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
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
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26389425Curator's Comment: Description was created based on several sources, including
https://www.mskcc.org/cancer-care/integrative-medicine/herbs/amygdalin
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26389425
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.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17359643 |
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Target ID: CHEMBL3464 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17359643 |
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Target ID: CHEMBL3038469 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25136960 |
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Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16880611 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Laetrile Approved UseCancer prevention, cancer treatment |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1702.52 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23735239/ |
20 mg/kg single, oral dose: 20 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
AMYGDALIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
127 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7092570/ |
50 mg/kg single, intravenous dose: 50 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: DIATRIZOATE MEGLUMINE |
AMYGDALIN plasma | Canis lupus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
18355.29 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23735239/ |
20 mg/kg single, oral dose: 20 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
AMYGDALIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.57 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7092570/ |
50 mg/kg single, intravenous dose: 50 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: DIATRIZOATE MEGLUMINE |
AMYGDALIN plasma | Canis lupus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23735239/ |
20 mg/kg single, oral dose: 20 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
AMYGDALIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
100% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7092570/ |
50 mg/kg single, intravenous dose: 50 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: DIATRIZOATE MEGLUMINE |
AMYGDALIN plasma | Canis lupus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Sample Use Guides
In Vivo Use Guide
Sources: http://vitaminb17.net/cancer-protocols-and-dosage
500mg Laetrile (Amygdalin) tablets per day ( two tablets at breakfast, lunch and dinner)
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17359643
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
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admin
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Edited
Mon Mar 31 18:10:46 GMT 2025
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Mon Mar 31 18:10:46 GMT 2025
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| Record UNII |
214UUQ9N0H
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4140 (Number of products:1)
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m1862
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AMYGDALIN
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1371051
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C28801
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |