Designer steroid profiles

[jbryand101b]

HALODROL-50

Nomenclature:
4-chloro-17a methyl-androst-1,4-diene-3,17b-diol

Anabolic/Androgenic Ratio:

Unknown.

Synonyms/Brand Names:

Gaspari Nutrition Halodrol-50, CEL H-drol, Purus Labs Halovar, EST Hemadrol, Mr Supps Helladrol, Hard Rock Halo-Plex, Pro Cycle Labs Halostane, Primordial Performance Turinabol

History:

This compound was originally released into the bodybuilding “supplement” market by Gaspari Nutrition as “Halodrol-50″. Their ex-product formulator Bruce Kneller tells the story:


“I spent over a year studying the original E. German docs on Oral Turinabol before I changed the ketone to a hydroxyl and launched it. The German doping machine kept amazing notes we had translated back in 2002-2004. Hundreds of pages. with dose of 5mg -500mg per day. Seeing out [sic] Halodrol was weaker than OT (and a precursor to it) I felt very comfortable in being able to predict how it would work.” [1]

The Halodrol-50 product listed the ingredient as “polydehydrogenated, polyhydroxylated halomethetioallocholane”, however it did not just contain the implied 4-chloro-17a methyl-androst 1,4-diene-3,17b-diol compound. As early as 2005 it was analysed by anti-doping expert Don Catlin and found to also contain the designer steroid Madol (desoxymethyltestosterone, or phera) which had then recently been detected in athletes as part of the BALCO scandal. [2]

While Catlin’s initial analysis revealed only the presence of madol and 4-chloro-17a methyl-androst 1,4-diene-3,17b-diol, more thorough testing of the Gaspari Nutrition product has since revealed that it also contained methyldrostanolone (superdrol) as well as oral turinabol and several similar analogues that are believed to be the result of crude synthesis techniques. [3]

The active compound has since appeared in numerous “dietary supplements” sold on the internet and in gyms and sports supplement shops.

Structure and Function:

Like many oral prohormones/designer steroids/anabolic steroids on the market, this compound has a 17a-methyl group. This functional group increases oral activity by preventing 17b-hydroxyl oxidation from occurring.
It has a covalent bond structure like that of Oral Turinabol. It differs from Oral Turinabol in that it has a hydroxyl function at carbon 3 instead of a ketone.

Though the nomenclature found on h-drol bottles says 4-chloro-17a methyl-androst 1,4-diene-3,17b-diol, the 3-hydroxyl is not planar; it must be either a 3b-hydroxyl or a 3a-hydroxyl. In truth commercial h-drol clones contain a mixture of 3a- and 3b-hydroxylated stereoisomers, due to the production process. Typically halodrol is made from Oral Turinabol using reducing agents such as sodium borohydride. The reaction method determines the ratio of isomers produced – which can be anywhere from 50:50 to 95:5 in favour of the 3b-ol.
This 3-hydroxyl is intended to be metabolised by the body back to a 3-ketone; h-drol is taken as a “prohormone” (precursor) to Oral Turinabol.

The 4-chloro modification also prevents Halodrol from aromatizing. The same substitution is found in the injectable steroid Clostebol and the oral steroid Turinabol: [4]


“After adminstration of 4-chloro-17b-hydroxyandrost-4-en-3-one-p-chlorophenoxyacetate (100 mg once intramuscularly) and of 4-chloro-17a-methyl-17b-hydroxyandrosta-1,4-dien-3-one (25mg orally daily) to endocrinologically healthy males, there was still no measurable increase in the excretion of estrogens in urine (1163).” [4]

Metabolism:

Oral Turinabol and Halodrol both have a 1,4-diene unconjugated system which will make the steroids very poor substrates for the 5a-reductase enzyme, thus making 5a-reduction highly unlikely. [5] It should be of note however that, like other 1,4-dienes, this compound will be subject to 5b-reduction.

There is some public skepticism regarding this compound’s ability to convert into Oral Turinabol, as there has yet to be a published study which examines the pharmacokinetic profile of Halodrol in humans. However, a recent in vitro study conducted by a team of researchers reveals the metabolism of Halodrol in equine (horse) liver. [6] The results of this study are discussed below:


“By far the most abundant metabolite observed by both LC-HRMS and GC-MS was an oxidized metabolite (−2H) proposed to be 3-keto-Halodrol (otherwise known as Turinabol). This is significant since it is therefore likely that Halodrol is a pro-drug for Turinabol (a 3-keto analogue of Halodrol) and that its metabolism could be very similar to this steroid.” [6]

Other routes of metabolism, from the same study, include oxidation and hydroxylation, A-ring reduction, and combinations thereof.

