upcScavenger » Alkene Derivatives » Wiki: Nandrolone

Nandrolone

( Alkene Derivatives )

Anabolic Esters Nandrolone Steroids

Rank: 100%

Wiki
Comments
Media

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen. It is also an anabolic steroid (AAS) which is medically used in the form of such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin).

(2025). 9781475720853, Springer. ISBN 9781475720853

(2000). 9783887630751, Taylor & Francis. . ISBN 9783887630751

(2025). 9780982828014, Molecular Nutrition Llc. . ISBN 9780982828014

(2005). 9780471899792, John Wiley & Sons. . ISBN 9780471899792

are used in the treatment of , cachexia (Skeletal muscle wasting syndrome), osteoporosis, breast cancer, and for other indications. They are now used by oral administration or instead are given by injection into muscle or fat.

of nandrolone esters include of virilization like acne, hirsutism, and voice deepening. They are synthetic androgens and anabolic steroids and hence are of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). Nandrolone has strong anabolic effects and weak effects, which give them a mild side effect profile and make them especially suitable for use in women and children.

(2012). 9783642663536, Springer Science & Business Media. . ISBN 9783642663536

There are metabolites of Nandrolone that act as long-lasting in the body, such as 5α-Dihydronandrolone.

Nandrolone esters were first described and introduced for medical use in the late 1950s. They are among the most widely used anabolic steroid worldwide. In addition to their medical use, nandrolone esters are used to improve physique and performance, and are said to be the most widely used anabolic steroid for such purposes.

(2015). 9780323321952, Elsevier Health Sciences. . ISBN 9780323321952

The drugs are controlled substances in many countries and so non-medical use is generally illicit.

Medical uses

Nandrolone esters are used clinically, although increasingly rarely, for people in catabolic states with major burns, cancer, and AIDS, and an ophthalmological formulation was available to support cornea healing.

The positive effects of nandrolone esters include muscle growth, appetite stimulation and increased red blood cell production, and bone density. Clinical studies have shown them to be effective in treating anemia, osteoporosis, and breast cancer.

Nandrolone sulfate has been used in an eye drop formulation as an ophthalmic medication.

Non-medical uses

Nandrolone esters are used for physique- and performance-enhancing purposes by competition , , and .

Side effects

of nandrolone esters include virilization among others. In women, nandrolone and have been reported to produce increased libido, acne, facial hair and body hair hair growth, voice deepening, and clitoral enlargement. However, the masculinizing effects of nandrolone and its esters are reported to be slighter than those of testosterone. Nandrolone has also been found to produce penile growth in prepubertal boys. Amenorrhea and menorrhagia have been reported as side effects of nandrolone cypionate.

Side effects of high doses of nandrolone may include cardiovascular toxicity as well as hypogonadism and infertility. Nandrolone may not produce scalp hair loss, although this is also theoretical.

Pharmacology

Pharmacodynamics

Nandrolone is an agonist of the AR, the biological target of like testosterone and . Unlike testosterone and certain other anabolic steroids, nandrolone is not potentiated in androgenic tissues like the scalp, skin, and prostate, hence deleterious effects in these tissues are lessened. This is because nandrolone is metabolized by 5α-reductase to the much weaker AR ligand 5α-dihydronandrolone (DHN), which has both reduced affinity for the androgen receptor (AR) relative to nandrolone in vitro and weaker AR agonistic potency in vivo. The lack of alkylation on the 17α-carbon drastically reduces the hepatotoxicity potential of nandrolone. Estrogen effects resulting from reaction with aromatase are also reduced due to lessened enzyme interaction, but effects such as gynecomastia and reduced libido may still occur at sufficiently high doses.

In addition to its AR agonistic activity, unlike many other anabolic steroids, nandrolone is also a potent progestogen. It binds to the progesterone receptor with approximately 22% of the affinity of progesterone. The progestogenic activity of nandrolone serves to augment its antigonadotropic effects, as antigonadotropic action is a known property of progestogens.Mauvais-Jarvis, P. "Progesterone and progestins: a general overview." (1983): 1-16.

Anabolic and androgenic activity

Nandrolone has a very high ratio of anabolic to androgenic activity. In fact, many nandrolone-like anabolic steroids and even nandrolone itself are said to have among the highest ratio of anabolic to androgenic effects of all anabolic steroids. This is attributed to the fact that whereas testosterone is potentiated via conversion into dihydrotestosterone (DHT) in androgenic tissues, the opposite is true with nandrolone and similar anabolic steroids (i.e., other 19-nortestosterone derivatives). As such, nandrolone-like anabolic steroids, namely nandrolone esters, are the most frequently used anabolic steroids in clinical settings in which anabolic effects are desired; for instance, in the treatment of AIDS-associated cachexia, severe , and chronic obstructive pulmonary disease. However, anabolic steroids with a very high ratio of anabolic to androgenic action like nandrolone still have significant androgenic effects and can produce symptoms of virilization like hirsutism and voice change in women and children with extended use.

Pharmacokinetics

The oral activity of nandrolone has been studied. With oral administration of nandrolone in rodents, it had about one-tenth of the potency of subcutaneous injection of nandrolone.

(1960). 9783034870405 ISBN 9783034870405

Nandrolone has very low affinity for human serum sex hormone-binding globulin (SHBG), about 5% of that of testosterone and 1% of that of DHT. It is metabolism by the enzyme 5α-reductase, among others. Nandrolone is less susceptible to metabolism by 5α-reductase and 17β-hydroxysteroid dehydrogenase than testosterone. This results in it being transformed less in so-called "androgenic" tissues like the skin, , and prostate gland and in the , respectively. of nandrolone include 5α-dihydronandrolone, 19-norandrosterone, and 19-noretiocholanolone, and these metabolites may be detected in urine.

