Trenbolone

Last updated
Trenbolone
Trenbolone.svg
Clinical data
Other namesTrienolone; Trienbolone; RU-2341; Δ9,11-Nandrolone; 19-Nor-δ9,11-testosterone; Estra-4,9,11-trien-17β-ol-3-one
AHFS/Drugs.com International Drug Names
License data
Pregnancy
category
  • X
Routes of
administration 		Intramuscular injection (as esters)
Drug class Androgen; Anabolic steroid; Progestogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Bioavailability Intramuscular: 80-100%[ citation needed ]
Metabolism Liver
Elimination half-life 6–8 hours[ citation needed ]
Excretion Urine
Identifiers
  • (8S,13S,14S,17S)-17-Hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.127.177 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H22O2
Molar mass 270.372 g·mol−1
3D model (JSmol)
  • O=C4\C=C2/C(=C1/C=C\[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
  • InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h8-10,15-17,20H,2-7H2,1H3/t15-,16+,17+,18+/m1/s1 Yes check.svgY
  • Key:MEHHPFQKXOUFFV-OWSLCNJRSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed.[ clarification needed ] [2] [3] [4] [5] [6] Trenbolone ester prodrugs, including trenbolone acetate (brand names Finajet, Finaplix, others) and trenbolone hexahydrobenzylcarbonate (brand names Parabolan, Hexabolan), are or have been marketed for veterinary and clinical use. [2] [3] [4] [6] [7] [8] Trenbolone acetate is used in veterinary medicine in livestock to increase muscle growth and appetite, while trenbolone hexahydrobenzylcarbonate was formerly used clinically in humans but is now no longer marketed. [2] [3] [4] [6] In addition, although it is not approved for clinical or veterinary use, trenbolone enanthate is sometimes sold on the black market under the nickname Trenabol. [6]

Contents

A vial of injectable trenbolone acetate. A vial of injectable Trenbolone..jpg
A vial of injectable trenbolone acetate.

Uses

Veterinary

Trenbolone, as trenbolone acetate, improves muscle mass, feed efficiency, and mineral absorption in cattle. [6]

Side effects

Sometimes human users may experience an event called "tren cough" shortly after or during an injection, where the user experiences a violent and extreme coughing fit, which can last for minutes.

Pharmacology

Pharmacodynamics

Trenbolone has both anabolic and androgenic effects. [6] Once metabolized, trenbolone esters have the effect of increasing ammonium ion uptake by muscles, leading to an increase in the rate of protein synthesis. It may also have the secondary effects of stimulating appetite and decreasing the rate of catabolism, as all anabolic steroids are believed to; however, catabolism likely increases significantly once the steroid is no longer taken. [9] At least one study in rats has shown trenbolone to cause gene expression of the androgen receptor (AR) at least as potent as dihydrotestosterone (DHT). This evidence tends to indicate trenbolone can cause an increase in male secondary sex characteristics without the need to convert to a more potent androgen in the body. [10]

Studies on metabolism are mixed, with some studies showing that it is metabolized by aromatase or 5α-reductase into estrogenic compounds, or into 5α-reduced androgenic compounds, respectively. [11] [12]

Trenbolone has potency five times as high as that of testosterone. [6] [13] Trenbolone also binds with high affinity to the progesterone receptor, [6] [13] [14] [15] Trenbolone binds to the glucocorticoid receptor, as well. [14]

Pharmacokinetics

To prolong its elimination half-life, trenbolone is administered as a prodrug as an ester conjugate such as trenbolone acetate, trenbolone enanthate, or trenbolone hexahydrobenzylcarbonate. [2] [3] [4] [6] Plasma lipases then cleave the ester group in the bloodstream leaving free trenbolone.[ citation needed ]

Trenbolone and 17-epitrenbolone are both excreted in urine as conjugates that can be hydrolyzed with beta-glucuronidase. [16] This implies that trenbolone leaves the body as beta-glucuronides or sulfates.

Chemistry

Trenbolone, also known as 19-nor-δ9,11-testosterone or as estra-4,9,11-trien-17β-ol-3-one, is a synthetic estrane steroid and a derivative of nandrolone (19-nortestosterone). [2] [3] [6] It is specifically nandrolone with two additional double bonds in the steroid nucleus. [2] [3] [6] Trenbolone esters, which have an ester at the C17β position, include trenbolone acetate, trenbolone enanthate, trenbolone hexahydrobenzylcarbonate, and trenbolone undecanoate. [2] [3] [6] [17]

Basic information about different types steroids included base trenbolone inside structure.
Name:Trenbolone Trenbolone acetate Trenbolone enanthate Trenbolone hexahydrobenzylcarbonate

(cyclohexylmethylcarbonate)

Structural [17] Trenbolone.svg Trenbolone acetate.svg Trenbolone enanthate.svg Trenbolone cyclohexylmethylcarbonate.svg
FormulaC18H22O2C20H24O3C25H34O3C26H34O4
Crystal system [17] monocrystalicmonocrystalicmonocrystalic
Elimination half life48–72 hours[ citation needed ]short

