U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C7H8NO2.Cl
Molecular Weight 173.597
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIGONELLINE HYDROCHLORIDE

SMILES

[Cl-].C[N+]1=CC(=CC=C1)C(O)=O

InChI

InChIKey=TZSYLWAXZMNUJB-UHFFFAOYSA-N
InChI=1S/C7H7NO2.ClH/c1-8-4-2-3-6(5-8)7(9)10;/h2-5H,1H3;1H

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19324944 | https://www.ncbi.nlm.nih.gov/pubmed/28816550 | https://www.ncbi.nlm.nih.gov/pubmed/23108405

Trigonelline is a pyridine derivative known to contribute indirectly to the formation of desirable flavor products, including furans, pyrazine, alkyl-pyridines, and pyrroles, during coffee roasting. The amount of trigonelline in arabica is higher than that in robusta green coffee beans, and thus it can be used as a marker compound to distinguish the coffee bean species. During the roasting process of coffee beans, trigonelline changes into N-methylpyridinium and nicotinic acid as its major products, which makes it a useful index of the degree of roasting. The importance of trigonelline in coffee is connected to nutritional aspects. It has been revealed in recent studies that the administration of trigonelline allows diabetic rats to avoid diabetes-related organ damage and live longer, which can make it a potentially strong candidate for industrial application as a pharmacological agent for the treatment of hyperglycemia, hyperlipidemia, and liver/kidney dysfunctions. In addition, the urinary concentrations of trigonelline and its thermal product N-methylpyridinium of coffee drinkers are higher than those of noncoffee drinkers, which indicates that trigonelline and N-methylpyridinium may have potential as dietary biomarkers that could be used as analytical probes to control compliance in human intervention studies on coffee. Trigonelline has been isolated from many plants: fenugreek seeds (Trigonella foenum-graecum, hence the name), garden peas, hemp seed, oats, potatoes, Stachys species, dahlia, Strophanthus species, and Dichapetalum cymosum. In a randomized cross-over trial, the critical effect of Trigonelline on glucose tolerance has been studied during a 2-hour oral glucose tolerance test (OGTT) in 15 overweight men. Results showed that glucose and insulin concentrations significantly reduced 15minutes after Trigonelline consumption compared with placebo.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Antiadhesive effect of green and roasted coffee on Streptococcus mutans' adhesive properties on saliva-coated hydroxyapatite beads.
2002 Feb 27
Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes.
2010 May
Characterization of organic anion-transporting polypeptide (Oatp) 1a1 and 1a4 null mice reveals altered transport function and urinary metabolomic profiles.
2011 Aug
Patents

Patents

Sample Use Guides

500 mg trigonelline
Route of Administration: Oral
Panc1 and Colo357 cells were used for activity evaluation. Cells were cultured in RPMI 1640 containing 10% FCS, 1% L-glutamine and 1% sodium pyruvate (all from PAA-Laboratories). Cells were cultured at 37 C, 5% CO2 and 85% humidity. ARE-luciferase assays conducted with Panc1 and Colo357 cells subject to trig (Trigonelline) treatment at various concentrations (0.01–10 mkM) for 16 h revealed a dose-dependent inhibition of ARE-driven luciferase expression by trig.
Name Type Language
TRIGONELLINE HYDROCHLORIDE
Common Name English
N-METHYLNICOTINIC ACID BETAINE HYDROCHLORIDE
Common Name English
TRIGONELLINE, CHLORIDE
Common Name English
N-METHYL-3-CARBOXYPYRIDINIUM CHLORIDE
Systematic Name English
NSC-66510
Code English
PYRIDINIUM, 3-CARBOXY-1-METHYL-, CHLORIDE
Systematic Name English
PYRIDINIUM, 3-CARBOXY-1-METHYL-, CHLORIDE (1:1)
Systematic Name English
3-CARBOXY-1-METHYLPYRIDINIUM CHLORIDE
Systematic Name English
Code System Code Type Description
FDA UNII
89A86B74I9
Created by admin on Sat Dec 16 00:30:06 GMT 2023 , Edited by admin on Sat Dec 16 00:30:06 GMT 2023
PRIMARY
CAS
6138-41-6
Created by admin on Sat Dec 16 00:30:06 GMT 2023 , Edited by admin on Sat Dec 16 00:30:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID30976921
Created by admin on Sat Dec 16 00:30:06 GMT 2023 , Edited by admin on Sat Dec 16 00:30:06 GMT 2023
PRIMARY
NSC
66510
Created by admin on Sat Dec 16 00:30:06 GMT 2023 , Edited by admin on Sat Dec 16 00:30:06 GMT 2023
PRIMARY
ECHA (EC/EINECS)
228-119-5
Created by admin on Sat Dec 16 00:30:06 GMT 2023 , Edited by admin on Sat Dec 16 00:30:06 GMT 2023
PRIMARY
PUBCHEM
134606
Created by admin on Sat Dec 16 00:30:06 GMT 2023 , Edited by admin on Sat Dec 16 00:30:06 GMT 2023
PRIMARY