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Mebolazine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
  • (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
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC42H68N2O2
Molar mass633.018 g·mol−1
3D model (JSmol)
  • 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=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
 ☒NcheckY (what is this?)  (verify)

Mebolazine (INNTooltip International Nonproprietary Name; brand namesDostalon andRoxilon; also known asdimethazine,dymethazine,di(methasterone) azine, or2α,17α-dimethyl-5α-androstan-17β-ol-3-one azine) is asynthetic,orally activeandrogen/anabolic steroid (AAS) and a17α-alkylatedderivative ofdihydrotestosterone (DHT) which is no longer marketed.[1][2] It has a unique and unusualchemical structure, being adimer ofmethasterone linked at the 3-position of the A-ring by anazinegroup, and reportedly acts as aprodrug of methasterone.[3]

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

See also

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References

[edit]
  1. ^Elks J (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, et al. (August 2016). "In vitro and in vivo metabolism studies of dimethazine".Biomedical Chromatography.30 (8):1202–1209.doi:10.1002/bmc.3668.PMID 26663462.
  3. ^Clemens R, Pressman P (2015). "Nutritional and Dietary Supplements: Code or Concern".Preventive Nutrition. Nutrition and Health. pp. 47–62.doi:10.1007/978-3-319-22431-2_3.ISBN 978-3-319-22430-5.
  4. ^Rahnema CD, Crosnoe LE, Kim ED (March 2015)."Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem".Andrology.3 (2):150–155.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. Archived fromthe original on July 29, 2013.
  6. ^"Criminal Investigations (2011) Dietary Supplements Manufacturer Sentenced". Department of Justice. Archived fromthe original on May 13, 2011.
Androgens
(incl.AASTooltip anabolic–androgenic steroid)
ARTooltip Androgen receptoragonists
Progonadotropins
Antiandrogens
ARTooltip Androgen receptorantagonists
Steroidogenesis
inhibitors
5α-Reductase
Others
Antigonadotropins
Others
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
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