Testosterone is commonly administered as an ester to improve its solubility and slow its release in the body. The document discusses several testosterone esters including enanthate, cypionate, propionate, and phenylpropionate. It describes their chemical structures, how they work, administration schedules, and common medical uses and side effects. Testosterone esters allow for sustained release over 1-3 weeks compared to hours for the non-esterified form. More carbons in the ester chain increase solubility in oil and prolong the active release time.

1. Lecture
Doping And Its Types
Testosterone Esters

2. Testosterone esters
Much of the testosterone that is prescribed for the purposes of
hormone therapy is in the form of testosterone "esters."
An ester is simply a name for a chemical compound that is
formed from reaction between a carboxylic acid and an alcohol.
A simple chemical diagram of this reaction is shown below in
Figure A.

3. Figure B shows the chemical structure of free
testosterone (chemical formula C19H28O2) as well as two
different esters of testosterone (testosterone cypionate
and testosterone enanthate).

4. • There are a number of different esters of testosterone, including the
commonly prescribed injectables of testosterone enanthate and
testosterone cypionate, as well others such as acetate, propionate,
phenylpropionate, isocaproate, caproate, decanoate, and undecanoate.
• Each of these different esters is a molecular chain composed of carbon,
hydrogen, and oxygen atoms.
• The main difference between the different esters is how many carbon
and hydrogen atoms make up the chain.
• For example, the propionate ester is composed of 3 carbons, 6
hydrogens, and 2 oxygens, whereas the cypionate ester is composed of 8
carbons, 14 hydrogens, and 2 oxygens.
• Esterification of testosterone is done in order to improve the solubility
of testosterone in oil, which in turn slows the release of the testosterone
from the site where it enters the body.
Testosterone esters

5. • Testosterone, in its free, non-esterified form, has poor solubility in either oil or
water-- though it can be suspended in water. Non-esterified testosterone is available
in an aqueous injectable form with the drug name "Aquaviron.
• " However, this form of testosterone stays active in the body for a very short period
of time (only a matter of hours). Because of this, it must be injected on a daily basis
in order to maintain a continuous level of testosterone in the blood. Therefore it is
rarely used for testosterone replacement therapy as an injectable.
• Once you have added an ester group to testosterone, it becomes even less soluble in
water and more soluble in oil. Additionally, as a general rule, the more carbon
atoms there are in an ester, the more soluble the ester is in oil. For example,
testosterone propionate (with 3 carbon atoms in the ester group) is less soluble in
oil than testosterone cypionate (with 8 carbon atoms in the ester group).
• So generally, the more carbons the ester group has, the more soluble in oil it
becomes, and the less soluble in water. The term for this ratio between oil and
water solubility is called the "partition coefficient"-- the higher the solubility in oil,
the higher the partition coefficient.
Testosterone esters

6. • Testosterone cypionate has a high partition coefficient. When injected into the body,
the drug remains in its esterified form in a deposit in the muscle tissue, depending on
the type of injection.
• From there, it will slowly enter the circulation as it is picked up in small quantities by
the blood. Once the esterified testosterone is brought into the blood stream,
"esterase enzymes" cleave off the ester chain in a process known as "hydrolization,"
thus leaving the testosterone in its free form to perform its various actions and
effects.
• When people speak of whether a particular testosterone ester is "fast acting" or
"slow acting," they are usually referring to the partition coefficient/solubility in oil.
• As described above, esters with more carbon atoms will generally be more soluble in
oil-- they are often referred to as "slow-acting" esters (they stay active in the system
longer).
• Esters that are less soluble in oil are often referred to as "fast-acting" forms of
testosterone, referring to the fact that they are more quickly available and used up in
the blood stream.
Testosterone esters

7. Testosterone Enanthate
• Testosterone enanthate has Chemical formula C26H40O3
• Testosterone enanthate, also known as testosterone heptanoate, is
an anabolic and androgenic steroid (AAS) drug used to treat low
testosterone levels.
• Anabolic drugs work by building muscles, while androgenic refers to
the enhancement of male sex characteristics.
• Used in medical procedures since the 1950s, testosterone enanthate is
marketed under numerous brand names, including Androfil,
Andropository, Cernos, Delatestryl, Depandro, Durathate, Everone,
Sustrone, Testanon, Testanova, Testrin, Testostroval, Testoviron, and
Testro.

