Metenolone enanthate

Last updated
Metenolone enanthate
Metenolone enanthate.png
Clinical data
Trade names Nibal Injection, Primobolan Depot
Other namesMethenolone enanthate; Metenolone heptanoate; Metenolone 17β-enanthate; NSC-64967; SH-601; SQ-16374; 1-Methyl-4,5α-dihydrotestosterone 17β-heptanoate; 1-Methyl-DHT heptanoate; 1-Methyl-5α-androst-1-en-17β-ol-3-one 17β-heptanoate
Routes of
administration 		Intramuscular injection
Drug class Androgen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
Elimination half-life IM Tooltip Intramuscular injection: 10.5 days [1]
Identifiers
  • [(5S,8R,9S,10S,13S,14S,17S)-1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] heptanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.005.584 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C27H42O3
Molar mass 414.630 g·mol−1
3D model (JSmol)
  • 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=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 Yes check.svgY
  • Key:TXUICONDJPYNPY-FRXWOFFRSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. [2] [3] [4] [5] [6] [7] It is given by injection into muscle. [6] Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. [5] [6] [3] A related drug, metenolone acetate, is taken by mouth. [6]

Contents

Side effects of metenolone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [6] The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). [6] [8] It has moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage. [6] [8] Metenolone enanthate is a metenolone ester and a long-lasting prodrug of metenolone in the body. [6]

Metenolone enanthate was introduced for medical use in 1962. [6] In addition to its medical use, metenolone enanthate is used to improve physique and performance. [6] The drug is a controlled substance in many countries and so non-medical use is generally illicit. [6] It remains marketed for medical use only in a few countries, such as Spain and Turkey. [5] [6]

Medical uses

Metenolone enanthate has been studied in the treatment of breast cancer. [9] [10]

Side effects

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity
of androgens/anabolic steroids
MedicationRatioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes:a = Ratio of androgenic to anabolic activity. Sources: See template.

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. [6] As an AAS, metenolone enanthate is antigonadotropic and can suppress the hypothalamic–pituitary–gonadal axis and produce reversible hypogonadism and infertility. [6] [11]

Pharmacokinetics

The biological half-life of metenolone enanthate is reported to be about 10.5 days by intramuscular injection. [1]

Parenteral durations of androgens/anabolic steroids
MedicationFormMajor brand namesDuration
Testosterone Aqueous suspensionAndronaq, Sterotate, Virosterone2–3 days
Testosterone propionate Oil solutionAndroteston, Perandren, Testoviron3–4 days
Testosterone phenylpropionate Oil solutionTestolent8 days
Testosterone isobutyrate Aqueous suspensionAgovirin Depot, Perandren M14 days
Mixed testosterone esters aOil solutionTriolandren10–20 days
Mixed testosterone esters bOil solutionTestosid Depot14–20 days
Testosterone enanthate Oil solutionDelatestryl14–28 days
Testosterone cypionate Oil solutionDepovirin14–28 days
Mixed testosterone esters cOil solutionSustanon 25028 days
Testosterone undecanoate Oil solutionAveed, Nebido100 days
Testosterone buciclate dAqueous suspension20 Aet-1, CDB-1781e90–120 days
Nandrolone phenylpropionate Oil solutionDurabolin10 days
Nandrolone decanoate Oil solutionDeca Durabolin21–28 days
Methandriol Aqueous suspensionNotandron, Protandren8 days
Methandriol bisenanthoyl acetate Oil solutionNotandron Depot16 days
Metenolone acetate Oil solutionPrimobolan3 days
Metenolone enanthateOil solutionPrimobolan Depot14 days
Note: All are via i.m. injection. Footnotes:a = TP, TV, and TUe. b = TP and TKL. c = TP, TPP, TiCa, and TD. d = Studied but never marketed. e = Developmental code names. Sources: See template.

