Trenbolone enanthate
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| Clinical data | |
|---|---|
| Other names | Trenabol; Trenbolone heptanoate; 19-Nor-δ9,11-testosterone 17β-enanthate; Estra-4,9,11-trien-17β-ol-3-one 17β-enanthate |
| Routes of administration | Intramuscular injection |
| Drug class | Androgen; Anabolic steroid; Androgen ester; Progestogen |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C25H34O3 |
| Molar mass | 382.544 g·mol−1 |
| 3D model (JSmol) | |
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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.[1][2] It is the C17β enanthate ester and a long-acting prodrug of trenbolone.[1] Trenbolone enanthate was never approved for medical or veterinary use but is used in scientific research[3][4] and has been sold on the internet black market as a designer steroid for bodybuilders and athletes.[5][6]
Side Effects
[edit]Trenbolone Enanthate being a potent anabolic steroid has several potential side effects stemming from its particularly strong androgenic properties and its regulation on human hormones.[7]
Psychological
[edit]Anabolic-androgenic steroid (AAS) users report significant psychological changes. Fluctuation in testosterone, a key AAS, affects the brain's structure and function, potentially leading to mood disorders and aggressive behavior.[8] Trenbolone Enanthate users have reported significant psychological changes, including increased aggression, mood instability, and impaired social interactions.[9] Prolonged use of AAS may also lead to psychological dependence, with approximately 1/3 of users experiencing withdrawal symptoms upon cessation.[10]
Reproductive health
[edit]Anabolic-androgenic steroids(AAS) impact male reproductive health. Their misuse can lead to a condition known as anabolic steroid-induced hypogonadism (ASIH), where natural testosterone production is suppressed. The decreased testosterone production leads to decreased sperm production and can cause prolonged infertility even after stopping use.[11] Chronic AAS use increases the risk of infertility due to its impact on hormonal balance, and some effects such as gynecomastia may not be reversible.[12]
Androgenic
[edit]Trenbolone Enanthate can include several androgenic side effects such as increased body hair growth, acne, and potential baldness in predisposed individuals.[7][13]
Gynecomastia
[edit]Gynecomastia is a condition that enlarges the breast tissue in males which is often produced as a side effect from the use of AAS.[10] AAS can disrupt the normal balance of estrogen and testosterone in the body due to the increase in testosterone, which can be aromatized into estrogen. Elevated levels of estrogen in males can be linked to both weight gain and gynecomastia.[14] While Trenbolone Enanthate is known for not aromatizing into estrogen,[15] trenbolone exhibits high progestogenic activity which is one of three natural developments of breast tissue in males, also leading to gynecomastia.[16][12]
Primary Uses
[edit]Bodybuilding
[edit]Trenbolone Enanthate is renowned for its capacity to promote significant muscle growth and strength gain. Its anabolic effects facilitate increased protein synthesis and nitrogen retention in muscle tissue.[13] Trenbolone Enanthate is also notable in the field of strength gain, with many users reporting marked improvements in their lifting capabilities in part due to the AAS' ability to increase red blood cell count and improve oxygenation of muscle tissue along with the increase in testosterone.[17] The compound is also often employed for its fat-burning properties.[18] It enhances the metabolic rate and promotes the conversion of fat into energy,[19] contributing to leaner muscle development during cutting cycles in body building.[18]
Enhanced Recovery
[edit]Trenbolone Enanthate is a potential treatment for muscle and bone loss without adverse effects commonly associated with testosterone, such as prostate growth or polycythemia.[20] Trenbolone Enanthate was hypothesized to offer benefits similar to selective androgen receptor modulators(SARMs) due to its inability to convert into more potent androgens in specific tissues.[20]
Veterinary Uses
[edit]In the veterinary field, Trenbolone Enanthate has a history of use for increasing muscle mass in livestock. This application is aimed at improving the lean muscle yield in animals prior to slaughter, enhancing the quality of meat production.[21]
History
[edit]Trenbolone was first synthesized in 1963 by L. Velluz and his co-workers, it was originally developed for veterinary use to improve muscle mass and feed efficiency in cattle;[22] however, trenbolone's potent anabolic and androgenic properties soon caught the attention of bodybuilders and athletes. The drug, however, has never been approved for human use, which has legal implications.[23]
