Perhaps one of the most
effective ways of building body mass is to intake androgenic-anabolic
steroids; although it’s positive effects are not limited to building
muscle and are reported to assist in other areas of athletic
performance such as endurance and speed.
However, because of adverse effects on the body, they are not
allowed to be taken without a medical prescription.
Steroids are derivatives of cholesterol and are defined as
“any of several fat-soluble organic compounds having as a basis 17
carbon atoms in four rings; many have important physiological
effects are essentially the development of masculine characteristics
in the human body while anabolic effects refer to synthesizing large
tissue from simple compounds (in this case amino acids form proteins).
Anabolic steroids can be taken in several ways; they can be
injected in to the muscle, they can be taken orally and they can be
taken through gels/creams that are applied to the skin.
As discussed previously,
steroid hormones are produced naturally within the body.
Anabolic steroids were originally developed to treat
hypogonadism-when sufficient testosterone is not produced by the body.
What occurs at the molecular level when anabolic-androgen
steroids are taken is the anabolic steroid diffuses across the cell
membrane and combines with the hormone receptor which initiates the
process of protein synthesis (refer to section II and Figure 7.1).
7.1-an anabolic steroid as it enters the cell and initiates protein
As mentioned previously,
steroids are produced naturally within the body and are fat-soluble
organic compounds with a tetracyclic framework derived from
cholesterol. The base
structure of steroids is shown below:
There are three major classes
of steroids, which are all produced in the adrenal cortex; glucocorticoids,
androgens (although the
androgens are mainly synthesized in the gonads-especially the testes
and ovaries). As androgens
is the class which influences muscle growth the most, these types of
steroids (such as testosterone-a key steroid which possesses both
anabolic and androgenic properties) will primarily be focused on.
The complicated process in
which cholesterol is converted to androgens (androstenedione and
dehydroepiandrosterone) and then testosterone is illustrated in Figure
7.3. Firstly, cholesterol
is modified by the cytochrome P-450 enzyme, resulting in pregnenolone (figure 7.2).
Pregnenolone is essentially the originator of androgens.
Through the use of the 17b-hydroxysteroid
dehydrogenase enzyme in the testes and ovaries, the androgens can be
converted to testosterone.
7.2-line structures for cholesterol and pregnenolone, respectively
7.3-eventual conversion from cholesterol to testosterone
7.4-structure of testosterone
common prohormones (synthetically produced chemicals which are taken
manually) are typically converted within the body into anabolic
steroids such as testosterone, dihydrotestosterone
(nortestosterone), and 1-testosterone, all of which
will be discussed subsequently.
Some of the more familiar prohormones advertised for are 4-androstenedione,
4-androstenediol (4-AD), 19-norandrostenedione, 19-norandrostenediol,
and 1-androstenediol (1-AD). Because
these are converted to steroids within the body and are not steroids
as such themselves, they are legal in the U.S. without perscription
until Janurary 19th, 2005 when laws banning prohormones
will be implemented.
Within the body, testosterone
can be converted to dihydrotestosterone (the most effective of male
steroids) by the 5α-reductase enzyme.
What occurs is the double bond between C4 and C5 is downgraded
to a single bond, thus allowing room for an additional hydrogen atom
to bond to the two carbon atoms. As
shown in Figure 7.5, the new hydrogen atom on C5 is trans to the
methyl group while the new hydrogen atom on the C4 can be either cis
or trans due to the already present hydrogen atom.
7.5-structure of dihydrotestosterone
Nandrolone is very similar in
structure to testosterone. Following
the reaction, a hydrogen atom has replaced the methyl group in C10.
Figure 7.6 shows the structure of nandrolone.
7.6-structure of nandrolone
is simply an isomer of testosterone, although it is claimed to be 700%
more anabolic and 200% more androgenic than testosterone.
The structure of 1-testosterone is illustrated in figure 7.7.
Figure 7.7- structure of
There are many negative
consequences due to taking steroids, although many are reversible upon
the termination of steroid intake.
