Chemistry:1-Testosterone

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Short description: Chemical compound
1-Testosterone
1-Testosterone.svg
1-Testosterone molecule ball.png
Clinical data
Other names1-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
UNII
ChEBI
Chemical and physical data
FormulaC19H28O2
Molar mass288.431 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 a 5α-reduced derivative of boldenone (Δ1-testosterone). 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

Pharmacology

Pharmacodynamics

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

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

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

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

References

  1. William Llewellyn (2009). Anabolics (9 ed.). Molecular Nutrition. p. 22,135. ISBN 978-0-9679304-7-3. https://books.google.com/books?id=3-FAQgAACAAJ. 
  2. "17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties". Toxicol. Lett. 165 (2): 149–55. August 2006. doi:10.1016/j.toxlet.2006.03.001. PMID 16621347. 
  3. "An efficient synthesis of 5α-androst-1-ene-3,17-dione". Steroids 71 (13–14): 1088–90. December 2006. 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". Recent Advances in Doping Analysis 13: 407–410. http://proceedings.live-record.de/proceedings_13_pdf/13_407.pdf. Retrieved 2011-06-18.