull Korean Chem Soc. 2010;31:483-6.
Human Urine	Detected and Quantified	<2				umol/mmol creatinine	Adult (>18 years old)	Male	Dimethylglycinuria	HMDB	10102904
Human Blood	Detected and Quantified	13.3	2.0			uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Blood	Detected and Quantified	1.5	0.5			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	17073580
Human Blood	Detected and Quantified	6.03	2.0			uM	Adult (>18 years old)	Female	Late-onset preeclampsia	HMDB	23159745
Human Blood	Detected and Quantified	11.2	3.1			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Blood	Detected and Quantified	7.6	3.3			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23159745
Human Urine	Detected and Quantified	22.2				umol/mmol creatinine	Adult (>18 years old)	Both	Trimethylaminuria	HMDB	9246418
Human Urine	Detected and Quantified			5	160	umol/mmol creatinine	Children (1-13 years old)	Both	Trimethylaminuria	HMDB	16601883
Human Urine	Detected and Quantified			87.2	322.7	umol/mmol creatinine	Adult (>18 years old)	Both	Trimethylaminuria	HMDB	7474897
Human Blood	Detected and Quantified	1.38	0.48			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Urine	Detected and Quantified			2	6	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human Urine	Detected and Quantified	<10				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	16601883
Human Urine	Detected and Quantified	<2				umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	10102904
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0679		0.0492	0.0866	uM	Adult (>18 years old)	Both	Normal	HMDB	8257730
Human Blood	Detected and Quantified	0.42	0.12			uM	Adult (>18 years old)	Both	Normal	HMDB	16401621
Human Saliva	Detected and Quantified	159		9.00	309	uM	Adult (>18 years old)	Both	Normal	HMDB	12097436
Human Urine	Detected and Quantified	2.5		0.3	19.4	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	26.55	7.07			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Urine	Detected and Quantified	40		20	60	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	25012580
Human Urine	Detected and Quantified	7.7	7.4			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9246418
Human Urine	Detected and Quantified	3.659	2.462			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	3.366	1.991			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			0.24	2.33	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Lee SK, Kim D-H, Jin C, Yoo HH. Determination of urinary trimethylamine and trimethylamine-N-oxide by liquid chromatography-tandem mass spectrometry using mixed-mode stationary phases. Bull Korean Chem Soc. 2010;31:483–6.
Human Saliva	Detected and Quantified	20.72	17.19			uM	Adult (>18 years old)	Both	Normal	HMDB	Zerihun T. Dame, Farid Aziat, Rupasri Mandal, Ram Krishnamurthy, Souhaila Bouatra, Shima Borzouie, An Chi Guo, Tanvir Sajed, Lu Deng, Hong Lin, Philip Liu, Edison Dong, David S. Wishart "The human saliva metabolome" Metabolomics (2015) DOI 10.1007/s11306-015-0840-5
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20300169
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	18052033
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	18085514
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21761941
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25670064
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17269711
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	27622378
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	25985090
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000906

