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

Details

Stereochemistry ACHIRAL
Molecular Formula C7H9N2O.Cl
Molecular Weight 172.612
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIGONELLAMIDE CHLORIDE

SMILES

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

InChI

InChIKey=BWVDQVQUNNBTLK-UHFFFAOYSA-N
InChI=1S/C7H8N2O.ClH/c1-9-4-2-3-6(5-9)7(8)10;/h2-5H,1H3,(H-,8,10);1H

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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
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
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 17:59:21 GMT 2023
Edited
by admin
on Fri Dec 15 17:59:21 GMT 2023
Record UNII
L54XNJ1D5G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIGONELLAMIDE CHLORIDE
MI  
Common Name English
TRIGONELLAMIDE CHLORIDE [MI]
Common Name English
MNA CHLORIDE
Brand Name English
METHYL NIACINAMIDE CHLORIDE [INCI]
Common Name English
METHYL NIACINAMIDE CHLORIDE
INCI  
INCI  
Official Name English
Code System Code Type Description
CAS
1005-24-9
Created by admin on Fri Dec 15 17:59:21 GMT 2023 , Edited by admin on Fri Dec 15 17:59:21 GMT 2023
PRIMARY
DRUG BANK
DBSALT002055
Created by admin on Fri Dec 15 17:59:21 GMT 2023 , Edited by admin on Fri Dec 15 17:59:21 GMT 2023
PRIMARY
PUBCHEM
70495
Created by admin on Fri Dec 15 17:59:21 GMT 2023 , Edited by admin on Fri Dec 15 17:59:21 GMT 2023
PRIMARY
MERCK INDEX
m11132
Created by admin on Fri Dec 15 17:59:21 GMT 2023 , Edited by admin on Fri Dec 15 17:59:21 GMT 2023
PRIMARY Merck Index
FDA UNII
L54XNJ1D5G
Created by admin on Fri Dec 15 17:59:21 GMT 2023 , Edited by admin on Fri Dec 15 17:59:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID10905552
Created by admin on Fri Dec 15 17:59:21 GMT 2023 , Edited by admin on Fri Dec 15 17:59:21 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY