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Chemical structure of Amygdalin

Amygdalin (from Greek: ἀμυγδάλη, almond), C₂₀H₂₇NO₁₁, is a glycoside isolated from bitter almonds by H. E. Robiquet 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." Image File history File links Unbalanced_scales. ... Image File history File links Broom_icon. ... Image File history File links Amygdalin. ... Image File history File links Amygdalin. ... Chemical structure refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. ... A glycoside is a molecule where a sugar group is bonded through its anomeric carbon to a nonsugar group by either an oxygen or a nitrogen atom. ... Apricot kernels are, like most nuts and seeds, very nutritious. ... Freiherr Justus von Liebig (May 12, 1803 in Darmstadt, Germany – April 18, 1873 in Munich, Germany) was a German chemist who made major contributions to agricultural and biological chemistry, and worked on the organization of organic chemistry. ... Friedrich Wöhler Friedrich Wöhler (July 31, 1800 - September 23, 1882) was a German chemist, best-known for his synthesis of urea, but also the first to isolate several of the elements. ... Ernst T. Krebs, Jr. ...

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.^[1] Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound with a distinctive perfume-like odor, and is the alcohol found in alcoholic beverages. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ... The chemical compound benzaldehyde (C6H5CHO) consists of a benzene ring with an aldehyde group attached to one carbon. ... Hydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid or Prussic acid. ... The chemical compound hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride (HCl). ... Mandelic acid, also called phenylglycollic acid, (C8H8O3) (C6H5•CH(OH)•OOH), is an isomer of cresotinic acid and oxymethylbenzoic acid. ... Ammonia is a compound with the formula NH3. ...

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. Dunstan 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]} Maltase, drawn from PDB 1OBB. Maltase (EC 3. ... The chemical compound benzaldehyde (C6H5CHO) consists of a benzene ring with an aldehyde group attached to one carbon. ... The cyanide ion, CN−. From the top: 1. ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... This article refers to the plant. ... Dhurrin is a cyanogenic glycoside occuring in plants. ... Species About 30 species, see text Sorghum is a genus of about 30 species of grasses raised for grain, native to tropical and subtropical regions of Eastern Africa, with one species native to Mexico. ...

Nomenclature

Amygdalin is also called laevomandelonitrile, or laetrile for short. This is a typical pharmaceutical abbreviation from laevomandelonitrile. 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]} Latin is an ancient Indo-European language originally spoken in Latium, the region immediately surrounding Rome. ...

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." ^[2] A patent is a set of exclusive rights granted by a state to a patentee (the inventor or assignee) for a fixed period of time in exchange for the regulated, public disclosure of certain details of a device, method, process or composition of matter (substance) (known as an invention) which...

Though it is sometimes sold as "Vitamin B17", it is not a vitamin, as no disease is associated with a dietary deficiency of laetrile. Retinol (Vitamin A) For the record label, see Vitamin Records Vitamins are nutrients required in very small amounts for essential metabolic reactions in the body. ...

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.^[2] Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these cells to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ... The Food and Drug Administration (FDA) is an agency of the United States Department of Health and Human Services and is responsible for regulating food (humans and animal), dietary supplements, drugs (human and animal), cosmetics, medical devices (human and animal) and radiation emitting devices (including non-medical devices), biologics, and...

The US 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. The National Institutes of Health (NIH) is the primary agency of the United States government responsible for medical research. ... The cyanide ion, CN−. From the top: 1. ...

While no double-blind clinical trials may have been conducted, a clinical trial was carried out in 1982 by the Mayo Clinic ^[3] 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. Double-blind describes an especially stringent way of conducting an experiment, usually on living, conscious, human subjects. ... Main campus in downtown Rochester, Minnesota. ... In probability theory and statistics, a median is a number dividing the higher half of a sample, a population, or a probability distribution from the lower half. ... Tumor or tumour literally means swelling, and is sometimes still used with that meaning. ... The cyanide ion, CN−. From the top: 1. ...

