Desoxymethyltestosterone (DMT), known by the nicknames Madol and Pheraplex, is a synthetic and orally active

anabolic–androgenic steroid Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone as well as synthetic androgens that are structurally related and have similar effects t ...

(AAS) and a 17α-methylated

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. F ...

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 includi ...

(DHT) which was never marketed for medical use. It was one of the first designer steroids to be marketed as a

performance-enhancing drug Performance-enhancing substances, also known as performance-enhancing drugs (PEDs), are substances that are used to improve any form of activity performance in humans. A well-known example of cheating in sports involves doping in sport, where bann ...

athlete An athlete (also sportsman or sportswoman) is a person who competes in one or more sports that involve physical strength, speed, or endurance. Athletes may be professionals or amateurs. Most professional athletes have particularly well-devel ...

s and

bodybuilder Bodybuilding is the use of progressive resistance exercise to control and develop one's muscles (muscle building) by muscle hypertrophy for aesthetic purposes. It is distinct from similar activities such as powerlifting because it focuses o ...

s. Desoxymethyltestosterone is sometimes abbreviated as DMT, though it should not be confused with the

hallucinogen Hallucinogens are a large, diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Most hallucinogens can be categorized ...

dimethyltryptamine ''N'',''N''-Dimethyltryptamine (DMT or ''N'',''N''-DMT, SPL026) is a substituted tryptamine that occurs in many plants and animals, including human beings, and which is both a derivative and a structural analog of tryptamine. It is used as a ...

, which is also known by the same acronym.

Side effects

Pharmacology

Pharmacodynamics

In animal studies, desoxymethyltestosterone has been found to bind to the

androgen receptor The androgen receptor (AR), also known as NR3C4 (nuclear receptor subfamily 3, group C, member 4), is a type of nuclear receptor that is activated by binding any of the androgenic hormones, including testosterone and dihydrotestosterone in th ...

(AR) about half as strongly as DHT, and to cause

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 that are typical of 17α-alkylated AAS, such as

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 ...

and

left ventricular hypertrophy Left ventricular hypertrophy (LVH) is thickening of the heart muscle of the left ventricle of the heart, that is, left-sided ventricular hypertrophy and resulting increased left ventricular mass. Causes While ventricular hypertrophy occurs na ...

when taken in higher doses. Desoxymethyltestosterone is unusual in that it is structurally a 2-

ene Ene or ENE may refer to: Ene * Ene (name), a given name and surname * Ene, a type of hydrocarbon involved in the Ene reaction and the Thiol-ene reaction * -ene'', a suffix used in the names of certain organic compounds (alkenes) * Ene, Spanish ...

compound, lacking the 3- keto group present in almost all commercial AAS (with

ethylestrenol Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such ...

being a rare and notable exception). This does not mean it is a weak compound, and clinical research has determined that it is a fairly potent oral agent. Rat studies indicate that desoxymethyltestosterone has an anabolic effect 160% that of testosterone while being only 60% as androgenic, giving it a Q ratio of 6.5:1. Because of this favorable ratio, experiments in orchiectomized rats have demonstrated that treatment with desoxymethyltestosterone resulted only in a stimulation of the weight of the levator ani muscle; the

prostate The prostate is both an Male accessory gland, accessory gland of the male reproductive system and a muscle-driven mechanical switch between urination and ejaculation. It is found only in some mammals. It differs between species anatomically, ...

and

seminal vesicle The seminal vesicles (also called vesicular glands, or seminal glands) are a pair of two convoluted tubular glands that lie behind the urinary bladder of some male mammals. They secrete fluid that partly composes the semen. The vesicles are 5� ...

weights remained unaffected leading the authors of one study to characterize desoxymethyltestosterone as a powerful AAS with attributes of a

selective androgen receptor modulator Selective Androgen Receptor Modulators or SARMs are a class of androgen receptor ligands that maintain some of the desirable effects of androgens, such as preventing osteoporosis and muscle loss while reducing risks of developing prostate cancer ...

(SARM) and some indication of

toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...

Chemistry

Desoxymethyltestosterone, also known as 3-desoxy-17α-methyl-δ²-5α-dihydrotestosterone (3-desoxy-17α-methyl-δ²-DHT) or as 17α-methyl-5α-androst-2-en-17β-ol, 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 A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...

and a 17α-alkylated

(DHT).

History

Desoxymethyltestosterone was invented in 1961 by Max Huffman who obtained a patent on the compound the same year. It was described in the scientific literature in 1963. However, it was never brought to market as a commercial drug. Desoxymethyltestosterone was rediscovered by chemist, AAS enthusiast, and amateur bodybuilder

Patrick Arnold Patrick Arnold (born 1966) is an American organic chemist known for introducing androstenedione, 1-androstenediol, and methylhexanamine into the dietary supplement market, and for creating the designer steroid tetrahydrogestrinone, also known a ...

in 2005. Arnold produced desoxymethyltestosterone and supplied it to Victor Conte of

Bay Area Laboratory Co-operative The Bay Area Laboratory Co-operative (BALCO) (1984–2003) was an American company led by founder and owner Victor Conte. In 2003, journalists Lance Williams and Mark Fainaru-Wada investigated the company's role in a drug sports scandal later re ...

(BALCO), an American nutritional supplement company and steroid supplier. DMT became a controlled substance in the US on January 4, 2010, and is classified as a Schedule III

anabolic steroid Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone (medication), testosterone as well as synthetic androgens that are structurally related ...

under the United States

Controlled Substances Act The Controlled Substances Act (CSA) is the statute establishing federal government of the United States, federal drug policy of the United States, U.S. drug policy under which the manufacture, importation, possession, use, and distribution of ...

along with

boldione Boldione, also known as androstadienedione or 1-dehydroandrostenedione, as well as 1,4-androstadiene-3,17-dione, is an important industrial precursor for various steroid hormones. In the United States the chemical is regulated as a Schedule III ...

and

dienedione Dienedione, also known as estra-4,9-diene-3,17-dione, is a synthetic, orally active anabolic-androgenic steroid (AAS) of the 19-nortestosterone group that was never introduced for medical use. It is thought to be a prohormone of dienolone. Th ...

. The substance had come under scrutiny after it was found to be present in several over-the-counter

bodybuilding supplements Bodybuilding supplements are dietary supplements commonly used by those involved in bodybuilding, weightlifting, mixed martial arts, and athletics for the purpose of facilitating an increase in lean body mass. Bodybuilding supplements may contain ...

References