Chemistry

Metenolone enanthate, or metenolone 17β-enanthate, is a synthetic androstane steroid and a derivative of DHT. [2] [3] [6] It is the C17β enanthate (heptanoate) ester of 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. [2] [3] [6]

Structural properties of major anabolic steroid esters
Anabolic steroidStructureEsterRelative
mol. weight		Relative
AAS contentb		Durationc
PositionMoietyTypeLengtha
Boldenone undecylenate
Boldenone undecylenate.svg
C17β Undecylenic acid Straight-chain fatty acid111.580.63Long
Drostanolone propionate
Drostanolone propionate.svg
C17β Propanoic acid Straight-chain fatty acid31.180.84Short
Metenolone acetate
Metenolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid21.140.88Short
Metenolone enanthate
Metenolone enanthate.png
C17β Heptanoic acid Straight-chain fatty acid71.370.73Long
Nandrolone decanoate
Nandrolone decanoate.svg
C17β Decanoic acid Straight-chain fatty acid101.560.64Long
Nandrolone phenylpropionate
Nandrolone phenylpropionate.svg
C17β Phenylpropanoic acid Aromatic fatty acid– (~6–7)1.480.67Long
Trenbolone acetate
Trenbolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid21.160.87Short
Trenbolone enanthate d
Trenbolone enanthate.svg
C17β Heptanoic acid Straight-chain fatty acid71.410.71Long
Footnotes:a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative androgen/anabolic steroid content by weight (i.e., relative androgenic/anabolic potency). c = Duration by intramuscular or subcutaneous injection in oil solution. d = Never marketed. Sources: See individual articles.

History

Metenolone enanthate was introduced for medical use in 1962 in the United States under the brand name Nibal Depot. [6] It was soon discontinued in the United States and was marketed instead in Europe in the 1960s and 1970s under the brand name Primobolan Depot. [6]

Society and culture

Generic names

Methenolone enanthate is the USAN Tooltip United States Adopted Name of metenolone enanthate, and methenolone is the BAN Tooltip British Approved Name of its active form, metenolone. [2] [3] [4] [5] Conversely, metenolone is the INN Tooltip International Nonproprietary Name of metenolone. [2] [3] [4] [5]

Brand names

Metenolone enanthate is or has been marketed under the brand names Nibal Injection and Primobolan Depot. [2] [3] [6] [5]

Availability

Metenolone enanthate is marketed in Spain and Turkey. [5] [6]

Doping in sports

There are known cases of doping in sports with metenolone enanthate by professional athletes.

Related Research Articles

<span class="mw-page-title-main">Methyltestosterone</span> Chemical compound

Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women. It is taken by mouth or held in the cheek or under the tongue.

<span class="mw-page-title-main">Metenolone</span> Chemical compound

Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate and metenolone enanthate. Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure. Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.

<span class="mw-page-title-main">Oxandrolone</span> Androgen and anabolic steroid

Oxandrolone, sold under the brand names Oxandrin and Anavar, among others, is an androgen and anabolic steroid (AAS) medication which is used to help promote weight gain in various situations, to help offset protein catabolism caused by long-term corticosteroid therapy, to support recovery from severe burns, to treat bone pain associated with osteoporosis, to aid in the development of girls with Turner syndrome, and for other indications. It is taken by mouth.

<span class="mw-page-title-main">Oxymetholone</span> Androgen and anabolic steroid

Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemia. It is also used to treat osteoporosis, HIV/AIDS wasting syndrome, and to promote weight gain and muscle growth in certain situations. It is taken by mouth.

<span class="mw-page-title-main">Metandienone</span> Androgen and anabolic steroid

Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol (D-Bol) among others, is an androgen and anabolic steroid (AAS) medication which is still quite often used because of its affordability and effectiveness for bulking cycles. It is also used non-medically for physique- and performance-enhancing purposes. It is often taken by mouth.

<span class="mw-page-title-main">Testosterone cypionate</span> Chemical compound

Testosterone cypionate, sold under the brand name Depo-Testosterone among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It is also used in hormone therapy for transgender men. It is given by injection into muscle or subcutaneously, once every one to four weeks, depending on clinical indication.

<span class="mw-page-title-main">Testosterone enanthate</span> Chemical compound

Testosterone enanthate is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It is also used in hormone therapy for transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks.

<span class="mw-page-title-main">Mesterolone</span> Chemical compound

Mesterolone, sold under the brand name Proviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels. It has also been used to treat male infertility, although this use is controversial. It is taken by mouth.

<span class="mw-page-title-main">Drostanolone propionate</span> Chemical compound

Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed. It is given by injection into muscle.

