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Dimethandrolone
Clinical data
Other names	CDB-1321; Dimethylnandrolone; 7α,11β-Dimethyl-19-nortestosterone; 7α,11β-Dimethylestr-4-en-17β-ol-3-one; 7α,11β-Dimethyl-19-norandrost-4-en-17β-ol-3-one
Routes of; administration	By mouth
Drug class	Androgen; Anabolic steroid; Progestogen
Identifiers
	IUPAC name (7R,8R,9S,10R,11S,13S,14S,17S)-17-hydroxy-7,11,13-trimethyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one;
CAS Number	226066-52-0 ; 366472-45-9 (undecanoate);
PubChem CID	9882863;
ChemSpider	8058538;
UNII	OD742D6TJ9;
CompTox Dashboard (EPA)	DTXSID001046859 ;
Chemical and physical data
Formula	C20H30O2
Molar mass	302.458 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1CC2=CC(=O)CCC2C3C1C4CCC(C4(CC3C)C)O;
	InChI InChI=1S/C20H30O2/c1-11-8-13-9-14(21)4-5-15(13)18-12(2)10-20(3)16(19(11)18)6-7-17(20)22/h9,11-12,15-19,22H,4-8,10H2,1-3H3/t11-,12+,15+,16+,17+,18-,19+,20+/m1/s1; Key:KVIKZOGGZHCGFH-RJMNTABLSA-N;

Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use.^[1]^[2]^[3]

Dimethandrolone is an AAS, and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone.^[1] It is also a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.^[1] Due to its androgenic and progestogenic activity, dimethandrolone has antigonadotropic effects.^[1] It has no estrogenic activity.^[1]^[4]

Dimethandrolone was first described in 1997.^[5] It was developed by the Contraceptive Development Branch of the National Institute of Child Health and Human Development, an agency in the United States government.^[1]^[6]

An ester and prodrug of dimethandrolone, dimethandrolone undecanoate (DMAU) (CDB-4521), is under development for potential use as a birth control pill for men and in androgen replacement therapy for men.^[1]^[2]^[3]^[7]

Side effects

Pharmacology

Pharmacodynamics

Dimethandrolone is an AAS, though it has also been described as a selective androgen receptor modulator (SARM).^[1]^[2]^[3] As an AAS, it is a potent agonist of the androgen receptor (AR).^[1]^[2]

Unlike testosterone and various other AAS, dimethandrolone is not metabolized by 5α-reductase.^[2] In addition, the 5α-reduced derivative of dimethandrolone, 5α-dihydrodimethandrolone (5α-DHDMA), possesses only 30 to 40% of the potency of dimethandrolone as an agonist of the AR, indicating that dimethandrolone does not require potentiation by 5α-reductase for its activity as an AAS and that even if it were a substrate for 5α-reductase, it would not be potentiated in androgenic tissues like the skin and prostate.^[2] As such, dimethandrolone and ester prodrugs of it like DMAU are thought to have a reduced risk of androgenic side effects and conditions such as benign prostatic hyperplasia, prostate cancer, pattern scalp hair loss, and acne relative to testosterone and certain other AAS.^[2]

Dimethandrolone is not a substrate for aromatase, and for this reason, is not converted into the corresponding aromatic A-ring derivative 7α,11β-dimethylestradiol, a potent estrogen.^[3]^[4] As such, dimethandrolone is not estrogenic.^[4] This is in contrast to nandrolone, which, although its rate of aromatization into the estrogen estradiol is reduced relative to that of testosterone, is still converted to a significant extent.^[4]

Similarly to nandrolone and other 19-nortestosterone derivatives, dimethandrolone is a potent progestogen in addition to AAS.^[1] This property may serve to augment its antigonadotropic activity, which in turn may improve its effectiveness as an antispermatogenic agent and male contraceptive.^[1] This is salient and potentially beneficial as male contraceptives based on androgens alone have failed to produce satisfactory azoospermia in around one-third of men.^[1]

Dimethandrolone has shown minimal potential for hepatotoxicity in animal studies, which is in accordance with the fact that it is not a 17α-alkylated AAS.^[6]

Chemistry

Dimethandrolone, also known as 7α,11β-dimethyl-19-nortestosterone or as 7α,11β-dimethylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a non-17α-alkylated derivative of nandrolone (19-nortestosterone).^[1]

Esters

Aside from the C17β undecanoate ester of dimethandrolone, DMAU (CDB-4521),^[1]^[2]^[3] a few other esters, such as dimethandrolone buciclate (CDB-4386A) and dimethandrolone dodecylcarbonate (CDB-4730), have also been developed.^[8]^[9]

Analogues

Other AAS that are closely related to dimethandrolone (besides nandrolone) include trestolone (also known as 7α-methyl-19-nortestosterone (MENT)) and 11β-methyl-19-nortestosterone (11β-MNT) and their respective C17β esters trestolone acetate and 11β-MNT dodecylcarbonate (11β-MNTDC).^[1]^[2]