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

synthetic Synthetic may refer to: Science * Synthetic biology * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic elements, chemical elements that are not naturally found on Earth and therefore have to be created in ...

, orally active anabolic-androgenic steroid (AAS) and a 17α-alkylated

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

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 a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...

" and putative prohormone 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 (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, and for this reason, poses no risk of

estrogen Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three ...

side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...

s like gynecomastia at any dosage. It is not extensively metabolized by 5α-reductase and exhibits relatively greater

anabolic Anabolism () is the set of metabolic pathways that construct macromolecules like DNA or RNA from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catab ...

than

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

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

acne Acne ( ), also known as ''acne vulgaris'', is a long-term Cutaneous condition, skin condition that occurs when Keratinocyte, dead skin cells and Sebum, oil from the skin clog hair follicles. Typical features of the condition include comedo, ...

, and increased growth of facial and

body hair Body hair or androgenic hair is terminal hair that develops on the human body during and after puberty. It is different from head hair and also from less visible vellus hair, which is much finer and lighter in color. Growth of androgenic hai ...

, 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 a medical term commonly used in three medical a ...

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 (DILI) is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdr ...

. CMA is closely related to chlorodehydromethylandrostenediol (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 network, global system of interconnected computer networks that uses the Internet protocol suite (TCP/IP) to communicate between networks and devices. It is a internetworking, network of networks ...

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 (dehy ...

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

References

Diols Anabolic–androgenic steroids Androstanes Hepatotoxins Organochlorides 1-Methylcyclopentanols Cyclohexenols {{genito-urinary-drug-stub

See also

References