Legality
[edit]Trenbolone Enanthate has never had regulatory approval for human use from any single health agency. Its legal status varies by country, however, it is commonly a controlled substance and non-prescribed use is highly illegal. For example, in the United States, the Drug Enforcement Administration (DEA) considers trenbolone and its esters (including its acetate and enanthate form) as Schedule III controlled substances similar to the likes of Australia where use of possession is a criminal offence.[24][25] However, trenbolone is considered a class C drug with no penalty for personal use or possession in the United Kingdom.[26] The legal framework surrounding trenbolone and its derivatives is complex and not universally consistent, reflecting the substance's potent effects and the concerns over its potential misuse. Sporting organizations, including the World Anti Doping Agency (WADA), closely monitor the use of such substances, especially in competitive events like the Olympics, due to these concerns.[27]
| Anabolic steroid | Structure | Ester | Relative mol. weight |
Relative AAS contentb |
Durationc | ||||
|---|---|---|---|---|---|---|---|---|---|
| Position | Moiety | Type | Lengtha | ||||||
| Boldenone undecylenate |  |
C17β | Undecylenic acid | Straight-chain fatty acid | 11 | 1.58 | 0.63 | Long | |
| Drostanolone propionate |  |
C17β | Propanoic acid | Straight-chain fatty acid | 3 | 1.18 | 0.84 | Short | |
| Metenolone acetate |  |
C17β | Ethanoic acid | Straight-chain fatty acid | 2 | 1.14 | 0.88 | Short | |
| Metenolone enanthate |  |
C17β | Heptanoic acid | Straight-chain fatty acid | 7 | 1.37 | 0.73 | Long | |
| Nandrolone decanoate |  |
C17β | Decanoic acid | Straight-chain fatty acid | 10 | 1.56 | 0.64 | Long | |
| Nandrolone phenylpropionate |  |
C17β | Phenylpropanoic acid | Aromatic fatty acid | – (~6–7) | 1.48 | 0.67 | Long | |
| Trenbolone acetate |  |
C17β | Ethanoic acid | Straight-chain fatty acid | 2 | 1.16 | 0.87 | Short | |
| Trenbolone enanthated | |
C17β | Heptanoic acid | Straight-chain fatty acid | 7 | 1.41 | 0.71 | Long | |
| Footnotes: a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative androgen/anabolic steroid content by weight (i.e., relative androgenic/anabolic potency). c = Duration by intramuscular or subcutaneous injection in oil solution. d = Never marketed. Sources: See individual articles. | |||||||||
See also
[edit]References
[edit]- ^ a b William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 724–. ISBN 978-0-9828280-1-4.
- ^ Underground Anabolics. Molecular Nutrition Llc. pp. 120–. ISBN 978-0-9828280-7-6.
- ^ Dalbo VJ, Roberts MD, Mobley CB, Ballmann C, Kephart WC, Fox CD, et al. (2016). "Testosterone and trenbolone enanthate increase mature myostatin protein expression despite increasing skeletal muscle hypertrophy and satellite cell number in rodent muscle". Andrologia. 49 (3): e12622. doi:10.1111/and.12622. PMID 27246614. S2CID 1852164.
- ^ Ye F, McCoy SC, Yarrow JF, Conover CF, Beck DT, Beggs LA, et al. (2013). "Effect of Trenbolone enanthate on protein degradation in levator ani/bulbocavernosus (LABC) muscle in orchiectomized rats". The FASEB Journal. 27: 939–15. doi:10.1096/fasebj.27.1_supplement.939.15. S2CID 88757206.
- ^ "Side effects of Trenbolone Enanthate". trenenanthate.net. 2020-01-24. Retrieved 2021-03-02.
- ^ El Osta R, Almont T, Diligent C, Hubert N, Eschwège P, Hubert J (2016). "Anabolic steroids abuse and male infertility". Basic Clin Androl. 26: 2. doi:10.1186/s12610-016-0029-4. PMC 4744441. PMID 26855782.
- ^ a b Stojko M, Nocoń J, Piłat P, Szpila G, Smolarczyk J, Żmudka K, et al. (August 2023). "Innovative Reports on the Effects of Anabolic Androgenic Steroid Abuse-How to Lose Your Mind for the Love of Sport". Medicina. 59 (8): 1439. doi:10.3390/medicina59081439. PMC 10456445. PMID 37629729.
- ^ Bertozzi G, Salerno M, Pomara C, Sessa F (July 2019). "Neuropsychiatric and Behavioral Involvement in AAS Abusers. A Literature Review". Medicina. 55 (7): 396. doi:10.3390/medicina55070396. PMC 6681542. PMID 31336641.
- ^ Piatkowski TM, Neumann DL, Dunn M (September 2023). "'My mind pretty much went to mush': A qualitative exploration of trenbolone in the performance and image enhancing drug community". Drug and Alcohol Review. 42 (6): 1566–1576. doi:10.1111/dar.13656. hdl:10072/422455. PMID 36992616.
- ^ a b Scarth M, Westlye LT, Havnes IA, Bjørnebekk A (May 2023). "Investigating anabolic-androgenic steroid dependence and muscle dysmorphia with network analysis among male weightlifters". BMC Psychiatry. 23 (1): 342. doi:10.1186/s12888-023-04781-1. PMC 10186641. PMID 37193971.