<span class="mw-page-title-main">Mestanolone</span> Chemical compound

Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer used. It is still available for use in Japan however. It is taken by mouth.

<span class="mw-page-title-main">Drostanolone</span> Chemical compound

Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. An androgen ester prodrug of drostanolone, drostanolone propionate, was formerly used in the treatment of breast cancer in women under brand names such as Drolban, Masteril, and Masteron. This has also been used non-medically for physique- or performance-enhancing purposes.

<span class="mw-page-title-main">1-Testosterone</span> Chemical compound

1-Testosterone, also known as δ1-dihydrotestosterone (δ1-DHT), as well as dihydroboldenone, is a synthetic anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of boldenone (Δ1-testosterone). It differs from testosterone by having a 1(2)-double bond instead of a 4(5)-double bond in its A ring. It was legally sold online in the United States until 2005, when it was reclassified as a Schedule III drug.

<span class="mw-page-title-main">Epitiostanol</span> Chemical compound

Epitiostanol, sold under the brand name Thiodrol, is an injected antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was described in the literature in 1965 and has been marketed in Japan as an antineoplastic agent for the treatment of breast cancer since 1977.

<span class="mw-page-title-main">Stenbolone</span> Chemical compound

Stenbolone is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. A C17β ester prodrug of stenbolone, stenbolone acetate, is used as an AAS for depot intramuscular injection under the brand names Anatrofin and Stenobolone.

<span class="mw-page-title-main">Methylstenbolone</span> Chemical compound

Methylstenbolone, known by the nicknames M-Sten, Methyl-Sten, and Ultradrol, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-methylated derivative of dihydrotestosterone (DHT) which was never introduced for medical use. It is a designer steroid and has been sold via the internet marketed as a dietary/nutritional supplement.

<span class="mw-page-title-main">Boldenone undecylenate</span> Chemical compound

Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. It was formerly used in humans as well. It is given by injection into muscle.

<span class="mw-page-title-main">Stenbolone acetate</span> Chemical compound

Stenbolone acetate, also known as 2-methyl-4,5α-dihydro-δ1-testosterone 17β-acetate or as 2-methyl-5α-androst-1-en-17β-ol-3-one 17β-acetate, is a synthetic, injected anabolic–androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT) which has been marketed in Spain.

<span class="mw-page-title-main">Metenolone acetate</span> Chemical compound

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.

<span class="mw-page-title-main">Androstanolone</span> Androgenic and anabolic steroid medication

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men. It is also used to treat breast development and small penis in males. Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

References

  1. 1 2 Pedro Ruiz; Eric C. Strain (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN   978-1-60547-277-5.
  2. 1 2 3 4 5 6 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 784–. ISBN   978-1-4757-2085-3.
  3. 1 2 3 4 5 6 7 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–661. ISBN   978-3-88763-075-1.
  4. 1 2 3 I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 178–. ISBN   978-94-011-4439-1.
  5. 1 2 3 4 5 6 7 "List of Androgens and anabolic steroids".
  6. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 633–. ISBN   978-0-9828280-1-4.
  7. ↑ J. Larry Jameson; Leslie J. De Groot (25 February 2015). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN   978-0-323-32195-2.
  8. 1 2 Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC   2439524 . PMID   18500378.
  9. ↑ Kennedy BJ, Yarbro JW (February 1968). "Effect of methenolone enanthate (NSC-64967) in advanced cancer of the breast". Cancer. 21 (2): 197–201. doi: 10.1002/1097-0142(196802)21:2<197::AID-CNCR2820210207>3.0.CO;2-R . PMID   4952912.
  10. ↑ Notter G (December 1975). "Treatment of disseminated carcinoma of the breast by metenolone enanthate". Acta Radiologica. 14 (6): 545–551. doi: 10.3109/02841867509132696 . PMID   1224996.
  11. ↑ van Breda E, Keizer HA, Kuipers H, Wolffenbuttel BH (Apr 2003). "Androgenic anabolic steroid use and severe hypothalamic-pituitary dysfunction: a case study". Int J Sports Med. 24 (3): 195–196. doi:10.1055/s-2003-39089. PMID   12740738. S2CID   260166539.


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