Trigonelline

Modify Date: 2024-01-03 12:50:58

Trigonelline structure	Common Name	Trigonelline
	CAS Number	535-83-1	Molecular Weight	137.136
	Density	1.2528 (rough estimate)	Boiling Point	251.96°C (rough estimate)
	Molecular Formula	C₇H₇NO₂	Melting Point	260ºC (dec.)
	MSDS	N/A	Flash Point	N/A

Use of Trigonelline

Trigonelline, an alkaloid with potential antidiabetic activity, is present in considerable amounts in coffee.

Name	N-methylnicotinate
Synonym	More Synonyms

Description	Trigonelline, an alkaloid with potential antidiabetic activity, is present in considerable amounts in coffee.
Related Catalog	Natural Products >> Alkaloid Research Areas >> Metabolic Disease
Target	Human Endogenous Metabolite
In Vitro	It is found that Trigonelline (TG) significantly rescues the morphology of the H9c2 cells. Treatment of cells with Trigonelline attenuates H2O2 induced cell deaths and improves the antioxidant activity. In addition, Trigonelline regulates the apoptotic gene caspase-3, caspase-9 and anti-apoptotic gene Bcl-2, Bcl-XL during H2O2 induced oxidative stress in H9c2 cells. For evident, flow cytometer results also confirms that Trigonelline significantly reduces the H2O2 induced necrosis and apoptosis in H9c2 cells. However, further increment of Trigonelline concentration against H2O2 can induce the necrosis and apoptosis along with H2O2[1].
In Vivo	Trigonelline decreases bone mineralization and tends to worsen bone mechanical properties in streptozotocin-induced diabetic rats. In nicotinamide/streptozotocin-treated rats, Trigonelline significantly increases bone mineral density (BMD) and tends to improve cancellous bone strength. Trigonelline differentially affects the skeletal system of rats with streptozotocin-induced metabolic disorders, intensifying the osteoporotic changes in streptozotocin-treated rats and favorably affecting bones in the non-hyperglycemic (nicotinamide/streptozotocin-treated) rats[2].
Cell Assay	The H9c2 cells are seeded in the 96 well at a density of 1×105 cells/well. The cells are treated with different concentrations of Trigonelline (TG) (25 to 150 μM) and hydrogen peroxide (25 to 125 μM). It is incubated at 37°C in 5% CO2 incubator for 24 h and 6 h respectively and then the culture is treated with the water soluble tetrazolium (WST) reagent incubated for 2 h to 4 h. The living cells absorb the WST then it is converted into an orange colour product. Then, the intensity of colour is measured at 450 nm using spectra count ELISA reader. For cardio protective activity, the cells are seeded and separated into six groups control, H2O2 alone, the rest of groups’ initially exposed to different concentration (25 to 125 μM) of Trigonelline for 48 hours. Then, 100 μM of H2O2 is added and incubated for 4 hours, after, read the absorbance at 450 nm for cell viability assay[1].
Animal Admin	Three-month-old female Wistar rats are used in this study. The animals are divided into five groups (n=10): Control rats, Streptozotocin-treated control rats, Streptozotocin-treated rats receiving Trigonelline (50 mg/kg p.o. daily), Nicotinamide/streptozotocin-treated control rats, and Nicotinamide/streptozotocin-treated rats receiving Trigonelline (50 mg/kg p.o. daily). Administration of Trigonelline starts two weeks after streptozotocin and lasts four weeks. Trigonelline is administered once daily by a stomach tube. All control rats receive tap water (the vehicle) at the same volume of 2 mL/kg p.o. The four-week period of Trigonelline administration is long enough to demonstrate skeletal effects of Trigonelline and other compounds of plant origin in rats. The rats are fasted overnight after the last Trigonelline or vehicle administration. The next day, the blood glucose level is measured and the rats are anesthetized with ketamine and xylazine, and then sacrificed by cardiac exsanguination[2].
References	[1]. Ilavenil S, et al. Trigonelline protects the cardiocyte from hydrogen peroxide induced apoptosis in H9c2 cells. Asian Pac J Trop Med. 2015 Apr;8(4):263-8. [2]. Joanna Folwarczna, et al. Effects of Trigonelline, an Alkaloid Present in Coffee, on Diabetes-Induced Disorders in the Rat Skeletal System. Nutrients. 2016 Mar; 8(3): 133.

