Trenbolone

Last updated

Trenbolone
Trenbolone.svg
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.com International Drug Names
License data
Pregnancy
category
  • X
Routes of
administration 		Intramuscular injection (as esters)
Drug class Androgen; Anabolic steroid; Progestogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Bioavailability Intramuscular: 80-100%[ citation needed ]
Metabolism Liver
Elimination half-life 6–8 hours[ citation needed ]
Excretion Urine
Identifiers
  • (8S,13S,14S,17S)-17-Hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.127.177 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H22O2
Molar mass 270.372 g·mol−1
3D model (JSmol)
  • O=C4\C=C2/C(=C1/C=C\[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)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 Yes check.svgY
  • Key:MEHHPFQKXOUFFV-OWSLCNJRSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

A vial of injectable trenbolone acetate. A vial of injectable Trenbolone..jpg
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

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 or 5α-reductase into estrogenic compounds, or into 5α-reduced androgenic compounds, respectively. [15] [16]

The potency of Trenbolone is not known, although it's often falsely believed to be five times high as that of 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 literature, is usually done in rats, which makes the 500/100 potency number inaccurate. Rats respond differently to androgens 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, which makes it unclear as to how large the relative potency actually is. [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

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] Trenbolone.svg Trenbolone acetate.svg Trenbolone enanthate.svg Trenbolone cyclohexylmethylcarbonate.svg
FormulaC18H22O2C20H24O3C25H34O3C26H34O4
Crystal system [25] monocrystalicmonocrystalicmonocrystalic
Elimination half life48–72 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 INN Tooltip International Nonproprietary Name and BAN Tooltip 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

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

See also

Related Research Articles

<span class="mw-page-title-main">Tetrahydrogestrinone</span> Synthetic and orally active anabolic–androgenic steroid (AAS)

Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profile athletes such as Barry Bonds and Dwain Chambers.

<span class="mw-page-title-main">Nandrolone</span> Androgenic Anabolic steroid

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are now used by oral administration or instead are given by injection into muscle or fat.

<span class="mw-page-title-main">Nandrolone decanoate</span> Anabolic steroid

Nandrolone decanoate, sold under the brand names Rolon and Deca-Durabolin, among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in menopausal women. It is given by injection into muscle or fat once every one to four weeks.

<span class="mw-page-title-main">Testosterone enanthate</span> Chemical compound

Testosterone enanthate is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It is also used in hormone therapy for women and transsexual men. It is given by injection into muscle or subcutaneously usually once every one to four weeks.

<span class="mw-page-title-main">Metenolone enanthate</span> Chemical compound

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<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

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<span class="mw-page-title-main">Trenbolone acetate</span> Chemical compound

Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle growth in cattle. It is given by injection into muscle.

<span class="mw-page-title-main">Metribolone</span> Chemical compound

Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.

<span class="mw-page-title-main">Anabolic steroid</span> Class of drugs

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<span class="mw-page-title-main">Trenbolone enanthate</span> Chemical compound

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<span class="mw-page-title-main">Nandrolone phenylpropionate</span> Anabolic steroid

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<span class="mw-page-title-main">Trimethyltrienolone</span> Chemical compound

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<span class="mw-page-title-main">Dimethyltrienolone</span> Anabolic–androgenic steroid

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<span class="mw-page-title-main">Trenbolone hexahydrobenzylcarbonate</span> Chemical compound

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<span class="mw-page-title-main">Metenolone acetate</span> Chemical compound

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.

<span class="mw-page-title-main">Trenbolone undecanoate</span> Chemical compound

Trenbolone undecanoate, or trenbolone undecylate, is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was never marketed. It is the C17β undecanoate (undecylate) ester and a long-acting prodrug of trenbolone. The drug was described by Roussel Uclaf in 1967 and was the first long-lasting ester of trenbolone to be developed. Subsequently, trenbolone hexahydrobenzylcarbonate, a roughly equivalent compound, was developed and introduced for use in humans in 1980, though it was discontinued in 1997. Trenbolone enanthate is another long-lasting ester of trenbolone. Similarly to trenbolone undecanoate, it was never marketed, but it has been sold on the black market as a designer steroid for bodybuilders and athletes.

<span class="mw-page-title-main">Trendione</span> Chemical compound

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References

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