Amygdalin

This was one of two molecules for this week.
May 27, 2019
We 鈥渜uacked鈥�, but we鈥檙e not ducks.
What molecules are we?
Image of Amygdalin 3D Image of Amygdalin
Image of Amygdalin 3D Image of Amygdalin

Amygdalin (on the left) and its companion molecule laetrile (right) burst into the headlines in the 1950s as purported cancer cures. As scientific research soon determined, they are not effective for treating cancer鈥攖hey are potent poisons.

Amygdalin occurs in many plants, notably in seeds of fruits in the Rosaceae family such as bitter almonds, apricots, and plums. Laetrile is a derivative of amygdalin formed by the hydrolytic removal of one glycoside group from the parent compound. The literature is a bit confusing because the names and laetrile sometimes are conflated. Both molecules are also erroneously termed vitamin B17.

Chemists Walter Norman Haworth and Birkett Wylam at Durham University (Newcastle upon Tyne, UK) elucidated the structure of amygdalin and synthesized it in 1923. Haworth was awarded the 1937 Nobel Prize in Chemistry for 1938.

From the 1950s through the 1970s, both compounds, under the name laetrile, were heavily promoted as a cure for many types of cancer. Rogue physicians and others established clinics in Mexico to which desperate patients flocked to receive the 鈥渃ure鈥� and other ineffective treatments. Science, however, prevailed: Laetrile was never approved by the US Food and Drug Administration or the European Commission.

The nitrile groups in amygdalin and laetrile are labile and easily removed as the cyanide ion by 尾-glucosidase enzymes in the human body. Cyanide, of course, is highly toxic; it is surprising that the compounds鈥� oral toxicity is given the mild hazard statement 鈥渉armful if swallowed鈥�.

In 1981, Irving J. Lerner at the University of Minnesota Medical School (Minneapolis) summarized the laetrile hoax thus: "All prior forms of cancer quackery . . . pale in comparison with the laetrile crusade, cancer quack promotion in medical history."聽

Amygdalin and laetrile* hazard information

GHS classification**: acute toxicity, oral, category 4
H302鈥擧armful if swallowedChemical Safety Warning

*No safety data sheet for laetrile is available. Hazards are assumed to be the same as for amygdalin.
**Globally Harmonized System of Classification and Labeling of Chemicals.聽

础尘测驳诲补濒颈苍听fast facts

CAS Reg. No.29883-15-6
Empirical formulaC20H27NO11
Molar mass457.43 g/mol
AppearanceWhite to beige powder
Melting point223鈥�226 潞C
Water solubility50 g/L

尝补别迟谤颈濒别听fast facts

CAS Reg. No.1332-94-1
Empirical formulaC14H15NO7
Molar mass309.27 g/mol
AppearanceWhite powder
Melting point214鈥�216 潞C
Water solubility83 g/L
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