1-testosterone

1-Testosterone
Legal status

Legal status	US: Schedule III
Pharmacokinetic data
Metabolism	Liver
Identifiers
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
CAS Number	65-06-5^N
PubChem (CID)	579094
DrugBank	DB01481^Y
ChemSpider	206590^Y
ChEBI	CHEBI:59714^Y
ECHA InfoCard	100.164.058
Chemical and physical data
Formula	C₁₉H₂₈O₂
Molar mass	288.42 g/mol
3D model (Jmol)	Interactive image
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^Y Key:OKJCFMUGMSVJBG-ABEVXSGRSA-N^Y
^NY (what is this?)

1-Testosterone (abbreviated as 1-Testo, 1-T), also known as 4,5α-dihydro-δ¹-testosterone (Δ¹-DHT) or 5α-androst-1-en-17β-ol-3-one, as well as dihydroboldenone, is an androgenic-anabolic steroid (AAS) 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 online 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 testosterone propionate, 1-testosterone also increases liver weight.

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

Two prohormones of 1-testosterone are 1-androstenediol and 1-androstenedione, the latter of which may be synthesized from stanolone acetate.

...
Wikipedia