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19-Nor-5-androstenedione
19-Nor-5-androstenedione, also known as estr-5-ene-3,17-dione, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of 19-nortestosterone (nandrolone) that was never introduced for medical use. It is an androgen prohormone of nandrolone and of other 19-norandrostanes. 19-Nor-5-androstenedione, 19-nor-5-androstenediol, and other 19-norandrostane prohormones were considered to be nutritional supplements and were sold over-the-counter in the United States as a result of the Dietary Supplement Health and Education Act of 1994 (DSHEA). However, they were banned from sports in 1999 by the International Olympic Committee (IOC) and are currently on the World Anti-Doping Agency (WADA) list of prohibited substances. In 2004, they became controlled substances in the U.S. as a result of the Anabolic Steroid Control Act of 2004. See also * 5-Androstenedione * Bolandiol (19-nor-4-androstenediol) * Bolandione (19-nor-4-androstenedione) * Bolenol (17α-ethyl- ...
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Androgen Prohormone
An androgen prohormone, or proandrogen, is a prohormone (or prodrug) of an anabolic-androgenic steroid (AAS). They can be prohormones of testosterone or of synthetic AAS, for example, nandrolone (19-nortestosterone). Dehydroepiandrosterone (DHEA), DHEA sulfate (DHEA-S), and androstenedione may all be considered proandrogens of testosterone. In the last two decades, prohormones have also been used by bodybuilders, athletes, and nonmedical users of AAS and other hormones to refer to substances that are expected to convert to active hormones in the body. The intent is to provide the benefits of taking an AAS without the legal risks, and to achieve the hoped-for benefits or advantages without use of AAS themselves. Many of these compounds are legal to manufacture, sell, possess and ingest eliminating the legal problems associated with schedule III AAS. This also enables chemists to further their legal research and get around the law (albeit for a short time). The typical definition ...
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19-nortestosterone
Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). Nandrolone esters are used in the treatment of anemias, cachexia (muscle wasting syndrome), osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat. Side effects of nandrolone esters include symptoms of masculinization like acne, increased hair growth, voice changes, and decreased sexual desire due to its ability to suppress endogenous testosterone synthesis while not being a sufficient androgen itself. They are synthetic androgens and anabolic steroids and hence are agonists of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). Nandrolone has strong anabolic effects and weak androgenic effects, which giv ...
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Nandrolone
Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). Nandrolone esters are used in the treatment of anemias, cachexia (muscle wasting syndrome), osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat. Side effects of nandrolone esters include symptoms of masculinization like acne, increased hair growth, voice changes, and decreased sexual desire due to its ability to suppress endogenous testosterone synthesis while not being a sufficient androgen itself. They are synthetic androgens and anabolic steroids and hence are agonists of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). Nandrolone has strong anabolic effects and weak androgenic effects, which g ...
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Bolandiol
Bolandiol (INN, also known as 19-nor-4-androstenediol, estr-4-ene-3β,17β-diol, or 3β-dihydronandrolone) is an anabolic-androgenic steroid (AAS) that was never marketed. However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed. Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses estrogenic and progestogenic activity. Bolandiol is on the World Anti-Doping Agency's list of prohibited substances, and is therefore banned from use in most major sports. It is a potential metabolic precursor to nandrolone. However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance. See also * 4-Androstenediol * 19-Nor-5-androstenediol * 19-Nor-5-androstenedione * Bolandione Bolandione, also known as 19-norandrostenedione, as well as 19-norandrost-4-en-3,17-dione or estr-4-ene-3,17-dione, is a precursor of the anabolic-androgenic steroid (AAS) nan ...
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Oral Administration
Oral administration is a route of administration where a substance is taken through the mouth. Per os abbreviated to P.O. is sometimes used as a direction for medication to be taken orally. Many medications are taken orally because they are intended to have a systemic effect, reaching different parts of the body via the bloodstream, for example. Oral administration can be easier and less painful than other routes, such as injection. However, the onset of action is relatively low, and the effectiveness is reduced if it is not absorbed properly in the digestive system, or if it is broken down by digestive enzymes before it can reach the bloodstream. Some medications may cause gastrointestinal side effects, such as nausea or vomiting, when taken orally. Oral administration can also only be applied to conscious patients, and patients willing and able to swallow. Terminology ''Per os'' (; ''P.O.'') is an adverbial phrase meaning literally from Latin "through the mouth" or "by mo ...
