Amygdalin possesses anticancer properties. There has been some advancement in amygdalin's anti-tumor mechanism [1]. Exonuclease 1, ATP-binding cassette, subfamily F, member 2, MRE11 meiotic recombination 11 homolog A, topoisomerase (DNA) I, and FK506 Binding protein 12-rapamycin-related protein 1 are among the genes that are specifically downregulated by amygdalin. RT-PCR analysis revealed that amygdalin treatment also decreased the mRNA levels of these genes in SNU-C4 human colon cancer cells [2].

Amygdalin functions as an analgesic with antinociceptive and anti-inflammatory properties, effectively relieving inflammatory pain. Amygdalin injected intramuscularly dramatically decreased formalin-induced tonic pain both early (in the first ten minutes following injection) and late (in the ten to thirty minute range). Later on, and in the dose range below 1 mg/kg, amygdalin decreases formalin-induced pain in a dose-dependent way [3].

Absorption, Distribution and Excretion
THE MAX CYANIDE LEVEL AFTER ORAL ADMIN OF AMYGDALIN TO MICE WAS REACHED AT ABOUT 1 1/2-2 HR & WAS WITHIN THE RANGE OF VALUES SEEN AFTER KCN ADMIN. THE ABILITY OF THE CONTENTS OF VARIOUS REGIONS OF THE GI TRACT & OF TUMOR TISSUE TO RELEASE CYANIDE FROM AMYGDALIN WAS ASSESSED. THE STOMACH & UPPER INTESTINE HAD LITTLE ACTIVITY WHILE THE LOWER INTESTINE & FECES RELEASED LARGE AMOUNTS. THERE WAS A LARGE VARIATION BETWEEN MICE.

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Metabolism / Metabolites
AMYGDALIN IS A CHEMICAL COMBINATION OF GLUCOSE, BENZALDEHYDE, & CYANIDE FROM WHICH THE LATTER CAN BE RELEASED BY THE ACTION OF BETA-GLUCOSIDASE OR EMULSIN. ALTHOUGH THESE ENZYMES ARE NOT FOUND IN MAMMALIAN TISSUES, THE HUMAN INTESTINAL MICROFLORA APPEARS TO POSSESS THESE OR SIMILAR ENZYMES CAPABLE OF EFFECTING CYANIDE RELEASE RESULTING IN HUMAN POISONING. FOR THIS REASON AMYGDALIN MAY BE AS MUCH AS 40 TIMES MORE TOXIC BY THE ORAL ROUTE AS COMPARED WITH IV INJECTION.
...PLANT GLYCOSIDES ARE CHARACTERIZED BY PRODN OF CYANIDE, TOGETHER WITH A SUGAR & AROMATIC ALDEHYDE, ON ENZYMIC OR ACID HYDROLYSIS. COMMON EXAMPLES ARE AMYGDALIN (GENTIOBIOSE + BENZALDEHYDE + HCN) WHICH IS PRESENT IN BITTER ALMONDS... AN ENZYME COMPLEX, EMULSIN, IS PRESENT TOGETHER WITH GLYCOSIDES IN PLANT TISSUES & CATALYZES THE HYDROLYSIS OF GLYCOSIDES, FIRST TO MANDELONITRILE OR P-HYDROXYMANDELONITRILE, & THEN TO BENZALDEHYDE OR P-HYDROXYBENZALDEHYDE, & HCN. ... THE ALDEHYDES ARE OXIDIZED TO CORRESPONDING AROMATIC ACIDS & EXCRETED AS PEPTIDE CONJUGATES.
...VARIOUS PRUNUS SPECIES CONTAIN...AMYGDALIN, WHICH IS HYDROLYZED BY ENZYME EMULSIN... IN INTACT PLANT NO SUCH ACTION TAKES PLACE; IT IS NOT UNTIL PLANT TISSUE IS DAMAGED OR STARTS TO DECAY THAT LIBERATION OF HCN BEGINS.
BREAKDOWN /OF GLYCOSIDES/ OFTEN OCCURS MORE READILY OR MORE RAPIDLY IN RUMEN THAN IN DIGESTIVE TRACT OF MONOGASTRIC ANIMALS. ALSO, SMALL MOLECULES CAN BE ABSORBED AT THE RUMEN & THUS ENTER CIRCULATION RAPIDLY. BREAKDOWN OF CYANOGENIC GLYCOSIDES, SUCH AS AMYGDALIN, FROM MEMBERS OF ROSE FAMILY...IS AN EXAMPLE.
For more Metabolism/Metabolites (Complete) data for AMYGDALIN (9 total), please visit the HSDB record page.
Beta-glucosidase, one of the enzymes that catalyzes the release of the cyanide from amygdalin, is present in human small intestine and in a variety of common foods. This leads to an unpredictable and potentially lethal toxicity when amygdalin or Laetrile is taken orally. (L402) Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

