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2D Structure
Also known as: 535-83-1, Trigenolline, N-methylnicotinate, Caffearine, Gynesine, Coffearine
Molecular Formula
C7H7NO2
Molecular Weight
137.14  g/mol
InChI Key
WWNNZCOKKKDOPX-UHFFFAOYSA-N
FDA UNII
3NQ9N60I00

trigonelline is a natural product found in Hypoestes phyllostachya, Schumanniophyton magnificum, and other organisms with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-methylpyridin-1-ium-3-carboxylate
2.1.2 InChI
InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
2.1.3 InChI Key
WWNNZCOKKKDOPX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C[N+]1=CC=CC(=C1)C(=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
3NQ9N60I00
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Trigonelline Chloride

2. Trigonelline Iodide

3. Trigonelline Ion

4. Trigonelline Tosylate

2.3.2 Depositor-Supplied Synonyms

1. 535-83-1

2. Trigenolline

3. N-methylnicotinate

4. Caffearine

5. Gynesine

6. Coffearine

7. Betain Nicotinate

8. 1-methylpyridinium-3-carboxylate

9. Trigonellin

10. Coffearin

11. Betaine Nicotinate

12. 1-methylpyridinio-3-carboxylate

13. Nicotinic Acid N-methylbetaine

14. 1-methylpyridin-1-ium-3-carboxylate

15. N-methylnicotinic Acid

16. Trigenelline

17. Caffearin

18. 1-methyl-3-pyridiniumcarboxylate

19. 3-carboxy-1-methylpyridinium Hydroxide Inner Salt

20. N'-methylnicotinate

21. Chebi:18123

22. 3nq9n60i00

23. Pyridinium, 3-carboxy-1-methyl-, Hydroxide, Inner Salt

24. 1-methyl-nicotinic Acid Anion(trigonelline)

25. 3-carboxy-1-methylpyridinium Hydroxide, Inner Salt

26. 1-methylpyridin-1-ium-3-carboxylic Acid

27. Ccris 1332

28. Einecs 208-620-5

29. Brn 3905114

30. Unii-3nq9n60i00

31. Hsdb 7684

32. 1-methylnicotinate

33. Trigonelline,(s)

34. N-methyl-nicotinate

35. 3-carboxy-1-methylpyridinium Inner Salt

36. N'-methylnicotinic Acid

37. 6138-40-5

38. Trigonelline [mi]

39. Trigonelline [hsdb]

40. 5-22-02-00143 (beilstein Handbook Reference)

41. Mls002153895

42. N-methylnicotinic Acid Betaine

43. Schembl195666

44. Spectrum1500880

45. Trigonelline [usp-rs]

46. Chembl350675

47. Dtxsid2026230

48. Hms2096h08

49. Hms2234k22

50. Hms3371k21

51. Hy-n0414

52. Bdbm50548713

53. Ccg-38517

54. Mfcd00054262

55. Nsc714350

56. Akos005067859

57. Nsc-714350

58. Sdccgmls-0066739.p001

59. Ncgc00095649-01

60. Ncgc00095649-02

61. Ncgc00095649-03

62. Ncgc00095649-04

63. Ncgc00095649-07

64. Ac-34290

65. As-17722

66. Smr001233244

67. Ab00052974

68. Cs-0008944

69. Ft-0689338

70. N2788

71. 1-methyl-5-(oxylatocarbonyl)pyridinium-3-ide

72. Pyridinium, 3-carboxy-1-methyl-, Inner Salt

73. A14825

74. C01004

75. 3-carboxy-1-methyl-pyridinium Hydroxide Inner Salt

76. Q928965

77. 3-carboxy-1-methylpyridinium, Hydroxide, Inner Salt

78. W-105723

79. Trigonelline (constituent Of Fenugreek Seed) [dsc]

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 137.14 g/mol
Molecular Formula C7H7NO2
XLogP31.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass137.047678466 g/mol
Monoisotopic Mass137.047678466 g/mol
Topological Polar Surface Area44 Ų
Heavy Atom Count10
Formal Charge0
Complexity130
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPL THER/ Fenugreek seeds are known for their characteristic smell of soup seasoning and as an ingredient of Indian curry. Traditionally the seeds are used as macerate for the treatment of diabetes, cough, and flatulence, to increase breast milk secretion, and for anti-inflammatory and aphrodisiac effects. The use is limited by its unpleasant smell and bitter taste which can be modified by adding mint leaves to the macerate. Antidiabetic properties are attributed mainly to galactomannan, 4-hydroxyisoleucin (4-OH-Ile), diosgenin and trigonelline. These substances demonstrate direct antidiabetic properties in clinical studies by increasing insulin secretion (4-OH-Ile), decreasing insulin resistance and glucose resorption from the GIT (galactomannan) and improvement in B-cells regeneration (trigonelline). Besides this main effect, the herb improves blood lipid spectre (4-OH-Ile, diosgenin), and has reno-protective (4-OH-Ile, trigonelline), neuroprotective (trigonelline) and antioxidant (diosgenin, trigonelline) effects. Antidiabetic efficacy of trigonelline is comparable to glibenclamide treatment and more effective than sitagliptine therapy. Given the large body of evidence and promising results in comparison with standard pharmacotherapy, fenugreek active substances have a potential to become a source of new antidiabetic medication.Key words: fenugreek Trigonella foenum-graecum diabetes mellitus type 2 biological activity.

PMID:26400229 Koupy D et al; Ceska Slov Farm 64 (3): 67-71 (2015)


/EXPL THER/ There is evidence that Trigonella foenum-graecum L. (fenugreek), a traditional Chinese herb, and its components are beneficial in the prevention and treatment of diabetes and central nervous system disease. The pharmacological activities of trigonelline, a major alkaloid component of fenugreek, have been more thoroughly evaluated than fenugreek's other components, especially with regard to diabetes and central nervous system disease. Trigonelline has hypoglycemic, hypolipidemic, neuroprotective, antimigraine, sedative, memory-improving, antibacterial, antiviral, and anti-tumor activities, and it has been shown to reduce diabetic auditory neuropathy and platelet aggregation. It acts by affecting beta cell regeneration, insulin secretion, activities of enzymes related to glucose metabolism, reactive oxygen species, axonal extension, and neuron excitability. However, further study of trigonelline's pharmacological activities and exact mechanism is warranted, along with application of this knowledge to its clinical usage. This review aims to give readers a survey of the pharmacological effects of trigonelline, especially in diabetes, diabetic complications and central nervous system disease. In addition, because of its pharmacological value and low toxicity, the reported adverse effects of trigonelline in experimental animal models and humans are briefly reviewed, and the pharmacokinetics of trigonelline are also discussed.

PMID:22680628 Zhou J et al; Curr Med Chem. 2012;19(21):3523-31 (2012)


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

... The concentration-time curves of trigonelline in rabbits after ... iv administration were shown to fit one-compartment and two-compartment open model, respectively. The main parameters after iv /administration/ of trigonelline were as follows: T1/2 alpha was 10.8 min, T1/2 beta was 44.0 min, K21 was 0.044 min-1, K10 was 0.026 min-1, K12 was 0.017 min-1, AUC was 931.0 mg.min/L . /It was concluded that/ trigonelline showed a middle rate of absorption and fast rate of elimination in rabbit...

PMID:12889128 Zhao HQ et al; Yao Xue Xue Bao 38 (4): 279-82 (2003)


5.2 Metabolism/Metabolites

... Trigonelline (N-methylnicotinic acid) /is a metabolite of nicotinamide/.

PMID:8082753 Berglund T; FEBS Lett 351 (2): 145-9 (1994)