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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.mskcc.org/cancer-care/integrative-medicine/herbs/amygdalin

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.

Originator

Curator's Comment: Amygdalin was first isolated in 1830 from bitter almond seeds (Prunus dulcis) by Pierre-Jean Robiquet and Antoine Boutron-Charlard.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Laetrile

Approved Use

Cancer prevention, cancer treatment

Sample Use Guides

500mg Laetrile (Amygdalin) tablets per day ( two tablets at breakfast, lunch and dinner)
Route of Administration: Oral
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
Created
by admin
on Fri Dec 15 15:50:50 UTC 2023
Edited
by admin
on Fri Dec 15 15:50:50 UTC 2023
Record UNII
214UUQ9N0H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMYGDALIN
HSDB   MI   WHO-DD  
Common Name English
LAETRILE
Common Name English
AMYGDALIN [HSDB]
Common Name English
(2R)-((6-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)(PHENYL)ACETONITRILE
Common Name English
Amygdalin [WHO-DD]
Common Name English
NSC-15780
Code English
AMYGDALIN [MI]
Common Name English
Classification Tree Code System Code
DSLD 4140 (Number of products:1)
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
Code System Code Type Description
EVMPD
SUB21889
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
CAS
29883-15-6
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
HSDB
3559
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
249-925-3
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
MERCK INDEX
m1862
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
AMYGDALIN
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
RXCUI
1371051
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C28801
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
FDA UNII
214UUQ9N0H
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
EVMPD
SUB14322MIG
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
SMS_ID
100000088499
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
PUBCHEM
656516
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
MESH
D000678
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
DAILYMED
214UUQ9N0H
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID00897159
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
NSC
15780
Created by admin on Fri Dec 15 15:50:50 UTC 2023 , Edited by admin on Fri Dec 15 15:50:50 UTC 2023
PRIMARY
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