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Biological Half-Life
PLASMA & URINE CONCN OF AMYGDALIN, WHOLE-BLOOD CONCN OF CN- & SCN- CONCN IN SERUM & URINE WERE DETERMINED IN CANCER PT FOLLOWING IV (4.5 G/SQUARE M) & ORAL (500-MG TABLET) ADMIN OF AMYGDALIN. FOLLOWING IV ADMIN, CONCN OF PARENT DRUG AS HIGH AS 1401 MUG/ML WERE OBSERVED WITH NO INCR IN PLASMA CONCN OF CN- OR SERUM CONCN OF SCN-. PLASMA ELIM OF AMYGDALIN WAS BEST DESCRIBED BY 2-COMPARTMENT OPEN MODEL WITH MEAN DISTRIBUTIVE PHASE T/2 OF 6.2 MIN, MEAN ELIM PHASE T/2 OF 120.3 MIN, & MEAN CLEARANCE OF 99.3 ML/MIN. FOLLOWING ORAL ADMIN OF AMYGDALIN, PLASMA CONCN WERE MUCH LOWER, WITH PEAK VALUES OF LESS THAN 525 NG/ML. CN- CONCN INCR TO VALUES AS HIGH AS 2.1 MUG/ML WHOLE BLOOD. SCN- CONCN DID NOT INCR FOR SEVERAL DAYS, PLATEAUING AT VALUES AS HIGH AS 38 MUG/ML SERUM.

Toxicity Summary
Amygdalin can be metabolized into hydrogen cyanide in the stomach causing discomfort or illness. (L402) Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

[1]. Advanced research on anti-tumor effects of amygdalin. J Cancer Res Ther. 2014 Aug;10 Suppl 1:3-7.

[2]. Amygdalin inhibits genes related to cell cycle in SNU-C4 human colon cancer cells. World J Gastroenterol. 2005 Sep 7;11(33):5156-61.

[3]. Antinociceptive effect of amygdalin isolated from Prunus armeniaca on formalin-induced pain in rats. Biol Pharm Bull. 2008 Aug;31(8):1559-64.

Amygdalin has been reported in Sorbus commixta, Prunus persica, and other organisms with data available.
Amygdalin is a cyanogenic glucoside isolated from almonds and seeds of other plants of the family Rosaceae. Amygdalin is converted by plant emulsin (a combination of a glucosidase and a nitrilase) or hydrochloric acid into benzaldehyde, D-glucose, and hydrocyanic acid. (NCI04)
Amygdalin is found in almond. Bitter glycoside of the Rosaceae, found especially in kernels of cherries, peaches and apricots. Amygdalin is present in cold pressed bitter almond oil from the above sources prior to enzymic hydolysis and steam distillation for food use Amygdalin , C20H27NO11, is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds, by Pierre-Jean Robiquet and A. F. Boutron-Charlard in 1803, and subsequently investigated by Liebig and Wohler in 1830, and others. Several other related species in the genus of Prunus, including apricot (Prunus armeniaca) and black cherry (Prunus serotina), also contain amygdalin. It was promoted as a cancer cure by Ernst T. Krebs under the name Vitamin B17, but studies have found it to be ineffective. Amygdalin is sometimes confounded with laevomandelonitrile, also called laetrile for short; however, amygdalin and laetrile are different chemical compounds.



Amygdalin has been shown to exhibit anti-nociceptive and apoptotic functions (A7778, A7779).



Amygdalin belongs to the family of Dihexoses. These are disaccharides containing two hexose carbohydrates.
A cyanogenic glycoside found in the seeds of Rosaceae.
See also: Amygdalin (annotation moved to).

C20H27NO11

457.42

457.158

29883-15-6

2180

White to off-white solid powder

1.6±0.1 g/cm3

743.3±60.0 °C at 760 mmHg

223-226 °C(lit.)

403.3±32.9 °C

0.0±2.6 mmHg at 25°C

1.650

-0.36

7

12

7

32

638

0

XUCIJNAGGSZNQT-SWRVSKMJSA-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-/m1/s1

[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy](phenyl)acetonitrile

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.47 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 2: 100 mg/mL (218.61 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

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 (Please use freshly prepared in vivo formulations for optimal results.)