1-Testosterone

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1-Testosterone
1-Testosterone.svg
Systematic (IUPAC) name
(5S,8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver
Identifiers
CAS Number 65-06-5 N
PubChem CID 579094
DrugBank DB01481 YesY
ChemSpider 206590 YesY
ChEBI CHEBI:59714 YesY
Chemical data
Formula C19H28O2
Molar mass 288.42 g/mol
 NYesY (what is this?)  (verify)
Not to be confused with Boldenone.

1-Testosterone (abbreviated as 1-Testo, 1-T), also known as 1,2-dehydro-4,5α-dihydrotestosterone or as 17β-hydroxy-5α-androst-1-en-3-one, is an androgen and anabolic steroid that differs from testosterone by having a 1(2)-double bond instead of a 4(5)-double bond in its A ring. It was legally sold as a prohormone in the United States until 2005, when it was reclassified as a Schedule III drug.

A 2006 study determined that 1-testosterone has a high androgenic and anabolic potency even without being metabolized, so it can be characterized as a typical anabolic steroid. 1-Testosterone binds in a manner that is highly selective to the androgen receptor (AR) and has a high potency to stimulate AR-dependent transactivation. In vivo, an equimolar dose of 1-testosterone has the same potency to stimulate the growth of the prostate, the seminal vesicles and the androgen-sensitive levator ani muscle as the reference anabolic steroid testosterone propionate, but unlike it, 1-testosterone also increases liver weight.[1]

Doping with 1-testosterone can be detected in urine samples using gas chromatography.[2]

A prodrug of 1-testosterone is Δ1-androstenedione, which may be synthesized from stanolone acetate.[3]

References[edit]

  1. ^ Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schänzer W, Thevis M, Vollmer G, Zierau O, Diel P (August 2006). "17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties". Toxicol. Lett. 165 (2): 149–55. doi:10.1016/j.toxlet.2006.03.001. PMID 16621347. 
  2. ^ S. Jain, A. Beotra and T. Kaur (2005). "A Case Study: Detection of 1-Testosterone in Urine by GC-MSD" (PDF). Recent Advances in Doping Analysis. 13: 407–410. 
  3. ^ Zhang H, Qiu Z (December 2006). "An efficient synthesis of 5α-androst-1-ene-3,17-dione". Steroids. 71 (13-14): 1088–90. doi:10.1016/j.steroids.2006.09.008. PMID 17123559.