- ^ El Osta R, Almont T, Diligent C, Hubert N, Eschwège P, Hubert J (2016-02-06). "Anabolic steroids abuse and male infertility". Basic and Clinical Andrology. 26 (1): 2. doi:10.1186/s12610-016-0029-4. PMC 4744441. PMID 26855782.
- ^ a b Swerdloff RS, Ng JC (2000). "Gynecomastia: Etiology, Diagnosis, and Treatment". In Feingold KR, Anawalt B, Blackman MR, Boyce A (eds.). Endotext. South Dartmouth (MA): MDText.com, Inc. PMID 25905330. Retrieved 2024-03-14.
- ^ a b 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.
- ^ Ding JB, Ng MZ, Huang SS, Ding M, Hu K (2021-12-10). Rehrer NJ (ed.). "Anabolic-Androgenic Steroid Misuse: Mechanisms, Patterns of Misuse, User Typology, and Adverse Effects". Journal of Sports Medicine. 2021: 7497346. doi:10.1155/2021/7497346. PMC 8683244. PMID 34926695.
- ^ Yarrow JF, Conover CF, McCoy SC, Lipinska JA, Santillana CA, Hance JM, et al. (April 2011). "17β-Hydroxyestra-4,9,11-trien-3-one (trenbolone) exhibits tissue selective anabolic activity: effects on muscle, bone, adiposity, hemoglobin, and prostate". American Journal of Physiology. Endocrinology and Metabolism. 300 (4): E650–E660. doi:10.1152/ajpendo.00440.2010. PMC 6189634. PMID 21266670.
- ^ Bauer ER, Daxenberger A, Petri T, Sauerwein H, Meyer HH (December 2000). "Characterisation of the affinity of different anabolics and synthetic hormones to the human androgen receptor, human sex hormone binding globulin and to the bovine progestin receptor". APMIS. 108 (12): 838–846. doi:10.1111/j.1600-0463.2000.tb00007.x. PMID 11252818. S2CID 22776408.
- ^ Bachman E, Travison TG, Basaria S, Davda MN, Guo W, Li M, et al. (June 2014). "Testosterone induces erythrocytosis via increased erythropoietin and suppressed hepcidin: evidence for a new erythropoietin/hemoglobin set point". The Journals of Gerontology. Series A, Biological Sciences and Medical Sciences. 69 (6): 725–735. doi:10.1093/gerona/glt154. PMC 4022090. PMID 24158761.
- ^ a b Donner DG, Beck BR, Bulmer AC, Lam AK, Du Toit EF (February 2015). "Improvements in body composition, cardiometabolic risk factors and insulin sensitivity with trenbolone in normogonadic rats". Steroids. 94: 60–69. doi:10.1016/j.steroids.2014.12.017. hdl:10072/156381. PMID 25554582.
- ^ Donner DG, Elliott GE, Beck BR, Bulmer AC, Lam AK, Headrick JP, et al. (2016). "Endocrinology". academic.oup.com. 157 (1): 368–381. doi:10.1210/en.2015-1603. PMID 26584015. Retrieved 2024-03-17.
- ^ a b Yarrow JF, Conover CF, McCoy SC, Lipinska JA, Santillana CA, Hance JM, et al. (April 2011). "17β-Hydroxyestra-4,9,11-trien-3-one (trenbolone) exhibits tissue selective anabolic activity: effects on muscle, bone, adiposity, hemoglobin, and prostate". American Journal of Physiology. Endocrinology and Metabolism. 300 (4): E650–E660. doi:10.1152/ajpendo.00440.2010. PMC 6189634. PMID 21266670.
- ^ Scanes CG (2018). "Impact of Agricultural Animals on the Environment". Animals and Human Society. Elsevier. pp. 427–449. doi:10.1016/b978-0-12-805247-1.00025-3. ISBN 978-0-12-805247-1.
- ^ "17β-Trenbolone". Molecule of the Week. American Chemical Society. 31 December 2013. Retrieved 2024-03-18.
- ^ "Is It Legal To Buy Tren?". Lex Digest. 2023-07-26. Retrieved 2024-03-18.
- ^ "Steroids Fast Facts". www.justice.gov. Retrieved 2024-03-18.
- ^ "Anabolic steroids". Healthdirect Australia. 2024-03-06. Retrieved 2024-03-18.
- ^ "Drugs penalties". GOV.UK. Retrieved 2024-03-18.
- ^ "The Prohibited List". World Anti Doping Agency. Retrieved 2024-03-18.
Further reading
[edit]- Yarrow JF, McCoy SC, Borst SE (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): 377–89. doi:10.1016/j.steroids.2010.01.019. PMID 20138077. S2CID 205253265.
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