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Derivatives: Removing unsourced content

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{{Short description|Chemical compound}}
{{Distinguish|Boldenone}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477208602
| IUPAC_name = (5''S'',8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-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 compound|synthetic]] [[anabolic–androgenic steroid]] (AAS) and a [[5α-reductase|5α-reduced]] [[chemical derivative|derivative]] of [[boldenone]] (Δ1-testosterone). It differs from [[testosterone (medication)|testosterone]] by having a 1(2)-[[double bond]] instead of a 4(5)-double bond in its [[:File:Steroid numbering.svg|A ring]].<ref name="Llewellyn2009">{{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}}</ref> It was legally sold online in the [[United States]] until 2005, when it was reclassified as a [[Controlled Substances Act#Schedule III controlled substances|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 vesicle]]s and the androgen-sensitive [[levator ani]] [[muscle]] as the reference anabolic steroid [[testosterone propionate]], but, unlike testosterone propionate, 1-testosterone also increases [[liver]] weight.<ref>{{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}}</ref>

==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 compound|synthetic]] [[androstane]] [[steroid]] and a [[chemical derivative|derivative]] of [[dihydrotestosterone]] (DHT).

===Derivatives===
Two [[prohormone]]s of 1-testosterone are [[1-androstenediol]] and [[1-androstenedione]], the latter of which may be [[chemical synthesis|synthesized]] from [[stanolone acetate]].<ref>{{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 }}</ref>

===Detection in body fluids===
[[Doping (sport)|Doping]] with 1-testosterone can be detected in urine samples using [[gas chromatography]].<ref>{{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 }}</ref>

==References==
{{Reflist|2}}

{{Androgen receptor modulators}}

{{DEFAULTSORT:Testosterone, 1-}}

[[Category:Abandoned drugs]]
[[Category:Secondary alcohols]]
[[Category:Anabolic–androgenic steroids]]
[[Category:Androstanes]]
[[Category:Ketones]]

1-Testosterone - Revision history

imported>IntentionallyDense: /* Derivatives */ Removing unsourced content