In 1974, the American Cancer Society officially labelled laetrile as "quackery," but advocates for laetrile claim a conspiracy with regard to this label.^[4] Pro-laetrile groups assert that financial motivations have tainted the published research. These advocates reason that a cure as cheap and plentiful as apricot kernels would not be welcomed by the pharmaceutical industry. So, even today, many American and Canadian cancer patients travel to Mexico for treatment with the substance, under the auspices of Dr. Ernesto Contreras. One of these patients was actor Steve McQueen, who died while undergoing treatment in Mexico after developing 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. Edward Griffin, author of "The Discovery of Noah’s Ark". The American Cancer Society (ACS) is a medical organization with a corporate attitude in the United States. ... This article or section does not cite its references or sources. ... Ernesto Contreras (1915–2003) was a Mexican doctor. ... Steve McQueen (March 24, 1930 – November 7, 1980) was an American movie actor, nicknamed The King of Cool. He was one of the biggest box-office draws of the 1960s and 1970s due to a popular anti-hero persona. ... The Village Voice is a New York City-based weekly newspaper featuring investigative articles, analysis of current affairs and culture, arts reviews and events listings for New York City. ... The National Cancer Institute (NCI) is part of the United States Federal governments National Institutes of Health. ... Cytochemistry is the biochemistry of cells, especially that of the macromolecules responsible for cell structure and function Categories: | ... G. Edward Griffin G. Edward Griffin, born on November 7, 1931, is an American political commentator, writer and documentary filmmaker, perhaps best known for his book The Creature from Jekyll Island that has been translated into Japanese. ...

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 firmly 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]

Famous case in history

Jason 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. This article or section does not cite its references or sources. ... It has been suggested that Renal anomalies and Renal plasma threshold be merged into this article or section. ... The pancreas is a retroperitoneal organ that serves two functions: exocrine - it produces pancreatic juice containing digestive enzymes endocrine - it produces several important hormones Anatomy The pancreas is a retroperitoneal organ located posterior to the stomach on the posterior abdominal wall. ... The spleen is an organ of the upper abdomen, where it functions in the destruction of old red blood cells and holding a reservoir of blood. ... Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these cells to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ... Binomial name Prunus armeniaca L. For other uses, see Apricot (disambiguation). ... Criminal law (also known as penal law) is the body of law that regulates governmental sanctions (such as imprisonment and/or fines) as retaliation for crimes against the social order. ...

Famous supporters of amygdalin

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. Andrew McNaughton of the McNaughton Foundation requested a scientific experiment by Dr. Burk of the (NCI), the results were a famous comment which was used in a G. Edward Griffin 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.” ^[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. The National Cancer Institute (NCI) is part of the United States Federal governments National Institutes of Health. ... Cytochemistry is the biochemistry of cells, especially that of the macromolecules responsible for cell structure and function Categories: | ... Andrew George Latta McNaughton, PC (February 25, 1887 - July 11, 1966) was a Canadian army officer, politician and diplomat. ... G. Edward Griffin G. Edward Griffin, born on November 7, 1931, is an American political commentator, writer and documentary filmmaker, perhaps best known for his book The Creature from Jekyll Island that has been translated into Japanese. ... Wikipedia does not have an article with this exact name. ...

Amygdalin research

On 6 September, 2000 the British Association Festival of Science released a news story about how cyanide can be used to target cancer cells. Dr Mahendra Deonarain explained how Imperial College scientists "engineered the enzyme", which the cassava plant, almond tree, and hydrangea, have. This enzyme produces "cyanide when it comes into contact with a particular sugar molecule." Dr Deonarain went on to explain that this system would be "Tumour Specific." ^[13] Royal School of Mines Entrance Imperial College London is a college of the University of London which focuses on science and technology, and is located in South Kensington in London. ... The cyanide ion, CN−. From the top: 1. ...

