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1,4,6-Androstatriene-3,17-dione

Chemical compound

| elimination_half-life = 48 hours

1,4,6-Androstatriene-3,17-dione (ATD) is a potent irreversible aromatase inhibitor that inhibits estrogen biosynthesis by permanently binding and inactivating aromatase in adipose and peripheral tissue. It is used to control estrogen synthesis.

ATD was present in some over-the-counter bodybuilding supplements until 2009, as well as Topical ATD solutions that work transdermally. The product was developed and commercialized in the dietary supplement market place by industry journeyman Bruce Kneller, who holds a United States Patent for use of the compound and related compounds (#7,939,517) and Gaspari Nutrition. ATD has many names in sports supplements including: 1,4,6 etiollochan-dione, 3, 17-keto-etiochol-triene, androst-1,4,6-triene-3,17-dione and many others. These all refer to CAS# 633-35-2.

ATD may cause a positive test for the anabolic steroid Boldenone, of which it is a possible metabolite and production contaminant. ATD is also prohibited in amateur and professional sports which forbids aromatase inhibitors.

A related agent is exemestane (Aromasin).

Synthesis

The synthesis of 1,4,6-Androstatriene-3,17-dione has been described: It is most congenially prepared from DHEA by oxidation with DDQ in a single step.

It is possible to use 1,4,6-Androstatriene-3,17-dione in the synthesis of estrone. However, the modern process seems to rely on Boldione.

References

(April 1981). "Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatriene-3,17-dione cause a time-dependent decrease in human placental aromatase activity". Endocrinology.
(December 2006). "Sex steroids modulate changes in social and sexual preference during juvenile development in zebra finches". Elsevier Inc.
(January 2009). "Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control". Rapid Communications in Mass Spectrometry.
Ma, E., Kim, E. (25 May 2005). "Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol". Molecules. 10 (3): 572–582. doi:10.3390/10030572.
Kim, E., Ma, E. (April 2007). "Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents". Steroids. 72 (4): 360–367. doi:10.1016/j.steroids.2006.12.008.
Turner, A. B. (1966). "Applications of high-potential quinones. Convenient syntheses of steroidal 1,4,6-trien-3-ones". Chemical Communications (London) (23): 845. doi:10.1039/c19660000845.
Burg Willem Jacob Van Der, US2879279 (1959 to Organon NV, Organon Inc).
Kaufmann, St., Pataki, J., Rosenkranz, G., Romo, J., Djerassi, C. (October 1950). "Steroids. VI. 1 The Wohl—Ziegler Bromination of Steroidal 1,4-Dien-3-ones. Partial Synthesis of ▵ 6 -Dehydroestrone and Equilenin". Journal of the American Chemical Society. 72 (10): 4531–4534. doi:10.1021/ja01166a054.
Rubin Martin, Emanuel B Hershberg & Schwenk Erwin, US2594349 (1952 to Merck Sharp and Dohme LLC).
田伟生, 史勇 & 汪昀, CN107602650 (2018 to Shanghai Institute of Organic Chemistry of CAS).

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