Metandienone

Structural formula
General
Non-proprietary name	Metandienone
other names	17 β - hydroxy -17 α -methylandrosta-1,4-dien-3-one
Molecular formula	C 20 H 28 O 2
External identifiers / databases
EC number	200-787-2
ECHA InfoCard	100,000,716
PubChem	6300
ChemSpider	6061
DrugBank	DB13586
Wikidata	Q417194
Drug information
ATC code	A14 AA03
Drug class	Steroid , anabolic
properties
Molar mass	300.44 g · mol -1
Physical state	firmly
Melting point	165 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	425 mg kg −1 ( LD 50 , rat , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Metandienone , also known as methandrostenolone, is an anabolic steroid and has been one of the most commonly abused anabolic steroids for years .

history

It was first synthesized in 1955 by the American doctor John Ziegler. He sold the rights in 1956 to Ciba-Geigy (Basel), who sold the preparation under the trade name Dianabol ^® from 1960 . Because of the side effects, Ciba withdrew Dianabol from the market in 1982. Metandienone is also no longer on the market in Germany . The drug is still available in Poland (trade name: Metanabol ^® ) and Romania (trade name: Naposim ^® ).

pharmacology

Metandienone is a 17 α -alkylated steroid due to its methylation . This alkylation means that metandienone is only subject to a slight first-pass effect , i.e. it can be taken orally . At the same time, it has a lower affinity both for androgen receptors and for sex hormone binding globulin (SHGB). Since only free androgens that are not bound to SHGB are effective, metandienone is significantly more active than testosterone . On the other hand, it aromatizes more easily to the corresponding estrogen .

Side effects

In addition to the anabolic effect, side effects include high blood pressure , acne , alopecia (hair loss on the head) and - in the course of aromatization as estrogen-related side effects - gynecomastia (formation of a female breast in men), an increase in subcutaneous fat and water retention in the tissue. Furthermore, especially in men, there are disorders of the gonadal control circuit, ie an impairment of hormone and sperm production and as a result temporary infertility. With prolonged use of metandienone - as with the use of other 17α-alkylated steroids - liver damage is to be expected.

Individual evidence

↑ ^a ^b ^c ^d Data sheet 17β-Hydroxy-17-methylandrosta-1,4-dien-3-one from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
↑ Werner Franke , Udo Ludwig : The betrayed sport . Munich 2007, ISBN 978-3-89883-185-7 , p. 29.
^ Andreas Singler, Gerhard Treutlein: Doping in top sport. Sports science analyzes of national and international performance development . Aachen 2007, ISBN 978-3-89899-192-6 , p. 183.
↑ Werner Franke , Udo Ludwig: The betrayed sport . Munich 2007, ISBN 978-3-89883-185-7 , p. 30.
↑ ABDA database (as of December 6, 2009).

[sigma-1] Data sheet 17β-Hydroxy-17-methylandrosta-1,4-dien-3-one from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).

[2] Werner Franke , Udo Ludwig : The betrayed sport . Munich 2007, ISBN 978-3-89883-185-7 , p. 29.

[3] Andreas Singler, Gerhard Treutlein: Doping in top sport. Sports science analyzes of national and international performance development . Aachen 2007, ISBN 978-3-89899-192-6 , p. 183.

[4] Werner Franke , Udo Ludwig: The betrayed sport . Munich 2007, ISBN 978-3-89883-185-7 , p. 30.

[5] ABDA database (as of December 6, 2009).