Trenbolone

Structural formula
General
Non-proprietary name	Trenbolone
other names	17 β -hydroxyestra-4,9,11-trien-3-one ( IUPAC )
Molecular formula	C 18 H 22 O 2
External identifiers / databases
CAS number 10161-33-8 EC number 600-229-1 ECHA InfoCard 100.127.177 PubChem 25015 Wikidata Q904833
Drug information
Drug class	Anabolic steroids
properties
Molar mass	270.37 g · mol -1
Physical state	firmly
Melting point	183-186 ° C from acetone + water
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 360 P: 201-308 + 313
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Trenbolone is a synthetically produced drug from the group of anabolic steroids with moderately androgenic and strongly anabolic effects. Trenbolone is no longer of any importance in human medicine. It is misused as a doping agent to build muscle and improve performance. As a derivative of nandrolone , it is a male sex hormone .

field of use

The substance was initially used in the form of trenbolone hexahydrobenzyl carbonate and later as trenbolone acetate for market products. The funds are mainly used in the USA and Canada to increase the fattening performance of heifers and oxen and are sometimes combined with estradiol and tylosin . Trenbolone is also highly effective in slaughter cows, but is prohibited everywhere. Trenbolone can be detected in milk and meat in cows treated with trenbolone acetate. The Finaplix veterinary steroid implant is currently available. It is a steroid implant with the ester acetate, which is mainly implanted in young cows.

history

Trenbolone was first synthesized in France in 1963 by the scientist Leon Valluz and colleagues on behalf of the pharmaceutical company Roussel Uclaf (now Sanofi ). It was launched two decades later as Finajet in the US and Finaject in France for veterinary medicine; here primarily in cattle breeding. In human medicine, Trenbolone was officially launched in 1987. The French pharmaceutical company Negma Laboratories introduced it under the brand name Parabolan . 1997 Negma Laboratories stopped production. Parabolan is the only trenbolone-containing supplement ever approved for humans. Parabolan was one of the most counterfeit medicines ever. Due to the high basic price of trenbolone at the time, the active ingredient nortestosterone decanoate was sometimes used instead of trenbolone in the counterfeits . Trenbolone preparations are nowadays manufactured and sold in “underground laboratories” for doping purposes. The trade in and sale of preparations containing trenbolone without authorization or permission is prohibited under the Medicines Act . Possession of more than 150 mg is classified as a "not small amount" according to the doping agent quantity regulation and is punishable.

Properties and mode of action

The name is derived from the structure: 17 β -hydroxyestra-4,9,11-trien-3-one, the 'trien' in the formula gives it its name and indicates another property of trenbolone, namely a total of three C. = C double bonds starting from the carbon atoms in positions 4, 9 and 11.

Trenbolone is a derivative of nandrolone , but has a stronger effect than nandrolone. However, the effects of Trenbolone differ significantly from that of Nandrolone. For example, trenbolone cannot be converted to estrogen by aromatization. The delta-9 group within the molecular structure occupies a bridge that would be necessary for the aromatization of the A-ring. Since this group is not removed by a metabolic process, estrogen conversion in the body is impossible. Even if nandrolone is only weakly aromatized, the estrogen level can nevertheless rise noticeably during its use. With Trenbolone, on the other hand, a reduction in the serum estrogen level is to be expected, as it suppresses the endogenous testosterone production, which in turn is the primary basic substance for the production of estradiol in the male body.

Even though trenbolone is a derivative of nandrolone, it is more androgenic than nandrolone itself. The first reason for this is that trenbolone binds more strongly with the androgenic receptor. This property is also characteristic of nandrolone, which is several times more active than testosterone in this respect. The ability of Trenbolone to bind to the androgenic receptor is increased by the double bonds at positions delta 9 and 11 in comparison to nandrolone and makes trenbolone a more potent agonist of the androgen receptor than nandrolone itself. To what extent the progesterone effect of trenbolone in simultaneous intake can cause water and fat deposits with flavoring drugs has not been clearly clarified and is controversial.

Trenbolone binds to the androgen receptor more strongly than testosterone . Trenbolone has about the same effectiveness as testosterone in terms of its anabolic effect (increase in mass), but it does not allow the prostate to grow due to the lack of conversion to DHT . Like testosterone, it influences the development of the male sexual organs and the build-up of protein in the muscles . In the average man, the ratio of testosterone to nandrolone in the body is 50: 1.

Trenbolone suppresses the formation of cortisol and thus has an inhibiting effect on muscle breakdown (anti-catabolic). Trenbolone displaces cortisol agonists just as well as z. B. the dexamethasone from the glucocorticoid receptor and inhibits the synthesis of cortisol, about 1.5 times as strong as testosterone. Trenbolone also prevents the conversion of the weaker cortisone into cortisol via the 11 β- HSD enzyme. According to psychological studies, a prevented cortisol effect and concentration leads to e.g. B. also to increased aggressive behavior.

Trenbolone also promotes muscle building and muscle regeneration by increasing the sensitivity to certain growth factors such as FGF and IGF-1 .

The strong anabolic effects of Trenbolone are based, among other things, on a significant increase in nitrogen storage in the muscles and an increase in IGF-1 secretion by the liver and in the muscle itself. According to studies, Trenbolone can double and cause IGF-1 secretion in the body At the same time, the satellite cells of the muscles, which are responsible for repairing muscle damage (e.g. through training or other stress) and for muscle growth, are more sensitive to IGF-1 and other growth factors.

Unlike testosterone, trenbolone cannot convert to estrogen in the human male body. This is possible with animals. In animal experiments, a conversion rate of 1.9% was found.

In the absence of estradiol , trenbolone is considered to be a nutrient-redistributing agent: if there is no competition with estradiol at the corresponding receptors, trenbolone causes fat tissue to break down while at the same time building up muscle tissue. In animal experiments, female cattle had their ovaries removed, which meant that no more estradiol was formed: after administration of trenbolone, a significant breakdown of fat and muscle tissue was observed. It was also observed that the muscle hardness increased. This is attributed to the fact that trenbolone acts on the mineral corticoid receptor. The double bond at carbon atom 9 also ensures muscle hardness, it prevents the trenbolone from aromatizing into estrogens.

As a nandrolone derivative, trenbolone suppresses the body's own hormone production within a short time, so that no more testosterone is produced in the male body, which means that a sufficient erection is not possible in the long term without additional testosterone injections. Due to the progesterone effect of trenbolone, erectile function is also impaired in men . Even with a 1: 1 dose of trenbolone to testosterone, a deterioration in erectile function can be observed in over 50% of those affected. The simultaneous use of sexual enhancers usually helps, but can lead to loss of sensation in the penis and difficult orgasm . Treatment with cabergoline has proven to be successful in the long term , as it suppresses progesterone and prolactin levels. Thus the cause and not the result is combated.

Trenbolone is now available in several esterified variants: acetate (short-term, approx. 1 day), enanthate (long-term, approx. 4.5–5 days) and: hexahydrobenzyl carbonate (medium, approx. 2.5–3 days). Hexahydrobenzyl carbonate is known by its brand name Parabolan .

Abuse in Sports

Since nandrolone and trenbolone have a much higher activity than testosterone and the relationship between virilizing effect and anabolic effect is shifted in favor of the metabolic effect, it is of greater interest as a doping agent . Trenbolone is a well-known doping agent and is often used by bodybuilders to build muscle. Its muscle-promoting effectiveness is 10– to 15 times stronger than that of testosterone, since, unlike testosterone, it builds up “lean” muscle mass, so it neither accumulates fat nor stores water. The weight gain is achieved almost exclusively through the increase in lean muscle mass. Furthermore, Trenbolone is said to cause a continuous increase in strength, which, compared to testosterone, is supposed to develop more slowly, but for a longer period of time. Trenbolone is also used by bodybuilders and strength athletes as part of a diet , as it inhibits the breakdown of muscle mass. Trenbolone is often mixed with testosterone or drostanolone to increase the effect. In conjunction with somatropin , insulin and / or IGF-1 injections, Trenbolone can lead to a massive gain in muscle mass. However, with this combination, in which an extremely high IGF-1 release is achieved, there is an acute risk of antibody formation and metabolic diseases. Trenbolone has a major impact on the body's production of hormones. Testosterone production is switched off, which can lead to an imbalance in the hormone level that lasts for months, especially after discontinuation without appropriate “withdrawal therapy”. An irreversible disruption of hormone production is possible.

Traceability

Trenbolone is on the World Anti-Doping Agency (WADA) prohibited list . After isolation from urine samples, nandrolone , methyltrenbolone and trenbolone can be detected sensitively using a combination of liquid chromatography (LC) and mass spectrometry (MS).

Before the Olympic Games in Beijing in 2008, trenbolone was detected in eleven weightlifters and a female athlete using the chromatographic method (HPLC-MS / MS). Characteristic product ions, especially in the case of analytes with a structural relationship between trenbolone and methyltrenbolone, provided indications of improper use.

Side effects

The following side effects have been observed with the use of trenbolone on men:

• Worsening of liver values and heart function (permanent damage is not uncommon in long-term users)
• profuse sweating (especially profuse)
• Sleep disorders (particularly severe)
• aggressions
• Increase in blood pressure
• increased risk of a heart attack
• Worsening of blood lipid levels and bleeding disorders
• Suppression of the body's own hormone production
• Reduction or shutdown of the libido .

In women, trenbolone, as a derivative of a male sex hormone, develops other side effects despite its only moderately androgenic effect:

• Deepening of the voice (darker, more masculine)
• Body hair growth
• facial hair
• missed periods
• Enlargement of the clitoris ( clitoral hypertrophy ) with possible infertility (cannot always be reversed)
• general masculinization of the body, for example facial features

In particular, no specific reason for the profuse sweating and sleep disorders could be determined so far, while some studies assume the reason for the accelerated metabolism, others assume the increased IGF emissions as the reason.

