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Amygdalin

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Amygdalin

Identifiers

CAS number

29883-15-6

PubChem

34751

MeSH

Amygdalin

Properties

Molecular formula

C20H27NO11

Molar mass

457.429

Hazards

Except where noted otherwise, data are given formaterials in their standard state(at 25 °C, 100 kPa)Infobox disclaimer and references

Amygdalin (from Greek: ἀμυγδάλη, almond), C20H27NO11, is a glycoside isolated from bitter almonds by Pierre-Robiquet[1] and A. F. Boutron-Charlard in 1830, and subsequently investigated by Liebig and Wöhler, and others. Some sources claim Ernst T. Krebs was the discoverer of the substance, and Krebs is generally credited with popularizing it as a purported cancer cure and as "Vitamin B17."

Contents

1 Chemistry 2 Nomenclature 3 Cancer cure

3.1 Fraud conviction 3.2 Supporters of amygdalin 3.3 Amygdalin research 3.4 Government regulation in the U.S.

4 References 5 External links

[edit] Chemistry

Amygdalin is extracted from almond cake by boiling ethanol; on evaporation of the solution and the addition of diethyl ether, amygdalin is precipitated as white minute crystals. Sulfuric acid decomposes it into d-glucose, benzaldehyde, and prussic acid (hydrogen cyanide); while hydrochloric acid gives mandelic acid, d-glucose, and ammonia.[2]

The decomposition induced by enzymes may occur in two ways. Maltase partially decomposes it, giving d-glucose and mandelic nitrile glucoside, C6H5CH(CN)O·C6H11O5; this compound is isomeric with sambunigrin, a glucoside found by E.E. Bourquelot and Danjou in the berries of the common elder, Sambucus nigra. Emulsin, on the other hand, decomposes it into benzaldehyde, cyanide, and two molecules of glucose; this enzyme occurs in the bitter almond, and consequently the seeds invariably contain free cyanide and benzaldehyde. An "amorphous amygdalin" is said to occur in the cherry-laurel. Closely related to these glucosides is dhurrin, C14H17O7N, isolated by W. and T. A. Henry from the common sorghum or "great millet," Sorghum vulgare; this substance is decomposed by emulsin or hydrochloric acid into d-glucose, cyanide, and p-hydroxybenzaldehyde.[citation needed]

[edit] Nomenclature

Amygdalin is also called laevomandelonitrile, or laetrile for short. Some claim that laetrile is derived from a Latin word meaning "joyfulness" as laetari is the Latin verb meaning "to rejoice or exult".[citation needed]

The National Cancer Institute explains that "the names Laetrile, laetrile, and amygdalin are often used in place of one another, but they are not the same product. The chemical make-up of Laetrile patented in the United States is different from the laetrile/amygdalin produced in Mexico. The patented laetrile is a partly synthetic (man-made) form of amygdalin, while the laetrile/amygdalin made in Mexico comes from crushed apricot pits."[3]

Though it is sometimes sold as "Vitamin B17", it is not a vitamin.

[edit] Cancer cure

Amygdalin has been advocated by some as a "cure" or a "preventative" for cancer, but due to a lack of scientifically accepted evidence of its efficacy, it has not been approved for this use by the United States' Food and Drug Administration.[3]

The U.S. government's National Institutes of Health reports that two clinical trials with laetrile have been published. One Phase I study found that amygdalin caused minimal side effects; the side effects that were seen were similar to the symptoms of cyanide poisoning. One Phase II study with 175 patients had some patients reporting improvements in symptoms, but all patients showed cancer progression 7 months after completing treatment, and it was determined no further tests were necessary.

While no double-blind clinical trials may have been conducted, a clinical trial was carried out in 1982 by the Mayo Clinic[4] and three other U.S. cancer centers under NCI sponsorship. Laetrile and "metabolic therapy" were administered as recommended by their promoters to 178 patients with advanced cancer for which there was no proven treatment. None were cured or stabilized or had any improvement of cancer-related symptoms. The median survival rate was about five months. In survivors after seven months, tumor size had increased. Several patients suffered from cyanide poisoning.

In 1974, the American Cancer Society officially labelled laetrile as "quackery," but advocates for laetrile claim a conspiracy with regard to this label.[citation needed] Pro-laetrile groups assert that financial motivations have tainted the published research.[citation needed] These advocates reason that a cure as cheap and plentiful as apricot kernels would not be welcomed by the pharmaceutical industry.[citation needed] So, even today, many American and Canadian cancer patients travel to Mexico for treatment with the substance, under the auspices of Dr. Ernesto Contreras.[citation needed] One of these patients was actor Steve McQueen, who died in Mexico, while undergoing treatment for mesothelioma. Laetrile's foremost advocates within the United States can be found in all spectra of the political and science field from alternative newspapers like The Village Voice to individuals like the one-time chief chemist of the National Cancer Institute's cytochemistry laboratory,[5] Dean Burk Ph.D.[6], and G. , author of "The Creature From Jekyll Island: A Second Look at the Federal Reserve".

