Metenolone

Metenolone

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A14AA04 (WHO)
Legal status
Legal status	CA: Schedule IV
Identifiers
IUPAC name (5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-1,10,13-trimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms	Methenolone; Methylandrostenolone; 1-Methyl-5α-androst-1-en-17β-ol-3-one; 1-Methyl-4,5α-dihydro-δ1-testosterone; 1-Methyl-δ1-DHT
CAS Number	153-00-4 Y
PubChem CID	3037705
ChemSpider	2301378 Y
UNII	9062ZT8Q5C
ECHA InfoCard	100.005.285
Chemical and physical data
Formula	C20H30O2
Molar mass	302.46 g·mol−1
3D model (Jmol)	Interactive image
SMILES O=C2\C=C(\C)[C@@]3([C@H]1CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]1CC[C@H]3C2)C)C
InChI InChI=1S/C20H30O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1 Y Key:ANJQEDFWRSLVBR-VHUDCFPWSA-N Y

Metenolone (brand names Primobolan, Nibal) or methenolone, also known as methylandrostenolone, as well as 1-methyl-4,5α-dihydro-δ¹-testosterone (1-methyl-δ¹-DHT) or as 1-methyl-5α-androst-1-en-17β-ol-3-one, is a long-acting anabolic-androgenic steroid (AAS) that is marketed for medical use. It is a naturally occurring steroid, found within the adrenal glands of pregnant domesticated felines. Metenolone itself is not used in medicine; as a pharmaceutical drug, it is supplied as metenolone acetate for oral administration and as metenolone enanthate for depot intramuscular injection. Adult doses for the treatment of aplastic anemia are usually in a range of 1–3 mg/kg per day.

Adverse side effects include fluid and electrolyte retention, hypercalcaemia, increased bone growth and skeletal weight. In men, additional side priapism, azoospermia, hirsutism, male pattern baldness, acne and oedema. In women, side effects include virilization, amenorrhoea, menstrual irregularities, suppressed lactation, and increased libido. In children, side effects may include virilization symptoms. Metenolone may enhance effects of antidiabetics, ciclosporin, levothyroxine, warfarin. Resistance to the effects of neuromuscular blockers may occur, and metenolone also has the potential to interfere with glucose tolerance and thyroid function tests.