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#Post#: 88--------------------------------------------------
Deca Durabolin
By: Road2HardCoreIron Date: April 26, 2018, 9:31 pm
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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.[15]:134
The positive effects of nandrolone esters include muscle growth,
appetite stimulation and increased red blood cell
production,[medical citation needed] and bone density.[16]
Clinical studies have shown them to be effective in treating
anemia, osteoporosis and some forms of neoplasia including
breast cancer, and also acts as progestin-based
contraceptives.[citation needed]
Nandrolone sulfate has been used in an eye drop formulation as
an ophthalmic medication.[1][11]
Non-medical uses[edit]
Nandrolone esters are used for physique- and
performance-enhancing purposes by competitive athletes,
bodybuilders, and powerlifters.[8]
Side effects[edit]
See also: Anabolic steroid § Adverse effects
Side effects of nandrolone esters include masculinization among
others.[8]
Other side effects of high doses of nandrolone can include
erectile dysfunction and cardiovascular damage, as well as
several ailments resulting from the drug's effect of lowering
levels of luteinizing hormone through negative
feedback.[citation needed]
Pharmacology[edit]
Pharmacodynamics[edit]
Nandrolone is an agonist of the AR, the biological target of
androgens like testosterone and DHT. Unlike testosterone and
certain other AAS, nandrolone is not potentiated in androgenic
tissues like the scalp, skin, and prostate, hence deleterious
effects in these tissues are lessened.[17] 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.[17]
The lack of alkylation on the 17α-carbon drastically
reduces the hepatotoxic potential of nandrolone.[medical
citation needed] Estrogen effects resulting from reaction with
aromatase are also reduced due to lessened enzyme
interaction,[18] but effects such as gynecomastia and reduced
libido may still occur at sufficiently high doses.[citation
needed]
In addition to its AR agonistic activity, unlike many other AAS,
nandrolone is also a potent progestogen.[19] It binds to the
progesterone receptor with approximately 22% of the affinity of
progesterone.[19] The progestogenic activity of nandrolone
serves to augment its antigonadotropic effects,[20][8] as
antigonadotropic action is a known property of
progestogens.[21][22]
Anabolic and androgenic activity[edit]
Nandrolone has a very high ratio of anabolic to androgenic
activity.[13] In fact, nandrolone-like AAS like nandrolone
itself and trenbolone are said to have among the highest ratio
of anabolic to androgenic effect of all AAS.[20] 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 AAS
(i.e., other 19-nortestosterone derivatives).[13] As such,
nandrolone-like AAS, namely nandrolone esters, are the most
frequently used AAS in clinical settings in which anabolic
effects are desired; for instance, in the treatment of
AIDS-associated cachexia, severe burns, and chronic obstructive
pulmonary disease.[20] However, AAS with a very high ratio of
anabolic to androgenic action like nandrolone still have
significant androgenic effects and can produce symptoms of
masculinization like hirsutism and voice deepening in women and
children with extended use.[13]
[show]
Relative affinities (%) of nandrolone and related steroids at
the AR[17][23]
Pharmacokinetics[edit]
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.[24] It is metabolized by the
enzyme 5α-reductase, among others.[23][additional
citation(s) needed] Nandrolone is less susceptible to metabolism
by 5α-reductase and 17β-hydroxysteroid dehydrogenase
than testosterone.[23] This results in it being transformed less
in so-called "androgenic" tissues like the skin, hair follicles,
and prostate gland and in the kidneys, respectively.[23]
Metabolites of nandrolone include 5α-dihydronandrolone,
19-norandrosterone, and 19-noretiocholanolone, and these
metabolites may be detected in urine.[25]
Chemistry[edit]
Nandrolone, 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 nandrolone.
See also: List of androgens/anabolic steroids
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,[26] is a naturally
occurring estrane (19-norandrostane) steroid and a derivative of
testosterone (androst-4-en-17β-ol-3-one).[1][11] It is
specifically the C19 demethylated (nor) analogue of
testosterone.[1][11] Nandrolone 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.[27] It can be detected during pregnancy in
women.[28] Nandrolone esters have an ester such as decanoate or
phenylpropionate attached at the C17β position.[1][11]
Derivatives[edit]
Esters[edit]
See also: List of androgen esters § Nandrolone esters
A variety of esters of nandrolone have been marketed and used
medically.[1][11] 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.[1][11][8]
Anabolic steroids[edit]
See also: List of androgens/anabolic steroids and List of
androgen esters § Esters of synthetic AAS
Nandrolone 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 nandrolone that have been
developed as AAS:[8]
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)-19-NEA 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[edit]
See also: List of progestogens § Testosterone derivatives
Nandrolone, together with ethisterone
(17α-ethynyltestosterone), is also the parent compound of a
large group of progestins, the norethisterone
(17α-ethynyl-19-nortestosterone) derivatives.[29][30] This
family is subdivided into two groups: the estranes and the
gonanes.[29] 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.[29]
Synthesis[edit]
19-Nortestosterone synthesis:[31] alternative:[32][33]
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,[34] 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[edit]
Treatment of 4 with decanoic anhydride and pyridine affords
nandrolone decanoate.[35]
Acylation of 4 with phenylpropionyl chloride yields nandrolone
phenpropionate.[36]
Detection in body fluids[edit]
Nandrolone 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,[37] beyond which an athlete 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.[38][39][40][41]
A number of nandrolone cases in athletics occurred in 1999,
which included high-profile athletes such as Merlene Ottey,
Dieter Baumann and Linford Christie.[42] 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.[43]
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
nandrolone.[44] 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 nandrolone 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.[45]
Mass spectrometry is also used to detect small samples of
nandrolone in urine samples, as it has a unique molar mass.
History[edit]
QV Nandrolone Deca, a form of nandrolone used by athletes.
Nandrolone was first synthesized in 1950.[1][26][15]:130[46] It
was first introduced, as nandrolone phenylpropionate, in 1959,
and then as nandrolone decanoate in 1962, followed by additional
esters.[47]
Society and culture[edit]
Generic names[edit]
Nandrolone is the generic name of the drug and its INN, BAN,
DCF, and DCIT.[1][11][2][48] The formal generic names of
nandrolone esters include nandrolone cyclohexylpropionate
(BANM), nandrolone cyclotate (USAN), nandrolone decanoate (USAN,
USP, BANM, JAN), nandrolone laurate (BANM), nandrolone
phenpropionate (USP), and nandrolone phenylpropionate (BANM,
JAN).[1][11][2][48]
Doping in sports[edit]
See also: List of doping in sport cases § Nandrolone esters
Nandrolone was probably among the first AAS to be used as a
doping agent in sports in the 1960s. It has been banned at the
Olympics since 1974.[15]:128 There are many known cases of
doping in sports with nandrolone esters by professional
athletes.
Research[edit]
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 bisphosphonates became
available.[49] They have also been studied in clinical trials
for chronic kidney failure, aplastic anemia, and as male
contraceptives.[15]:134
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