Mebolazine

Mebolazine (INN; brand names Dostalon and Roxilon; also known as dimethazine, dymethazine, di(methasterone) azine, or 2α,17α-dimethyl-5α-androstan-17β-ol-3-one azine) is a synthetic, orally active androgen/anabolic steroid (AAS) and a 17α-alkylated derivative of dihydrotestosterone (DHT) which is no longer marketed.[1][2] It has a unique and unusual chemical structure, being a dimer of methasterone linked at the 3-position of the A-ring by an azine group, and reportedly acts as a prodrug of methasterone.[3]

Mebolazine
Clinical data
Trade namesDostalon, Roxilon
Other namesDimethazine; Dymethazine; Dimethasterone azine; Di(methasterone) azine; 2α,17α-Dimethyl-5α-androstan-17β-ol-3-one azine
Identifiers
IUPAC name
  • (3Z)-3-[(Z)-(17-Hydroxy-2,10,13,17-tetramethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-ylidene)hydrazinylidene]-2,10,13,17-tetramethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC42H68N2O2
Molar mass633.018 g·mol−1
3D model (JSmol)
SMILES
  • C[C@@]23[C@](CC[C@]4([H])[C@@]([H])3CC[C@@]5(C)[C@]([H])4CC[C@@](C)5O)([H])C/C([C@H](C)C2)=N/N=C1[C@H](C)C[C@@]6(C)[C@](CC[C@]7([H])[C@@]([H])6CC[C@@]8(C)[C@]([H])7CC[C@@](C)8O)([H])C/1
InChI
  • InChI=1S/C42H68N2O2/c1-25-23-37(3)27(9-11-29-31(37)13-17-39(5)33(29)15-19-41(39,7)45)21-35(25)43-44-36-22-28-10-12-30-32(38(28,4)24-26(36)2)14-18-40(6)34(30)16-20-42(40,8)46/h25-34,45-46H,9-24H2,1-8H3/b43-35-,44-36-/t25-,26-,27+,28+,29-,30-,31+,32+,33+,34+,37+,38+,39+,40+,41+,42+/m1/s1 N
  • Key:POPWFGNRCCUJGU-QQZDHCPGSA-N N
 NY (what is this?)  (verify)

Since 2008, mebolazine has been used illegally as an ingredient is some dietary supplements,[4] including vitamin B supplements, and in the United States the Food and Drug Administration has taken legal action against such manufacturers.[5][6]

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 756–. ISBN 978-1-4757-2085-3.
  2. Geldof L, Tudela E, Lootens L, van Lysebeth J, Meuleman P, Leroux-Roels G, van Eenoo P, Deventer K (2016). "In vitro and in vivo metabolism studies of dimethazine". Biomed. Chromatogr. 30 (8): 1202–9. doi:10.1002/bmc.3668. PMID 26663462.
  3. Clemens, Roger; Pressman, Peter (2015). "Nutritional and Dietary Supplements: Code or Concern". Preventive Nutrition: 47–62. doi:10.1007/978-3-319-22431-2_3. ISBN 978-3-319-22430-5.
  4. Rahnema, C. D.; Crosnoe, L. E.; Kim, E. D. (2015). "Designer steroids - over-the-counter supplements and their androgenic component: Review of an increasing problem". Andrology. 3 (2): 150–5. doi:10.1111/andr.307. PMID 25684733. S2CID 6999218.
  5. See, for example: "FDA Warns Consumers About Health Risks With Healthy Life Chemistry Dietary Supplement". Food and Drug Administration.
  6. "Criminal Investigations (2011) Dietary Supplements Manufacturer Sentenced". Department of Justice.


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