(2010). 9781135258252, Routledge. . ISBN 9781135258252

Single intramuscular injections of 100 mg nandrolone phenylpropionate or nandrolone decanoate have been found to produce an anabolic effect for 10 to 14 days and 20 to 25 days, respectively.

(2016). 9781483273006, Elsevier Science. . ISBN 9781483273006

Conversely, unesterified nandrolone has been used by intramuscular injection once daily.

Chemistry

Nandrolone, 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,

(1967). 9780323146111, Elsevier Science. . ISBN 9780323146111

is a natural compound estrane (19-norandrostane) steroid and a derivative of testosterone (androst-4-en-17β-ol-3-one). It is specifically the C19 demethylation (nor-) analogue of testosterone. Nandrolone is an endogenous intermediate in the biosynthesis of estradiol from testosterone via aromatase in including humans and is present in the body naturally in trace amounts. It can be detected during pregnancy in women. Nandrolone esters have an ester such as decanoate or phenylpropionate attached at the C17β position.

Derivatives

Esters

A variety of esters of nandrolone have been marketed and used medically. The most commonly used esters are nandrolone decanoate and to a lesser extent nandrolone phenylpropionate. Examples of other nandrolone esters that have been marketed and used medically include nandrolone cyclohexylpropionate, nandrolone cypionate, nandrolone hexyloxyphenylpropionate, nandrolone laurate, nandrolone sulfate, and nandrolone undecanoate.

Anabolic steroids

Nandrolone is the parent compound of a large group of anabolic steroids. Notable examples include the non-17α-alkylated trenbolone and the 17α-alkylated ethylestrenol (ethylnandrol) and metribolone (R-1881), as well as the 17α-alkylated norboletone and tetrahydrogestrinone (THG). The following is list of derivatives of nandrolone that have been developed as anabolic steroids:

Non-17α-alkylated derivatives

Marketed

Bolandiol (19-nor-4-androstenediol)
Norclostebol (4-chloro-19-NT)
Oxabolone (4-hydroxy-19-NT)
Trenbolone (δ^9,11-19-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-δ^2,5(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-δ^9,11-19-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-δ^9,11-19-NT)
Norboletone (17α-ethyl-18-methyl-19-NT)
Tetrahydrogestrinone (THG; 17α-ethyl-18-methyl-δ^9,11-19-NT)

Progestins

Nandrolone, together with ethisterone (17α-ethynyltestosterone), is also the parent compound of a large group of , the norethisterone (17α-ethynyl-19-nortestosterone) derivatives.

(2003). 9781592593750, Springer Science & Business Media. . ISBN 9781592593750

This family is subdivided into two groups: the and the . 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

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 nandrolone ( 4).

Esters

Treatment of 4 with decanoic anhydride and pyridine affords nandrolone decanoate..
Acylation of 4 with phenylpropionyl chloride yields nandrolone phenpropionate.

Detection in body fluids

Nandrolone use is directly detectable in hair or indirectly detectable in urine by testing for the presence of 19-norandrosterone, a metabolite. The IOC has set a limit of 2.0 μg/L of 19-norandrosterone in urine as the upper limit, beyond which an sportsperson is suspected of doping. In the largest nandrolone 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.

(2025). 9780962652370, Biomedical Publications. . ISBN 9780962652370

A number of nandrolone 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 nandrolone 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 C. J. Hunter as the reason for his positive test, though in 2004 he admitted to a federal grand jury that he had injected nandrolone. A possible cause of incorrect urine test results is the presence of metabolites from other anabolic steroids, though modern urinalysis can usually determine the exact anabolic steroid used by analyzing the ratio of the two remaining nandrolone metabolites. As a result of the numerous overturned verdicts, the testing procedure was reviewed by UK Sport. In October 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 amounts of nandrolone in urine samples.

History

Nandrolone was first synthesized in 1950. It was first introduced, as nandrolone phenylpropionate, in 1959, and then as nandrolone decanoate in 1962, followed by additional esters.

(1983). 9789211302301, United Nations Publications. . ISBN 9789211302301

Society and culture

Generic names

Nandrolone is the generic term of the drug and its , , , and .

(2012). 9789401144391, Springer Science & Business Media. . ISBN 9789401144391

The formal generic names of nandrolone esters include nandrolone cyclohexylpropionate (), nandrolone cyclotate (), nandrolone decanoate (, , , ), nandrolone laurate (), nandrolone phenpropionate (), and nandrolone phenylpropionate (, ).

Doping in sports

Nandrolone was probably among the first anabolic steroids to be used as a doping agent in sports in the 1960s. It has been banned at the Olympics since 1974.

(2025). 9783540790884, Springer. ISBN 9783540790884

There are many known cases of doping in sports with nandrolone esters by professional .

Research

Nandrolone esters have been studied in several indications. They were intensively studied for osteoporosis, and increased calcium uptake and decreased bone loss, but caused virilization in about half of the women who took them and were mostly abandoned for this use when better drugs like the became available. They have also been studied in for chronic kidney failure, aplastic anemia, and as male contraceptives.

Nandrolone

( Alkene Derivatives )

Account

Navigation

Statistics

Nandrolone ( Alkene Derivatives )

Account

Navigation

Statistics

Nandrolone

( Alkene Derivatives )