References:
[1] Modern Fitness Forum: Turinabol by Primordial Performance
[2] Washington Post: Steroids Detected In Dietary Tablets
[3] Gauthier J, Poirier D, Ayotte C. Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes. Steroids. 2012 May;77(6):635–43.
[4] Krüskemper, Hans Ludwig. 1968. Anabolic Steroids. Academic Press.
[5] Fragkaki AG, Angelis YS, Tsantili-Kakoulidou A, Koupparis M, Georgakopoulos C. Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine. J. Steroid Biochem. Mol. Biol. 2009 May;115(1-2):44–61.
[6] Clarke A. The use of in vitro technologies and high-resolution/accurate-mass LC-MS to screen for metabolites of ‘designer’ steroids in the equine. Drug Test Anal 3:74 (2011)

 

[jbryand101b]

Re: Designer steroid profiles by henryv

triumphalis methyldiazirinol

Structural Image: cant post pics for some reason.

Nomenclature:
3,3-azo-17a-methyl-5a-androstan-17b-ol or
3,3-azo-17α-methyl-5α-androstan-17β-ol

Synonyms:
Methyldiazirinol


History:
This compound was first synthesized by researchers at Lederle Laboratories, a subsidiary of American Cyanamid, who were examining a series of diazirines and diaziridines (the steroid in question is a diazirine). Their results were reported in 1965. [1] They patented the invention in 1966. [2]
Lederle/American Cyanamid also synthesized (appropriately enough) some 2a-cyano-substituted compounds similar to the Anabolic Innovations ‘prohormone’ Cynostane, [3][4] though their major contribution to the field of steroids was the 16-oxygenated corticosteroid triamcinolone in the late 1950s. [5]



US Patent #19640392022 [2]
Methyldiazirinol was one of the many steroids listed in Julius Vida’s Androgens and Anabolic Agents. In a section detailing “Compounds displaying decreased androgenic activity coupled with increased anabolic activity”, the 3,3-azo steroid is listed alongside steroids such as oxandrolone (anavar), methenolone (primobolan), stanozolol (winstrol) and norbolethone (one version of “the Clear”). [6]



Prog Med Chem. 1991;28:233-300. [7]
Anabolic:Androgenic Ratio:
According to the Lederle Laboratories researchers, the 3,3-azo has an oral anabolic:androgenic ratio of 300:20 (levator ani:ventral prostate) when compared to methyl testosterone, giving it a “Q factor” of 15.



Androgens and Anabolic Agents. 1969. Academic Press, p90. [6]
This gives it a dissociation of anabolic to androgenic effects similar to the recently-banned methasterone (superdrol), which was reported to have an anabolic:androgenic ratio of 400:20.


3,3-azo vida
Androgens and Anabolic Agents. 1969. Academic Press, p194. [8]

Structure and Function:
Many active steroids (including the natural androgens testosterone and DHT) have a ketone function at the three position (usually written in the nomenclature as a “3-one”). It was once believed that this was necessary for anabolic activity, but since 1959 many steroids have been discovered that have significant activity despite the absence of a 3-ketone.
◾Stanozolol (Winstrol) has a pyrazole heterocyclic ring fused to the steroid at carbons 2 and 3.
◾Furazabol has a furazane ring at the same position.
◾Methylepitiostanol (“Epistane”) has an episulphide moiety at carbons 2 and 3.
◾Methyldiazirinol has a diazirine moiety at carbon 3.

methyldiazirinol comparison
Heterocyclic steroids

Receptor bonding in these cases has been improved by the substitution of the 3-ketone for a more highly nucleophilic heteroatom; either sulphur or nitrogen. Methylepithiostanol has a sulphur atom in the place of the oxygen function of the natural steroids, while stanozolol, furazabol, and methyldiazirinol possess a nitrogen atom.

Stability
Diazirines are not terribly stable chemical structures, being known to be susceptible to decay from both ultraviolet light and heat. This relative instability is partly due to the ring strain on three membered rings, and partly due to the nucleophilic nature of the nitrogen atoms.
Instability in UV light is not something that is unique to diazirines, or to this steroid; many steroids have been found to be subject to photodegradation, including testosterone, testosterone propionate, methyltestosterone, nandrolone, dienolone, and trenbolone. [9][10][11][12]
The American Cyanomid Company discovered that the 3,3-azo steroids pyrolized largely to 2-ene compounds at 135°+ (via a singlet state carbene), though that is not expected to happen in vivo. This degradation with heat is not unique to methyldiazirinol either; the structurally similar steroid methylepitiostanol (epistane) also pyrolizes under heat (to the same 2-ene compound, desoxymethyltestosterone), making accurate testing by GC/MS impossible. [13][14]
In practice this ‘instability’ is likely to be of little consequence. The Lederle researchers found that “Unlike the diaziridines, the diazirines were found to be very stable, relatively nonpolar compounds”. [1] The same storage advice should be heeded as with all other steroidal products: keep in a cool, dark, dry place.

Availability
Methyldiazirinol was never commercialised by its inventors, though they continued to explore the possibilities of the diazirine group in other (non-steroidal) molecules. [15][16]

triumphalis methyldiazirinolIn 2013 methyldiazirinol was released onto the dietary supplement market as Iron Legion Triumphalis.



References:
[1] Church RFR, Kende AS, Weiss MJ. Diazirines. I. Some Observations on the Scope of the Ammonia-Hydroxylamine-O-sulfonic Acid Diaziridine Synthesis. The Preparation of Certain Steroid Diaziridines and Diazirines. J. Am. Chem. Soc. 1965 Jun 1;87(12):2665–71.
[2] Church RFR. 2,2 And 3,3-Hydrazi-Steroids of the Androstane and Pregnane Series. 1969
[3] Kissman H, Hoffman A, Weiss M. Communications- Synthesis of Certain Steroidal α-Cyano Ketones. J. Org. Chem. 1961 Jul 1;26(7):2610–1.
[4] Kissman HM, Hoffman AS, Weiss MJ. The Synthesis of Certain α-Cyano Keto Steroids. J. Org. Chem. 1962 Sep 1;27(9):3168–75.
[5] Bernstein S. Historic reflection on steroids: Lederle and personal aspects. Steroids. 1992 Aug;57(8):392–402.
[6] Androgens and Anabolic Agents. 1969. Academic Press, p90.
[7] Singh H, Jindal DP, Yadav MR, Kumar M. Heterosteroids and drug research. Prog Med Chem. 1991;28:233–300.
[8] Androgens and Anabolic Agents. 1969. Academic Press, p194.
[9] Albini A, Fasani E, Albini A, Fasani E. Photochemistry of drugs: An overview and practical problems. Drugs Photochemistry and Photostability. 2007.
[10] Van der Merwe PJ, Pieterse JW. Stability of zeranol, nandrolone and trenbolone in bovine urine. Analyst. 1994 Dec;119(12):2651–3.
[11] Debono M. The photodimerization of 17β-hydroxy-estra-4,9(10)-dien-3-one. Steroids. 1968 Oct;12(4):485–9.
[12] Qu S, Kolodziej EP, Cwiertny DM. Phototransformation rates and mechanisms for synthetic hormone growth promoters used in animal agriculture. Environ. Sci. Technol. 2012 Dec 18;46(24):13202–11.
[13] Okano M, Sato M, Ikekita A, Kageyama S. Analysis of non-ketoic steroids 17α-methylepithiostanol and desoxymethyl- testosterone in dietary supplements. Drug Testing and Analysis. 2009;1(11-12):518–25.
[14] Does “Epistane” convert to “Phera”? – Total Flex Blog.
[15] Church RFR, Weiss MJ. Diazirines. II. Synthesis and properties of small functionalized diazirine molecules. Observations on the reaction of a diaziridine with the iodine-iodide ion system. J. Org. Chem. 1970 Aug 1;35(8):2465–71.
[16] Church RFR, Maleike RR, Weiss MJ. Diazirines. 3. Synthesis of a series of diazirine-containing molecules and their pharmacological evaluation. J. Med. Chem. 1972 May 1;15(5):514–8.

