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Chlorodehydromethylandrostenediol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Chlorodehydromethylandrostenediol
Clinical data
Other namesCDMA; Halodrol; Halodrol-50
Routes of
administration
Oral[1]
Identifiers
  • (3S,8R,9S,10R,13S,14S,17S)-4-Chloro-10,13,17-trimethyl-3,6,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC20H29ClO2
Molar mass336.90 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CCC4=C([C@H](C=C[C@]34C)O)Cl
  • InChI=1S/C20H29ClO2/c1-18-9-8-16(22)17(21)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,16,22-23H,4-7,10-11H2,1-3H3/t12-,13+,14+,16+,18-,19+,20+/m1/s1
  • Key:ZHWBNJVZZYSUJZ-HADYEQCDSA-N

Chlorodehydromethylandrostenediol (CDMA), also known as4-chloro-17α-methylandrost-1,4-diene-3β,17β-diol, is asynthetic,orally activeanabolic-androgenic steroid (AAS) and a17α-alkylatedderivative of4-androstenediol that was never marketed.[1] It was first encountered in 2005 when it was introduced as a "dietary supplement" and putativeprohormone under the nameHalodrol-50 by industry veteran, Bruce Kneller while working with the dietary supplement company, Gaspari Nutrition.[1][2] The drug was the subject of a scathing and highly critical article byThe Washington Post in November 2006.[1] CDMA was voluntarily discontinued by Gaspari Nutrition in mid-2006, likely fearing government sanctions if it continued to sell the product.[1] During the brief period of time that CDMA was sold online, it was an extremely well-selling product; its total sales are estimated to have been greater than twenty five million dollars, and by some estimates, CDMA may have been the best-selling hormonal product ever sold "over-the-counter" (i.e., without aprescription) in theUnited States.[1]CDMA continued to be sold online until the 2014 prohormone ban as generic versions known as clones.

Although CDMA was sold as a "prohormone" or "prosteroid" ofchlorodehydromethyltestosterone (CDMT), 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.[1] Due to the presence of achloro group at the C4 position, CDMA cannot bearomatized, and for this reason, poses no risk ofestrogenicside effects likegynecomastia at anydosage.[1] It is not extensivelymetabolized by5α-reductase and exhibits relatively greateranabolic thanandrogenic activity, but is still capable of producing androgenic side effects likeoily skin,acne, and increased growth offacial andbody hair, as well asvirilization in women.[1] As with other 17α-alkylated AAS, CDMA poses a risk ofhepatotoxicity.[1][3]

CDMA is closely related tochloromethylandrostenediol (CMA; Promagnon), which was also developed by industry veteran Bruce Kneller and was also briefly sold on theInternet in 2005 and 2006, though by a different company (Peak Performance Laboratories).[1] Both compounds were derived from CDMT (brand name Oral Turinabol), a popular AAS that was introduced in the 1960s.[1]

See also

[edit]

References

[edit]
  1. ^abcdefghijklWilliam Llewellyn (1 November 2008).Anabolics: Anabolic Steroid Reference Guide. William Llewellyn. pp. 260, 365.ISBN 978-0-9679304-7-3.
  2. ^Kazlauskas R (18 December 2009)."Designer Steroids".Doping in Sports. Handbook of Experimental Pharmacology. Vol. 195. Springer Science & Business Media. pp. 155–185.doi:10.1007/978-3-540-79088-4_7.ISBN 978-3-540-79088-4.PMID 20020364.
  3. ^Kafrouni MI, Anders RA, Verma S (July 2007)."Hepatotoxicity associated with dietary supplements containing anabolic steroids".Clinical Gastroenterology and Hepatology.5 (7):809–812.doi:10.1016/j.cgh.2007.02.036.PMID 17509944.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists

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