Drostanolone

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Drostanolone
Clinical data
Trade namesDrolban, Masteril, Masteron, others (all as drostanolone propionate)
Other namesDromostanolone; 2α-Methyl-4,5α-dihydrotestosterone; 2α-Methyl-DHT; 2α-Methyl-5α-androstan-17β-ol-3-one
Routes of
administration		Intramuscular injection (as drostanolone propionate)
Drug classAndrogen; Anabolic steroid
Legal status
Legal status
Identifiers
  • (2R,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy- 2,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17- tetradecahydrocyclopenta[a]phenanthren-3-one
JSmol)
  • C[C@@H]1C[C@]2([C@@H](CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)CC1=O)C
  • InChI=1S/C20H32O2/c1-12-11-20(3)13(10-17(12)21)4-5-14-15-6-7-18(22)19(15,2)9-8-16(14)20/h12-16,18,22H,4-11H2,1-3H3/t12-,13+,14+,15+,16+,18+,19+,20+/m1/s1 ☒N
  • Key:IKXILDNPCZPPRV-RFMGOVQKSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Drostanolone, or dromostanolone, is an

physique- or performance-enhancing purposes.[4]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

Like other AAS, drostanolone is an

17α-alkylated, it is not known to cause hepatotoxicity.[4]

Chemistry

See also:
List of androgens/anabolic steroids

Drostanolone, also known as 2α-methyl-5α-dihydrotestosterone (2α-methyl-DHT) or as 2α-methyl-5α-androstan-17β-ol-3-one, is a

derivative of DHT.[2][3][4] It is specifically DHT with a methyl group at the C2α position.[2][3][4]

History

Drostanolone and its ester drostanolone propionate were first described in 1959.[4][6] Drostanolone propionate was first introduced for medical use in 1961.[7]

Society and culture

Generic names

Drostanolone is the

INNTooltip International Nonproprietary Name, BANTooltip British Approved Name, and DCFTooltip Dénomination Commune Française.[2][3] It has also been referred to as dromostanolone.[2][3]

Legal status

Drostanolone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[8]

Potential side effects

Like other AAS, drostanolone can cause a variety of side effects, including:

  • Virilization: This refers to the development of masculine characteristics in women, such as deepening of the voice, increased body hair growth, and clitoral enlargement.
  • Acne: AAS can increase sebum production, leading to acne.
  • Hair loss: Drostanolone can accelerate male pattern baldness.
  • Cardiovascular issues: AAS can negatively affect cholesterol levels and increase the risk of cardiovascular disease.
  • Liver damage: Although drostanolone is not 17α-alkylated, high doses or prolonged use can still potentially damage the liver.
  • Mood swings: AAS can cause aggression, irritability, and mood swings.

Non-medical uses

Drostanolone is used by some bodybuilders and athletes to increase muscle mass and strength. It is often used during "cutting cycles" to help preserve muscle mass while losing body fat. However, the use of AAS for non-medical purposes is not recommended due to the potential for serious side effects.

Synthesis

Bolazine is when react 2 eq. with hydrazine to give dimer

Thieme Synthesis:[9][10][11][12][13]

Treatment of DHT (androstan-17β-ol-3-one, stanolone) [521-18-6] (1) with methyl formate and the strong base sodium methoxide gives [4033-95-8] (2). The newly added formyl function in the product is shown in the enol form. Catalytic hydrogenation reduces that function to a methyl group (3). The addition of hydrogen from the bottom face of the molecule leads to the formation of β-methyl isomer where the methyl group occupies the higher-energy axial position. Strong base-induced equilibration of the methyl group leads to the formation of the sterically favoured equatorial α-methyl isomer, affording dromostanolone (4).

References

  1. ^ 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.
  2. ^
    ISBN 978-1-4757-2085-3
    .
  3. ^
    ISBN 978-3-88763-075-1
    .
  4. ^
    ISBN 978-0-9828280-1-4
    .
  5. PMID 1242823
    .
  6. ISSN 0002-7863
    .
  7. ISBN 978-0-8155-1856-3
    .
  8. ISBN 978-1-4200-0346-8
    .
  9. doi:10.1021/ja01511a040
    .
  10. ^ Volovel'skii, L.N. et al, Zh. Obschch. Khim., 1966, 46, 1772.
  11. ^ US 2908693, Ringold HJ, Rosenkranz G, issued 1959, assigned to Syntex SA 
  12. ^ US 3118915, Ringold HJ, Rosenkranz G, issued 1964, assigned to Roche Palo Alto LLC 
  13. ^ GB 1005896  US 3249627, issued 1966, assigned to Ormonoterapia Richter Spa 

External links

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