Methyltestosterone

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Methyltestosterone
Methyltestosterone.svg
Systematic (IUPAC) name
17b-hydroxy-17a-methylandrost-4-ene-3-one
Clinical data
Trade names Virilon
AHFS/Drugs.com monograph
Legal status Schedule III (US)
Routes oral
Pharmacokinetic data
Metabolism Liver
Half-life 6-8 hours
Excretion 90% urine / 10% feces
Identifiers
CAS number 58-18-4 YesY
ATC code G03BA02
PubChem CID 6010
DrugBank DB06710
ChemSpider 5788 YesY
UNII V9EFU16ZIF YesY
ChEBI CHEBI:27436 N
ChEMBL CHEMBL1395 YesY
Chemical data
Formula C20H30O2 
Mol. mass 302.451
 N (what is this?)  (verify)

Methyltestosterone (brand names:[1] Android, Testred, Virilon) is a 17-alpha-alkylated anabolic steroid used to treat men with a testosterone deficiency.[2] It bears close structural similarity to testosterone, but has a methyl group at C17 in order to increase oral bioavailability.

Confiscated methyltestosterone.

Synthesis[edit]

Preparation of methyltestosterone.

Reaction of DHEA (androstenolone) with methylmagnesium bromide to produce methandriol from addition to the α face. Reaction of methandriol with aluminum isopropoxide in the presence of cyclohexanone (Oppenauer oxidation) oxidizes the alcohol at position 3; the double bond shifts into conjugation.[3]

Chromium trioxide can also be used to do the oxidation step.[4][5][6]

References[edit]

  1. ^ "Methyltestosterone Oral : Uses, Side Effects, Interactions, Pictures, Warnings & Dosing". WebMD. Retrieved 2012-02-13. 
  2. ^ "Truestar health". 
  3. ^ Ruzicka, L. (1935). "Sexualhormone X. Herstellung des 17-Methyl-testosterons und anderer Androsten- und Androstanderivate. Zusammenh�nge zwischen chemischer Konstitution und m�nnlicher Hormonwirkung". Helvetica Chimica Acta 18 (1): 1487–1498. doi:10.1002/hlca.193501801203.  edit
  4. ^ L. Ruzicka, A. Wettstein, U.S. Patent 2,143,453 (1939).
  5. ^ 8. K. Miescher, A. Wettstein, U.S. Patent 2,374,369 (1945).
  6. ^ K. Miescher, A. Wettstein, U.S. Patent 2,374,370 (1945).