Anabolic steroid
Trenbolone
Other names Trienolone; 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
Routes of administration
Intramuscular injection (as
esters )
Drug class
Androgen ;
Anabolic steroid ;
Progestogen
ATC code
Legal status
Bioavailability
Intramuscular : 80-100%[
citation needed ]
Metabolism
Liver
Elimination half-life 6–8 hours[
citation needed ]
Excretion
Urine
(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
Formula C 18 H 22 O 2
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
Y Key:MEHHPFQKXOUFFV-OWSLCNJRSA-N
Y
N Y
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(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
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.
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.
[9] 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.
[10]
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.
[11]
[12]
Trenbolone has potency five times as high as that of
testosterone .
[6]
[13] Trenbolone also binds with high
affinity to the
progesterone receptor ,
[6]
[13]
[14]
[15] Trenbolone binds to the
glucocorticoid receptor , as well.
[14]
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.
[16] 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]
[17]
History
Trenbolone was first
synthesized in 1963.
[19]
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]
[20]
Legal status
Some
bodybuilders and
athletes use trenbolone hexahydrobenzylcarbonate and other esters (acetate, enanthate) for their muscle-building and otherwise performance-enhancing effects.
[21]
[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 .
[22] Trenbolone is classified as a Schedule 4 drug in
Canada
[23] and a class C drug with no penalty for personal use or possession in the
United Kingdom .
[24] Use or possession of steroids without a prescription is a crime in
Australia .
[25]
Doping in sports
There are known cases of doping in sports with trenbolone esters by
professional
athletes .
See also
References
^
Anvisa (2023-03-31).
"RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
Diário Oficial da União (published 2023-04-04).
Archived from the original on 2023-08-03. Retrieved 2023-08-15 .
^
a
b
c
d
e
f
g
h
i Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer.
ISBN
978-1-4757-2085-3 .
^
a
b
c
d
e
f
g
h
i
Index Nominum 2000: International Drug Directory . Taylor & Francis. January 2000. p. 1591.
ISBN
978-3-88763-075-1 .
^
a
b
c
d
e
f Morton IK, Hall JM (6 December 2012).
Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Science & Business Media. pp. 279–.
ISBN
978-94-011-4439-1 .
^
"Trenbolone" .
^
a
b
c
d
e
f
g
h
i
j
k
l
m Llewellyn W (2011).
Anabolics . Molecular Nutrition Llc. pp. 491–499, 618–, 724–.
ISBN
978-0-9828280-1-4 .
^ Nichols W, Hutcheson J, Streeter M, Corrigan M, Nuttelman B.
"Implant Strategies for Finishing Cattle using Revalor® (trenbolone acetate and estradiol), Finaplix® (trenbolone) and/or Ralgro® (zeranol)" (PDF) . Merck Animal Health.
^ Kicman AT (June 2008).
"Pharmacology of anabolic steroids" . British Journal of Pharmacology . 154 (3): 502–521.
doi :
10.1038/bjp.2008.165 .
PMC
2439524 .
PMID
18500378 .
^ Fahey TD (March 1998).
"Anabolic Steroids: Mechanisms and Effects" . Encyclopedia of sports medicine and science. Internet Society for Sport Science .
^ Wilson VS, Lambright C, Ostby J, Gray LE (December 2002).
"In vitro and in vivo effects of 17beta-trenbolone: a feedlot effluent contaminant" . Toxicological Sciences . 70 (2): 202–211.
doi :
10.1093/toxsci/70.2.202 .
PMID
12441365 .
^ Yarrow JF, McCoy SC, Borst SE (June 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): 377–389.
doi :
10.1016/j.steroids.2010.01.019 .
PMID
20138077 .
S2CID
205253265 .
^ Gettys TW, D'Occhio MJ, Henricks DM, Schanbacher BD (January 1984). "Suppression of LH secretion by oestradiol, dihydrotestosterone and trenbolone acetate in the acutely castrated bull". The Journal of Endocrinology . 100 (1): 107–112.
doi :
10.1677/joe.0.1000107 .
PMID
6361192 .
^
a
b Nicholas Mascie-Taylor CG, Rosetta L (13 January 2011).
Reproduction and Adaptation: Topics in Human Reproductive Ecology . Cambridge University Press. pp. 69–.
ISBN
978-1-139-49430-4 .
^
a
b
APMIS.: Supplementum . Munksgaard. 2001. p. 5339.
ISBN
9788716164575 .
^ McKerns KW (13 March 2013).
Reproductive Processes and Contraception . Springer Science & Business Media. pp. 171–.
ISBN
978-1-4684-3824-6 .
^ Schänzer W (July 1996).
"Metabolism of anabolic androgenic steroids" . Clinical Chemistry . 42 (7): 1001–1020.
doi :
10.1093/clinchem/42.7.1001 .
PMID
8674183 .
^
a
b
c
d
e
f 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 .
S2CID
216299984 .
^ Ruiz P, Strain EC (2011).
Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook . Lippincott Williams & Wilkins.
ISBN
978-1-60547-277-5 .
^ Schänzer W (July 1996).
"Metabolism of anabolic androgenic steroids" . Clinical Chemistry . 42 (7): 1001–1020.
doi :
10.1093/clinchem/42.7.1001 .
PMID
8674183 .
^ Food and Agriculture Organization of the United Nations (1990).
Residues of Some Veterinary Drugs in Animals and Foods: Monographs Prepared by the Thirty-Fourth Meeting of the Joint FAO/WHO Expert Committee on Food Additives, Geneva, 30 January-8 February 1989 . Food & Agriculture Org. pp. 88–.
ISBN
978-92-5-102933-6 .
^
"Trenbolone hexahydrobenzylcarbonate use in bodybuilding" . 20 November 2021.
^
"Controlled Substances Act" . United States Food and Drug Administration. 11 June 2009. Retrieved 17 June 2016 .
^
"Controlled Drugs and Substances Act" . laws-lois.justice.gc.ca . Archived from
the original on 2012-09-15.
^
"Consideration of the Anabolic Steroids" . London: Advisory Council on the Misuse of Drugs. September 2010. Archived from
the original on 2011-09-22.
^
"Australian Institute of Criminology - Steroids" . Archived from
the original on 2012-03-23. Retrieved 2011-08-22 .
Further reading
Androgens (incl.
AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor
antagonists
Steroidogenesis inhibitors
Antigonadotropins
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 ,
medroxyprogesterone acetate ,
megestrol acetate )
Others
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins:
6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g.,
levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g.,
norethisterone acetate ,
norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g.,
nandrolone decanoate ,
nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g.,
trenbolone acetate ,
trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )