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{{Short description|Chemical compound}}
{{Mergefrom | Boli (steroid) |discuss=Talk:Methenolone enanthate#Merge proposal |date=February 2009 }}
{{Refimprove|date=March 2008}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | verifiedrevid = 400299068
| Watchedfields = changed
| IUPAC_name = (5α,17β)-1-methyl-3-oxoandrost-1-en-17-yl heptanoate
⚫ | verifiedrevid = 447451529
⚫ | IUPAC_name = phenanthren-17-yl] heptanoate
| image = Metenolone enanthate.png | image = Metenolone enanthate.png
| width = 250px


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Nibal Injection, Primobolan Depot
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = Schedule III | legal_US = Schedule III
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration = ]
| class = ]; ]; ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| elimination_half-life = {{abbrlink|IM|Intramuscular injection}}: 10.5 days<ref name="RuizStrain2011">{{cite book| vauthors = Westreich LM | chapter = Anabolic-Androgenic Steroids| veditors = Ruiz P, Strain EC |title=Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook | chapter-url = https://books.google.com/books?id=w4ZUJAdleTsC&pg=PA358 |year=2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-60547-277-5|pages=358–}}</ref>
| elimination_half-life = 10.5 days
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 303-42-4 | CAS_number = 303-42-4
| ATC_prefix = none | ATC_prefix =
| ATC_suffix = | ATC_suffix =
| PubChem = 248271 | PubChem = 248271
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 217360 | ChemSpiderID = 217360
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 0SPD480WFH
| synonyms = Methenolone 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


<!--Chemical data--> <!--Chemical data-->
| C=27 | H=42 | O=3 | C=27 | H=42 | O=3
⚫ | SMILES = O=C2\C=C(\C)3(1CC4((OC(=O)CCCCCC)CC41CC3C2)C)C
| molecular_weight = 414.621 g/mol
⚫ | smiles = O=C2\C=C(\C)3(1CC4((OC(=O)CCCCCC)CC41CC3C2)C)C
| InChI = 1/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
| InChIKey = TXUICONDJPYNPY-FRXWOFFRBE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TXUICONDJPYNPY-FRXWOFFRSA-N | StdInChIKey = TXUICONDJPYNPY-FRXWOFFRSA-N
⚫ | synonyms = <small>phenanthren-17-yl] heptanoate</small>
}} }}
<!-- Definition and medical uses -->
'''Metenolone enanthate''', or '''methenolone enanthate''', sold under the brand names '''Primobolan Depot''' and '''Nibal Injection''', is an ] and ] (AAS) medication which is used mainly in the treatment of ] due to ].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA784|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=784–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA660|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=659–661}}</ref><ref name="MortonHall2012">{{cite book | vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA178|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=178–}}</ref><ref name="Drugs.com">{{Cite web|url=https://www.drugs.com/international/metenolone.html|title=List of Androgens and anabolic steroids}}</ref><ref name="Llewellyn2011">{{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT625|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=633–}}</ref><ref name="JamesonGroot2015">{{cite book| vauthors = Handelsman DJ | chapter = Androgen Physiology, Pharmacology, and Abuse | veditors = Jameson JL, De Groot LJ |title=Endocrinology: Adult and Pediatric E-Book| chapter-url = https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2388|date=25 February 2015|publisher=Elsevier Health Sciences|isbn=978-0-323-32195-2|pages=2388–}}</ref> It is given by ].<ref name="Llewellyn2011" /> 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.<ref name="Drugs.com" /><ref name="Llewellyn2011" /><ref name="IndexNominum2000" /> A related drug, ], is taken ].<ref name="Llewellyn2011" />


