1-Testosterone

1-Testosterone
Systematic (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
Clinical data
Legal status	Schedule III (US)
Pharmacokinetic data
Metabolism	Liver
Identifiers
CAS Number	65-06-5
PubChem	CID 579094
DrugBank	DB01481^Y
ChemSpider	206590^Y
ChEBI	CHEBI:59714^Y
Chemical data
Formula	C₁₉H₂₈O₂
Molar mass	288.42 g/mol
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
(verify)

Δ¹-Testosterone (17β-hydroxy-5α-androst-1-en-3-one, 1-Testo, 1-T) is an androgen and anabolic steroid 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 as a prohormone in the United States until 2005, when it was reclassified as a Schedule III drug.

A 2006 study determined that Δ¹-testosterone has a high androgenic and anabolic potency even without being metabolized, so it can be characterized as a typical anabolic steroid. Δ¹-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 it, Δ¹-testosterone also increases liver weight.^[1]

Doping with Δ¹-testosterone can be detected in urine samples using gas chromatography.^[2]

A prodrug of Δ¹-testosterone is Δ¹-androstenedione, which may be synthesized from stanolone acetate.^[3]

References

↑ 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.
↑ 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.
↑ 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.

Androgens and antiandrogens

Androgens

Agonists	Anabolic steroids (see here instead) Androgenic progestins (e.g., norethisterone, levonorgestrel, medroxyprogesterone acetate) Androstanolone Androstenediol Androstenedione DHEA DHEA sulfate Dihydrotestosterone Fluoxymesterone Mesterolone Methyltestosterone Testosterone^# Testosterone acetate Testosterone capropate Testosterone cypionate Testosterone decanoate Testosterone enanthate Testosterone isocaproate Testosterone phenylpropionate Testosterone propionate Testosterone undecanoate Tibolone

SARMs	AC-262,356^§ Andarine^§ BMS-564,929^§ Enobosarm (ostarine)^§ LGD-2226^§ LGD-3303^§ S-23^§ S-40503^§

Antiandrogens

Antagonists

Enzyme inhibitors

5α-Reductase	Alfatradiol Chlormadinone acetate Dutasteride Finasteride Saw palmetto extract

CYP17A1	Abiraterone acetate Cyproterone acetate Danazol Galeterone^† Gestrinone Ketoconazole Orteronel^† Spironolactone VT-464^†

Others	Abiraterone acetate Aminoglutethimide Cyproterone acetate Danazol Gestrinone Ketoconazole Mitotane Trilostane

Antigonadotropins

Anabolic steroids (e.g., nandrolone, oxandrolone)
Estrogens (e.g., estradiol)
GnRH agonists (e.g., leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Progestogens (incl. allylestrenol, chlormadinone acetate, cyproterone acetate, delmadinone acetate, dydrogesterone, medroxyprogesterone acetate, megestrol acetate, nomegestrol acetate, norethisterone acetate, progesterone, spironolactone)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Anabolic steroids (A14)

Androstane (carbon 19 present)	Adrenosterone Androisoxazole Bolasterone (Myagen) Bolazine Boldione Boldenone undecylenate (Equipoise) 4-Chlordehydromethyltestosterone (Turinabol) 4-Hydroxytestosterone Calusterone Clostebol Danazol Desoxymethyltestosterone (Madol) DHT Drostanolone (Masteron) Enestebol Epitiostanol Fluoxymesterone (Halotestin) Formebolone Furazabol (Miotolan) Hydroxystenozole Mebolazine Mesabolone Mestanolone Mesterolone (Proviron) Metandienone (methandrostenolone) Methandriol Metenolone Methenolone enanthate (Primobolan) Methasterone (Superdrol) Methyltestosterone Methyldiazirinol Oxandrolone (Anavar) Oxymetholone (Anadrol) Oxymesterone Prostanozol Quinbolone (Anabolicum Vister) Roxibolone Silandrone Stanozolol (Strombafort Winstrol) Stenbolone Testosterone`s (Sustamed Sustanon) 1-Testosterone Thiomesterone

Estrene (carbon 19 absent)	Bolenol Ethyldienolone Ethylestrenol Mibolerone (Cheque Drops) Metribolone (R1881) Nandrolone (Deca Durabolin) Norboletone (Genabol) Norclostebol Norethandrolone Normethandrone (methylestrenolone) Oxabolone cipionate Propetandrol Tetrahydrogestrinone (The Clear) Trenbolone (Fina) Trestolone

Prohormones	1-Androstenediol 1,4-Androstadienedione 4-Androstenediol 4-Androstenedione 19-Norandrostenediol 19-Norandrostenedione DHEA

