:1-Testosterone
{{Short description|Chemical compound}}
{{Distinguish|Boldenone}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477208602
| 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
| image = 1-Testosterone.svg
| width = 225px
| image2 = 1-Testosterone molecule ball.png
| width2 = 225px
| tradename =
| pregnancy_category =
| legal_US = Schedule III
| routes_of_administration =
| class = Androgen; Anabolic steroid
| bioavailability =
| protein_bound =
| metabolism = Liver
| elimination_half-life =
| excretion = Urine
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 65-06-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Y984BV1Q0G
| PubChem = 579094
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01481
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 206590
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 59714
| synonyms = 1-Testo; 1-T; δ1-Dihydrotestosterone; δ1-DHT; Dihydroboldenone
| C=19 | H=28 | O=2
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OKJCFMUGMSVJBG-ABEVXSGRSA-N
}}
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.{{cite book|author=William Llewellyn|title=Anabolics|edition=9|url=https://books.google.com/books?id=3-FAQgAACAAJ|date=2009|publisher=Molecular Nutrition|isbn=978-0-9679304-7-3|page=22,135}} It was legally sold online in the United States until 2005, when it was reclassified as a Schedule III drug.
Side effects
{{See also|Anabolic steroid#Adverse 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.{{cite journal |vauthors=Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schänzer W, Thevis M, Vollmer G, Zierau O, Diel P |title=17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties |journal=Toxicol. Lett. |volume=165 |issue=2 |pages=149–55 |pmid=16621347 |doi=10.1016/j.toxlet.2006.03.001|date=August 2006}}
Chemistry
{{See also|List of androgens/anabolic steroids}}
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.{{cite journal |vauthors=Zhang H, Qiu Z |title=An efficient synthesis of 5α-androst-1-ene-3,17-dione |journal=Steroids |volume=71 |issue=13–14 |pages=1088–90 |pmid=17123559 |doi=10.1016/j.steroids.2006.09.008|date=December 2006|s2cid=53258890 }}
=Detection in body fluids=
Doping with 1-testosterone can be detected in urine samples using gas chromatography.{{cite journal | author = S. Jain, A. Beotra and T. Kaur | url = http://proceedings.live-record.de/proceedings_13_pdf/13_407.pdf | title = A Case Study: Detection of 1-Testosterone in Urine by GC-MSD | journal = Recent Advances in Doping Analysis | volume = 13 | year = 2005 | pages = 407–410 | access-date = 2011-06-18 | archive-url = https://web.archive.org/web/20110825032543/http://proceedings.live-record.de/proceedings_13_pdf/13_407.pdf | archive-date = 2011-08-25 | url-status = dead }}
References
{{Reflist|2}}
{{Androgen receptor modulators}}
{{DEFAULTSORT:Testosterone, 1-}}