Amygdalin

• CAT Number: R019890
• CAS Number: 29883-15-6
• Molecular Formula: C20H27NO11
• Molecular Weight: 457.43
• Purity: ≥95%
• Storage: 3 years -20C powder
• InChI: 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
• InChIKey: XUCIJNAGGSZNQT-SWRVSKMJSA-N
• SMILES: N#CC(O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O)C3=CC=CC=C3

Amygdalin is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds. Several other related species in the genus of Prunus, including apricot and black cherry also contain amygdalin. Since the early 1950s, both amygdalin and a modified form named laetrile or Vitamin B17 have been promoted as cancer cures. However, neither of these compounds nor any other derivatives are vitamins in any sense, and studies have found them to be clinically ineffective in the treatment of cancer, as well as dangerously toxic. They are potentially lethal when taken by mouth, because certain enzymes (in particular, glucosidases that occur in the gut and in various kinds of seeds, edible or inedible) act on them to produce cyanide. The promotion of laetrile to treat cancer has been described in the medical literature as a canonical example of quackery, and as "the slickest, most sophisticated, and certainly the most remunerative cancer quack promotion in medical history." Amygdalin is extracted from almonds or apricot kernels by boiling in ethanol; on evaporation of the solution and the addition of diethyl ether, amygdalin is precipitated as white minute crystals.

Reference

1:Effect of Natural β-Glucosidase Inhibitors in Reducing Toxicity of Amygdalin in Persicae Semen. Liu C, Li X, Yang H, Mao X, Wang J, Gao W.Phytother Res. 2017 May;31(5):771-777. doi: 10.1002/ptr.5798. Epub 2017 Apr 9. PMID: 28393463 2:Protective Effect of Amygdalin on LPS-Induced Acute Lung Injury by Inhibiting NF-κB and NLRP3 Signaling Pathways. Zhang A, Pan W, Lv J, Wu H.Inflammation. 2017 Jun;40(3):745-751. doi: 10.1007/s10753-017-0518-4. PMID: 28303417 3:Antimutagenic, Antirecombinogenic, and Antitumor Effect of Amygdalin in a Yeast Cell-Based Test and Mammalian Cell Lines. Todorova A, Pesheva M, Iliev I, Bardarov K, Todorova T.J Med Food. 2017 Apr;20(4):360-366. doi: 10.1089/jmf.2016.0108. Epub 2017 Feb 1. PMID: 28146364 4:Laetrile/Amygdalin (PDQ®): Health Professional Version. PDQ Integrative, Alternative, and Complementary Therapies Editorial Board.PDQ Cancer Information Summaries [Internet]. Bethesda (MD): National Cancer Institute (US); 2002-.2016 Dec 21. PMID: 26389425 Free Books & Documents5:Laetrile/Amygdalin (PDQ®): Patient Version. PDQ Integrative, Alternative, and Complementary Therapies Editorial Board.PDQ Cancer Information Summaries [Internet]. Bethesda (MD): National Cancer Institute (US); 2002-.2016 Nov 4. PMID: 26389167 Free Books & Documents6:Apricot and other seed stones: amygdalin content and the potential to obtain antioxidant, angiotensin I converting enzyme inhibitor and hypocholesterolemic peptides. García MC, González-García E, Vásquez-Villanueva R, Marina ML.Food Funct. 2016 Nov 9;7(11):4693-4701. PMID: 27783077 7:Pharmacokinetic Effects of Cinnamic Acid, Amygdalin, Glycyrrhizic Acid and Liquiritin on Ephedra Alkaloids in Rats. Tang Y, Zheng M, Chen YL, Chen J, He Y.Eur J Drug Metab Pharmacokinet. 2017 Jun;42(3):527-535. doi: 10.1007/s13318-016-0368-8. PMID: 27514823 8:Correlation between the transdermal characteristics of pseudoephedrine and amygdalin in majiepingchuan in vitro. Kong H, Qu H, Qu B, Zeng W, Zhao Y, Wang X, Wang Q.J Tradit Chin Med. 2016 Apr;36(2):238-42. PMID: 27400480 Free Article9:Amygdalin, quackery or cure? Blaheta RA, Nelson K, Haferkamp A, Juengel E.Phytomedicine. 2016 Apr 15;23(4):367-76. doi: 10.1016/j.phymed.2016.02.004. Epub 2016 Feb 17. Review. PMID: 27002407 10:[An LC-MS/MS method for the simultaneous determination of amygdalin and paeoniflorin in human urine and application to urinary excretion study]. Li XB, Shi FG, Jian LY, Ding L.Yao Xue Xue Bao. 2015 Oct;50(10):1330-5. Chinese. PMID: 26837182