Androgenics

Receptor
(ligands)

Agonists	4-Chlordehydromethyltestosterone 4-Hydroxytestosterone 5α-Androst-1-ene-3,17-dione 7β-Hydroxyepiandrosterone 11-Ketotestosterone 17-((1-Oxoheptyl)oxy)androstan-3-one 17-((1-Oxopentyl)oxy)androstan-3-one 17-(1-Oxopropoxy)androstan-3-one 17β-Hydroxyandrost-2-ene-2-carbonitrile 19-Norandrostenediol 19-Norandrostenedione 19-Norandrosterone 19-Nordehydrotestosterone Δ¹-Androstenediol Δ¹-Testosterone Δ^1,4-Androstenedione Δ⁴-Androstenediol Δ⁴-Androstenedione Δ^4-Tibolone Δ⁴-Androstenediol Δ⁴-Androstenedione Adrenosterone Androisoxazole Androstanolone Bolandiol Bolasterone Bolazine Boldenone Boldione Bolenol Bolmantalate Calusterone Cl-4AS-1 Clostebol Cloxotestosterone Cortexolone 17α-propionate Danazol Desogestrel Desoxymethyltestosterone DHEA DHEA sulfate Dihydrotestosterone Drostanolone Enestebol Epitiostanol Ethisterone Ethyldienolone Ethylestrenol Fluoxymesterone Formebolone Furazabol Hexabolan Hydroxystenozole Levonorgestrel Mebolazine Medroxyprogesterone acetate Mepitiostane Mesabolone Mestanolone Mesterolone Metandienone/Methandrostenolone Metenolone Metenolone acetate Metenolone enanthate Methandriol Methandriol propionate Methasterone Methylestrenolone Methyltestosterone Metribolone Mibolerone Nandrolone Nandrolone caproate Nandrolone cypionate Nandrolone cyclohexane carboxylate Nandrolone cyclohexylpropionate Nandrolone cyclotate Nandrolone decanoate Nandrolone furylpropionate Nandrolone hexyloxyphenylpropionate Nandrolone hydrogen succinate Nandrolone laurate Nandrolone phenylpropionate Nandrolone propionate Nandrolone undecyclate Norboletone Norclostebol Norethandrolone Norethisterone Norgestrel Oxabolone Oxabolone cypionate Oxandrolone Oxendolone Oxymesterone Oxymetholone Penmesterol Propetandrol Quinbolone Quingestanol acetate Roxibolone Silandrone Stanozolol Stenbolone Stenbolone acetate Testolactone Testosterone Testosterone acetate Testosterone capropate Testosterone cypionate Testosterone decanoate Testosterone enanthate Testosterone isocaproate Testosterone ketolaurate Testosterone nicotinate Testosterone phenylpropionate Testosterone propionate Testosterone undecanoate Tetrahydrogestrinone Thiomesterone Tibolone Tiomesterone Trenboloneca Trenbolone acetate Trestolone

Mixed (SARMs)	AC-262,356 Andarine BMS-564,929 Enobosarm (ostarine) LGD-2226 LGD-3303 LGD-4033 RAD140 S-23 S-40503 TFM-4AS-1

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Abiraterone Abiraterone acetate Apalutamide AZD-3514 Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) Benorterone Bicalutamide BMS-641,988 BOMT Canrenoic acid Canrenone Chlormadinone acetate Cimetidine Cioteronel Clometerone Cyproterone Cyproterone acetate Delanterone DDT (via metabolite p,p’-DDE) Dieldrin Dienogest Drospirenone Endosulfan Enzalutamide EPI-001 Epitestosterone Fenarimol Flutamide Galeterone Guggulsterone Hydroxyflutamide Inocoterone Ketoconazole Lavender oil Linuron Megestrol acetate Mespirenone Methiocarb Metogest Mifepristone Nilutamide Nomegestrol Nordinone Norgestimate ODM-201 ONC1-13B ORM-15341 Osaterone Oxendolone PF-998425 Potassium canrenoate Prochloraz Procymidone R-2956 Rosterolone RU-58642 RU-58841 Spironolactone Topilutamide (fluridil) Topterone Valproic acid Vinclozolin VT-464 Zanoterone

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Precursors/prohormones	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycortisol (cortodoxone) DHEA DHEA sulfate Δ⁵-Androstenediol Δ⁴-Androstenedione

Indirect	Antigonadotropins (e.g., estrogens, progestogens, prolactin) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Estrogenics • Glucocorticoids • Mineralocorticoids • Progestogenics

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