Chemical structure of d-gluconodimethylamino acetic acid, a structure of "pangamic acid" proposed in 1951 | |
Names | |
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IUPAC name 6-O-(N,N-dimethylglycinyl)-D-gluconic acid | |
Systematic IUPAC name (2R,3S,4R,5R)-6-[(Dimethylamino)acetyl]-2,3,4,5-tetrahydroxyhexanoic acid | |
Other names dimethylglycine d-gluconic acid ester | |
Identifiers | |
3D model (JSmol) | |
PubChem CID | |
UNII | |
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Properties | |
C10H19NO8 | |
Molar mass | 281.261 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Pangamic acid, also called pangamate, is the name given to a chemical compound discovered by Ernst T. Krebs Sr. His son, Ernst T. Krebs Jr., promoted it as a medicinal compound for use in treatment of a wide range of diseases. They also termed this chemical "vitamin B15", though it is not a true vitamin, has no nutritional value, [1] has no known use in the treatment of any disease, and has been called a "quack remedy". Although a number of compounds labelled "pangamic acid" have been studied or sold (including the 1951 d-gluconodimethylamino acetic acid), no chemical compound, including those claimed by the Krebses to be pangamic acid, has been scientifically verified to have the characteristics that defined the original description of the compound.
The Krebses derived the term "pangamic" to describe this compound which they asserted to be ubiquitous and highly concentrated in seeds (pan meaning "universal" and gamic meaning "seed"). [2]
Pangamic acid is the name given to the chemical compound with the empirical formula C
10H
19O
8N and a molecular weight of 281 which appeared to be an ester derived from d-gluconic acid and dimethylglycine. In 1943, the Krebses applied for a patent for a process for extracting this chemical compound which they reported had been previously isolated from apricot seeds, and received the patent in 1949. [3] A 1951 paper by the Krebses reported the first isolation of this compound using this patented process, but did not include enough information to confirm that this compound was actually isolated. [4] In 1955, the Krebses received a patent for another synthesizing process for "N-substituted glycine esters of gluconic acid", [5] but the patent contained no supporting data to confirm the process was able to synthesize compounds described by the patent, including pangamic acid. [2]
Subsequent attempts at synthesizing this ester by other researchers found Krebs' purported methods of producing pangamic acid were not reproducible, and research into pangamic acid have focused on compounds of various chemical compositions. A review noted that of all the chemicals described in research about pangamic acid, "[n]ot a single product labeled 'pangamate' or 'B15' has been established in a scientifically verifiable manner to conform to the empiric formula" described by the Krebses. [2] Analysis of a sample of a compound called "pangamic acid" which was provided by a co-worker of the Krebses in the 1950s showed only lactose upon further evaluation by nuclear magnetic resonance spectroscopy. [1] Thus, "pangamic acid" is more a label used to describe one of any number of chemical compounds rather than a particular substance. [2]
Chemical compounds sold as "pangamic acid" for medicinal purposes have also had various chemical compositions, and suppliers of "pangamic acid" have regularly changed the identity of the chemical compounds sold under this label. [6] One anecdote noted that the Food and Drug Administration (FDA) has seized lots of "calcium pangamate" sold by General Nutrition Center (GNC), which agreed to stop selling the compound in those bottles after the FDA filed suit to stop sales. Afterwards, it was noted that GNC was still selling something in the same bottles with the same labels, likely a different compound. [1] Due to ambiguity in situations like this, the FDA considers it "not an identifiable substance". [6]
To summarize, substances that have been claimed to be pangamic acid include: [2]
The Krebses' original patent claimed pangamic acid could be used for detoxification as well as treatment of asthma, skin conditions, joint pain, and nerve pain, with none of these claims supported by evidence in the patent application. Early promotion for pangamic acid included use by race horses as well as humans. Although given the name "Vitamin B15" by the Krebses, there is no evidence that it meets the definition of a vitamin as there is no evidence it is a nutrient needed by the body. [6]
Much of the clinical research on pangamic acid took place in the former Soviet Union, though that research often did not describe which of the many compounds called "pangamic acid" was used in the study. This research was also of limited quality due to being overwhelmingly anecdotal in nature (as opposed to controlled experimentation) and ignoring short and long term safety in human use. [6]
Although more recent[ when? ] claims include treatment of a wide variety of conditions including cancer, heart disease, schizophrenia as well as providing improvement in oxygen utilization, there is no significant evidence for any of these claims or that it is safe for human use. One review noted that it meets "the criteria that define a quack remedy". [6]
Positive results from mutagenicity analysis via the Ames test of compounds commonly found in preparations labelled "pangamic acid" including diisopropylamine dichloroacetate, diisopropylamine, [7] dichloroacetate, [8] as well as dimethylglycine mixed with sodium nitrite [1] suggests there may be concern for the development of cancer with the use of these substances.
The FDA has recommended seizing any chemicals advertised as pangamic acid and restraining the importation and interstate shipment of pangamic acid on the grounds that pangamic acid and pangamic acid products are unsafe for use and have no known nutritional properties. [9] Pangamic acid's distribution in Canada has been prohibited by the then-named Canadian Food and Drug Directorate. [6]
Amygdalin is a naturally occurring chemical compound found in many plants, most notably in the seeds of apricots, bitter almonds, apples, peaches, cherries and plums, and in the roots of manioc.