While some people believe that cancer is related to such a lack of "B17," and thus that it can be used as cancer treatment, it has not been established as medical fact. The lack of information and the self-medication of patients with amygdalin causes severe problems in cancer treatment.[7]

A review of the clinical evidence was published in 2006 with the conclusion "Therefore, the claim that laetrile has beneficial effects for cancer patients is not supported by sound clinical data."[8]

[edit] Fraud conviction

Vale was the nation's leading spokesman for the legalization of laetrile. He was a national arm wrestling champion after he was cured of kidney, pancreatic and spleen cancer, purportedly by eating apricot seeds. However, in 2004 he was convicted[9] of fraud and sentenced to 63 months in prison for his methods of marketing laetrile, for defrauding the U.S. government by claiming that he qualified for Legal Aid, and for criminal contempt. Representatives of the Memorial Sloan-Kettering Cancer Center testified on the side of the prosecution during Vale's criminal trial.

[edit] Supporters of amygdalin

This section needs additional citations for verification.Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (October 2007)

Dr Dean Burk, biochemist with a Ph.D. from Cornell Medical College,[6] became Head of National Cancer Institute (NCI) Cytochemistry Section in 1937 and headed this department for over three decades. McNaughton of the McNaughton Foundation requested a scientific experiment by Dr. Burk of the (NCI), the results were used in a G. documentary "A World Without Cancer"[10] that “When we add "laetrile" (amygdaline) to a cancer culture under the microscope,†“providing the enzyme glucosidase also is present, we can see the cancer cells dying off like flies.â€[11] He also claimed in Congressional testimony that laetrile was less toxic than sugar.[12] Dr Dean Burk then went on to become a life long supporter of laetrile / amygdaline as a Cancer prevention and cure.

[edit] Amygdalin research

This section needs additional citations for verification.Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (October 2007)

Cancer researcher Kanematsu Sugiura (who had a 4-volume set of his collected scientific papers published in 1965) performed three sets of experiments between September 1972 and June 1973 "to determine the effects of amygdalin...upon mice with spontaneous mammary tumors."[citation needed] In an internal report to his colleagues at Sloan-Kettering Institute, he said that "The results clearly show that amygdalin significantly inhibits the appearance of lung metastases in mice bearing spontaneous mammary tumors and increases significantly the inhibition of the growth of the primary tumor over the appearance of inhibition in the untreated animals."[citation needed]

In 1977, Dr. Vern L. van Breeman of Salisbury State College, land, reported that the addition of apricot kernels [rich in Laetrile] to standard food in pilot experiments with special strains of mice bred to develop breast cancer and leukemia showed impressive differences both in terms of developing the disease and increased survival times between the animals that [ate] the kernels and those that did not. When he reported his early findings... seven of the animals in the leukemia control group and five in the breast cancer [control] group had died, while none of the mice on the kernels had. Ultimately only one of the mammary cancer mice developed a slow-growing tumor, and, while the leukemia results were less impressive in terms of total symptoms, leukemia-prone mice that ate apricot kernels enjoyed life extensions up to 50% over what would normally be expected."[citation needed]

[edit] Government regulation in the U.S.

Laetrile is a compound that has been used as an anticancer treatment in humans worldwide. It is not approved by the U.S. Food and Drug Administration (FDA) as a treatment for cancer or any other medical condition. The drug is made and used as a cancer treatment in Mexico.[13]

Since laetrile has not been approved as a treatment for cancer in the United States by the FDA,[13] doctors may not prescribe it specifically to cure cancer. However in certain US states the use of laetrile is authorized.[14] In Montana this "does not prevent a physician from prescribing laetrile as a dietary supplement to a patient not suffering from any known malignancy, disease, illness, or physical condition."[15], while in Indiana "a physician can prescribe or administer amygdalin (laetrile) instead of or in addition to customary or accepted modes of therapy in the treatment of a malignancy, a disease, an illness, or a physical condition of a patient" who has signed a written informed request.[16]

In the United States, the Food and Drug Administration continues to seek jail sentences for vendors selling laetrile for cancer treatment, calling it a "highly toxic product that has not shown any effect on treating cancer."[17]

Amygdalin is commonly manufactured in Mexico. But due to the controversial status of amygdalin, it may be banned or difficult to locate in some locations.