8. • Use of testosterone enanthate has been shown to significantly
increase strength within 6-12 weeks of administration
• It is a slow-acting ester with a release time between 7-9 days.
• . Testosterone enanthate is typically injected anywhere
between once every week to once every three weeks.
• Testosterone enanthate is available by prescription only and is
classified as a prohibited substance by the World Anti-Doping
Agency
Testosterone Enanthate

9. Common Side Effects
As a substance designed to alter hormone levels, testosterone
enanthate has both its clear benefits and risks. According to the FDA,
the most common side effects associated with testosterone
enanthate use include:
• Injection site pain and swelling
• Headaches
• Dizziness
• Mood changes, including aggression
• Depression or anxiety
• Increased or decreased libido
• Generalized tingling sensations
• Oily skin and acne
• Thinning hair
• Weight gain

10. Adverse Reactions
Less common but potentially more serious are side effects
associated with the long-term use or overuse of testosterone
enanthate. Some are related to the androgenic effects of the drug;
others can affect the heart and liver by elevating the cholesterol and
liver enzyme levels.
• Male-pattern hair loss
• Male-pattern hair growth in women
• Male breast enlargement
• Deepening voice in women
• Menstrual irregularities
• Difficulty urinating or frequent urination at night in men
• Severe psychiatric symptoms, including major depression,
paranoia, or psychosis

11. Testosterone Propionate
INTRODUCTION
Testosterone propionate was discovered in 1936 and was introduced for
medical use in 1937
This type of testosterone is a slow-releasing anabolic steroid with a short half-
life of 4-5.
It is used in short Testosterone Propionate cycles in the range of 8 – 10 weeks,
sometimes in as little as even 6 weeks.
This is due to the shorter time required for optimal blood plasma levels to be
achieved because of the faster release. It will result in the fastest peak plasma
levels of Testosterone.
The high level will be followed by a crash in T levels if you do not inject twice
or thrice a week to maintain stable levels.
This testosterone ester can peak in the blood within hours of being administered
and metabolized over three days.
C22H32O3

12. • Propionate requires frequent injections compared to other types of
testosterone such as cypionate or enanthate.
• Injections should be administered every two to three days.
• Competition bodybuilders like to use Testosterone Propionate along
with Stanozolol and Trenbolone, as well as Growth Hormone,
which ensures optimal muscle protection even during the toughest
diets and heaviest exercise phases. However, this combination
should only be used by ambitious athletes.
• For amateur bodybuilders who have no competitive ambitions, the
sole use of Testosterone Propionate is usually completely
sufficient and low side effects.

13. Testosterone Cypionate C27H40O3
Introduction
1. Testosterone Cypionate was first created in the mid-1950s, and was released on
the prescription drug market under the brand name Depo-Testosterone
2. Testosterone Cypionate is most likely the second most popular esterified
variant (the first being Testosterone Enanthate).
3. It is an injectable form of Testosterone with a slow rate of release and a longer
half-life.
4. However, the release rates and half-life of both Testosterone Cypionate and
Testosterone Enanthate are very much identical and the two compounds are
easily interchangeable (for example, an individual can easily run a 10 week
cycle of Testosterone and switch between Testosterone Enanthate and
Testosterone Cypionate seamlessly).

14. 5. Testosterone Cypionate possesses a half-life of approximately 8-
10 days while Testosterone Enanthate possesses a half-life of
approximately 7-9 days – hardly much difference.
6. the most common difference that we know about the
difference between testosterone enanthate and testosterone
cypionate is that the latter lasts longer.
7. In addition to the difference in the effect of the two,
testosterone enanthate and cypionate has a difference in their
chemical structure as well. The Testosterone enanthate has 7-
carbons whereas Testosterone cypionate has 8-carbons.
8. Testosterone cypionate comes only in the form of an injectable
solution given into your muscle. You can give this medication to
yourself at home after your doctor shows you how.

15. When it needs to take
Testosterone cypionate is used to treat symptoms of hypogonadism in males. In
this condition, males don't produce enough of the sex hormone testosterone.
Testosterone cypionate works to treat hypogonadism in males by replacing the
testosterone your body is unable to make.

16. Testosterone Phenylpropionate
Testosterone phenylpropionate, Chemical formula C28H36O3, otherwise called
testosterone hydrocinnamate, is an engineered anabolic-androgenic steroid
which was once in the past promoted in Romania. Testosterone
phenylpropionate is a slow-acting ester, with a release time of 1-3 weeks.
Testosterone phenylpropionate was first released into the market in 1955 by
Sicomed Pharmaceutical house but was selling under the name brand Testolent.
Testosterone phenylpropionate is a drug that should be administered through
injection. After the injection, the drug remains active for about five days when
then you can take another dose. The drug can be used independently or
administered with other testosterone esters for testosterone treatments in a
patient with affirmed testosterone insufficiency.

17. Additionally, by taking testosterone phenylpropionate, bodybuilders report
increment of craving, forcefulness, and quality.
Testosterone Phenylpropionate Half life
Testosterone phenylpropionate is an injectable drug with a half-life of 3 to 4
days. You will be required to take your dose once in 4 days. A professional
health practitioner should administer the injection.

