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Details

Stereochemistry ACHIRAL
Molecular Formula C7H9N2O
Molecular Weight 137.1592
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of TRIGONELLAMIDE

SMILES

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

InChI

InChIKey=LDHMAVIPBRSVRG-UHFFFAOYSA-O
InChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1

HIDE SMILES / InChI

Molecular Formula C7H9N2O
Molecular Weight 137.1592
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including http://www.hmdb.ca/metabolites/HMDB0000699 | https://www.ncbi.nlm.nih.gov/pubmed/13121916 | https://www.ncbi.nlm.nih.gov/pubmed/17641676 | https://www.ncbi.nlm.nih.gov/pubmed/19837120

Trigonellamide (1-Methylnicotinamide) is a metabolite of nicotinamide and is produced primarily in the liver by nicotinamide N-methyltransferase. Trigonellamide may be an endogenous activator of prostacyclin (PGI2) production and thus may regulate thrombotic as well as inflammatory processes in the cardiovascular system. The mechanisms of action of Trigonellamide involve the activation of PGI2 release driven by cyclooxygenase 2 (COX-2). PGI2 releasing capacity of 1- Trigonellamide was shown to afford not only anti-thrombotic but also fibrinolytic, anti-inflammatory and gastroprotective effects. Interestingly, Trigonellamide did not directly either affect the activity of leucocytes or release PGI2 in the perfused rat hindquarters model. Still, Trigonellamide, due to its PGI2 releasing capacity, might serve as a hepatoprotective agent that protects against Concanavalin-A induced liver injury through the downregulation of interleukin-4 (IL-4) and tumor necrosis factor-α signalization (TNF-α). In addition to its anti-platelet, anti-thrombotic and anti-inflammatory activities, 1-MNA has also been shown to restore endothelial function in diabetic hyperglycemic rats, as well as to improve endothelial function in humans. PGI2 displays anti-metastatic activity, and the PGI2 releasing activity of Trigonellamide, the potential application of exogenous Trigonellamide to prevent metastatic cancer.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Liver function test in pregnancy; effect of trigonellamide (N1-methylnicotinamide chloride) on pyruvic, lactic, and amino acids in the blood in liver insufficiency in pregnancy.
1953 Jul
Patents

Patents

Sample Use Guides

30 mg 1-MNA (Trigonellamide ) or 90 mg 1-MNA (Trigonellamide ) three times daily for twelve weeks.
Route of Administration: Oral
Primary cultures of granule neurons were prepared from cerebella of 7-day-old rats. The cells were used for experiments on the 6th to 8lh day in vitro (DIV). To verify the intrinsic neurotoxicity of MNA (Trigonellamide), on DIV 6 or 7 these substance was added directly to the cell growth medium and culturing was continued for 24 h under standard conditions. The acute neurotoxicity of D,L-homocysteine was induced at DIV 7 by replacing the BME growth medium with Locke 25 buffer containing aliquots of freshly prepared D,L-homocysteine alone or with MNA as required. After 30 min, the Locke medium was replaced with the original growth medium and the cultures continued for 24 h. In other experiments, MNA were present in the growth medium for 24 h before and after acute exposure to Hey. To examine sub-acute Hey neurotoxicity, this amino acid was applied at different concentrations directly to cultures for 24 h. In these experiments NAM or MNA, if present, were added 24 h before Hey.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:53:45 GMT 2023
Edited
by admin
on Fri Dec 15 17:53:45 GMT 2023
Record UNII
UM47085BXC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIGONELLAMIDE
Common Name English
1-METHYLNICOTINAMIDE
Systematic Name English
PYRIDINIUM, 3-(AMINOCARBONYL)-1-METHYL-
Systematic Name English
TRIGONELLINAMIDE
Common Name English
1-MNA
Common Name English
TRIA-662
Common Name English
N1-METHYLNICOTINAMIDE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID10185019
Created by admin on Fri Dec 15 17:53:45 GMT 2023 , Edited by admin on Fri Dec 15 17:53:45 GMT 2023
PRIMARY
PUBCHEM
457
Created by admin on Fri Dec 15 17:53:45 GMT 2023 , Edited by admin on Fri Dec 15 17:53:45 GMT 2023
PRIMARY
CHEBI
16797
Created by admin on Fri Dec 15 17:53:45 GMT 2023 , Edited by admin on Fri Dec 15 17:53:45 GMT 2023
PRIMARY
FDA UNII
UM47085BXC
Created by admin on Fri Dec 15 17:53:45 GMT 2023 , Edited by admin on Fri Dec 15 17:53:45 GMT 2023
PRIMARY
DRUG BANK
DB11710
Created by admin on Fri Dec 15 17:53:45 GMT 2023 , Edited by admin on Fri Dec 15 17:53:45 GMT 2023
PRIMARY
CAS
3106-60-3
Created by admin on Fri Dec 15 17:53:45 GMT 2023 , Edited by admin on Fri Dec 15 17:53:45 GMT 2023
PRIMARY
WIKIPEDIA
1-Methylnicotinamide
Created by admin on Fri Dec 15 17:53:45 GMT 2023 , Edited by admin on Fri Dec 15 17:53:45 GMT 2023
PRIMARY
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