Amygdalin
Medicinal Chemistry
Molecular Weight
457.43
Molecular Formula
C20H27NO11
IUPAC Name
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
Pharmacognosy
Biological Source
Prunus dulcis (Bitter almond), Prunus armeniaca (Apricot pits)
Active Constituents
Amygdalin
Pharmacology & Synthesis
Mechanism of Action
Hydrolized by beta-glucosidase to release toxic hydrogen cyanide (HCN).
Pharmacokinetics (ADME)
A: Rapidly absorbed orally.
D: Wide distribution.
M: Hydrolysis in GI tract to HCN and benzaldehyde.
E: Renal (as thiocyanate).
Pharmacodynamics
Produces systemic cyanide toxicity; no proven clinical efficacy for cancer.
Synthesis Pathway
Biosynthesized from phenylalanine.
Safety, Warnings & Interactions
Adverse Effects
Cyanide poisoning (nausea, vomiting, coma, respiratory failure, death).
Contraindications
Not approved for medical use.
Drug Interactions
Ascorbic acid (increases cyanide release).
Pharmaceutics & Compendia
Dosage Forms
Tablets, Injection (illicit)