Trenbolone

In this article we are going to delve into the topic of Trenbolone. Trenbolone is a topic that has generated great interest in various areas of society, from politics to science. Throughout history, Trenbolone has been the subject of multiple research and debate, leading to greater understanding and knowledge on the topic. In this article we will explore different perspectives and approaches related to Trenbolone, as well as its impact on today's society. From its origin to its future implications, Trenbolone is a highly relevant topic that deserves to be analyzed in depth.

Not to be confused with Trestolone.

Trenbolone
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.comInternational Drug Names
License data
Pregnancy
category
  • X
Routes of
administration		Intramuscular injection (as esters)
Drug classAndrogen; Anabolic steroid; Progestogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
BioavailabilityIntramuscular: 80-100%[citation needed]
MetabolismLiver
Elimination half-life6–8 hours[citation needed]
ExcretionUrine
Identifiers
  • (8S,13S,14S,17S)-17-Hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1H-cyclopentaphenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.127.177 Edit this at Wikidata
Chemical and physical data
FormulaC18H22O2
Molar mass270.372 g·mol−1
3D model (JSmol)
  • O=C4\C=C2/C(=C1/C=C\3((O)CC31CC2)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 checkY
  • Key:MEHHPFQKXOUFFV-OWSLCNJRSA-N checkY
 ☒NcheckY (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]

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

See also: Anabolic steroid § Adverse 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.

"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 exist several theories on why this phenomenon happens.[9]

It is possible that the androgenic effect from steroids activates a variety of lipid-like active compounds which are called prostaglandins.[10] 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.).[11] The bradykinin peptide is well known to promote a cough reaction associated with ACE inhibitor medications prescribed for hypertension.[12]

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.[13] 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.[14]

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.[15][16]

The potency of Trenbolone is not known, although it's often falsely believed to be five times higher than testosterone.[17][18] 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.[19][20] Trenbolone also binds with high affinity to the progesterone receptor,[6][21][22][23] and binds to the glucocorticoid receptor as well.[22]

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.[24] This implies that trenbolone leaves the body as beta-glucuronides or sulfates.

Chemistry

See also: List of androgens/anabolic steroids

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][25]

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

(cyclohexylmethylcarbonate)

Structural[25]
Formula C18H22O2 C20H24O3 C25H34O3 C26H34O4
Crystal system[25] monocrystalic monocrystalic monocrystalic
Elimination half life 48–72 hours[citation needed] short

1–2 days;[25] 3 days[26]

long

11 days[25]

8 days[25]

History

Trenbolone was first synthesized in 1963.[27]

Society and culture

Generic names

Trenbolone is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.[2][3][4] It has also been referred to as trienolone or trienbolone or tren.[2][3][4][28]

Some bodybuilders and athletes use trenbolone hexahydrobenzylcarbonate and other esters (acetate, enanthate) for their muscle-building and otherwise performance-enhancing effects.[29][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.[30] Trenbolone is classified as a Schedule 4 drug in Canada[31] and a class C drug with no penalty for personal use or possession in the United Kingdom.[32] Use or possession of steroids without a prescription is a crime in Australia.[33]

Doping in sports

See also: List of doping in sport cases § Trenbolone esters

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

Environmental persistence

Early studies suggested that the metabolites of trenbolone acetate would degrade through phototransformation. However, a 2013 paper found that the endocrine-disrupting metabolites were able to reform at night, resulting in a diurnal cycling of the compounds.[34] The environmental persistence of the steroid metabolites results in the contamination of water supplies and the disruption of aquatic reproductive processes. Due to its nocturnal reformation, researchers have referred to trenbolone as the "vampire steroid".[35][36]

See also

References

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  36. ^ Gravitz L (April 8, 2014). "'Vampire' Steroids Rise After Dark". Discover Magazine.

Further reading