Metenolone, or methenolone, is an

androgen An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This in ...

and anabolic steroid (AAS) which is used in the form of

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

s such as metenolone acetate (brand name Primobolan, Nibal) and metenolone enanthate (brand name Primobolan Depot, Nibal Injection).

Metenolone ester This is a list of androgen esters, including esters (as well as ethers) of natural androgens like testosterone and dihydrotestosterone (DHT) and synthetic anabolic–androgenic steroids (AAS) like nandrolone (19-nortestosterone). Esters of nat ...

s are used mainly in the treatment of

anemia Anemia or anaemia (British English) is a blood disorder in which the blood has a reduced ability to carry oxygen due to a lower than normal number of red blood cells, or a reduction in the amount of hemoglobin. When anemia comes on slowly, t ...

due to bone marrow failure. Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.

Side effect In medicine, a side effect is an effect, whether therapeutic or adverse, that is secondary to the one intended; although the term is predominantly employed to describe adverse effects, it can also apply to beneficial, but unintended, consequence ...

s of metenolone esters include symptoms of masculinization like

acne Acne, also known as ''acne vulgaris'', is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and ...

, increased hair growth, voice changes, and increased

sexual desire Sexual desire is an emotion and motivational state characterized by an interest in sexual objects or activities, or by a drive to seek out sexual objects or to engage in sexual activities. It is an aspect of sexuality, which varies significantly f ...

. Metenolone esters are synthetic androgens and anabolic steroids and hence are agonists of the androgen receptor (AR), the

biological target A biological target is anything within a living organism to which some other entity (like an endogenous ligand or a drug) is directed and/or binds, resulting in a change in its behavior or function. Examples of common classes of biological targets ...

of androgens like

testosterone Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristi ...

and

dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone. The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues includ ...

(DHT). They have moderate

anabolic Anabolism () is the set of metabolic pathways that construct molecules from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking ...

effects and weak

ic effects, as well as no

estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal ac ...

ic effects or risk of

liver damage Liver disease, or hepatic disease, is any of many diseases of the liver. If long-lasting it is termed chronic liver disease. Although the diseases differ in detail, liver diseases often have features in common. Signs and symptoms Some of the si ...

. Metenolone esters are

androgen ester An androgen or anabolic steroid ester is an ester of an androgen/anabolic steroid (AAS) such as the natural testosterone or dihydrotestosterone (DHT) or the synthetic nandrolone (19-nortestosterone). Esterification renders AAS into metabolism-re ...

s and prodrugs of metenolone in the body. Metenolone esters were introduced for medical use in the early 1960s. In addition to their medical use, metenolone esters are used to improve physique and performance. The drugs are

controlled substance A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Single ...

s in many countries and so non-medical use is generally illicit. They have mostly been discontinued for medical use and have limited availability.

Medical uses

Metenolone, as its esters, is used almost exclusively in the treatment of

due to bone marrow failure. It has also been used to treat wasting syndromes due to major surgery,

infection An infection is the invasion of tissues by pathogens, their multiplication, and the reaction of host tissues to the infectious agent and the toxins they produce. An infectious disease, also known as a transmissible disease or communicable dis ...

, long-term corticosteroid therapy,

malnutrition Malnutrition occurs when an organism gets too few or too many nutrients, resulting in health problems. Specifically, it is "a deficiency, excess, or imbalance of energy, protein and other nutrients" which adversely affects the body's tissues ...

, or other causes. It has also been used to treat osteoporosis and sarcopenia, to inhibit the natural loss of muscle mass with aging, and to promote

weight gain Weight gain is an increase in body weight. This can involve an increase in muscle mass, fat deposits, excess fluids such as water or other factors. Weight gain can be a symptom of a serious medical condition. Description Weight gain occurs w ...

in underweight

premature Premature may refer to: * ''Premature'' (2014 film), an American comedy film * ''Premature'' (2019 film), an American romantic drama film * '' PREMature'', a 2015 British television drama miniseries See also * Premature aging, of an organism * ...

infants and children.

Side effects

s of metenolone and its esters include

virilization Virilization or masculinization is the biological development of adult male characteristics in young males or females. Most of the changes of virilization are produced by androgens. Virilization is most commonly used in three medical and biology ...

among others.

Pharmacology

Pharmacodynamics

Due to its

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betwee ...

between the C1 and C2 positions, metenolone is resistant to

metabolism Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run c ...

by 3α-hydroxysteroid dehydrogenase (3α-HSD). As such, unlike DHT and the closely related DHT derivatives mestanolone (17α-methyl-DHT) and

mesterolone Mesterolone, sold under the brand name Proviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels. It has also been used to treat male infertility, although this ...

(1α-methyl-DHT), metenolone has considerable anabolic effects.

Pharmacokinetics

Metenolone has very low affinity for human serum

sex hormone-binding globulin Sex hormone-binding globulin (SHBG) or sex steroid-binding globulin (SSBG) is a glycoprotein that binds to androgens and estrogens. When produced by the Sertoli cells in the seminiferous tubules of the testis, it has also been called androgen ...

(SHBG), about 16% of that of testosterone and 3% of that of DHT.

Chemistry

Metenolone, also known as 1-methyl-4,5α-dihydro-δ¹-testosterone (1-methyl-δ¹-DHT) or as 1-methyl-5α-androst-1-en-17β-ol-3-one, is a synthetic

androstane Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane. File:androstane.png, 5α-Androstane File:androstane 5beta.png, 5β-Androstane Pharmacology ...

steroid and

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

(DHT). A closely related AAS is

(1α-methyl-DHT).

Society and culture

Generic names

''Metenolone'' is the generic name of the drug and its , while ''methenolone'' is its . It has also been referred to as ''methylandrostenolone''. This synonym should not be confused with ''methandrostenolone'', which is another name for a different AAS known as

metandienone Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol (D-Bol) among others, is an androgen and anabolic steroid (AAS) medication which is still quite often used because of its affordability and eff ...

Doping in sports

Metenolone and its esters are banned from use in sports governed by the

World Anti-Doping Agency The World Anti-Doping Agency (WADA; french: Agence mondiale antidopage, AMA) is a foundation initiated by the International Olympic Committee based in Canada to promote, coordinate, and monitor the fight against drugs in sports. The agency's key ...

. The NBA and NBPA also banned the use of metenolone and its esters under the Anti-Drug Program. There are known cases of doping in sports with metenolone esters by

professional A professional is a member of a profession or any person who works in a specified professional activity. The term also describes the standards of education and training that prepare members of the profession with the particular knowledge and ski ...

athletes.

References

External links

Primobolan (methenolone acetate) - William Llewellyn's Anabolic.org

Primobolan Depot (methenolone enanthate) - William Llewellyn's Anabolic.org
{{Androgen receptor modulators Secondary alcohols Androgens and anabolic steroids Androstanes Enones World Anti-Doping Agency prohibited substances