<!-- Side effects and mechanism -->
'''Methenolone enanthate''', or metenolone enanthate, is a ] (DHT) based ]. It is an ] derivative of ] sold commonly under the brand names '''Primobolan''' (] form) or Primobolan Depot (]). When it interacts with the ] ] it does not form any ]s.{{Citation needed|date=April 2008}} It is used by people who are very susceptible to ] side effects, having lower ] properties than ]. Methenolone, in form of enanthate and acetate, is available as an ] or as an oral respectively. The injection is naturally regarded as having a higher ]. It is an ] ester which is quite long-acting. Because it by-passes ] breakdown on the first pass, it also has a higher survival rate.{{Citation needed|date=April 2008}} The tablets are in a short-lived ] form. Methenolone is not 17-alpha-alkylated, but 1-methylated for oral ]. This reduces the stress on the ], but also the availability.{{Citation needed|date=February 2009}} It is considered one of the ''safer'' steroids, meaning it has few side effects.{{Citation needed|date=February 2009}} Methenolone has no ] side effects, and its effects on ] levels are minimal.{{Citation needed|date=February 2009}} In doses of 200 ] per week or less (]) ] is rarely altered.{{Citation needed|date=February 2009}} It is possibly one of the ''safer'' ] for females due to very low ] effects in short-term usage.{{Citation needed|date=April 2008}} Methenolone is also not overly suppressive of the HPTA axis, although how suppressive is debatable.{{Citation needed|date=April 2008}} For this reason, many ] use it '''in between''' ]s during their "off-time" to help maintain their gains and ]. The long term safety of such a practice is possibly dangerous and can lead to permanent suppression of the HPTA axis.<ref>
]s of metenolone enanthate include ]s of ] like ], ], ], and increased ].<ref name="Llewellyn2011" /> The drug is a ] androgen and anabolic steroid and hence is an ] of the ] (AR), the ] of androgens like ] and ] (DHT).<ref name="Llewellyn2011" /><ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = Br. J. Pharmacol. | volume = 154 | issue = 3 | pages = 502–21 | year = 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref> It has moderate ] effects and weak ]ic effects, as well as no ]ic effects or risk of ].<ref name="Llewellyn2011" /><ref name="pmid18500378" /> Metenolone enanthate is a ] and a long-lasting ] of ] in the body.<ref name="Llewellyn2011" />
{{cite web

|url=http://www.thieme-connect.com/ejournals/abstract/sportsmed/doi/10.1055/s-2003-39089;jsessionid=983072189C7F586850656C57C8FA4D80.jvm5
<!-- History, society, and culture -->
|title=Androgenic Anabolic Steroid Use and Severe Hypothalamic-Pituitary Dysfunction: a Case Study
Metenolone enanthate was introduced for medical use in 1962.<ref name="Llewellyn2011" /> In addition to its medical use, metenolone enanthate is used to ].<ref name="Llewellyn2011" /> The drug is a ] in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2011" /> It remains marketed for medical use only in a few countries, such as ] and ].<ref name="Drugs.com" /><ref name="Llewellyn2011" />
|publisher=www.thieme-connect.com

|accessdate=2008-03-19
==Medical uses==
|last=
Metenolone enanthate has been studied in the treatment of ].<ref name="KennedyYarbro1968">{{cite journal | vauthors = Kennedy BJ, Yarbro JW | title = Effect of methenolone enanthate (NSC-64967) in advanced cancer of the breast | journal = Cancer | volume = 21 | issue = 2 | pages = 197–201 | date = February 1968 | pmid = 4952912 | doi = 10.1002/1097-0142(196802)21:2<197::AID-CNCR2820210207>3.0.CO;2-R | doi-access = free }}</ref><ref name="Notter1975">{{cite journal | vauthors = Notter G | title = Treatment of disseminated carcinoma of the breast by metenolone enanthate | journal = Acta Radiologica | volume = 14 | issue = 6 | pages = 545–551 | date = December 1975 | pmid = 1224996 | doi = 10.3109/02841867509132696 | doi-access = free }}</ref>
|first=

}}
==Side effects==
{{See also|Anabolic steroid#Adverse effects}}

==Pharmacology==

===Pharmacodynamics===
{{Relative androgenic to anabolic activity in animals}}

As a derivative of DHT, metenolone, the active form of metenolone enanthate, is not ], and so has no propensity for producing ]ic ]s like ].<ref name="Llewellyn2011" /> As an AAS, metenolone enanthate is ] and can suppress the ] and produce reversible ] and ].<ref name="Llewellyn2011" /><ref name="pmid12740738">{{cite journal | journal = Int J Sports Med | date = Apr 2003 | volume = 24 | issue = 3 | pages = 195–196 | title = Androgenic anabolic steroid use and severe hypothalamic-pituitary dysfunction: a case study |vauthors=van Breda E, Keizer HA, Kuipers H, Wolffenbuttel BH | pmid= 12740738 | doi=10.1055/s-2003-39089| s2cid = 260166539 }}</ref>

===Pharmacokinetics===
The ] of metenolone enanthate is reported to be about 10.5&nbsp;days by ].<ref name="RuizStrain2011" />

{{Parenteral durations of androgens/anabolic steroids}}

==Chemistry==
{{See also|List of androgens/anabolic steroids|List of androgen esters}}

