(R)-Amygdalin

Chemical compound
trends
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chemical structure
alias
D-mandelonitrile-beta-D-glucosido-6-beta-D-glucoside
D-(-)-mandelonitrile-beta-D-gentiobioside
D-amygdalin
(2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-acetonitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-ethanenitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
mass
457.158 dalton
chemical formula
C₂₀H₂₇NO₁₁
media
canonical SMILES
C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O
isomeric SMILES
OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H](C#N)C3=CC=CC=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
NCI Thesaurus ID
C28801
Wikipedia creation date
2/25/2002
Wikipedia incoming links count
Wikipedia opening text
Amygdalin (from Ancient Greek: ἀμυγδαλή amygdálē "almond") is a naturally occurring chemical compound best known for falsely being promoted as a cancer cure. It is found in many plants, but most notably in the seeds (kernels) of apricots, bitter almonds, apples, peaches, and plums. Amygdalin is classified as a cyanogenic glycoside because each amygdalin molecule includes a nitrile group, which can be released as the toxic cyanide anion by the action of a beta-glucosidase. Eating amygdalin will cause it to release cyanide in the human body, and may lead to cyanide poisoning. Since the early 1950s, both amygdalin and a modified form named laetrile have been promoted as alternative cancer treatments, often under the misnomer vitamin B17 (neither amygdalin nor laetrile is a vitamin). Scientific study has found them to be clinically ineffective in treating cancer, as well as potentially toxic or lethal when taken by mouth due to cyanide poisoning. The promotion of laetrile to treat cancer has been described in the medical literature as a canonical example of quackery, and as "the slickest, most sophisticated, and certainly the most remunerative cancer quack promotion in medical history".
Wikipedia redirect
Laetrile
Vitamin B17
Vitamin b17
Nitriloside
Nitrilosides
Layatril
Layatryl
Laetari
Neoamygdalin
Laetril
C20H27NO11
C₂₀H₂₇NO₁₁
Leotril
Wikipedia URL
CAS Registry Number
ChEBI ID
ChEMBL ID
ChemSpider ID
DSSTOX substance identifier
EC number
249-925-3
ECHA InfoCard ID
Freebase ID
Human Metabolome Database ID
InChIKey
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KNApSAcK ID
Library of Congress authority ID
MassBank Accession ID
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PubChem CID
Reaxys registry number
66856
Römpp online ID
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external links