Methyldiazinol

Methyldiazinol
Clinical data
Other names	Methyldiazirinol; 3,3-Azo-17α-methyl-5α-dihydrotestosterone; 3,3-Azo-17α-methyl-DHT; 3,3-Azo-17α-methyl-5α-androstan-17β-ol; 3-Azi-17α-methyl-5α-androstan-17β-ol
Routes of; administration	By mouth
Drug class	Androgen; Anabolic steroid
Identifiers
	IUPAC name (5S,8R,9S,10S,13S,14S,17S)-10,13,17-Trimethylspiro[2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,3'-diazirine]-17-ol;
CAS Number	2429-17-6;
PubChem CID	112500385;
ChemSpider	52084890;
UNII	7AA03AP597;
CompTox Dashboard (EPA)	DTXSID201189902 ;
Chemical and physical data
Formula	C20H32N2O
Molar mass	316.489 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CCC3(C[C@@H]1CC[C@@H]4[C@@H]2CC[C@]5([C@H]4CC[C@]5(C)O)C)N=N3;
	InChI InChI=LMNFACKYKJIJHJ-PHFHYRSDSA-N; Key:1S/C20H32N2O/c1-17-10-11-20(21-22-20)12-13(17)4-5-14-15(17)6-8-18(2)16(14)7-9-19(18,3)23/h13-16,23H,4-12H2,1-3H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1;

Methyldiazinol (also known as 3,3-azo-17α-methyl-5α-dihydrotestosterone, 3-azi-17α-methyl-DHT, or 3,3-azo-17α-methyl-5α-androstan-17β-ol) is a synthetic and orally active androgen/anabolic steroid (AAS) which was never marketed.^[1]^[2] It is a 17α-methylated derivative of dihydrotestosterone (DHT); specifically, it is the C3 azi (i.e., 3,3-azo) analogue of mestanolone (17α-methyl-DHT).^[1]^[2] The drug has been found to possess a high ratio and dissociation of myotrophic to androgenic activity; relative to methyltestosterone, its ratio was 15 (3:0.2), among the highest observed.^[1]^[2]

References

^ ^a ^b ^c Kochakian CD (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. p. 385. ISBN 978-3-642-66353-6. Methyldiazinol: 3-Azi-17-methyl-5α-androstan-17β-ol: The 3-azi derivative of methandrostanolone was noted by CHURCH et al. (1965) to have a wide myotrophic:androgenic dissociation (3: 0.2) 15 relative to methyltestosterone orally, among the highest noted.
^ ^a ^b ^c Church RF, Kende AS, Weiss MJ (1965). "Diazirines. I. Some Observations on the Scope of the Ammonia-Hydroxylamine-O-sulfonic Acid Diaziridine Synthesis. The Preparation of Certain Steroid Diaziridines and Diazirines". Journal of the American Chemical Society. 87 (12): 2665–2671. doi:10.1021/ja01090a025. ISSN 0002-7863.

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Clinical data

Other names	Methyldiazirinol; 3,3-Azo-17α-methyl-5α-dihydrotestosterone; 3,3-Azo-17α-methyl-DHT; 3,3-Azo-17α-methyl-5α-androstan-17β-ol; 3-Azi-17α-methyl-5α-androstan-17β-ol
Routes of administration	By mouth
Drug class	Androgen; Anabolic steroid
Identifiers
IUPAC name (5S,8R,9S,10S,13S,14S,17S)-10,13,17-Trimethylspiro[2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,3'-diazirine]-17-ol
CAS Number	2429-17-6
PubChem CID	112500385
ChemSpider	52084890
UNII	7AA03AP597
CompTox Dashboard (EPA)	DTXSID201189902
Chemical and physical data
Formula	C₂₀H₃₂N₂O
Molar mass	316.489 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CCC3(C[C@@H]1CC[C@@H]4[C@@H]2CC[C@]5([C@H]4CC[C@]5(C)O)C)N=N3
InChI InChI=LMNFACKYKJIJHJ-PHFHYRSDSA-N Key:1S/C20H32N2O/c1-17-10-11-20(21-22-20)12-13(17)4-5-14-15(17)6-8-18(2)16(14)7-9-19(18,3)23/h13-16,23H,4-12H2,1-3H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1