 

[jbryand101b]

Re: Designer steroid profiles by henryv

MAX LMG

Nomenclature:
18-methyl-3-methoxy-estra-2,5(10)-dien-17-one or
13β-ethyl-3-methoxy-gona-2,5(10)-dien-17-one

Synonyms:
Methoxygonadiene, methoxydienone, Max-LMG, M-LMG

History:
This compound first appears in patents dating to the 1960s filed by researchers Gordon Alan Hughes and Herchel Smith at Wyeth Laboratories, in which they synthesized a number of 13-alkylated 19-nor compounds, including some that would become the first synthetic contraceptives. [1][2] These patents would prove so profitable that after retiring from Wyeth, Smith was able to donate hundreds of millions of dollars to universities in the UK and US. [3]

Methoxygonadiene is a chemical intermediate in the synthesis of steroids such as Norbolethone, 18-methyl-nortestosterone, and Norgestrel/Levonorgestrel. [1]


Preparation of Norbolethone from Methoxydienone
Preparation of Norbolethone from Methoxydienone. [1]
Grignard methylation and acid-catalyzed hydrolysis of methoxygonadiene yields the steroid Norbolethone. Norbolethone was originally developed by Wyeth, and later made famous by its use as a then-undetectable doping agent in the ‘BALCO’ scandal.

This ready availability as a chemical intermediate, and its association with the BALCO scandal, are likely to be how it found its way into the “designer steroid” supplement market in 2005, when it was released by ALRI as Max-LMG (LMG stands for “Lean Mass Generator”).
alri-max-lmg__Anabolic and Androgenic Activity:
Methoxygonadiene is believed to act as a ‘prodrug’, deriving pharmacological activity by being metabolised to an active compound. Methoxygonadiene is unlikely to have any ‘intrinsic’ anabolic activity due to the lack of a 17b-hydroxyl function.

methoxygonadiene proposed metabolism
Proposed scheme of metabolism of methoxygonadiene

The diagram above illustrates the commonly suggested metabolic route. According to the scheme proposed, after ingestion methoxydienone’s enol ether group (methoxy) will undergo hydrolysis to the 3-ketone and the remaining 5(10) double bond should isomerize readily under acidic conditions in the body to produce a 4-en-3-one conjugation. It will then further convert to the biologically active 17b-hydroxyl steroid, 18-methyl-19-nortestosterone.

18-methyl-19-nortestosterone is a potent anabolic by injection, holding an A:A ratio of approximately 54:27 (LA:VP vs. testosterone propionate). [4] and 90:625 (LA:VP vs. 19-nortestosterone). [5] No data is available on the oral activity of either methoxygonadiene or 18-methyl-19-nortestosterone.

Structure and Function:
Methoxydienone belongs to a class of steroids called gonanes. The most basic gonane is a steroid devoid of the C-10 and C-13 methyl groups and is generally referred to as the ‘steroid nucleus’.

gonane
Structure of the steroid nucleus; the simplest gonane.

Herchel Smith and Richard Edgren originally described hormones such as methoxygonadiene and norbolethone as “13-substituted bisnortestosterones”, though they soon switched to the gonane nomenclature system to avoid confusion.


“We initially started calling them 13-substituted, bisnor testosterones… However this became very cumbrous from a nomenclature standpoint and to get some consistency in our work, at least internally, we followed the IUPAC recommendations, starting from the gonane nucleus and building from there.” – Richard Edgren [5]

Since by the strictest definition all steroids can be considered gonanes, Edgren has expressed a preference for the term “carbon 18-homologated 19-nortestosterones”, or alternatively “levonorgestrel family of progestins” for 18-methyl hormones such as methoxygonadiene. [6]

When this was released as a dietary supplement in 2005, the accompanying advertising copy declared:


“Max LMG is structurally related to the so-called abortion pill RU-486…”

In fact it’s almost entirely unrelated, structurally, to the “abortion pill” RU-486 (Mifepristone), as can be seen by even a cursory glance at the molecular structures.

methoxygonadiene, mifepristone, and norgestrel
Left to right: methoxygonadiene, mifepristone (RU-486), and norgestrel.

It’s possible that the confusion may have arisen because Wyeth’s oral contraceptive Nordette (which contained ethinyl estradiol and levonorgestrel) was marked “Wyeth” on one side, and “486″ on the other. Since levonorgestrel can be made from methoxygonadiene, a comparison with that compound would have been much more appropriate.

nordette


“…being a 5-alpha-reduced analog prevents conversion to DHT. It is important to remember that being 5-alpha-reduced also means it is related to DHT.”

