{{Short description|Anabolic steroid}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-10,13,17-Trimethylspiro[2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1''H''-cyclopenta[''a'']phenanthrene-3,3'-diazirine]-17-ol | image = Methyldiazirinol.svg | image_class = skin-invert-image | width = 225px
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth | class = Androgen; Anabolic steroid
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number_Ref = | CAS_number = 2429-17-6 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 112500385 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 52084890 | UNII = 7AA03AP597 | KEGG = | ChEBI = | ChEMBL = | synonyms = 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
<!--Chemical data--> | C=20 | H=32 | N=2 | O=1 | 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 | StdInChI_Ref = | StdInChI = LMNFACKYKJIJHJ-PHFHYRSDSA-N | StdInChIKey_Ref = | StdInChIKey = 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.<ref name="Kochakian2012">{{cite book| vauthors = Kochakian CD |title=Anabolic-Androgenic Steroids|url=https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA385|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-66353-6|page=385|quote=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.}}</ref><ref name="ChurchKende1965">{{cite journal| vauthors = Church RF, Kende AS, Weiss MJ |title=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=Journal of the American Chemical Society|volume=87|issue=12|year=1965|pages=2665–2671|issn=0002-7863|doi=10.1021/ja01090a025|bibcode=1965JAChS..87.2665C }}</ref> 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).<ref name="Kochakian2012" /><ref name="ChurchKende1965" /> 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.<ref name="Kochakian2012" /><ref name="ChurchKende1965" />
== See also == * List of androgens/anabolic steroids
== References == {{Reflist}}
{{Androgen receptor modulators}}
Category:Abandoned drugs Category:Tertiary alcohols Category:Androgens Category:Androstanes Category:Hepatotoxins Category:Diazirines
{{Genito-urinary-drug-stub}} {{Androgen-stub}}