Methenolone enanthate

Metenolone enanthate
Clinical data

Trade names	Nibal Injection, Primobolan Depot
Synonyms	Methenolone enanthate; Metenolone heptanoate; NSC-64967; SH-601; SQ-16374
Routes of administration	Intramuscular injection
Legal status
Legal status	US: Schedule III
Pharmacokinetic data
Biological half-life	IM: 4–5 days
Identifiers
IUPAC name (5α,17β)-1-Methyl-3-oxoandrost-1-en-17-yl heptanoate
CAS Number	303-42-4^Y
PubChem CID	248271
ChemSpider	217360^Y
UNII	0SPD480WFH
ECHA InfoCard	100.005.584
Chemical and physical data
Formula	C₂₇H₄₂O₃
Molar mass	414.621 g/mol
3D model (JSmol)	Interactive image
SMILES O=C2\C=C(\C)[C@@]3([C@H]1CC[C@@]4([C@@H](OC(=O)CCCCCC)CC[C@H]4[C@@H]1CC[C@H]3C2)C)C
InChI InChI=1S/C27H42O3/c1-5-6-7-8-9-25(29)30-24-13-12-22-21-11-10-19-17-20(28)16-18(2)27(19,4)23(21)14-15-26(22,24)3/h16,19,21-24H,5-15,17H2,1-4H3/t19-,21-,22-,23-,24-,26-,27-/m0/s1^Y Key:TXUICONDJPYNPY-FRXWOFFRSA-N^Y
^NY (what is this?)

Metenolone enanthate (brand names Nibal Injection, Primobolan Depot), or methenolone enanthate, is an injected anabolic-androgenic steroid (AAS) of the dihydrotestosterone (DHT) group. It is a C17β ester of metenolone, and acts as a prodrug of metenolone in the body. Whereas metenolone enanthate is the form of metenolone used for intramuscular injection, metenolone acetate is the form used for oral administration.

As a derivative of DHT, metenolone, the active form of metenolone enanthate, is not aromatized, and so has no propensity for producing estrogenic side effects like gynecomastia. As an AAS, metenolone enanthate is antigonadotropic and can suppress the hypothalamic-pituitary-gonadal axis and reversible hypogonadism and infertility.

Metenolone enanthate, also known as metenolone 17β-enanthate, is a synthetic androstane steroid and a derivative of DHT. It is the C17β ester metenolone, which itself is 1-methyl-δ¹-4,5α-dihydrotestosterone (1-methyl-δ¹-DHT) or 1-methyl-5α-androst-1-en-17β-ol-3-one.

Methenolone enanthate is the USAN of metenolone enanthate, and methenolone is the BAN of its active form, metenolone. Conversely, metenolone is the INN of metenolone.

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