Methoxygonadiene is not 5-alpha-reduced, or even remotely related to DHT. It has a double bond from C5-C10, which it’s believed may isomerise in vivo to the more thermodynamically stable C4-C5 position.


“Naturally the lack of estrogenic activity translates into low water retention and solid gains.”

Contrary to the assertion above, this compound is noted by users for a high degree of water retention – and is certain to aromatise. Ironically, both of the compounds sold by ALRI under the name “LMG” (Lean Mass Generator) were renowned for doing the opposite: Ergomax LMG (desoxymethyltestosterone; “Pheraplex”) was also usually characterized as a “wet bulker” that caused significant water retention.

References:
[1] US Patent US3959322: Synthesis of 13-alkyl-gon-4-ones. Smith, Herchel
[2] US Patent US3547909: Hughes GA. Synthesis of Gona-2,5(10)-Dienes. 1970.
[3] Herchel Smith Biography – University of Cambridge
[4] Buzby GC, Walk CR, Smith H. Totally Synthetic Steroid Hormones. X. Some (±)-13β-Ethyl-7α-methylgonane Derivatives. J. Med. Chem. 1966 Sep 1;9(5):782–4.
[5] Biological effects of synthetic gonanes. Edgren RA, Peterson DL, Jones RC, Nagra CL, Smith H, Hughes GA. Recent Prog Horm Res. 1966;22:305-49.
[6] Nomenclature of the gonane progestins. Edgren RA, Stanczyk FZ. Contraception. 1999 Dec;60(6):313

 

[jbryand101b]

Re: Designer steroid profiles by henryv

METHYL STENBOLONE

Nomenclature:

2,17α-dimethyl-5α-androsta-1-en-17β-ol-3-one, or 2,17a-Dimethyl-17b-hydroxy-5a-androst-1-en-3-one

Anabolic/Androgenic Ratio:

660:90-170 vs. methyltestosterone by oral administration. [1]

Synonyms:

Methyl stenbolone, methyl sten, 17a-methyl-stenbolone, m-sten, ultradrol

History:

In 1966, researchers at Searle Laboratories set about methodically testing the myotrophic (anabolic) and androgenic effects of a series of A-ring modified androstane derivatives. [2] The compounds they explored reads like a who’s who of designer steroids.
Methyl-1-testosterone (M1T), desoxymethyltestosterone (phera), 17a-methyl-1-androstenediol (Alpha One), and a variety of other 1- and 2-dehydro compounds were explored for activity.

The researchers proudly announced that “Even the least active compound in Table 6 possessed a higher relative myotrophic potency than previously has been obtained with several clinically interesting compounds which have been studied under identical conditions, i.e. oxymetholone, oxandrolone, stanozolol, and methandrostenolone.” (anadrol, anavar, winstrol, and dianabol). [2]



Key:
IIe = methyltestosterone
IIa = methyl-1-testosterone
IVd = methyl stenbolone
IIf = alpha one (17a-methyl-1-androstenediol)
IIIa = phera (desoxymethyltestosterone)

As you can see from the table above, methyl sten has somewhere between 2/3 and 3/4 the anabolic activity of methyl-1-testosterone, and a similar A:A ratio (by oral administration to castrated rats).

It can also be found in an earlier paper by two of the same authors, [3] however at the time it was only studied for activity by intramuscular injection, so the figures it quotes are irrelevant for our purposes. It does, however, give a recipe for producing the compound from superdrol.



Methylsten™ is listed as one of the ingredients in a proprietary blend in a now-discontinued product called Mass Tabs by IDS, though testing has shown that this product (at least the later, bottled batches) in fact contained superdrol. [4][5]

Structure and Function:

Structurally resembling the bastard child of M1T and superdrol, methyl sten is a DHT-derivative that is dimethylated at C-2 and C-17 (like superdrol) and has a 1-ene (like methyl-1-test).

It’s important to note that while methyl stenbolone is dimethylated at C-2 and C-17 like superdrol, the spatial configuration is different due to the presence of a delta-1 double bond (the C-2 methyl group is therefore planar). This means that methyl sten is a 2,17a-dimethyl rather than a 2a,17a-dimethyl compound.

