Testosterone Chemical Structure

by Benjamin Bunting BA(Hons) PGCert

Ben Bunting BA(Hons) PGCert Sports and Exercise Nutrition Level 2 Strength and Conditioning CoachWritten by Ben Bunting: BA, PGCert. (Sport & Exercise Nutrition) // British Army Physical Training Instructor // S&C Coach.

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The primary androgen hormone in males is testosterone. In humans, the hormone testosterone is important in the development and growth of male reproductive tissue, such as the testicles and the prostate.

It also promotes secondary sexual characteristics, such as an increased muscle mass and bone density, as well the growth of hair. 

What is testosterone?

Testosterone, 17b-hydroxyandrost-4-en-3-one, is a naturally occurring androgen in men.

It is primarily a precursor of estradiol in women, but it also has other hormone effects. It is quickly metabolized to relatively inactive 17-1s, preventing significant oral activity.

The primary androgen hormone in males is testosterone. In humans, the hormone testosterone is important in the development and growth of male reproductive tissue, such as the testicles and the prostate.

It also promotes secondary sexual characteristics, such as an increased muscle mass and bone density, and hair growth.

It's associated with aggression, sex desire, dominance and courtship displays, as well as a variety of other behavioral characteristics.

The testosterone hormone is also involved in the health and well-being of both men and women. It has an impact on mood, cognition and social behavior, metabolism, energy output and the cardiovascular system.

Men with low testosterone levels may experience abnormalities such as frailty and fragility, an increase in adipose tissue, depression and anxiety, problems with sexual performance, and even bone loss. 

Men with high testosterone levels may experience hyperandrogenism. They are also at a higher risk for heart failure and prostate cancer.

The steroid testosterone is an androstane steroid that contains a ketone at position three and a group of hydroxyls at position seventeen.

In the liver, it is converted to inactive metabolites. It acts by binding to the androgen-receptor and activating it.

The testicles and ovaries are the primary sources of testosterone in humans and other vertebrates.

In adult males testosterone levels are typically seven to eight time higher than in adult females.

The daily testosterone production in men is approximately 20 times higher than in women, due to the greater metabolism of the hormone in males. The hormone is also more sensitive in females.

As well as its role as an organic hormone, testosterone can be used to treat hypogonadism and breast cancer. It is also prescribed to treat gender dysphoria.

In older men, testosterone can be used to compensate for the testosterone deficiency. Illicitly, it is used to improve physique and performance in athletes.

The World Anti-Doping Agency classifies it as "anabolic agent substance S1" that is "prohibited in all circumstances".

Description

Testosterone, an endogenous metabolite from androstenedione & estradiol, is a reference material for analytical purposes. 

The use of anabolic steroids such as testosterone has been known to improve the performance of athletes.

In the United States, testosterone is classified as a Schedule 3 compound. This product is for research and forensic purposes.

Testosterone is a certified material classified as an anabolic-androgenic steroid. Testosterone is an endogenous metabolite from androstenedione and estradiol.

Anabolic steroids such as testosterone have been used by athletes to improve their performance. 

The structure of testosterone

The gonads produce testosterone (by the Leydig cell in the testes of men and the ovaries of women), but small amounts are also produced in the adrenal glands by both sexes.

Androgens are substances that stimulate the development of masculine characteristics.

The androstanoid testosterone is an androstanoid with 17beta hydroxy and 3-oxo group, as well as unsaturation between C-4-C-5.

It is an androgen as well as a human metabolite.

It is a 17beta hydroxy steroid.

The steroid testosterone is an androstane steroid that contains a ketone at position three and a group of hydroxyls at position seventeen. 

It is produced in several steps by cholesterol, and then converted to inactive metabolites in the liver. 

Testosterone is an androstane steroid that contains a ketone at position three and a group of hydroxyls at position seventeen.

The hormones testosterone, estrogen and progesterone are all considered lipids.

Chemical Properties

Powder is white and crystalline with no smell. Its melting temperature is 155°C, its specific rotary power [a]24D+109deg (4%) and the absorbance of its ethanol solution at wavelength 240nm is highest. 

It is soluble (1:5) in ethanol, soluble (1:100) in ether and insoluble (1:500) in water. LD50 (large mice, venal blood transfusion): 326mg/kg It has been shown in studies that it can cause cancerous effects latently on test animals.

Pharmacokinetics

It can bind to plasma sex-hormone binding globulins and albumins, but not specifically. In peripheral tissue, it can be converted to estradiol or estrone.

The liver is the main site of testosterone degradation, where the A-ring is repaired. It is then converted to 17-ketosteroid by 17b-Hydroxysteroid Dehydrogenase.

It is excreted along with androsterone and epiandrosterone. The majority of metabolites excreted in urine by binding with glucuronic acids are 17-ketosteroids.

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Synthesis

Testosterone, 17-hydroxyandrost-4-ene-3-one (29.1.5), is made in a number of ways from different substances, including cholesterol, although it is most often made from androstenolone acetate.

In the given example, reduction by sodium borohydride or hydrogen over Raney nickel leads to the formation of 3-acetoxy-5-androsten-17-ol (29.1.1).

The hydroxyl group formed by reduction is then acylated in pyridine by benzoyl chloride, resulting in a diester.

Aluminum isopropylate is used to convert the alcohol to a ketone (29.1.4), while cyclohexanone is used as hydrogen acceptor.

This isomerization occurs simultaneously as the double bond is moved from C5"CC6 position to C4"CC5. The remaining ester group of the molecule is hydrolyzed with an alkali to give the desired testosterone.

The acylation is required to convert the testosterone ester into its corresponding propionate (enantate), cypionate (and a few others).

Applicable to Specific Diseases

Osteoporosis is a condition that affects the bones.

  • The FDA has not approved testosterone replacement therapy for osteoporosis prevention or treatment. 
  • This treatment should not be solely used for these indications, but it may be helpful to reduce bone loss for patients who need therapy for hypogonadal symptomatology. 
  • Women who received oral methyltestosterone 1,25 or 2.5mg daily or testosterone implant 50mg every three months showed increased BMD in a few studies. 
  • In some studies, men who were hypogonadal or older men with normal hormones or mild hormonal deficiencies showed an increased BMD when they received different salt forms of the testosterone. 
  • There are several testosterone products available, including oral, intramuscular and transdermal gels.
  • The patient should be evaluated 1 to 2 weeks after initiation, and then 3 to 6 times thereafter.

Can chemicals destroy testosterone?

A 2020 study looked into whether chemicals could affect testosterone.

It found that men aged over 60 were found to have lower levels of total, bioavailable, and free testosterone when exposed to high molecular weight polymers.

The results suggest that different phthalate metabolites may affect males differently depending on their age. 

Takeaway

The powder is white and crystalline with no smell. Its melting temperature is 155°C, its specific rotary power [a]24D+109deg (4%) and the absorbance of ethanol solutions at wavelengths of 240nm is highest. 

It is soluble (1:5) in ethanol, soluble (1:100) in ether and insoluble (1:100) in water. LD50 (Large mouse, venal blood transfusion): 326mg/kg It has been shown in studies that it can cause cancerous effects latently on test animals.

Indications and uses

Testosterone, a 19-carbon steroid hormone, is the primary male sex hormonal in mammals. 

It is the primary male sex hormone secreted from the testes. It is also the most potent male sex hormone. 

This androgen is responsible for the development of sex organs and secondary sex characteristics in humans and animals, as well as the maturation of sperm and protein metabolism to strengthen muscles. 

Testosterone is responsible for the growth and development male sex traits and organs. It is used primarily in the treatment of male menopause, impotence and eunuchism.

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