1-Testosterone

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1-Testosterone
1-Testosterone.svg
1-Testosterone molecule ball.png
Clinical data
Synonyms1-Testo; 1-T; δ1-Dihydrotestosterone; δ1-DHT; Dihydroboldenone
Drug classAndrogen; Anabolic steroid
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
ExcretionUrine
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.164.058 Edit this at Wikidata
Chemical and physical data
FormulaC19H28O2
Molar mass288.42 g/mol g·mol−1
3D model (JSmol)
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1-Testosterone (abbreviated and nicknamed as 1-Testo, 1-T), also known as δ1-dihydrotestosterone (δ1-DHT), as well as dihydroboldenone, is a synthetic anabolic–androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT) which was never marketed. It differs from testosterone by having a 1(2)-double bond instead of a 4(5)-double bond in its A ring.[1] It was legally sold online in the United States until 2005, when it was reclassified as a Schedule III drug.

Side effects[edit]

Pharmacology[edit]

Pharmacodynamics[edit]

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.[2]

Chemistry[edit]

1-Testosterone, IUPAC name 17β-hydroxy-5α-androst-1-en-3-one, also known as 4,5α-dihydro-δ1-testosterone (Δ1-DHT) or as 5α-androst-1-en-17β-ol-3-one, is a synthetic androstane steroid and a derivative of dihydrotestosterone (DHT).

Derivatives[edit]

Two prohormones of 1-testosterone are 1-androstenediol and 1-androstenedione, the latter of which may be synthesized from stanolone acetate.[3]

Mesabolone is a ketal made from 1-testosterone.

1-Testosterone also is known to be used to synthesize mestanolone and metenolone.[citation needed]

Methyl-1-testosterone is the 17α-methyl derivative of 1-testosterone.

Detection in body fluids[edit]

Doping with 1-testosterone can be detected in urine samples using gas chromatography.[4]

References[edit]

  1. ^ William Llewellyn (2009). Anabolics (9 ed.). Molecular Nutrition. p. 22,135. ISBN 978-0-9679304-7-3.
  2. ^ 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.
  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.
  4. ^ 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. Archived from the original (PDF) on 2011-08-25. Retrieved 2011-06-18.