Vitamin C is a water-soluble vitamin found in citrus and other fruits, berries and vegetables. It is also a generic prescription medication and in some countries is sold as a non-prescription dietary supplement. As a therapy, it is used to prevent and treat scurvy, a disease caused by vitamin C deficiency.
Vitamins are organic molecules that are essential to an organism in small quantities for proper metabolic function. Essential nutrients cannot be synthesized in the organism in sufficient quantities for survival, and therefore must be obtained through the diet. For example, vitamin C can be synthesized by some species but not by others; it is not considered a vitamin in the first instance but is in the second. Most vitamins are not single molecules, but groups of related molecules called vitamers. For example, there are eight vitamers of vitamin E: four tocopherols and four tocotrienols.
Vitamin K is a family of structurally similar, fat-soluble vitamers found in foods and marketed as dietary supplements. The human body requires vitamin K for post-synthesis modification of certain proteins that are required for blood coagulation or for controlling binding of calcium in bones and other tissues. The complete synthesis involves final modification of these so-called "Gla proteins" by the enzyme gamma-glutamyl carboxylase that uses vitamin K as a cofactor.
Vitamin B6 is one of the B vitamins, and is an essential nutrient for humans. The term essential nutrient refers to a group of six chemically similar compounds, i.e., "vitamers", which can be interconverted in biological systems. Its active form, pyridoxal 5′-phosphate, serves as a coenzyme in more than 140 enzyme reactions in amino acid, glucose, and lipid metabolism.
Retinol, also called vitamin A1, is a fat-soluble vitamin in the vitamin A family that is found in food and used as a dietary supplement. Retinol or other forms of vitamin A are needed for vision, cellular development, maintenance of skin and mucous membranes, immune function and reproductive development. Dietary sources include fish, dairy products, and meat. As a supplement it is used to treat and prevent vitamin A deficiency, especially that which results in xerophthalmia. It is taken by mouth or by injection into a muscle. As an ingredient in skin-care products, it is used to reduce wrinkles and other effects of skin aging.
Biotin (also known as vitamin B7 or vitamin H) is one of the B vitamins. It is involved in a wide range of metabolic processes, both in humans and in other organisms, primarily related to the utilization of fats, carbohydrates, and amino acids. The name biotin, borrowed from the German Biotin, derives from the Ancient Greek word βίοτος (bíotos; 'life') and the suffix "-in" (a suffix used in chemistry usually to indicate 'forming'). Biotin appears as a white, needle-like crystalline solid.
A nutrient is a substance used by an organism to survive, grow and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi and protists. Nutrients can be incorporated into cells for metabolic purposes or excreted by cells to create non-cellular structures such as hair, scales, feathers, or exoskeletons. Some nutrients can be metabolically converted into smaller molecules in the process of releasing energy such as for carbohydrates, lipids, proteins and fermentation products leading to end-products of water and carbon dioxide. All organisms require water. Essential nutrients for animals are the energy sources, some of the amino acids that are combined to create proteins, a subset of fatty acids, vitamins and certain minerals. Plants require more diverse minerals absorbed through roots, plus carbon dioxide and oxygen absorbed through leaves. Fungi live on dead or living organic matter and meet nutrient needs from their host.
A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources, or that are synthetic. The classes of nutrient compounds in supplements include vitamins, minerals, fiber, fatty acids, and amino acids. Dietary supplements can also contain substances that have not been confirmed as being essential to life, and so are not nutrients per se, but are marketed as having a beneficial biological effect, such as plant pigments or polyphenols. Animals can also be a source of supplement ingredients, such as collagen from chickens or fish for example. These are also sold individually and in combination, and may be combined with nutrient ingredients. The European Commission has also established harmonized rules to help insure that food supplements are safe and appropriately labeled.
Olestra is a fat substitute food additive that adds no metabolizable calories to products. It has been used in the preparation of otherwise high-fat foods, thereby lowering or eliminating their fat content.
B vitamins are a class of water-soluble vitamins that play important roles in cell metabolism and synthesis of red blood cells. They are a chemically diverse class of compounds.
Nootropics, colloquially brain supplements, smart drugs and cognitive enhancers, are natural, semisynthetic or synthetic compounds which purportedly improve cognitive functions, such as executive functions, attention or memory.
Auxotrophy is the inability of an organism to synthesize a particular organic compound required for its growth. An auxotroph is an organism that displays this characteristic; auxotrophic is the corresponding adjective. Auxotrophy is the opposite of prototrophy, which is characterized by the ability to synthesize all the compounds needed for growth.
Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active. The compound was first synthesised by Adolf von Baeyer.
Ernst Theodore Krebs Jr. was an American promoter of various substances as alternative cures for cancer, including pangamic acid and amygdalin. He also co-patented the semi-synthetic chemical compound closely related to amygdalin called laetrile, which was also promoted as a cancer preventative and cure. His medical claims about these compounds are not supported by scientific evidence and are widely considered quackery.
Chromium(III) picolinate is a chemical compound with the formula Cr(C5H4N )3, commonly abbreviated as CrPic3. It is a bright-red coordination compound derived from chromium(III) and picolinic acid.
Dimethylglycine (DMG) is a derivative of the amino acid glycine with the structural formula (CH3)2NCH2COOH. It can be found in beans and liver, and has a sweet taste. It can be formed from trimethylglycine upon the loss of one of its methyl groups. It is also a byproduct of the metabolism of choline.
Calcium pangamate is a mineral supplement. It is sometimes used as a synonym for pangamic acid.