1-Testosterone

1-Testosterone

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
Clinical data
Legal status	Schedule III (US)
Pharmacokinetic data
Metabolism	Liver
Identifiers
CAS Number	65-06-5
PubChem	CID 579094
DrugBank	DB01481
ChemSpider	206590
ChEBI	CHEBI:59714
Chemical data
Formula	C19H28O2
Molar mass	288.42 g/mol
SMILES O=C4\C=C/[C@]1([C@@H](CC[C@@H]2[C@@H]1CC[C@@]3([C@@H](O)CC[C@@H]23)C)C4)C
InChI InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,12,14-17,21H,3-6,8,10-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1 Key:OKJCFMUGMSVJBG-ABEVXSGRSA-N
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Δ¹-Testosterone (17β-hydroxy-5α-androst-1-en-3-one, 1-Testo, 1-T) 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 Δ¹-testosterone has a high androgenic and anabolic potency even without being metabolized, so it can be characterized as a typical anabolic steroid. Δ¹-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, Δ¹-testosterone also increases liver weight.^[1]

Doping with Δ¹-testosterone can be detected in urine samples using gas chromatography.^[2]

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

References

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.