Desoxymethyltestosterone

Desoxymethyltestosterone

Clinical data
Pregnancy category	X
Routes of administration	Oral
ATC code	None
Legal status
Legal status	UK: Class C US: Schedule III
Identifiers
IUPAC name (5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
Synonyms	Desoxymethyltestosterone; Madol; Pheraplex; 17α-Methyl-5α-androst-2-en-17β-ol; NSC-63329; SC-11977
CAS Number	3275-64-7 Y
PubChem CID	18651
ChemSpider	17611 Y
Chemical and physical data
Formula	C20H32O
Molar mass	288.46748 g/mol
3D model (Jmol)	Interactive image
SMILES O[C@@]4([C@@]2([C@H]([C@@H]1CC[C@@H]3[C@]([C@H]1CC2)(C)C\C=C/C3)CC4)C)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 Y Key:FRVHJVATKMIOPQ-PAPWGAKMSA-N Y

Desoxymethyltestosterone (nicknames Madol, Pheraplex), also known as 3-deketo-17α-methyl-4,5α-dihydro-δ²-testosterone or as 17α-methyl-5α-androst-2-en-17β-ol, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a 17α-methylated derivative of dihydrotestosterone (DHT). It was one of the first designer steroids to be marketed as a performance-enhancing drug to athletes and bodybuilders.

Desoxymethyltestosterone is sometimes abbreviated as DMT, though it should not be confused with the hallucinogen dimethyltryptamine, which is also known by the same acronym.

In animal studies, desoxymethyltestosterone has been found to bind to the androgen receptor (AR) about as half as strongly as DHT, and caused side effects that are typical of 17α-alkylated AAS, such as liver damage when taken in higher dosages as well as left ventricular hypertrophy.

Desoxymethyltestosterone is unusual in that it is structurally a 2-ene compound, lacking the 3-keto group present in almost all commercial AAS (with ethylestrenol being a notable and one of the few exceptions). This does not mean it is a weak compound, and clinical research has determined that it is a fairly potent oral agent. Rat studies indicate that desoxymethyltestosterone has an anabolic effect 160% that of testosterone while being only 60% as androgenic, giving it a Q ratio of 6.5:1. Because of this favorable ratio, experiments in orchiectomized rats have demonstrated that treatment with desoxymethyltestosterone resulted only in a stimulation of the weight of the levator ani muscle; the prostate and seminal vesicle weights remained unaffected leading the authors of one study to characterize desoxymethyltestosterone as a powerful AAS with attributes of a selective androgen receptor modulator (SARM) and some indication of toxicity.