Androsta-1,4-diene-3,17-dione
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Androsta-1,4-diene-3,17-dione
Boldione, also known as androstadienedione or 1-dehydroandrostenedione, as well as 1,4-androstadiene-3,17-dione, is an important industrial precursor for various steroid hormones. In the United States the chemical is regulated as a Schedule III Controlled Substance. Uses Androstadienedione is an important industrial-scale precursor for a wide variety of steroid hormones within the estrane and androstane classifications. Preparation Androstadienedione is obtained in high yield from both plant and animal sterols by biotransformation. The chemical is a common byproduct derived from other processes (e.g. vegetable oil deodorization and the production of lanolin from wool processing). The product is produced in a single step via a simultaneous side-chain cleavage at the C17 position and an alcohol oxidation in the C3 position. Regulation United States In 2004 the United States Congress passed the Anabolic Steroid Control Act of 2005 which placed 36 steroids and over- ...
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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 mouth ...
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Side Chain
In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called the "main chain" or backbone. The side chain is a hydrocarbon branching element of a molecule that is attached to a larger hydrocarbon backbone. It is one factor in determining a molecule's properties and reactivity. A side chain is also known as a pendant chain, but a pendant group (side group) has a different definition. Conventions The placeholder R is often used as a generic placeholder for alkyl (saturated hydrocarbon) group side chains in chemical structure diagrams. To indicate other non-carbon groups in structure diagrams, X, Y, or Z are often used. History The ''R'' symbol was introduced by 19th-century French chemist Charles Frédéric Gerhardt, who advocated its adoption on the grounds that it would be widely recognizable and intelligible given its correspondence in multiple European languages to the initial letter of "root" or "residue": ...
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Androstanes
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. Also, and ...
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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. Also, and ...
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World Anti-Doping Agency
The World Anti-Doping Agency (WADA; french: Agence mondiale antidopage, AMA) is a foundation initiated by the International Olympic Committee based in Canada to promote, coordinate, and monitor the fight against drugs in sports. The agency's key activities include scientific research, education, development of anti-doping capacities, and monitoring of the World Anti-Doping Code, whose provisions are enforced by the UNESCO International Convention Against Doping in Sport. The aims of the Council of Europe Anti-Doping Convention and the United States Anti-Doping Agency are also closely aligned with those of WADA. History The World Anti-Doping Agency is a foundation created through a collective initiative led by the International Olympic Committee (IOC). It was set up on 10 November 1999 in Lausanne, Switzerland, as a result of what was called the "Declaration of Lausanne", to promote, coordinate and monitor the fight against drugs in sports. Since 2002, the organization's head ...
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Dienedione
Dienedione, also known as estra-4,9-diene-3,17-dione, is a synthetic, orally active anabolic-androgenic steroid (AAS) of the 19-nortestosterone group that was never introduced for medical use. It is thought to be a prohormone of dienolone. The drug became a controlled substance in the US on January 4, 2010, and is classified as a Schedule III anabolic steroid under the United States Controlled Substances Act. Previous to this, it was sold as a bodybuilding supplement within the United States, and often mistakenly marketed as a prohormone for trenbolone, a veterinary steroid. Prior to its scheduling, it was part of a number of supplements that were seized during FDA enforcement of Bodybuilding.com for selling unapproved new drugs. The actual active metabolite, dienolone, is almost identical to trenbolone structurally, but lacks the C11 double bond. See also * Androstenedione * Bolandiol * Bolandione * Boldione Boldione, also known as androstadienedione or 1-dehydroandrosten ...
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Desoxymethyltestosterone
Desoxymethyltestosterone (DMT), known by the nicknames Madol and Pheraplex, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-methylated derivative of dihydrotestosterone (DHT) which was never marketed for medical use. It was one of the first designer steroids to be marketed as a performance-enhancing drug to athletes and bodybuilders. Desoxymethyltestosterone is sometimes abbreviated as DMT, though it should not be confused with the hallucinogen dimethyltryptamine, which is also known by the same acronym. Side effects Pharmacology Pharmacodynamics In animal studies, desoxymethyltestosterone has been found to bind to the androgen receptor (AR) about half as strongly as DHT, and to cause side effects that are typical of 17α-alkylated AAS, such as liver damage and left ventricular hypertrophy when taken in higher doses. Desoxymethyltestosterone is unusual in that it is structurally a 2-ene compound, lacking the 3- keto group present in almost ...
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Controlled Substances Act
The Controlled Substances Act (CSA) is the statute establishing federal government of the United States, federal drug policy of the United States, U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United States Congress as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970 and signed into law by President Richard Nixon. The Act also served as the national implementing legislation for the Single Convention on Narcotic Drugs. The legislation created five schedules (classifications), with varying qualifications for a substance to be included in each. Two federal agencies, the Drug Enforcement Administration (DEA) and the Food and Drug Administration (FDA), determine which substances are added to or removed from the various schedules, although the statute passed by Congress created the initial listing. Congress has sometimes scheduled other substances th ...
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Anabolic Steroid Control Act Of 2005
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 chemica ...
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Oxidation Of Secondary Alcohols To Ketones
The oxidation of secondary alcohols to ketones is an important redox, oxidation reaction in organic chemistry. When a secondary alcohol is oxidised, it is converted to a ketone. The hydrogen from the hydroxyl group is lost along with the hydrogen bonded to the carbon attached to oxygen. The remaining oxygen then forms double bonds with the carbon. This leaves a ketone, as R1–COR2. Ketones are quite resistant to further oxidation as it would require breaking an adjacent C–C bond, but with strong oxidants this may occur and produces Ester, esters or Carboxylic acid, carboxylic acids. The reaction can occur using a variety of oxidants. Potassium dichromate A secondary alcohol can be oxidised into a ketone using acidified potassium dichromate and heating under reflux. The orange-red dichromate ion, Cr2O72−, is reduced to the green Cr3+ ion. This reaction was once used in an alcohol breath test. PCC (Pyridinium chlorochromate) Pyridinium chlorochromate (PCC), when used in an ...
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Steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene. The steroid core structure is typically composed of seventeen carbon atoms, bonded in four " fused" rings: three six-member cyclohexane rings (rings A, B and C in the first illustration) and one five-member cyclopentane ring (the D ring). Steroids vary by the functional groups attached to this four-ring core and by the oxidation state of the rings. Sterols are forms of steroids with a hydroxy group at position three and a skeleton derived from cholestane. ''A ...
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Bond Cleavage
In chemistry, bond cleavage, or bond fission, is the splitting of chemical bonds. This can be generally referred to as dissociation when a molecule is cleaved into two or more fragments. In general, there are two classifications for bond cleavage: ''homo''lytic and ''hetero''lytic, depending on the nature of the process. The triplet and singlet excitation energies of a sigma bond can be used to determine if a bond will follow the homolytic or heterolytic pathway. A metal−metal sigma bond is an exception because the bond's excitation energy is extremely high, thus cannot be used for observation purposes. In some cases, bond cleavage requires catalysts. Due to the high bond-dissociation energy of C-H bonds, around , a large amount of energy is required to cleave the hydrogen atom from the carbon and bond a different atom to the carbon. Homolytic cleavage In homolytic cleavage, or homolysis, the two electrons in a cleaved covalent bond are divided equally between th ...
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