<unk> , with the differences from testosterone highlighted in red. The methyl group in testosterone at the C19 position has been removed, and the C17β position is where esters are attached to<unk> .<unk> , also known as 19-nortestosterone (19-NT) or as estrenolone, as well as estra-4-en-17β-ol-3-one or 19-norandrost-4-en-17β-ol-3-one, is a naturally occurring estrane (19-norandrostane) steroid and a derivative of testosterone (androst-4-en-17β-ol-3-one). It is specifically the C19 demethylated (nor) analogue of testosterone.<unk>  is an endogenous intermediate in the production of estradiol from testosterone via aromatase in mammals including humans and is present in the body naturally in trace amounts. It can be detected during pregnancy in women.<unk>  esters have an ester such as decanoate or phenylpropionate attached at the C17β position. Derivatives Esters A variety of esters of<unk>  have been marketed and used medically. The most commonly used esters are<unk>  decanoate and to a lesser extent<unk>  phenylpropionate. Examples of other<unk>  esters that have been marketed and used medically include<unk>  cyclohexylpropionate,<unk>  cypionate,<unk>  hexyloxyphenylpropionate,<unk>  laurate,<unk>  sulfate, and<unk>  undecanoate. Anabolic steroids<unk>  is the parent compound of a large group of AAS. Notable examples include the non-17α-alkylated trenbolone and the 17α-alkylated ethylestrenol (ethylnandrol) and metribolone (R-1881), as well as the 17α-alkylated designer steroids norboletone and tetrahydrogestrinone (THG). The following is list of derivatives of<unk>  that have been developed as AAS: ; Non-17α-alkylated derivatives * Marketed * Bolandiol (19-nor-4-androstenediol) * Norclostebol (4-chloro-19-NT) * Oxabolone (4-hydroxy-19-NT) * Trenbolone (δ9,11-19-NT) * Never marketed * 7α-Methyl-19-nor-4-androstenedione (MENT dione, trestione) * 11β-Methyl-19-nortestosterone (11β-MNT; 11β-methyl-19-NT) * 19-Nor-5-androstenediol * 19-Nor-5-androstenedione * Bolandione (19-nor-4-androstenedione) * Dienedione (δ9-19-nor-4-androstenedione) * Dienolone (δ9-19-NT) * Dimethandrolone (7α,11β-dimethyl-19-NT) * Methoxydienone (18-methyl-δ2,5(10)- 3β-methyl ether) * Trestolone (MENT; 7α-methyl-19-NT) ; 17α-Alkylated derivatives * Marketed * Ethylestrenol (ethylnandrol; 3-deketo-17α-ethyl-19-NT) * Mibolerone (7α,17α-dimethyl-19-NT) * Norethandrolone (17α-ethyl-19-NT) * Normethandrone (methylestrenolone; 17α-methyl-19-NT) * Propetandrol (17α-ethyl-19-NT 3β-propionate) * Never marketed * Bolenol (3-deketo-17α-ethyl-19-nor-5-androstenediol) * Dimethyltrienolone (7α,17α-dimethyl-δ9,11-19-NT) * Ethyldienolone (17α-ethyl-δ9-19-NT) * Methyldienolone (17α-methyl-δ9-19-NT) * Methylhydroxynandrolone (MOHN, MHN; 4-hydroxy-17α-methyl-19-NT) * Metribolone (methyltrienolone, R-1881; 17α-methyl-δ9,11-19-NT) * Norboletone (17α-ethyl-18-methyl-19-NT) * Tetrahydrogestrinone (THG; 17α-ethyl-18-methyl-δ9,11-19-NT) Progestins<unk> , together with ethisterone (17α-ethynyltestosterone), is also the parent compound of a large group of progestins, the norethisterone (17α-ethynyl-19-nortestosterone) derivatives. This family is subdivided into two groups: the estranes and the gonanes. The estranes include norethisterone (norethindrone), norethisterone acetate, norethisterone enanthate, lynestrenol, etynodiol diacetate, and noretynodrel, while the gonanes include norgestrel, levonorgestrel, desogestrel, etonogestrel, gestodene, norgestimate, dienogest (actually a 17α-cyanomethyl-19-nortestosterone derivative), and norelgestromin. Synthesis 19-Nortestosterone synthesis: alternative: The elaboration of a method for the reduction of aromatic rings to the corresponding dihydrobenzenes under controlled conditions by A. J. Birch opened a convenient route to compounds related to the putative 19-norprogesterone. This reaction, now known as the Birch reduction, is typified by the treatment of the monomethyl ether of estradiol (1) with a solution of lithium metal in liquid ammonia in the presence of alcohol as a proton source. Initial reaction constituents of 1,4-dimetalation of the most electron deficient positions of the aromatic ring–in the case of an estrogen, the 1 and 4-positions. Rxn of the intermediate with the proton source leads to a dihydrobenzene; a special virtue of this sequence in steroids is the fact that the double bind at 2 is in effect becomes an enol ether moiety. Treatment of this product (2) with weak acid, oxalic acid for e.g., leads to the hydrolysis of the enol ether, producing β,γ-unconjugated ketone 3. Hydrolysis under more strenuous conditions (mineral acids) results in migration/conjugation of the olefin to yield<unk>  (4). Esters * Treatment of 4 with decanoic anhydride and pyridine affords<unk>  decanoate. * Acylation of 4 with phenylpropionyl chloride yields<unk>  phenpropionate. Detection in body fluids<unk>  use is directly detectable in hair or indirectly detectable in urine by testing for the presence of 19-norandrosterone, a metabolite. The International Olympic Committee has set a limit of 2.0 μg/L of 19-norandrosterone in urine as the upper limit, beyond which an athlete is suspected of doping. In the largest<unk>  study performed on 621 athletes at the 1998 Nagano Olympic Games, no athlete tested over 0.4 μg/L. 19-Norandrosterone was identified as a trace contaminant in commercial preparations of androstenedione, which until 2004 was available without a prescription as a dietary supplement in the U.S. A number of<unk>  cases in athletics occurred in 1999, which included high-profile athletes such as Merlene Ottey, Dieter Baumann and Linford Christie. However, the following year the detection method for<unk>  at the time was proved to be faulty. Mark Richardson, a British Olympic relay runner who tested positive for the substance, gave a significant amount of urine samples in a controlled environment and delivered a positive test for the drug, demonstrating that false positives could occur, which led to an overhaul of his competitive ban. Heavy consumption of the essential amino acid lysine (as indicated in the treatment of cold sores) has allegedly shown false positives in some and was cited by American shotputter C. J. Hunter as the reason for his positive test, though in 2004 he admitted to a federal grand jury that he had injected<unk> . A possible cause of incorrect urine test results is the presence of metabolites from other AAS, though modern urinalysis can usually determine the exact AAS used by analyzing the ratio of the two remaining<unk>  metabolites. As a result of the numerous overturned verdicts, the testing procedure was reviewed by UK Sport. On October 5, 2007, three-time Olympic gold medalist for track and field Marion Jones admitted to use of the drug, and was sentenced to six months in jail for lying to a federal grand jury in 2000. Mass spectrometry is also used to detect small samples of<unk>  in urine samples, as it has a unique molar mass.
Nandrolone
Oxandrolone
Norethandrolone
Androstanolone
Gestrinone
Norbormide
Androstanolone benzoate
Allenestrol