(1S,2S,7S,10R,11S,14S,15S)-2,14,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadec-4-en-14-ol

• ChemBase ID: 172467
• Molecular Formular: C20H32O
• Molecular Mass: 288.46748
• Monoisotopic Mass: 288.24531564
• SMILES: C1=CC[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C)C)C
• Canonical SMILES: C[C@]12CC=CC[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C)O)C
• InChI: InChI=1S/C20H32O/c1-18-11-5-4-6-14(18)7-8-15-16(18)9-12-19(2)17(15)10-13-20(19,3)21/h4-5,14-17,21H,6-13H2,1-3H3/t14-,15-,16+,17+,18+,19+,20+/m1/s1
• InChIKey: FRVHJVATKMIOPQ-PAPWGAKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7S,10R,11S,14S,15S)-2,14,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-4-en-14-ol
• IUPAC Traditional name: desoxymethyltestosterone
• Synonyms: (5α,17β)-17-Μethylandrost-2-en-17-ol; 17-Methyl-5α-androst-2-en-17β-ol; 17α-Methylandrost-2-en-17β-ol; Ba 2665; Desoxymethyltesterone; Madol; NSC 63329; SC 11977; Madol

Database IDs

• CAS Number: 3275-64-7
• PubChem SID: 164228377
• PubChem CID: 18651

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.50913
• LogD (pH = 7.4): 4.5091305
• Log P: 4.5091305
• Molar Refractivity: 88.7165 cm^3
• Polarizability: 35.055073 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 144-146°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M108000

It is an anabolic steroid recently identified to be misused as a doping agent. The potency of Madol (DMT) to transactivate androgen receptor (AR) dependent reporter gene expression was two times lower as compared to dihydrotestosterone (DHT).

REFERENCES

• Zierau, O., et al.: Planta Med., 69, 856 (2003)
• Takahashi, M., et al.: Endocr. J., 51, 425 (2003)
• Labrie, F., et al.: J. Endocrinol., 184, 427 (2003)
• Friedel, A., et al.: Toxicol. Lett., 164, 16 (2003)