At the University of Nebraska and Auburn University in Alabama, eligible employees can be reimbursed for the cost of laetrile, if prescribed.[18][19]

[edit] References

This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.

^ A chronology of significant historical developments in the biological sciences. Botany Online Internet Hypertextbook. University of Hamburg, Department of Biology (2002-08-18). Retrieved on 2007-08-06. ^ J. W. , V. K. Krieble (1909). "The hydrolysis of amygdalin by acids. Part I". Journal of the Chemical Society 95 (11): 1369 - 1377. doi:10.1039/CT9099501369. ^ a b What is laetrile?, National Cancer Institute, Retrieved on 14 January 2007 ^ Moertel, C.G., (1982). "A clinical trial of amygdalin (laetrile) in the treatment of human cancer.". N. Engl. J. Med. (306): 201-206. ^ Dean Burk, 84, Noted Chemist At National Cancer Institute, Dies, Washington Post, 9 October 1988 ^ a b Dr Dean Burk, The Moss Reports ^ Schraub S. (2000). "Unproven methods in cancer: a worldwide problem". Supportive Care in Cancer 8: 10-15. doi:10.1007/s005209900057. ^ Milazzo, Stefania; Stephane Lejeune, Edzard Ernst (2006-11-15). "Laetrile for cancer: a systematic review of the clinical evidence". Supportive Care in Cancer. doi:10.1007/s00520-006-0168-9. ^ New York Man Sentenced to 63 Months for Selling Fake Cancer Cure, Medical News Today, 22 June 2004, Retrieved on 14 January 2007 ^ , G. . A World Without Cancer - The Story Of Vitamin B17 (Video). ^ Vitamin B17 “..cancer cells were dying like flies.â€, Cancer Tutor - Alternative Cancer Treatments Information Center ^ , , MD. The Rise and Fall of Laetrile. Quackwatch. Retrieved on 2007-02-12. ^ a b Is laetrile approved by the FDA for use as a cancer treatment in the United States?, National Cancer Institute, Retrieved on 14 January 2007 ^ Mennenga, Jerry (1978-04-02). Laetrile: Legal but undefined and unavailable. Illinois Issues. Retrieved on 2007-01-14. ^ Montana Code: Laetrile not endorsed -- permitted as a dietary supplement, Montana State Government, Montata Code Annotated 2005, Retrieved on 14 January 2007 ^ Prescription or administration permitted with written informed request, Indiana State Government, Information Maintained by the Office of Code Revision Indiana Legislative Services Agency, Chapter 23. Drugs: Use of Amygdalin (Laetrile), Retrieved on 14 January 2007 ^ US FDA (June 22, 2004). Lengthy Jail Sentence for Vendor of Laetrile—A Quack Medication to Treat Cancer Patients. FDA News ^ Health Care Reimbursement Account (PDF). University of Nebraska. Retrieved on 2007-01-14. ^ Payroll and Employee Benefits, Auburn University, Retrieved on 14 January 2007

[edit] External links

National Cancer Institute - Laetrile A clinical trial of amygdalin (Laetrile) in the treatment of human cancer. - Moertel C and others in New England Journal of Medicine 306:201-206, 1982 Cancer Research UK on Laetrile British Association Festival Of Science BBC news story Unproven Methods of Cancer Management: Laetrile - American Cancer Society

U.S. Supreme Court UNITED STATES v. RUTHERFORD, 442 U.S. 544 (1979). Finding: The Federal Food, Drug, and Cosmetic Act makes no express exception for drugs used by the terminally ill and no implied exemption is necessary to attain congressional objectives or to avert an unreasonable reading of the terms "safe" and "effective" in 201 (p) (1).

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Analogues of nucleic acids:

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Analogues of nucleic acids:

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α-Glycoside | β-Glycoside | 1,4-Glycoside | 1,6-Glycoside

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Aglycone:

Alcoholic glycoside | Anthraquinone glycoside | Coumarin glycoside | Cyanogenic glycoside | Flavonoid glycoside | Phenolic glycoside | Saponin | Cardiac glycoside | Steviol glycoside | Thioglycoside | Glycosylamine | Bufanolide | Cardenolide

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Categories: Cleanup from September 2006 | All pages needing cleanup | Articles needing additional references from October 2007 | All articles with unsourced statements | Articles with unsourced statements since February 2007 | Articles with unsourced statements since October 2007 | Glycosides | Alternative medicine | Medical ethics

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