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Theobromine: Chocolate's Caffeine Cousin

Dateline: 06/19/00

By Alan Bruzel

Beans from the cacao tree, Theobroma cacao (pronounced keh-COW), are the source of the world's chocolate. (Those who disparage chocolate's appeal should recall this plant's name derives from the Greek theos, god, and broma, food). The principal alkaloid of the cacao bean is theobromine, a close structural relative of caffeine. Theobromine possesses one less methyl group than does caffeine, the major alkaloid of coffee and tea. Cacao beans have between 1.5 to 3% theobromine and a seven-fold lesser amount of caffeine; coffee and tea contain about 4% caffeine with theobromine being a minor constituent of tea and not present in coffee.

Caffeine	Theobromine

In humans, theobromine has a ten-fold less stimulating effect than does caffeine. This is not the case in dogs, whose metabolic machinery removes theobromine very slowly, and who are therefore vulnerable to cardiac and central nervous system distress from this alkaloid (and from caffeine, as well). A toxic dose is estimated as between 100 to 200 milligrams of theobromine per kilogram (2.2 pounds) of a dog's body weight.

Theobromine levels vary in commercial chocolate. Milk chocolate contains about 200 milligrams per 100 grams (3.5 ounces), unsweetened baking chocolate has about 1400 milligrams per 100 grams, and cocoa has 2600 milligrams per 100 grams. The blissful state experienced by some chocolate devotees has not yet been linked to one specific ingredient; chocolate possesses a medley of bioactive molecules (including serotonin, phenylethylamine, and anandamide) that may, in combination, play a soothing sonata upon the senses.

What the Web Has to Say about:
Theobromine: Chocolate's Caffeine Cousin

Chocolate and Anxiety
Theobromine and other physiologically active substances in chocolate. From About.com's Panic/Anxiety Disorders Guide.

Chocolate Toxicity in Dogs
Toxic amounts and recommended veterinary treatment. From The Wolfdogs Resource.

Coffee and Caffeine FAQs
With additional information on theobromine and theophylline.

Extraction of Theobromine from Cocoa
Laboratory exercise isolates theobromine, and then alkylates it to caffeine. From The Australian National University.

Health and Happiness – Does Chocolate Have It All Wrapped Up?
History of chocolate and its bioactive ingredients. From Caroline Long, International Food Information Service.

Theobromine
Amounts of this compound in chocolate candy, cocoa, and chocolate milk. From Hershey Foods Corporation.

Theobromine
More data are required before assessing this compound's carcinogenic potential. From the International Agency for Research on Cancer, World Health Organization.

When Money Grew on Trees
Follow chocolate from the Mayans to the Europeans to your supermarket. From About.com's Botany Guide.

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