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Trimethylamine

METLIN ID

3772

PubChem Compound

1146

PDB ID

Not Available

ChEBI ID

18139

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Zeisel SH, daCosta KA, LaMont JT: Mono-, di- and trimethylamine in human gastric fluid: potential substrates for nitrosodimethylamine formation. Carcinogenesis. 1988 Jan;9(1):179-81. doi: 10.1093/carcin/9.1.179. [PubMed:3335043 ]
Al-Waiz M, Ayesh R, Mitchell SC, Idle JR, Smith RL: A genetic polymorphism of the N-oxidation of trimethylamine in humans. Clin Pharmacol Ther. 1987 Nov;42(5):588-94. doi: 10.1038/clpt.1987.201. [PubMed:3677545 ]
Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. doi: 10.1021/ac00101a004. [PubMed:7762816 ]
Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. doi: 10.1016/0731-7085(93)80171-v. [PubMed:8257730 ]
Hillier SL: Diagnostic microbiology of bacterial vaginosis. Am J Obstet Gynecol. 1993 Aug;169(2 Pt 2):455-9. doi: 10.1016/0002-9378(93)90340-o. [PubMed:8357044 ]
Mitchell SC, Zhang AQ, Barrett T, Ayesh R, Smith RL: Studies on the discontinuous N-oxidation of trimethylamine among Jordanian, Ecuadorian and New Guinean populations. Pharmacogenetics. 1997 Feb;7(1):45-50. doi: 10.1097/00008571-199702000-00006. [PubMed:9110361 ]
Maschke S, Wahl A, Azaroual N, Boulet O, Crunelle V, Imbenotte M, Foulard M, Vermeersch G, Lhermitte M: 1H-NMR analysis of trimethylamine in urine for the diagnosis of fish-odour syndrome. Clin Chim Acta. 1997 Jul 25;263(2):139-46. doi: 10.1016/s0009-8981(97)00060-0. [PubMed:9246418 ]
Thithapandha A: A pharmacogenetic study of trimethylaminuria in Orientals. Pharmacogenetics. 1997 Dec;7(6):497-501. doi: 10.1097/00008571-199712000-00008. [PubMed:9429235 ]
Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. doi: 10.1177/154405910208100613. [PubMed:12097436 ]
Dzik-Jurasz AS, Prescot AP, Leach MO, Collins DJ: Non-invasive study of human gall bladder bile in vivo using (1)H-MR spectroscopy. Br J Radiol. 2003 Jul;76(907):483-6. doi: 10.1259/bjr/30212020. [PubMed:12857709 ]
Kenyon S, Carmichael PL, Khalaque S, Panchal S, Waring R, Harris R, Smith RL, Mitchell SC: The passage of trimethylamine across rat and human skin. Food Chem Toxicol. 2004 Oct;42(10):1619-28. doi: 10.1016/j.fct.2004.05.007. [PubMed:15304308 ]
Chao CK, Zeisel SH: Formation of trimethylamine from dietary choline by Streptococcus sanguis I, which colonizes the mouth. J Nutr Biochem. 1990 Feb;1(2):89-97. doi: 10.1016/0955-2863(90)90055-p. [PubMed:15539190 ]
Leys D, Basran J, Talfournier F, Chohan KK, Munro AW, Sutcliffe MJ, Scrutton NS: Flavin radicals, conformational sampling and robust design principles in interprotein electron transfer: the trimethylamine dehydrogenase-electron-transferring flavoprotein complex. Biochem Soc Symp. 2004;(71):1-14. doi: 10.1042/bss0710001. [PubMed:15777008 ]
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Lam CW, Law CY, To KK, Cheung SK, Lee KC, Sze KH, Leung KF, Yuen KY: NMR-based metabolomic urinalysis: a rapid screening test for urinary tract infection. Clin Chim Acta. 2014 Sep 25;436:217-23. doi: 10.1016/j.cca.2014.05.014. Epub 2014 Jun 6. [PubMed:24909875 ]
Lam CW, Law CY, Sze KH, To KK: Quantitative metabolomics of urine for rapid etiological diagnosis of urinary tract infection: evaluation of a microbial-mammalian co-metabolite as a diagnostic biomarker. Clin Chim Acta. 2015 Jan 1;438:24-8. doi: 10.1016/j.cca.2014.07.038. Epub 2014 Aug 6. [PubMed:25108210 ]
Wang Z, Roberts AB, Buffa JA, Levison BS, Zhu W, Org E, Gu X, Huang Y, Zamanian-Daryoush M, Culley MK, DiDonato AJ, Fu X, Hazen JE, Krajcik D, DiDonato JA, Lusis AJ, Hazen SL: Non-lethal Inhibition of Gut Microbial Trimethylamine Production for the Treatment of Atherosclerosis. Cell. 2015 Dec 17;163(7):1585-95. doi: 10.1016/j.cell.2015.11.055. [PubMed:26687352 ]
Fennema D, Phillips IR, Shephard EA: Trimethylamine and Trimethylamine N-Oxide, a Flavin-Containing Monooxygenase 3 (FMO3)-Mediated Host-Microbiome Metabolic Axis Implicated in Health and Disease. Drug Metab Dispos. 2016 Nov;44(11):1839-1850. doi: 10.1124/dmd.116.070615. Epub 2016 May 17. [PubMed:27190056 ]
Rath S, Heidrich B, Pieper DH, Vital M: Uncovering the trimethylamine-producing bacteria of the human gut microbiota. Microbiome. 2017 May 15;5(1):54. doi: 10.1186/s40168-017-0271-9. [PubMed:28506279 ]

Showing metabocard for Trimethylamine (MMDBc0000168)

MOL for #<Metabolite:0x00007fa4e2d0f7f8>

3D MOL for #<Metabolite:0x00007fa4e2d0f7f8>

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PDB for #<Metabolite:0x00007fa4e2d0f7f8>

3D PDB for #<Metabolite:0x00007fa4e2d0f7f8>

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Structure for #<Metabolite:0x00007fa4e2d0f7f8>

3D Structure for #<Metabolite:0x00007fa4e2d0f7f8>