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Anabolic Steroid Control Act Of 2004
Anabolism () is the set of metabolic pathways that construct molecules from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking-down aspect. Anabolism is usually synonymous with biosynthesis. Pathway Polymerization, an anabolic pathway used to build macromolecules such as nucleic acids, proteins, and polysaccharides, uses condensation reactions to join monomers. Macromolecules are created from smaller molecules using enzymes and cofactors. Energy source Anabolism is powered by catabolism, where large molecules are broken down into smaller parts and then used up in cellular respiration. Many anabolic processes are powered by the cleavage of adenosine triphosphate (ATP). Anabolism usually involves reduction and decreases entropy, making it unfavorable without energy input. The starting materials, called the precursor molecules, are joined using the chemic ...
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Prodrugs
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug is absorbed, distributed, metabolized, and excreted ( ADME). Prodrugs are often designed to improve bioavailability when a drug itself is poorly absorbed from the gastrointestinal tract. A prodrug may be used to improve how selectively the drug interacts with cells or processes that are not its intended target. This reduces adverse or unintended effects of a drug, especially important in treatments like chemotherapy, which can have severe unintended and undesirable side effects. History Many herbal extracts historically used in medicine contain glycosides (sugar derivatives) of the active agent, which are hydrolyzed in the intestines to release the active and more bioavailable aglycone. For example, salicin is a β-D-glucopyrano ...
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Estranes
Estrane is a C18 steroid derivative, with a gonane core. ''Estrenes'' are estrane derivatives that contain a double bond, with an example being nandrolone. ''Estratrienes'' (estrins) are estrane derivatives that contain three double bonds, for instance estrin (estra-1,3,5(10)-triene). The estrogen steroid hormones estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development o ..., estrone, and estriol are estra-1,3,5(10)-trienes. See also * Androstane * Pregnane References Estranes {{Steroid-stub ...
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Diketones
In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical (dialdehydes, diketones, diesters, ''etc.'') or unsymmetrical (keto-esters, keto-acids, ''etc.''). 1,2-Dicarbonyls 1,2-Dialdehyde The only 1,2-dialdehyde is glyoxal, . Like many alkyldialdehydes, glyoxal is encountered almost exclusively as its hydrate and oligomers thereof. These derivatives often behave equivalently to the aldehydes since hydration is reversible. Glyoxal condenses r ...
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Androgens And Anabolic Steroids
An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes the embryological development of the primary male sex organs, and the development of male secondary sex characteristics at puberty. Androgens are synthesized in the testes, the ovaries, and the adrenal glands. Androgens increase in both males and females during puberty. The major androgen in males is testosterone. Dihydrotestosterone (DHT) and androstenedione are of equal importance in male development. DHT ''in utero'' causes differentiation of the penis, scrotum and prostate. In adulthood, DHT contributes to balding, prostate growth, and sebaceous gland activity. Although androgens are commonly thought of only as male sex hormones, females also have them, but at lower levels: they function in libido and sexual arousal. Al ...
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Methandriol
Methandriol (brand names Anabol, Crestabolic, Cytobolin, Diandren, Durabolic, Madiol, Mestenediol, Methabolic, Methydiol, Sterabolic, Stenediol), also known as methylandrostenediol, is an androgen and anabolic steroid (AAS) medication which was developed by Organon and is used in both oral and injectable (as methandriol dipropionate, methandriol propionate, or methandriol bisenanthoyl acetate) formulations. It is an orally active 17α-alkylated AAS and a derivative of the endogenous androgen prohormone androstenediol. Medical uses Methandriol has been used in the treatment of breast cancer in women. It has been reported to be almost as virilizing as comparable doses of testosterone propionate and methyltestosterone in women. Available forms Methandriol (brand name Androteston M, Notandron, Protandren) was previously marketed as 25 mL and 50 mg/mL aqueous suspensions for use by intramuscular injection. Chemistry Methandriol, also known as 17α-methyl-5-androst ...
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Chloromethylandrostenediol
Chloromethylandrostenediol (CMA), also known as 4-chloro-17α-methyl-androst-4-ene-3β,17β-diol, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a 17α-alkylated derivative of 4-androstenediol that was never marketed. It was first encountered in 2005 when it was introduced as a " dietary supplement" and putative prohormone under the name Promagnon by an online vendor called Peak Performance Laboratories. CMA was voluntarily discontinued by Gaspari Nutrition in late 2006, likely fearing government sanctions if it continued to sell the product. Although CMA was sold as a "prohormone" or "prosteroid" of chloromethyltestosterone (CMT; also known more commonly as methylclostebol), it is likely that the conversion is far from complete and that much of the activity of the drug may be attributable to its unchanged form. Due to the presence of a chloro group at the C4 position, CMA cannot be aromatized, and for this reason, poses no risk of estrogenic side effect ...
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