Chloromethylandrostenediol (CMA), also known as 4-chloro-17α-methyl-androst-4-ene-3β,17β-diol, is a synthetic, 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-alkylated

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 ...

of 4-androstenediol that was never marketed. It was first encountered in 2005 when it was introduced as a "

dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...

" and putative

prohormone A prohormone is a committed Precursor (chemistry), precursor of a hormone consisting of peptide hormones synthesized together that has a minimal hormonal effect by itself because of its expression-suppressing structure, often created by protein fol ...

under the name Promagnon by an online vendor called Peak Performance Laboratories. CMA was voluntarily discontinued by Gaspari Nutrition in late 2006, likely fearing government sanctions if it continued to sell the product. Although CMA was sold as a "prohormone" or "prosteroid" of

chloromethyltestosterone Methylclostebol, also known as 4-chloro-17α-methyltestosterone or as 4-chloro-17α-methylandrost-4-en-17β-ol-3-one, is a synthetic, orally active anabolic-androgenic steroid (AAS) and designer steroid that has been sold on the Internet as a ...

(CMT; also known more commonly as methylclostebol), it is likely that the conversion is far from complete and that much of the activity of the drug may be attributable to its unchanged form. Due to the presence of a chloro group at the C4 position, CMA cannot be

aromatized Aromatization is a chemical reaction in which an aromaticity, aromatic system is formed from a single nonaromatic precursor. Typically aromatization is achieved by dehydrogenation of existing cyclic compounds, illustrated by the conversion of cycl ...

, and for this reason, poses no risk of

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 acti ...

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 like

gynecomastia Gynecomastia (also spelled gynaecomastia) is the abnormal non-cancerous enlargement of one or both breasts in males due to the growth of breast tissue as a result of a hormone imbalance between estrogens and androgens. Updated by Brent Wisse ( ...

at any dosage. It is not extensively

metabolized 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 cell ...

by 5α-reductase and exhibits relatively greater

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 ...

than

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 inc ...

ic activity, but is still capable of producing androgenic side effects like

oily skin The human skin is the outer covering of the body and is the largest organ of the integumentary system. The skin has up to seven layers of ectodermal tissue guarding muscles, bones, ligaments and internal organs. Human skin is similar to mos ...

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 ...

, and increased growth of

facial A facial is a family of skin care treatments for the face, including steam, exfoliation (physical and chemical), extraction, creams, lotions, facial masks, peels, and massage. They are normally performed in beauty salons, but are also a comm ...

and body hair, as well as

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 ...

in women. As with other 17α-alkylated AAS, CMA may pose a risk of

hepatotoxicity Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn fro ...

. CMA is closely related to

chlorodehydromethylandrostenediol Chlorodehydromethylandrostenediol (CDMA), also known as 4-chloro-17α-methylandrost-1,4-diene-3β,17β-diol, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a 17α-alkylated derivative of 4-androstenediol that was never mar ...

(CDMA; Halodrol-50) which was developed by industry veteran Bruce Kneller, and was also briefly sold on the

Internet The Internet (or internet) is the global system of interconnected computer networks that uses the Internet protocol suite (TCP/IP) to communicate between networks and devices. It is a '' network of networks'' that consists of private, pub ...

in 2005 and 2006, though by a different company (Giant Sports). Both drugs were derived from

chlorodehydromethyltestosterone Chlorodehydromethyltestosterone (CDMT; brand name Oral Turinabol), also known as 4-chloro-17β-hydroxy17α-methylandrosta-1,4-dien-3-one, is an anabolic–androgenic steroid (AAS). It is the 4-chloro-substituted derivative of metandienone (dehyd ...

(CDMT; brand name Oral Turinabol), a popular AAS that was introduced in the 1960s.

References

Diols Androgens and anabolic steroids Androstanes Hepatotoxins Organochlorides World Anti-Doping Agency prohibited substances 1-Methylcyclopentanols Cyclohexenols {{genito-urinary-drug-stub

See also

References