1–2 days; [17] 3 days [18]

long

11 days [17]

8 days [17]

History

Trenbolone was first synthesized in 1963. [19]

Society and culture

Generic names

Trenbolone is the generic name of the drug and its INN Tooltip International Nonproprietary Name and BAN Tooltip British Approved Name. [2] [3] [4] It has also been referred to as trienolone or trienbolone or tren. [2] [3] [4] [20]

Some bodybuilders and athletes use trenbolone hexahydrobenzylcarbonate and other esters (acetate, enanthate) for their muscle-building and otherwise performance-enhancing effects. [21] [6] Such use is illegal in the United States and several European and Asian countries. The DEA classifies trenbolone and its esters as Schedule III controlled substances under the Controlled Substances Act. [22] Trenbolone is classified as a Schedule 4 drug in Canada [23] and a class C drug with no penalty for personal use or possession in the United Kingdom. [24] Use or possession of steroids without a prescription is a crime in Australia. [25]

Doping in sports

There are known cases of doping in sports with trenbolone esters by professional athletes.

See also

Related Research Articles

<span class="mw-page-title-main">Tetrahydrogestrinone</span> Synthetic and orally active anabolic–androgenic steroid (AAS)

Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profile athletes such as Marion Jones, Barry Bonds, and Dwain Chambers.

<span class="mw-page-title-main">Methyltestosterone</span> Chemical compound

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<span class="mw-page-title-main">Nandrolone decanoate</span> Anabolic steroid

Nandrolone decanoate, sold under the brand name ROLON among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in menopausal women. It is given by injection into muscle or fat once every one to four weeks.

<span class="mw-page-title-main">Testosterone enanthate</span> Chemical compound

Testosterone enanthate is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It is also used in hormone therapy for transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks.

<span class="mw-page-title-main">Metenolone enanthate</span> Chemical compound

Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.

<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

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<span class="mw-page-title-main">Trenbolone acetate</span> Chemical compound

Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle growth in cattle. It is given by injection into muscle.

<span class="mw-page-title-main">Trestolone</span> Chemical compound

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

<span class="mw-page-title-main">Metribolone</span> Chemical compound

Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.

<span class="mw-page-title-main">Trenbolone enanthate</span> Chemical compound

Trenbolone enanthate, known by the nickname Trenabol, is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone which was never marketed. It is the C17β enanthate ester and a long-acting prodrug of trenbolone. Trenbolone enanthate was never approved for medical or veterinary use but is used in scientific research and has been sold on the internet black market as a designer steroid for bodybuilders and athletes.

<span class="mw-page-title-main">Nandrolone phenylpropionate</span> Anabolic steroid

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<span class="mw-page-title-main">Trimethyltrienolone</span> Chemical compound

Trimethyltrienolone (TMT), also known by its developmental code name R-2956 or RU-2956, is an antiandrogen medication which was never introduced for medical use but has been used in scientific research.

<span class="mw-page-title-main">Dimethandrolone</span> Chemical compound

Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use.

<span class="mw-page-title-main">Dimethyltrienolone</span> Anabolic–androgenic steroid

Dimethyltrienolone is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use. It has among the highest known affinity of any AAS for the androgen receptors, and has been said to be perhaps the most potent AAS to have ever been developed.

<span class="mw-page-title-main">Trenbolone hexahydrobenzylcarbonate</span> Chemical compound

Trenbolone hexahydrobenzylcarbonate, or trenbolone cyclohexylmethylcarbonate, sold under the brand names Parabolan and Hexabolan, is a synthetic, injected anabolic–androgenic steroid (AAS) of the nandrolone group and an androgen ester – specifically, the C17β hexahydrobenzylcarbonate (cyclohexylmethylcarbonate) ester of trenbolone – which was marketed in France for medical use in humans but has since been discontinued.

<span class="mw-page-title-main">Metenolone acetate</span> Chemical compound

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.

<span class="mw-page-title-main">Trenbolone undecanoate</span> Chemical compound

Trenbolone undecanoate, or trenbolone undecylate, is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was never marketed. It is the C17β undecanoate (undecylate) ester and a long-acting prodrug of trenbolone. The drug was described by Roussel Uclaf in 1967 and was the first long-lasting ester of trenbolone to be developed. Subsequently, trenbolone hexahydrobenzylcarbonate, a roughly equivalent compound, was developed and introduced for use in humans in 1980, though it was discontinued in 1997. Trenbolone enanthate is another long-lasting ester of trenbolone. Similarly to trenbolone undecanoate, it was never marketed, but it has been sold on the black market as a designer steroid for bodybuilders and athletes.

