Nandrolone, structure

Chemical Name 170-hydroxyestr-4-en-3-one 3-phenylpropionate Common Name 19-nortestosterone (3-phenylpropionate Structural Formula See Nandrolone Decanoate for the steroid structure Chemical Abstracts Registry No. 62-90-8 434-22-0 (Base)... 

Kuuranne, T, Aitio, O., Vahermo, M., Elovaara, E. and Kostiainen, R. (2002). Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of methyltestosterone (17 alpha-methylan-drost-4-en-17 beta-ol-3-one) and nandrolone (est-4-en-17 beta-ol-3-one) metabolites. Bioconjug. Chem., 13, 194-199. 

Because of these side effects, researchers have developed compounds that produce the same effects as those obtained from natural testosterone, but without the compound s harmful side effects. Some of those compounds increase the natural production of testosterone in the body when they are ingested. Others are derivatives of testosterone, compounds with similar chemical structures, but minor changes that reduce side effects. These derivatives include compounds such as dihydrotestosterone, androstenedione (also known as andro), dehy-droepiandrosterone (DHEA), clostebol, and nandrolone. Today most derivatives of testosterone and testosterone-producing compounds are banned by sports organizations, both because of their harmful side effects and because of the unfair advantages they provide athletes who use them. 

Highly selective MIP-coated quartz crystal microbalance (QCM) sensors have been prepared for nandrolone [16], a performance-enhancing substance that has been banned in international sports. The authors hope to address the need for a sensor to rapidly detect this substance of abuse. MIP was prepared with a 4-vinylphenol carbonate ester of the template, but also in the presence of methacrylic acid to target the ketone functionality. The sensor was able to detect nandrolone down to 0.2 ppm and was highly selective over closely related structures such as testosterone and epitestosterone. 

Anabolic steroids, such as stanozolol, nandrolone, and tetrahydrogestrinone have the same effect on the body as testosterone, but they are more stable, so they are not metabolized as quickly. Tetrahydrogestrinone (also called THG or The Clear), the performance-enhancing drug used by track star Marion Jones during the 2000 Sydney Olympics, was considered a designer steroid because it was initially undetected in urine tests for doping. After its chemical structure and properties were determined, it was added to the list of banned anabolic steroids in 2004. 

Nandrolone is very similar in structure to the male hormone testosterone (see p489 and p507), differing by one methyl group, and has many of the same effects in terms of increasing muscle mass, without some of the more unwanted side effects such as increased body hair or aggressive behavior. As such, it has been actively examined in clinical tests as a possible treatment for... 

Track-and-field athlete Daniel Plaza said that he had prolonged sex with his pregnant wife, as pregnant women may produce nandrolone. In fact, the female pregnancy hormone, progesterone, is structurally quite similar to nandrolone. 

The members of this group listed in Table 31, all have a keto-group in position 3, a double bond between C atoms 4 and 5, and an OH group at the 17 position, although this is esterified in some cases. Testosterone, methyltestosterone, fluoxymesterone and methandienone are all based on the androstane structure, having methyl groups in both the 10 and 13 positions and norethandrolone and nandrolone have a methyl group at C 13 only. In addition, methandienone has a second double bond in the... 

Figure 4.5 Structures of selected steroidal analytes 5a-androstan-17P-ol-3-one (1), 5P-androstan-17P-ol-3-one (2), 17a-methyl-5a-androstan-17P-ol-3-one (3), la-methyl-5a-androstan-17P-ol-3-one (4), testosterone (5), nandrolone (6), 1-testosterone (7), metenolone (8), 5a-androst-l-ene-3,17-dione (9), metandienone (10), 18-nor-17P-hydroxymethyl,17a-methyl-androst-l,4,13-trien-3-one (metandienone metabolite) (11), androsta-4,6-dien-17P-ol-3-one (12), androsta-4,9-dien-17P-ol-3-one (13), trenbo-lone (14), methyltrienolone (15), tetrahydrogestrinone (THG, 16), and stanozolol (17).

Oxymetholone is an anabolic steroid and it is similar in structure to nandrolone (a synthetic androgen analogue) ... 

---