Caffine Chemically

[Guest guest]

A groovy Caffine article

 

Chemically speaking, what is caffeine?

 

Caffeine is an alkaloid. There are numerous compounds called alkaloids,

among them we have the methylxanthines, with three distinguished compounds:

caffeine, theophylline, and theobromine, found in cola nuts, coffee, tea,

cacao beans, mate and other plants. These compounds have different

biochemical effects, and are present in different ratios in the different

plant sources. These compounds are very similar and differ only by the

presence of methyl groups in two positions of the chemical structure. They

are easily oxidized to uric acid and other methyluric acids which are also

similar in chemical structure.

 

Caffeine:

Sources: Coffee, tea, cola nuts, mate, guarana.

Effects: Stimulant of central nervous system, cardiac muscle, and

respiratory system, diuretic Delays fatigue.

 

 

Theophylline:

Sources: Tea

Effects: Cariac stimulant, smooth muscle relaxant, diuretic, vasodilator

 

 

Theobromine:

Sources: Principle alkaloid of the cocoa bean (1.5-3%) Cola nuts and tea

Effects: Diuretic, smooth muscle relaxant, cardiac stimulant, vasodilator.

 

 

(Info from Merck Index)

 

The presence of the other alkaloids in colas and tea may explain why these

sometimes have a stronger kick than coffee. Colas, which have lower caffeine

contents than coffee are, reportedly, sometimes more active. Tea seems the

strongest for some. Coffee seems more lasting for mental alertness and

offers fewer jitters than the others.

 

A search in CAS and produced these names and synonyms:

 

RN 58-08-2 REGISTRY

CN 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl- (9CI) (CA INDEX

NAME)

OTHER CA INDEX NAMES:

CN Caffeine (8CI)

OTHER NAMES:

CN 1,3,7-Trimethyl-2,6-dioxopurine

CN 1,3,7-Trimethylxanthine

CN 7-Methyltheophylline

CN Alert-Pep

CN Cafeina

CN Caffein

CN Cafipel

CN Guaranine

CN Koffein

CN Mateina

CN Methyltheobromine

CN No-Doz

CN Refresh'n

CN Stim

CN Thein

CN Theine

CN Tri-Aqua

 

MF C8 H10 N4 O2

 

The correct name is the first one, 1H-Purine-2,6-dione,

3,7-dihydro-1,3,7-trimethyl- (This is the " inverted name " ) The " uninverted

name " is 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

 

Merck Index excerpt...

 

Caffeine: 3,7-dihydro- 1,3,7-trimethyl- 1H-purine- 2,6-dione;

1,3,7-trimethylxanthine; 1,3,7-trimethyl- 2,6-dioxopurine; coffeine; thein;

guaranine; methyltheobromine; No-Doz.

 

C8H10N4O2; mol wt 194.19. C 49.48%, H 5.19%, N 28.85%, O 16.48%.

 

Occurs in tea, coffee, mate leaves; also in guarana paste and cola nuts:

Shuman, U.S. pat. 2,508,545 (1950 to General Foods). Obtained as a

by-product from the manuf of caffeine-free coffee: Barch, U.S. pat.

2,817,588 (1957 to Standard Brands); Nutting, U.S. pat. 2,802,739 (1957 to

Hill Bros. Coffee); Adler, Earle, U.S. pat. 2,933,395 (1960 to General

Foods).

 

Crystal structure: Sutor, Acta Cryst. 11, 453, (1958). Synthesis: Fischer,

Ach, Ber. 28, 2473, 3135 (1895); Gepner, Kreps, J. Gen. Chem. USSR 16, 179

(1946); Bredereck et al., Ber. 83, 201 (1950); Crippa, Crippa, Farmaco Ed.

Sci. 10, 616 (1955); Swidinsky, Baizer, U.S. pats. 2,785,162 and 2,785,163

(1957 to Quinine Chem. Works); Bredereck, Gotsmann, Ber. 95, 1902 (1962).

 

Hexagonal prisms by sublimation, mp 238 C. Sublimes 178 C. Fast sublimation

is obtained at 160-165 C under 1mm press. at 5 mm distance. d 1.23. Kb at 19

C: 0.7 x 10^(-14). Ka at 25 C: <1.0 x 10^(-14). pH of 1% soln 6.9. Aq solns

of caffeine salts dissociate quickly. Absorption spectrum: Hartley, J. Chem.

Soc. 87, 1802 (1905). One gram dissolves in 46 ml water, 5.5 ml water at 80

C, 1.5 ml boiling water, 66 ml alcohol, 22 ml alcohol at 60 C, 50 ml

acetone, 5.5 ml chloroform, 530 ml ether, 100 ml benzene, 22 ml boiling

benzene. Freely sol in pyrrole; in tetrahydrofuran contg about 4% water;

also sol in ethyl acetate; slightly in petr ether. Soly in water is

increased by alkali benzoates, cinnamates, citrates, or salicylates.

 

Monohydrate, felted needles, contg 8.5% H2O. Efflorescent in air; complete

dehydration takes place at 80 C. LD50 orally in rats: 200 mg/kg.

 

Acetate, C8H10N4O2.(CH3COOH)2, granules or powder; acetic acid odor; acid

reaction. Loses acetic acid on exposure to air. Soluble in water or alcohol

with hydrolysis into caffeine and acetic acid. Keep well stoppered.

 

Hydrochloride dihydrate, C8H10N4O2.HCl.2H2O, crystals, dec 80-100 C with

loss of water and HCl. Sol in water and in alcohol with dec.

 

Therap Cat: Central stimulant.

 

Therap Cat (Vet): Has been used as a cardiac and respiratory stimulant and

as a diuretic.

 

Return to Index