Interactions with other means

Combining Trenbolone with other abused substances like Clenbuterol , Ephedrine and Drostanolone increases undesirable effects like heart strain, excessive sweating and the deterioration of blood lipid levels.

Individual evidence

1. ^ The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals. 14th edition. Merck & Co., Whitehouse Station, NJ, USA, 2006, ISBN 0-911910-00-X .
2. ↑ ^{a b} Trenbolone data sheet from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
3. ↑ FTW Publishing: Kultsteroide. Vol. 1: Trenbolone. FTW Publishing Verlag, 2008, p. 8.
4. ↑ The addiction to body drugs. In: FOCUS magazine. No. 11 (1996).
5. ^ F. Neumann: Pharmacological and endocrinological studies on anabolic agents. In: Environmental quality and safety. Supplement. Number 5, 1976, pp. 253-264, PMID 782871 . (Review).
6. ↑ T. Ojasoo, JP Raynaud: Unique steroid congeners for receptor studies. In: Cancer Research . Volume 38, Number 11 Pt 2, November 1978, pp. 4186-4198, PMID 359134 . (Review).
7. ↑ CS Freeman, YJ Topper: Progesterone and glucocorticoid in relation to the growth and differentiation of mammary epithelium. In: Journal of Toxicology and Environmental Health . Volume 4, number 2-3, 1978 Mar-May, pp. 269-282, doi: 10.1080 / 15287397809529661 . PMID 96271 .
8. ↑ ^{a b c d} V. S. Wilson, C. Lambright et al. a .: In vitro and in vivo effects of 17β-trenbolone: ​​a feedlot effluent contaminant. In: Toxicological Sciences . Volume 70, Number 2, December 2002, pp. 202-211, PMID 12441365 .
9. ↑ ^{a b} NCBI: 2-methylestra-4,9-dien-3-one-17-ol
10. ↑ K. McBurnett, BB Lahey et al. a .: Low salivary cortisol and persistent aggression in boys referred for disruptive behavior. In: Archives of General Psychiatry . Volume 57, Number 1, January 2000, pp. 38-43, PMID 10632231 .
11. ^ RE Allen, LK Boxhorn: Regulation of skeletal muscle satellite cell proliferation and differentiation by transforming growth factor-beta, insulin-like growth factor I, and fibroblast growth factor. In: Journal of Cellular Physiology . Volume 138, Number 2, February 1989, pp. 311-315, doi: 10.1002 / jcp.1041380213 . PMID 2918032 .
12. ↑ SH Thompson, LK Boxhorn u. a .: Trenbolone alters the responsiveness of skeletal muscle satellite cells to fibroblast growth factor and insulin-like growth factor I. In: Endocrinology. Volume 124, Number 5, May 1989, pp. 2110-2117, doi: 10.1210 / endo-124-5-2110 . PMID 2707149 .
13. ↑ E. Kamanga-Sollo, MS Pampusch and a .: IGF-I mRNA levels in bovine satellite cell cultures: effects of fusion and anabolic steroid treatment. In: Journal of cellular physiology. Volume 201, Number 2, November 2004, pp. 181-189, doi: 10.1002 / jcp.20000 . PMID 15334653 .
14. ↑ M. Tóth, T. Zakár: Different binding of testosterone, 19-nortestosterone and their 5 alpha-reduced derivatives to the androgen receptor of the rat seminal vesicle: a step toward the understanding of the anabolic action of nortesterone. In: Endocrinology. Volume 80, Number 2, October 1982, pp. 163-172, PMID 7160340 .
15. ^ ME White, BJ Johnson et al. a .: Growth factor messenger RNA levels in muscle and liver of steroid-implanted and nonimplanted steers. In: Journal of animal science. Volume 81, Number 4, April 2003, pp. 965-972, PMID 12723086 .
16. ^ Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for TRENBOLONE ACETATE , accessed December 9, 2014.
17. ↑ A. Lazaro, J. Gallego-Delgado et al. a .: Long-term blood pressure control prevents oxidative renal injury. In: Antioxidants & Redox Signaling . Volume 7, number 9-10, 2005 Sep-Oct, pp 1285-1293, doi: 10.1089 / ars.2005.7.1285 . PMID 16115034 .
18. ^ S. Guddat, W. Schänzer, P. Wachsmuth, M. Thevis: Doping control screening procedure for Trenbolone analogues in human urine by LC- (APCI) -MS / MS. In: W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (eds.): Recent advances in doping analysis (15). Sportverlag Strauss, Cologne, 2007, pp. 397-400, ISBN 3-939390-13-5 .
19. ↑ M. Thevis, W. Schänzer: Doping prevention : methods, analytics, development tendencies. In: German magazine for sports medicine. Volume 61, number 7-8, 2010, pp. 153-156.
20. ↑ D. Sinner: The Black Book - Anabolic Steroids. BMS-Verlag, 2007, ISBN 978-3-00-020944-4 , pp. 659-660.

Web links

• Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for TRENBOLONE ACETATE

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