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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H27NO11
Molecular Weight 457.4285
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMYGDALIN

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

InChI

InChIKey=XUCIJNAGGSZNQT-JHSLDZJXSA-N
InChI=1S/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2/t10-,11+,12+,13+,14+,15-,16-,17+,18+,19+,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H27NO11
Molecular Weight 457.4285
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Amygdalin is a naturally occurring cyanogenic glycoside derived from nuts, plants, and the pits of certain fruits, primarily apricots. Bitter almonds containing amygdalin are used in Traditional Chinese Medicine to remove “blood stasis” and to treat abscesses. Amygdalin was first used as a cancer treatment in Russia in 1845, and in the United States in the 1920s. Laetrile is another name for the natural product amygdalin. Hydrogen cyanide is thought to be the main anticancer compound formed from laetrile (Amygdalin) via in situ release. Cyanide from the hydrolysis of amygdalin is believed to be cytotoxic with actions selective against cancerous cells, but results from animal studies were mostly negative. Other animal studies suggest it may help to relieve pain due to its anti-inflammatory and analgesic effects. One study suggested amygdalin can inhibit tumor growth, but subsequent tests were unable to confirm this observation. Laetrile (Amygdalin) has shown little anticancer activity in animal studies and no anticancer activity in human clinical trials. In 1970, an IND application to study laetrile was filed by the McNaughton Foundation (San Ysidro, California). This request was initially approved but later rejected because preclinical evidence in animals showed that laetrile was not likely to be effective as an anticancer agent. The side effects associated with laetrile toxicity mirror the symptoms of cyanide poisoning, including liver damage, difficulty walking (caused by damaged nerves), fever, coma, and death. Laetrile (Amygdalin) is not approved for use in the United States.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Laetrile

PubMed

Sample Use Guides

In Vivo Use Guide
500mg Laetrile (Amygdalin) tablets per day ( two tablets at breakfast, lunch and dinner)
Route of Administration: Oral
In Vitro Use Guide
The levels of COX-2 mRNA were decreased to 19.64%, 16.83% and 13.24% in mouse BV2 microglial cells treated with amygdalin extract at concentrations of 10 ug/ml, 100 ug/ml and 100 uM ASA, respectively
Substance Class Chemical
Record UNII
214UUQ9N0H
Record Status Validated (UNII)
Record Version