BBC News published another article on April 12, 1999 explaining the work of Professor Monica Hughes. She focused on the Cassava plant and Tapioca which is derived from it. "It is one of many plants which manufactures cyanide to deter animals who might want to eat it." and that "It does this by producing a chemical called linamarin which releases hydrogen cyanide when it is broken down by the linamarase enzyme."^[14] Professor Hughes' research has been funded by the European Union, but her funding has now run out and she is looking for other sources. This is despite the fact that Spanish researchers claim/found that a brain tumour in a rat was totally eradicated after one week of the genetic treatment that Dr Monica is working on. They found that the system allowed the localised release of small doses of cyanide through the breakdown of linamarin by linamarase. " In 1977, Dr. Vern L. van Breeman of Salisbury State College, Maryland, 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]} Binomial name Manihot esculenta Crantz The cassava or manioc (Manihot esculenta) is a woody shrub of the Euphorbiaceae (spurge family) that is extensively cultivated as an annual crop in tropical and subtropical regions for its edible starchy tuberous root, a major source of carbohydrate. ... Tapioca is an essentially flavourless starchy ingredient, or fecula, produced from treated and dried cassava (manioc) root and used in cooking. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ...

Veteran 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]}

Government regulations

Laetrile is a compound that has been used as an anticancer treatment in humans worldwide. It is not approved by the US 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. ^[15]

Since laetrile has not been approved as a treatment for cancer in the United States by the FDA,^[15] doctors may not prescribe it specifically to cure cancer. However in certain US states the use of laetrile is authorized.^[16] 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."^[17], 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. ^[18] The United States Food and Drug Administration is the government agency responsible for regulating food, dietary supplements, drugs, cosmetics, medical devices, biologics and blood products in the United States. ...

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." ^[19] The Food and Drug Administration (FDA) is an agency of the United States Department of Health and Human Services and is responsible for regulating food (humans and animal), dietary supplements, drugs (human and animal), cosmetics, medical devices (human and animal) and radiation emitting devices (including non-medical devices), biologics, and...

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.^[20][21]

References

This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain. Encyclopædia Britannica, the 11th edition The Encyclopædia Britannica Eleventh Edition (1910–1911) is perhaps the most famous edition of the Encyclopædia Britannica. ... The public domain comprises the body of all creative works and other knowledge—writing, artwork, music, science, inventions, and others—in which no person or organization has any proprietary interest. ...

The Journal of the Chemical Society was a scientific journal published from 1862 to 1877. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... The National Cancer Institute (NCI) is part of the United States Federal governments National Institutes of Health. ... ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Medical News Today is a web-based outlet for medical news headlines, targeted to both physicians and the general public. ... Quackwatch is the primary website of Quackwatch, Inc. ... 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the Anno Domini (common) era. ... February 12 is the 43rd day of the year in the Gregorian Calendar. ... The current BBC News logo BBC News and Current Affairs is a major arm of the BBC responsible for the corporations newsgathering and production of news programmes on BBC television, radio and online. ... The current BBC News logo BBC News and Current Affairs is a major arm of the BBC responsible for the corporations newsgathering and production of news programmes on BBC television, radio and online. ... The National Cancer Institute (NCI) is part of the United States Federal governments National Institutes of Health. ... 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the Anno Domini (common) era. ... January 14 is the 14th day of the year in the Gregorian calendar. ... Seal of the University of Nebraska The University of Nebraska is one of two public university systems in the state of Nebraska, USA. The system has four universities and a technical college: University of Nebraska-Lincoln University of Nebraska at Omaha University of Nebraska at Kearney University of Nebraska Medical... 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the Anno Domini (common) era. ... January 14 is the 14th day of the year in the Gregorian calendar. ... Auburn University (AU or Auburn) is a state university located in Auburn, Alabama, in the United States. ...

External links

• Personal Experiences
• 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
• British Association Festival Of Science BBC news story
• Unproven Methods of Cancer Management: Laetrile - American Cancer Society