18. Testosterone decanoate
Testosterone decanoate is an androgen and anabolic steroid and a testosterone
ester. It is a component of Sustanon, along with testosterone
propionate, testosterone phenylpropionate, and testosterone isocaproate. The
medication has not been marketed as a single-drug preparation. Testosterone
decanoate has been investigated as a potential long-acting injectable male
contraceptive. It has a longer duration of action than testosterone enanthate, but
its duration is not as prolonged as that of testosterone undecanoate. The
molecular formula of Testosterone decanoate is C29H46O3.
It is the fourth compound of Sustanon 250 has the longest half-life and is thus
the most powerful one. Its half-life extends for more than two weeks. It may
also have an active life of a month thus you may need to inject it after a month.
But, this only happens in the case of hormone replacement therapy.

19. Testosterone caproate
Testosterone caproate (TCa), also known as testosterone hexanoate, is
an androgen and anabolic steroid and a testosterone ester that is no longer
marketed. The molecular formula of Testosterone caproate is C25H38O3.
Testosterone isocaproate
Testosterone isocaproate, sold under the brand names Sustanon 100, Sustanon
250, and Omnadren 250, is an androgen and anabolic steroid medication and a
testosterone ester which has been used as a component of mixed testosterone
ester preparations.
Also known as isohexane,4-methylvaleric acid, and isocaproic acid. The half-
life if this compound is 7-9 days. If it is used as a single testosterone
supplement, then you need to inject it after every week.

20. Stanozolol
In 1962, Stanozolol was brought to market in the US by Winthrop under the
tradename "Winstrol" is a synthetic anabolic steroid derived from
dihydrotestosterone.
t was developed by Winthrop Laboratories (Sterling Drug) in 1962, and has been
approved by the FDA for human use.
Unlike most injectable anabolic steroids, stanozolol is not esterified and is sold
as an aqueous suspension, or in oral tablet form. The drug has a high oral
bioavailability,
Stanozolol has been used in both animal and human patients for a number of
conditions. In humans, it has been demonstrated to be successful in treating
anaemia and hereditary angioedema.
Veterinarians may prescribe the drug to improve muscle growth, red blood cell
production, increase bone density and stimulate the appetite of debilitated or
weakened animals

21. Stanozolol is one of the anabolic steroids commonly used as performance-enhancing drugs and
is banned from use in sports competition under the auspices of the International Association of
Athletics Federations (IAAF) and many other sporting bodies. Additionally, stanozolol has been
used in US horse racing.
Stanozolol is subject to non-medically supervised off-label use by some athletes for its anabolic
properties frequently presenting with concomitant reduction of body fat.
Commonly used by athletes and bodybuilders alike to lose fat while retaining lean body mass. It
is usually used in a "cutting or leaning out" cycle, to help preserve lean body mass while
metabolizing adipose, although it has not been proven conclusively that it has any special fat-
burning properties.
It is presented most commonly as a 50 mg/mL injection. However, recently 75 mg/ml 100 mg/mL
versions have become available
Stanozolol is metabolized in the liver, ultimately becoming glucuronide and sulfate
conjugates. Its biological half-life is reported to be 9 hours when taken by mouth and 24
hours when given by intramuscular injection in the form of an aqueous suspension.

22. Clenbuterol
Clenbuterol is a compound that belongs to a class of drugs called beta 2-
agonists. Drugs in this category can cause dilation of the bronchial muscles.
Beta2-agonists are often used to treat asthma.
In addition to being used to treat asthma, clenbuterol has become popular as a
weight loss supplement. That’s because of its effect on muscle growth and fat
reduction.
Clenbuterol isn’t a steroid, but it has some properties similar to those of
anabolic steroids, such as promoting an increase in muscle mass. Due to these
properties, clenbuterol has been used in livestock to increase the amount of lean
muscle.

23. Clenbuterol has been observed to both increase muscle mass and reduce body
fat. Additionally, it remains in the body with an active effect for up to about six
days after consumption (detectable traces can remain longer). Because of these
properties, it’s often used as a weight loss supplement or to enhance athletic
performance.
Clenbuterol has a half-life of up to 39 hours.
People taking clenbuterol for weight loss or performance enhancement often use
anabolic steroids or growth hormones as well.

24. Clenbuterol usage
The FDA hasn’t approved clenbuterol for use in humans. A liquid form of the
drug is approved by the FDA for treatment of airway obstruction in horses.
Outside of the United States, clenbuterol is available by prescription only for
the treatment of asthma.

25. Clenbuterol side effects
Clenbuterol can have negative side effects when overused or misused. These
can include:
 increased heart rate
 rapid breathing
 heart palpitations (A heart palpitation is the sensation that your heart has
skipped a beat or added an extra beat.)
 chest pain
 tremor
 anxiety
 electrolyte imbalance