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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 marketed.[1] It was first encountered in 2005 when it was introduced as a "dietary supplement" and putative prohormone under the name Halodrol-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 by The 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 a prescription) in the United States.[1]CDMA continued to be sold online until the 2014 prohormone ban as generic versions known as clones.

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
  • 1338221-84-3
PubChem CID
  • 29976098
ChemSpider
  • 29976098
UNII
  • K6PH0FVE0K
Chemical and physical data
FormulaC20H29ClO2
Molar mass336.90 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

Although CDMA was sold as a "prohormone" or "prosteroid" of chlorodehydromethyltestosterone (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 a chloro group at the C4 position, CDMA cannot be aromatized, and for this reason, poses no risk of estrogenic side effects like gynecomastia at any dosage.[1] It is not extensively metabolized by 5α-reductase and exhibits relatively greater anabolic than androgenic activity, but is still capable of producing androgenic side effects like oily skin, acne, and increased growth of facial and body hair, as well as virilization in women.[1] As with other 17α-alkylated AAS, CDMA poses a risk of hepatotoxicity.[1][3]

CDMA is closely related to chloromethylandrostenediol (CMA; Promagnon), which was also developed by industry veteran Bruce Kneller and was also briefly sold on the Internet 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

References

  1. ^ a b c d e f g h i j k l William Llewellyn (1 November 2008). Anabolics: Anabolic Steroid Reference Guide. William Llewellyn. pp. 260, 365. ISBN 978-0-9679304-7-3.
  2. ^ Detlef Thieme; Peter Hemmersbach (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 179–. ISBN 978-3-540-79088-4.
  3. ^ Kafrouni MI, Anders RA, Verma S (2007). "Hepatotoxicity associated with dietary supplements containing anabolic steroids". Clin. Gastroenterol. Hepatol. 5 (7): 809–12. doi:10.1016/j.cgh.2007.02.036. PMID 17509944.


chlorodehydromethylandrostenediol, cdma, also, known, chloro, 17α, methylandrost, diene, 17β, diol, synthetic, orally, active, anabolic, androgenic, steroid, 17α, alkylated, derivative, androstenediol, that, never, marketed, first, encountered, 2005, when, int. Chlorodehydromethylandrostenediol CDMA also known as 4 chloro 17a methylandrost 1 4 diene 3b 17b diol is a synthetic orally active anabolic androgenic steroid AAS and a 17a alkylated derivative of 4 androstenediol that was never marketed 1 It was first encountered in 2005 when it was introduced as a dietary supplement and putative prohormone under the name Halodrol 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 by The 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 a prescription in the United States 1 CDMA continued to be sold online until the 2014 prohormone ban as generic versions known as clones ChlorodehydromethylandrostenediolClinical dataOther namesCDMA Halodrol Halodrol 50Routes ofadministrationOral 1 IdentifiersIUPAC name 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 diolCAS Number1338221 84 3PubChem CID29976098ChemSpider29976098UNIIK6PH0FVE0KChemical and physical dataFormulaC 20H 29Cl O 2Molar mass336 90 g mol 13D model JSmol Interactive imageSMILES C C 12CC C H 3 C H C H 1CC C 2 C O CCC4 C C H C C C 34C O ClInChI 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 s1Key ZHWBNJVZZYSUJZ HADYEQCDSA NAlthough CDMA was sold as a prohormone or prosteroid of chlorodehydromethyltestosterone 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 a chloro group at the C4 position CDMA cannot be aromatized and for this reason poses no risk of estrogenic side effects like gynecomastia at any dosage 1 It is not extensively metabolized by 5a reductase and exhibits relatively greater anabolic than androgenic activity but is still capable of producing androgenic side effects like oily skin acne and increased growth of facial and body hair as well as virilization in women 1 As with other 17a alkylated AAS CDMA poses a risk of hepatotoxicity 1 3 CDMA is closely related to chloromethylandrostenediol CMA Promagnon which was also developed by industry veteran Bruce Kneller and was also briefly sold on the Internet 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 Edit1 Androstenediol Bolenol Clostebol MethandriolReferences Edit a b c d e f g h i j k l William Llewellyn 1 November 2008 Anabolics Anabolic Steroid Reference Guide William Llewellyn pp 260 365 ISBN 978 0 9679304 7 3 Detlef Thieme Peter Hemmersbach 18 December 2009 Doping in Sports Springer Science amp Business Media pp 179 ISBN 978 3 540 79088 4 Kafrouni MI Anders RA Verma S 2007 Hepatotoxicity associated with dietary supplements containing anabolic steroids Clin Gastroenterol Hepatol 5 7 809 12 doi 10 1016 j cgh 2007 02 036 PMID 17509944 This article about a steroid is a stub You can help Wikipedia by expanding it vte This drug article relating to the genito urinary system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Chlorodehydromethylandrostenediol amp oldid 1084541799, wikipedia, wiki, book, books, library,

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