Density	1.2528 (rough estimate)
Boiling Point	251.96°C (rough estimate)
Melting Point	260ºC (dec.)
Molecular Formula	C₇H₇NO₂
Molecular Weight	137.136
Exact Mass	137.047684
PSA	44.01000
LogP	-3.91
Index of Refraction	1.554
Storage condition	2~8℃

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YF6825000

CHEMICAL NAME :: Trigonelline

CAS REGISTRY NUMBER :: 535-83-1

BEILSTEIN REFERENCE NO. :: 3905114

LAST UPDATED :: 199712

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C7-H7-N-O2

MOLECULAR WEIGHT :: 137.15

WISWESSER LINE NOTATION :: T6KJ A1 CVQ &Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 1 mmol/plate

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 391,171,1997

Hazard Codes	Xi
Safety Phrases	24/25

1-Methylpyrrole

CAS#:96-54-8

Carbon dioxide

CAS#:124-38-9

Carbon

CAS#:7440-44-0

Trigonelline

CAS#:535-83-1

Detail

Literature: Journal of the American Chemical Society, , vol. 119, # 22 p. 5091 - 5094

Pyridinium, 3-c...

CAS#:6138-42-7

Trigonelline

CAS#:535-83-1

Literature: Monatshefte fuer Chemie, , vol. 22, p. 373 Monatshefte fuer Chemie, , vol. 21, p. 927 Anm. Monatshefte fuer Chemie, , vol. 24, p. 200

Nicotinic acid

CAS#:59-67-6

methyl iodide

CAS#:74-88-4

Trigonelline

CAS#:535-83-1

Literature: Journal fuer Praktische Chemie (Leipzig), , vol. <2> 130, p. 11,18

Pyridinium,3-(a...

CAS#:6456-44-6

Trigonelline

CAS#:535-83-1

Literature: Tetrahedron, , vol. 36, p. 785 - 789

Nicotinamide

CAS#:98-92-0

Trigonelline

CAS#:535-83-1

Literature: Tetrahedron, , vol. 36, p. 785 - 789

Nicotinic acid

CAS#:59-67-6

Trigonelline

CAS#:535-83-1

Literature: Journal of Molecular Structure, , vol. 614, # 1-3 p. 97 - 108

Ethyl nicotinate

CAS#:614-18-6

methyl iodide

CAS#:74-88-4

Trigonelline

CAS#:535-83-1

Literature: Chemische Berichte, , vol. 77/79, p. 362,365

Precursor 9
CAS#:96-54-8 1-Methylpyrrole CAS#:124-38-9 Carbon dioxide CAS#:7440-44-0 Carbon CAS#:6138-42-7 Pyridinium, 3-c...
CAS#:59-67-6 Nicotinic acid CAS#:74-88-4 methyl iodide CAS#:6456-44-6 Pyridinium,3-(a... CAS#:98-92-0 Nicotinamide
CAS#:614-18-6 Ethyl nicotinate
DownStream 10
CAS#:74-89-5 methylamine CAS#:626-67-5 1-Methylpiperidine CAS#:5657-70-5 1-methylpiperid... CAS#:499-04-7 Arecaidine
CAS#:695-36-3 1,5-dimethyl-3,... CAS#:695-35-2 Piperidine,1,3-... CAS#:59-67-6 Nicotinic acid CAS#:110-86-1 Pyridine
CAS#:74-87-3 Chloromethane CAS#:694-55-3 1-methyl-5,6-di...