<span class="mw-page-title-main">Trendione</span> Chemical compound

Trendione, also known as estra-4,9,11-triene-3,17-dione, is an androgen prohormone as well as metabolite of the anabolic steroid trenbolone. Trendione is to trenbolone as androstenedione is to testosterone. The compound is inactive itself, showing more than 100-fold lower affinity for the androgen and progesterone receptors than trenbolone. It is a designer steroid and has been sold on the internet as a "nutritional supplement". Trendione is listed in the United States Designer Anabolic Steroid Control Act of 2014.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

References

  1. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. 1 2 3 4 5 6 7 8 9 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN   978-1-4757-2085-3.
  3. 1 2 3 4 5 6 7 8 9 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 1591. ISBN   978-3-88763-075-1.
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  5. ↑ "Trenbolone".
  6. 1 2 3 4 5 6 7 8 9 10 11 12 13 Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 491–499, 618–, 724–. ISBN   978-0-9828280-1-4.
  7. ↑ Nichols W, Hutcheson J, Streeter M, Corrigan M, Nuttelman B. "Implant Strategies for Finishing Cattle using Revalor® (trenbolone acetate and estradiol), Finaplix® (trenbolone) and/or Ralgro® (zeranol)" (PDF). Merck Animal Health.
  8. ↑ Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC   2439524 . PMID   18500378.
  9. ↑ Fahey TD (March 1998). "Anabolic Steroids: Mechanisms and Effects". Encyclopedia of sports medicine and science. Internet Society for Sport Science.
  10. ↑ Wilson VS, Lambright C, Ostby J, Gray LE (December 2002). "In vitro and in vivo effects of 17beta-trenbolone: a feedlot effluent contaminant". Toxicological Sciences. 70 (2): 202–211. doi: 10.1093/toxsci/70.2.202 . PMID   12441365.
  11. ↑ Yarrow JF, McCoy SC, Borst SE (June 2010). "Tissue selectivity and potential clinical applications of trenbolone (17beta-hydroxyestra-4,9,11-trien-3-one): A potent anabolic steroid with reduced androgenic and estrogenic activity". Steroids. 75 (6): 377–389. doi:10.1016/j.steroids.2010.01.019. PMID   20138077. S2CID   205253265.
  12. ↑ Gettys TW, D'Occhio MJ, Henricks DM, Schanbacher BD (January 1984). "Suppression of LH secretion by oestradiol, dihydrotestosterone and trenbolone acetate in the acutely castrated bull". The Journal of Endocrinology. 100 (1): 107–112. doi:10.1677/joe.0.1000107. PMID   6361192.
  13. 1 2 Nicholas Mascie-Taylor CG, Rosetta L (13 January 2011). Reproduction and Adaptation: Topics in Human Reproductive Ecology. Cambridge University Press. pp. 69–. ISBN   978-1-139-49430-4.
  14. 1 2 APMIS.: Supplementum. Munksgaard. 2001. p. 5339. ISBN   9788716164575.
  15. ↑ McKerns KW (13 March 2013). Reproductive Processes and Contraception. Springer Science & Business Media. pp. 171–. ISBN   978-1-4684-3824-6.
  16. ↑ Schänzer W (July 1996). "Metabolism of anabolic androgenic steroids". Clinical Chemistry. 42 (7): 1001–1020. doi: 10.1093/clinchem/42.7.1001 . PMID   8674183.
  17. 1 2 3 4 5 6 Borodi G, Turza A, Camarasan PA, Ulici A (2020). "Structural studies of Trenbolone, Trenbolone Acetate, Hexahydrobenzylcarbonate and Enanthate esters". Journal of Molecular Structure. 1212: 128127. Bibcode:2020JMoSt121228127B. doi:10.1016/j.molstruc.2020.128127. ISSN   0022-2860. S2CID   216299984.
  18. ↑ Ruiz P, Strain EC (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. ISBN   978-1-60547-277-5.
  19. ↑ Schänzer W (July 1996). "Metabolism of anabolic androgenic steroids". Clinical Chemistry. 42 (7): 1001–1020. doi: 10.1093/clinchem/42.7.1001 . PMID   8674183.
  20. ↑ Food and Agriculture Organization of the United Nations (1990). Residues of Some Veterinary Drugs in Animals and Foods: Monographs Prepared by the Thirty-Fourth Meeting of the Joint FAO/WHO Expert Committee on Food Additives, Geneva, 30 January-8 February 1989. Food & Agriculture Org. pp. 88–. ISBN   978-92-5-102933-6.
  21. ↑ "Trenbolone hexahydrobenzylcarbonate use in bodybuilding". 20 November 2021.
  22. ↑ "Controlled Substances Act". United States Food and Drug Administration. 11 June 2009. Retrieved 17 June 2016.
  23. ↑ "Controlled Drugs and Substances Act". laws-lois.justice.gc.ca. Archived from the original on 2012-09-15.
  24. ↑ "Consideration of the Anabolic Steroids". London: Advisory Council on the Misuse of Drugs. September 2010. Archived from the original on 2011-09-22.
  25. ↑ "Australian Institute of Criminology - Steroids". Archived from the original on 2012-03-23. Retrieved 2011-08-22.

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