Chemistry:Trenbolone enanthate

Short description: Chemical compound

Trenbolone enanthate

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
Legal status
Legal status	UK: Class C US: Schedule III
Identifiers
IUPAC name [(8S,13S,14S,17S)-13-Methyl-3-oxo-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl] heptanoate
CAS Number	1629618-98-9
PubChem CID	20112041
ChemSpider	16788271
UNII	FF02TM6THR
Chemical and physical data
Formula	C25H34O3
Molar mass	382.544 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(C=CC3=C4CCC(=O)C=C4CC[C@@H]23)C
InChI InChI=1S/C25H34O3/c1-3-4-5-6-7-24(27)28-23-13-12-22-21-10-8-17-16-18(26)9-11-19(17)20(21)14-15-25(22,23)2/h14-16,21-23H,3-13H2,1-2H3/t21-,22+,23+,25+/m1/s1 Key:HGSFRISGULOJBX-FVEXOFTDSA-N

Trenbolone enanthate 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 black market for use by bodybuilders and athletes under the name Trenabol.

Side effects

As trenbolone enanthate is a rather potent AAS, it has several potential side effects:

Psychological

Anabolic-androgenic steroid (AAS) users report significant psychological changes. AAS-induced fluctuations in testosterone, affect the brain's structure and function, potentially leading to mood disorders and aggressive behavior. Trenbolone enanthate users have reported significant psychological changes, including increased aggression, mood instability, and impaired social interactions. Prolonged use of AAS may also lead to psychological dependence, with approximately 1/3 of users experiencing withdrawal symptoms upon cessation.

Reproductive health

Anabolic-androgenic steroids 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. 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.

Androgenic

Trenbolone enanthate can include several androgenic side effects such as increased body hair growth, acne, and potential baldness in predisposed individuals.

Gynecomastia

Gynecomastia is a condition that enlarges the breast tissue in males which is often produced as a side effect from the use of AAS. 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. While Trenbolone enanthate is known for not aromatizing into estrogen, trenbolone exhibits high progestogenic activity which is one of three natural developments of breast tissue in males, also leading to gynecomastia.

Primary uses

Bodybuilding

Trenbolone enanthate is renowned for its capacity to promote significant muscle growth and strength gain. Its anabolic effects facilitate increased protein synthesis and hydrogen retention in muscle tissue. 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. The compound is also often employed for its fat-burning properties. It enhances the metabolic rate and promotes the conversion of fat into energy, contributing to leaner muscle development during cutting cycles in body building.

Enhanced recovery

Trenbolone enanthate is a potential treatment for muscle and bone loss without adverse effects commonly associated with testosterone, such as prostate growth or polycythemia. 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.

Veterinary uses

In the veterinary field, Trenbolone acetate has a history of use for increasing muscle mass in livestock. Trenbolone enanthate however has never been approved for veterinary use. The application of Trenbolone acetate is aimed at improving the lean muscle yield in animals prior to slaughter, enhancing the quality of meat production.

History

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; 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.

Legality

Trenbolone enanthate has never had regulatory approval for human use from any single health agency. It is commonly considered a controlled substance and use is generally illegal. For example, in the United States, the Drug Enforcement Administration (DEA) considers trenbolone esters Schedule III controlled substances similar to the likes of Australia wherein possession of trenbolone esters is a criminal offence. However, this compound is considered a class C drug with no penalty for personal use or possession in the United Kingdom or Canada. Sporting organizations, including the World Anti Doping Agency (WADA), closely monitor the use of such substances, especially in competitive events like the Olympics.

See also

• List of androgen esters § Trenbolone esters

Further reading

• "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. 2010. doi:10.1016/j.steroids.2010.01.019. PMID 20138077. 

{{Navbox

| name = Androgens and antiandrogens
| title = Androgens and antiandrogens
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| listclass = hlist
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| group1 = Androgens
(incl. AAS)

| list1 =

AR agonists

Testosterone derivatives: Androstenediol dipropionate Boldenone undecylenate Clostebol Clostebol acetate Clostebol caproate Clostebol propionate Cloxotestosterone acetate Prasterone (dehydroepiandrosterone, DHEA) Prasterone enanthate (DHEA enanthate) Prasterone sulfate (DHEA sulfate) Quinbolone Testosterone# Testosterone esters (e.g., testosterone cypionate, testosterone enanthate]], testosterone propionate]], testosterone undecanoate]], testosterone ester mixture]]s (Deposterona, Omnadren, Sustanon, Testoviron Depot)) Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT) Androstanolone esters Bolazine capronate Drostanolone propionate (dromostanolone propionate) Epitiostanol Mepitiostane Mesterolone Metenolone acetate (methenolone acetate) Metenolone enanthate (methenolone enanthate) Stenbolone acetate 19-Nortestosterone derivatives: Bolandiol dipropionate Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norclostebol Norclostebol acetate Oxabolone cipionate (oxabolone cypionate) Trenbolone acetate Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate) 17α-Alkylated testosterone derivatives: Bolasterone Calusterone Chlorodehydromethyltestosterone (CDMT) Fluoxymesterone Formebolone Metandienone (methandienone, methandrostenolone) Methandriol (methylandrostenediol) Methandriol bisenanthoyl acetate Methandriol dipropionate Methandriol propionate Methyltestosterone Methyltestosterone 3-hexyl ether Oxymesterone Penmesterol Tiomesterone (thiomesterone) 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole Furazabol Mebolazine (dimethazine) Mestanolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol Mibolerone Norethandrolone Normethandrone (methylestrenolone, normethisterone) Propetandrol (propethandrol) 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone) 17α-Ethynyltestosterone derivatives: Danazol Gestrinone Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), [[Chemistry:Lynestrlynestrenol, Norgestrienone|norgestrienone]]) Tibolone Progesterone derivatives: Medroxyprogesterone acetate

Progonadotropins

Antiestrogens (e.g., tamoxifen, Chemistry:Clomifene

| group2 = Antiandrogens
| list2 = {{Navbox|child
| groupstyle = text-align:center;
| groupwidth = 9em;

  | group1 = AR antagonists
  | list1 =

• Steroidal: Abiraterone acetate
• Canrenone
• Chlormadinone acetate
• Cyproterone acetate
• Delmadinone acetate
• Dienogest
• Drospirenone
• Medrogestone
• Megestrol acetate
• Nomegestrol acetate
• Osaterone acetate
• Oxendolone
• Potassium canrenoate
• Spironolactone

• Nonsteroidal: Apalutamide
• Bicalutamide
• Cimetidine
• Darolutamide
• Enzalutamide
• Flutamide
• Ketoconazole
• Nilutamide
• Seviteronel^†
• Topilutamide (fluridil)

  | group2 = Steroidogenesis
inhibitors

| list2 =

5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel† Spironolactone

  | group3 = Antigonadotropins
  | list3 =

• D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
• Estrogens (e.g., bifluranol, [[diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
• GnRH agonists (e.g., leuprorelin)
• GnRH antagonists (e.g., cetrorelix)
• Progestogens (incl., chlormadinone acetate, [[cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

  | group4 = Others
  | list4 =

• Androstenedione immunogens: Androvax (androstenedione albumin)
• Ovandrotone albumin (Fecundin)

}}

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| list3 =

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

See also

Androgen receptor modulators

Estrogens and antiestrogens

Progestogens and antiprogestogens

List of androgens/anabolic steroids

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