Amygdalin

Title: Amygdalin
CAS Registry Number: 29883-15-6
CAS Name: [(6-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]benzeneacetonitrile
Additional Names: amygdaloside; mandelonitrile-b-gentiobioside; D-mandelonitrile-b-D-glucosido-6-b-D-glucoside
Manufacturers' Codes: NSC-15780
Molecular Formula: C20H27NO11
Molecular Weight: 457.43
Percent Composition: C 52.51%, H 5.95%, N 3.06%, O 38.47%
Literature References: The name amygdalin is currently used interchangeably with laetrile. Cyanogenic glycoside which occurs in seeds of Rosaceae; principally in bitter almonds; also in peaches and apricots. Most common constituent of Laetrile® preparations. Structure and synthesis: W. N. Haworth, B. Wylam, J. Chem. Soc. 123, 3120 (1923); Kuhn, Ber. 56, 857 (1923); R. Campbell, W. N. Haworth, J. Chem. Soc. 125, 1337 (1924); Hudson, J. Am. Chem. Soc. 46, 483 (1924); Zemplén, Kunz, Ber. 57, 1357 (1924); Kuhn, Sobotka, ibid. 1767; Baumann, Pigman, The Carbohydrates, W. Pigman, Ed. (Academic Press, New York, 1957) p 550. Enzymic hydrolysis studies: Haisman, Knight, Biochem. J. 103, 528 (1967). The term Laetrile® has also been applied to mandelonitrile b-glucuronide. Purported prepn: E. T. Krebs, E. T. Krebs, Jr., GB 788855 (1958) and US 2985664 (1961). Synthesis, characterization and comparison of mandelonitrile b-glucuronide with amygdalin: C. Fenselau et al., Science 198, 625 (1977). Pharmacology and cyanide toxicity studies of amygdalin (laetrile): C. G. Moertel et al., J. Am. Med. Assoc. 245, 591 (1981); M. M. Ames et al., Cancer Chemother. Pharmacol. 6, 51 (1981). Pharmacokinetics: A. G. Rauws et al., Arch. Toxicol. 49, 311 (1982). Determn methods in tissues and fluids: J. Balkon, J. Anal. Toxicol. 6, 244 (1982). Amygdalin (laetrile) is a toxic drug that is not effective as a cancer treatment: C. G. Moertel et al., N. Engl. J. Med. 306, 201 (1982). Review of the controversial use of amygdalin (laetrile): V. Herbert, Am. J. Clin. Nutr. 32, 1121-1158 (1979).
Derivative Type: Trihydrate
Properties: Orthorhombic columns from water, mp 200°; mp about 220° when anhydr. The once melted and solidif substance remelts at 125-130°. [a]D20 -42° (anhydr basis). One gram dissolves in 12 ml water, in 900 ml alcohol, in 11 ml boiling alcohol. Very sol in boiling water; almost insol in ether. pH of satd aq soln ~7.
Melting point: mp 200°; mp about 220° when anhydr; remelts at 125-130°
Optical Rotation: [a]D20 -42° (anhydr basis)
NOTE: The misleading term vitamin B17, has sometimes been applied to amygdalin.
Amyl Chloride Amyl Nitrite Amylbenzene Amylene Amylene Dichloride

Amygdalin
Identifiers
CAS number 29883-15-6 N
PubChem 34751
ChemSpider 570897 YesY
UNII 214UUQ9N0H YesY
MeSH Amygdalin
ChEBI CHEBI:17019 YesY
ChEMBL CHEMBL461727 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C20H27NO11
Molar mass 457.43 g mol−1
Hazards
NFPA 704
NFPA 704.svg
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Related compounds
Related compounds vicianin
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Amygdalin (from Ancient Greek: ἀμυγδαλή amygdálē "almond"), C20H27NO11, is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds, by Pierre-Jean Robiquet and Antoine Boutron-Charlard, in 1830[1] and subsequently investigated by Liebig and Wöhler in 1830. Several other related species in the genus of Prunus, including apricot (Prunus armeniaca) and black cherry (Prunus serotina),[2] also contain amygdalin.

Since the early 1950s, both amygdalin and a modified form named laetrile or Vitamin B17 have been promoted as cancer cures. However, neither of these compounds nor any other derivatives are vitamins in any sense,[3] and studies have found them to be clinically ineffective in the treatment of cancer, as well as dangerously toxic. They are potentially lethal when taken by mouth, because certain enzymes (in particular, glucosidases that occur in the gut and in various kinds of seeds, edible or inedible) act on them to produce cyanide.[4][5][6][7][8] The promotion of laetrile to treat cancer has been described in the medical literature as a canonical example of quackery,[9][10][11] and as "the slickest, most sophisticated, and certainly the most remunerative cancer quack promotion in medical history."[3]