Following is a list of possible adverse effects from steroids:
of hormonal production in the body
in sperm cell production and shrinkage of the testicles in men
or loss of hair
of breasts in men (gynecomastia)
of the clitoris and decrease of breast size in women
of the skin in women
in sex drive
stunt in adolescences
to tendons, ligaments and/or muscles
diseases such as heart attack and stroke
of blood flow
tumour and cysts can form on the liver, possibly rupturing and
resulting in internal bleeding
and hepatitis due to sharing and/or non-sterile needles
effects can include rage and delusions
The reason for gynecomastia in
men is due to the conversion of testosterone (or another androgenic
steroid) to an estrogen (the primary female sex hormone) through a
reaction called aromatization (because ring ‘A’ becomes an
aromatic ring), where the enzyme aromatase acts as a catalyst.
For example, testosterone can be converted in to an estrogen
called estradiol, a type of estrogen.
Figure 7.8- structure of
the estrogen, estradiol
Below is a table illustrating
the characteristics of the prohormones mentioned earlier.
Note that conversion rate signifies the amount of the steroid
that is converted to testosterone.
Table 7.1- characteristics
of prohormones (as cited from Wikipedia, original author unknown. Retrieved from the
Research indicates a conversion
rate of about 5.6%, which means that of the amount taken orally,
5.6% is converted to testosterone.
Relatively high rate of
aromatization to estrogen, and consequently higher risk of
side-effects such as gynecomastia brought on by excessive
Exhibits significant androgenic
properties, which may result in side effects such as male
pattern baldness, acne, and enlarged prostate.
Conversion rate of about
15.76%, almost triple that of androstenedione, due to
utilization of a different enzymatic pathway.
No direct conversion to
estrogen, though some secondary aromatization does occur through
Appears to be less androgenic
than its cousin, since it does not metabolize into the potent
androgen dihydrotestosterone (DHT).
Only slightly less anabolic
Low rate of aromatization to
Low occurrence of androgenic
Same as -dione, except
(as with the
), the conversion rate is higher.
Very high conversion rate,
owing to the fact that the liver serves primarily to
"activate" the compound as it passes through rather
than to break it down and excrete it, as is the case with other
Cannot aromatize to estrogen
either directly or through any of its metabolic products.
However,1-Testosterone is highly andronergic being a
Dihydrotestosterone derivative. Many side effects associated
with excessive levels of DHT, including male pattern baldness,
testicular shrinkage, benign prostate hypertrophy and acne can
occur with 1-AD usage. (Journal of Organic chem. vol, 27 1962
Because steroid abuse is a developing issue in the athletic
community, testing for steroids have become mandated in events such as
the Olympics. To detect
the presence of steroids within the body, a urine sample is collected
from a human, which is then analyzed by a gas chromatograph
and mass spectrometer (GC/MS). A
chromatograph is essentially device which is used in combination with
a mass spectrometer and is used to separate mixtures before the sample
is analyzed by the mass spectrometer.
A mass spectrometer is a device which allows the identification
of a (unknown) compound based on its mass.
7.9 – a gas chromatograph. The
injector is heated resulting in the inputted chemical becoming a gas.
In the column, the mixture is then separated due to their
volatility and the separated chemicals are carried through the tube by
an inert gas. Less
volatile chemicals will travel with a greater speed than those with
more volatility. This
diagram is copyrighted by the
7.10 – a mass spectrometer. Once
the mixture has been separated and have entered the mass spectrometer,
the chemicals are bombarded with electrons by the ionization source,
causes the molecules to form radical cations and subsequently break
into smaller pieces. The
cations are then accelerated and then pass through a magnetic plate
and are deflected. The less the mass is, the more deflection occurs
(see Figure 7.11). This
diagram is copyrighted by the
7.11 – deflection of ions in a mass spectrometer
Figure 7.12 -mass spectrum (a) and total ion chromatogram (b) of oxymetholone, an anabolic steroid.