Trigonelline is an alkaloid

Alkaloid

Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

 with chemical formula

Chemical formula

A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 ₇₇₂. It is an inner salt formed by the addition of a methyl group

Methyl group

Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...

 to the nitrogen atom of niacin

Niacin

"Niacin" redirects here. For the neo-fusion band, see Niacin .Niacin is an organic compound with the formula and, depending on the definition used, one of the forty to eighty essential human nutrients.Niacin is one of five vitamins associated with a pandemic deficiency disease: niacin deficiency...

. Trigonelline is a product of the metabolism of niacin (vitamin B₃) which is excreted in the urine.

Trigonelline occurs in many plants, it was isolated from fenugreek

Fenugreek

Fenugreek is a plant in the family Fabaceae. Fenugreek is used both as a herb and as a spice . The leaves and sprouts are also eaten as vegetables...

 seeds (Trigonella foenum-graecum, thus the name), garden peas, hemp seed, oats, potatoes, Stachys

Stachys

Stachys is one of the largest genera in the flowering plant family Lamiaceae. Estimates of the number of species in the genus vary from about 300, to about 450. The type species for the genus is Stachys sylvatica. Stachys is in the subfamily Lamioideae...

 species, dahlia

Dahlia

Dahlia is a genus of bushy, tuberous, perennial plants native to Mexico, Central America, and Colombia. There are at least 36 species of dahlia, some like D. imperialis up to 10 metres tall. Dahlia hybrids are commonly grown as garden plants...

, Strophanthus

Strophanthus

Strophanthus is a genus of 35-40 species of flowering plants in the family Apocynaceae, native mainly to tropical Africa, extending to South Africa, with a few species in Asia, from southern India to the Philippines and southern China. The name derives from the long twisted threadlike segments of...

 species and Dichapetalum cymosum

Dichapetalum cymosum

Dichapetalum cymosum, commonly known as Gifblaar from Afrikaans, or occasionally its English translation, poison leaf, is a small prostrate shrub occurring in the northern parts of Southern Africa. It is notable as a common cause of lethal cattle poisoning in this region and is considered one of...

. Holtz, Kutscher and Theilmann have recorded its presence in a number of animals.

Trigonelline is also found in coffee

Coffee

Coffee is a brewed beverage with a dark,init brooo acidic flavor prepared from the roasted seeds of the coffee plant, colloquially called coffee beans. The beans are found in coffee cherries, which grow on trees cultivated in over 70 countries, primarily in equatorial Latin America, Southeast Asia,...

, where it may help to prevent dental caries

Dental caries

Dental caries, also known as tooth decay or a cavity, is an irreversible infection usually bacterial in origin that causes demineralization of the hard tissues and destruction of the organic matter of the tooth, usually by production of acid by hydrolysis of the food debris accumulated on the...

 by preventing the bacteria

Bacteria

Bacteria are a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals...

 Streptococcus mutans

Streptococcus mutans

Streptococcus mutans is a facultatively aerobic, Gram-positive coccus-shaped bacterium commonly found in the human oral cavity and is a significant contributor to tooth decay.The microbe was first described by J Kilian Clarke in 1924.-Introduction:...

from adhering to teeth. Higher levels of trigonelline is found in robusta coffee.

Trigonelline crystallises as a monohydrate from alcohol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

 in hygroscopic prisms, mp. 130 °C or 218 °C (dry, dec.). It is readily soluble in water or warm alcohol, less so in cold alcohol, and slightly so in chloroform

Chloroform

Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...

 or ether. The salts crystallise well, the monohydrochloride, in leaflets, sparingly soluble in dry alcohol. The picrate

Picrate

A picrate is a salt or an ester of picric acid . But it could also be an additional compound which picric acid forms with many aromatic hydrocarbons, aromatic amines, aliphatic amines, alkalines, and other compounds. These additional compounds are also called picrates even though they are not a...

 forms shining prisms, mp. 198-200 °C, soluble in water but sparingly soluble in dry alcohol or ether. The alkaloid forms several aurichlorides: the normal salt, B•HCl•AuCl₃, is precipitated when excess of gold chloride

Gold chloride

Gold chloride can refer to:* Gold chloride , AuCl* Gold chloride , AuCl2* Gold chloride , AuCl3* Chloroauric acid, HAuCl4...

is added to the hydrochloride, and after crystallisation from dilute hydrochloric acid containing some gold chloride, has mp. 198 °C. Crystallised from water or very dilute hydrochloric acid, slender needles of B₄•3 HAuCl₄, mp. 186 °C, are obtained.