Metenolone enanthate, or metenolone 17β-enanthate, is a ] ] ] and a ] of DHT.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> It is the C17β ] (heptanoate) ] of ], which itself is 1-methyl-δ<sup>1</sup>-4,5α-dihydrotestosterone (1-methyl-δ<sup>1</sup>-DHT) or 1-methyl-5α-androst-1-en-17β-ol-3-one.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />

{{Structural properties of major anabolic steroid esters}}

==History==
Metenolone enanthate was introduced for medical use in 1962 in the ] under the brand name Nibal Depot.<ref name="Llewellyn2011" /> It was soon discontinued in the United States and was marketed instead in ] in the 1960s and 1970s under the brand name Primobolan Depot.<ref name="Llewellyn2011" />

==Society and culture==

===Generic names===
''Methenolone enanthate'' is the {{abbrlink|USAN|United States Adopted Name}} of metenolone enanthate, and ''methenolone'' is the {{abbrlink|BAN|British Approved Name}} of its active form, metenolone.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /> Conversely, ''metenolone'' is the {{abbrlink|INN|International Nonproprietary Name}} of metenolone.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />


===Brand names===
</ref>
Metenolone enanthate is or has been marketed under the brand names Nibal Injection and Primobolan Depot.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /><ref name="Drugs.com" />


===Availability===
==Use by Major League Baseball players==
Metenolone enanthate is marketed in ] and ].<ref name="Drugs.com" /><ref name="Llewellyn2011" />


===Doping in sports===
In February 2009, '']'' reported that ] tested positive for two ], ] and Primobolan, while playing for the Texas Rangers in 2003. He claims to have purchased them over the counter, in the Dominican Republic. However, "boli" is an illegal substance in the Dominican.<ref name="SIsteroids">{{cite news|work=Sports Illustrated|url=http://sportsillustrated.cnn.com/2009/baseball/mlb/02/07/alex-rodriguez-steroids/index.html | title= Alex Rodriguez tested positive for steroids in 2003|date=February 2009 |accessdate=2009-02-09}} By Selena Roberts and David Epstein.</ref><ref name="NYTsteroids">{{cite news|url=http://www.nytimes.com/2009/02/08/sports/baseball/08arod.html |title=Alex Rodriguez Said to Test Positive in 2003 |date=2009-02-07|accessdate=2009-02-09|first=Michael S.|last=Schmidt|work=New York Times}}</ref> In an interview with ESPN two days after the SI revelations, Rodriguez admitted to using banned substances from 2001 to 2003, citing "an enormous amount of pressure to perform," but said he had not since then used banned performance-enhancing substances.<ref name="ESPNadmission">{{cite news|work=ESPN|title=A-Rod admits, regrets use of PEDs |url=http://sports.espn.go.com/mlb/news/story?id=3894847 |first=Peter|last=Gammons |date=2009-02-09|accessdate=2009-02-09}}</ref><ref name="NYTadmission">{{cite news|work=New York Times|url=http://www.nytimes.com/2009/02/10/sports/baseball/10rodriguez.html | title=Rodriguez Admits to Using Performance-Enhancing Drugs |first=Michael S. |last=Schmidt |date=2009-02-09 |accessdate=2009-02-09}}</ref> He said he did not know the name(s) of the particular substance(s) he was using, and would not specify whether he took them in injectable form.<ref name="ESPNadmission"/>
{{See also|List of doping in sport cases#Metenolone esters}}


There are known cases of doping in sports with metenolone enanthate by ] ]s.
Primobolan, which has no approved prescriptive use,<ref name="SIsteroids"/> is the same ] to which ] allegedly tested positive in 2000 and 2001 (though such 'evidence' was dismissed as inadmissible hearsay).<ref name="NYTsteroids"/> A weak steroid on its own, it is generally used in conjunction with other steroids.<ref name="StarLedgersteroids"/> The drug is generally preferred in injected rather than oral form due to its cost.<ref name="StarLedgersteroids">{{cite news|title=What is Primobolan? | url=http://www.nj.com/yankees/index.ssf/2009/02/what_is_primobolan.html |first=Brendan |last=Prunty|work=Star-Ledger | date=2009-02-07|accessdate=2009-02-09}}</ref>


==References== ==References==
{{reflist}} {{Reflist|30em}}


==External links==
{{Anabolic steroids}}
* {{Webarchive|url=https://web.archive.org/web/20190629144018/https://anabolic.org/primobolan-depot-methenolone-enanthate/ |date=2019-06-29 }}


⚫ ]


{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}


]
{{gastrointestinal-drug-stub}}
⚫ ]
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