Trenbolone

Overview

Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed for human use. 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. 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. In addition, although it is not approved for clinical or veterinary use, trenbolone enanthate is sometimes sold on the black market under the name trenabol.[1–7] WP⚠ Wikipedia itself has flagged this text: clarification needed.

Uses, dosage and effects

Veterinary

Trenbolone, as trenbolone acetate, improves muscle mass, feed efficiency, and mineral absorption in cattle.[5] WP

Risks and side effects

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 and in some cases even longer. WP

"Tren cough", despite its name, is not exclusive to trenbolone. It can occur when injecting any oil-steroid solutions, if the solution accidentally is injected intravenously. When the oil-steroid solution gets into the bloodstream, the steroid oil solution travels into the lungs, therefore causing a coughing fit. There are several theories on why this phenomenon happens.[8] WP

It is possible that the androgenic effect from steroids activates a variety of lipid-like active compounds which are called prostaglandins. Many of these prostaglandins are inflammatory and vasoconstrictive. Prostaglandins are signalled through two varying pathways cyclooxygenase (COX) (Also known as: prostaglandin-endoperoxide synthase) and lipoxygenases (LOX) (also known as: EC 1.13.11.34, EC 1.13.11.33, etc.). The bradykinin peptide is well known to promote a cough reaction associated with ACE inhibitor medications prescribed for hypertension.[9][10][11] WP

Pharmacology

Pharmacodynamics

Trenbolone has both anabolic and androgenic effects. 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. 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.[5][12][13] WP

Studies on metabolism are mixed, with some studies showing that it is metabolized by aromatase into estrogenic compounds, or by 5α-reductase into 5α-reduced androgenic compounds.[14][15] WP

The potency of trenbolone is not known, although it's often falsely believed to be five times higher than testosterone. This is based on a book by William Llewellyn but has not been definitively proven. Trenbolone was never approved for human use, and therefore limited data on the subject exists. The relevant studies are usually done in rats, which makes the 500/100 potency number inaccurate. Rats respond differently and are less sensitive to androgens. While some literature report a 5 fold higher potency, two other scientific reviews report a 3 fold higher potency. Trenbolone also binds with high affinity to the progesterone receptor, and binds to the glucocorticoid receptor as well.[5][14][16–20] WP

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. Plasma lipases then cleave the ester group in the bloodstream leaving free trenbolone.[1][2][3][5] WP⚠ Wikipedia itself has flagged this text: citation needed.

Trenbolone and 17-epitrenbolone are both excreted in urine as conjugates that can be hydrolyzed with beta-glucuronidase. This implies that trenbolone leaves the body as beta-glucuronides or sulfates.[21] WP

History

History

Trenbolone was first synthesized in 1963.[21] WP

Legal status

Generic names

Trenbolone is the generic name of the drug and its INN (International Nonproprietary Name) and BAN (British Approved Name). It has also been referred to as trienolone or trienbolone or tren.[1][2][3][22] WP

Legal status

Some bodybuilders and athletes use trenbolone hexahydrobenzylcarbonate and other esters (acetate, enanthate) for their muscle-building and otherwise performance-enhancing effects. 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. Trenbolone is classified as a Schedule 4 drug in Canada and a class C drug with no penalty for personal use or possession in the United Kingdom. Use or possession of steroids without a prescription is a crime in Australia.[5][23–27] WP

Doping in sports

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

Chemistry

Formula

C18H22O2 PC

CAS number

10161-33-8 PC

Molar mass (g/mol)

270.4 PC

IUPAC name (computed by PubChem)

(8S,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-one PC

SMILES

C[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O PC

InChIKey

MEHHPFQKXOUFFV-OWSLCNJRSA-N PC

PubChem CID

25015

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014
2. Other Index Nominum 2000: International Drug Directory. January 2000
3. Other Morton IK, Hall JM. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012
4. Other Trenbolone
5. Other Llewellyn W. Anabolics. 2011
6. Other 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)
7. Journal / agency Kicman AT. Pharmacology of anabolic steroids. British Journal of Pharmacology. June 2008. doi:10.1038/bjp.2008.165 · PMID 18500378 · PMC2439524
8. Journal / agency Russell M, Storck A, Ainslie M. Acute respiratory distress following intravenous injection of an oil-steroid solution. Canadian Respiratory Journal. 2011. doi:10.1155/2011/743151 · PMID 22059184 · PMC3205107
9. Journal / agency Notelovitz M. Androgen effects on bone and muscle. Fertility and Sterility. April 2002. doi:10.1016/s0015-0282(02)02968-0 · PMID 12007900
10. Journal / agency Kam PC, See AU. Cyclo-oxygenase isoenzymes: physiological and pharmacological role. Anaesthesia. May 2000. doi:10.1046/j.1365-2044.2000.01271.x · PMID 10792135
11. Journal / agency Fox AJ, Lalloo UG, Belvisi MG, Bernareggi M, Chung KF, Barnes PJ. Bradykinin-evoked sensitization of airway sensory nerves: a mechanism for ACE-inhibitor cough. Nature Medicine. July 1996. doi:10.1038/nm0796-814 · PMID 8673930
12. Other Fahey TD. Encyclopedia of sports medicine and science. Internet Society for Sport Science. March 1998
13. Journal / agency Wilson VS, Lambright C, Ostby J, Gray LE. In vitro and in vivo effects of 17beta-trenbolone: a feedlot effluent contaminant. Toxicological Sciences. December 2002. doi:10.1093/toxsci/70.2.202 · PMID 12441365
14. Journal / agency Yarrow JF, McCoy SC, Borst SE. 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. June 2010. doi:10.1016/j.steroids.2010.01.019 · PMID 20138077
15. Journal / agency Gettys TW, D'Occhio MJ, Henricks DM, Schanbacher BD. Suppression of LH secretion by oestradiol, dihydrotestosterone and trenbolone acetate in the acutely castrated bull. The Journal of Endocrinology. January 1984. doi:10.1677/joe.0.1000107 · PMID 6361192
16. Other Wiebe JP. Reproduction and Adaptation: Topics in Human Reproductive Ecology. 2011-01-13
17. Journal / agency Neumann F. Pharmacological and endocrinological studies on anabolic agents. Environmental Quality and Safety. Supplement. 1976. PMID 782871
18. Other Nicholas Mascie-Taylor CG, Rosetta L. Reproduction and Adaptation: Topics in Human Reproductive Ecology. 13 January 2011
19. Other APMIS.: Supplementum. 2001
20. Other McKerns KW. Reproductive Processes and Contraception. 13 March 2013
21. Journal / agency Schänzer W. Metabolism of anabolic androgenic steroids. Clinical Chemistry. July 1996. doi:10.1093/clinchem/42.7.1001 · PMID 8674183
22. Other Food and Agriculture Organization of the United Nations. 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. 1990
23. Other Trenbolone hexahydrobenzylcarbonate use in bodybuilding. 20 November 2021
24. Journal / agency Controlled Substances Act. 11 June 2009
25. Other Controlled Drugs and Substances Act
26. Other Consideration of the Anabolic Steroids. September 2010
27. Other Australian Institute of Criminology - Steroids

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.