A more recent (2009) paper on the effects of structural modifications to steroids concluded that the addition of a 2-methyl function to a 1-ene steroid had little effect on the relative potency of the compound. [6]



You’ll note however that this is view is taken virtually word for word from the 1961 study that only examined the activity of the compounds by IM injection and is therefore questionable when discussing their oral activity. [3]



Metabolism:

Since it’s DHT-derived, aromatisation is impossible. 5a-reduction is also impossible, since it’s already 5a-reduced. The 17a-methyl group greatly increases the bioavailability of the compound by oral administration.

The combination of delta 1-dehydrogenation and 2-methylation is likely to make the A-ring very resistant to metabolism. 3z-,16z-, and 18-hydroxylated metabolites are likely to be the only ones detectable after administration, other than the unchanged compound. [7][8]

Effects:

It is a strong oral steroid in the vein of pheraplex, superdrol, and M1T. It should be an excellent “bulking” compound at an appropriate dosage.

Side Effects:

It is inevitable that the compound will display some degree of hepatotoxicity. This is discussed in some detail on the manufacturer’s blog, which is recommended reading. [9]

Dosages:

The only confirmed product on the market to contain this compound comes in 4mg caps and recommends dosing at two caps per day (8mg), and not to exceed three caps per day (12mg). In practice some users are dosing up to 24mg.



References
[1] Vida J.: Androgens and Anabolic Agents. Academic Press, New York (1969) p. 212.
[2] Acta Endocrinol 1966 53 627-634 & 635-643
[3] J. Org. Chem., 1962, 27 (1), pp 248–253
[4] Test results IDS mass tabs – ThermoLife International Forums
[5] Affidavit for bodybuilding.com raid: image 1, image 2, image 3
[6] Steroids 74 (2009) 172–197
[7] J. Steroid Biochem. Mol. Biol. 115 (2009) 44-61.
[8] J. Steroid Biochem. Mol. Biol. 101 (2006) 161–178.
[9] Antaeus Labs: A few words on the hepatotoxicity of 17a-methylated androgens/anabolics

 

[jbryand101b]

Re: Designer steroid profiles by henryv

HALOTESTIN

There is talk about possibly releasing a pro hormone to this compound...

Fluoxymesterone

Posted on September 23, 2012 by admin


Structure:



Brand Names:

Halotestin, Ultandren, Androfluorene, Android-F, Ora-Testryl, Stenox

Nomenclature:

9α-fluoro-11β-hydroxy-17α-methyl-17β-hydroxyandrost-4-en-3-one, or
9α-fluoro-17α-methyl-11β,17β-dihydroxyandrost-4-en-3-one, or
9α-fluoro-11β-hydroxymethyltestosterone.



History:

The Upjohn team developed an interest in the anabolic potential of steroids after observation of extensive clinical trials of “deponortestonate” (their own injectable nandrolone product) and proceeded to develop and test a number of novel compounds.

One of Upjohn’s most significant discoveries was made in the 1950s, when they discovered a microbiological fermentation technique for introducing an oxygen atom at the 11th carbon atom of a steroid. [1] Not only did this enable large-scale production of corticosteroids like cortisone, but it also paved the way for the creation of halotestin.

The results of experiments on rats given some of the 11-oxygenated steroids prepared by Upjohn can be seen below: [2]

Steroid Anabolic potency

17α-methyltestosterone 100
11β-hydroxy-17α-methyltestosterone 300
17β-hydroxy-17α-methyl-5α-androstan-3-one
(Methyl DHT) 43
11β,17β-dihydroxy-17α-methyl-5α-androstan-3-one 730
17α-methyl-5α-androsta-3β,17β-diol 35
17α-methyl-5α-androsta-3β,11β,17β-triol 1130

As you can see from the figures, all of the 11-oxygenated steroids were found to be significantly stronger than their non-oxygenated counterparts.

9α-halogenated corticosteroid derivatives were first described by Fried and Sabo in 1953 [3] and were found to have enhanced glucocorticoid and anti-inflammatory activity. With this in mind, Lyster et al at Upjohn synthesized and tested a variety of 9α-halogenated 11β-hydroxylated testosterone derivatives. [4]

Steroid Anabolic Androgenic
9α-fluoro-11β-hydroxy-testosterone 30 <10
9α-chloro-11β-hydroxy-17a-methyltestosterone <10 <10
9α-fluoro-11β-hydroxy-17a-methyltestosterone (fluoxymesterone) 2000 950

They found that while a 9-chloro group abolished activity, the 9α-fluoro substituted steroid produced a remarkable increase in the oral anabolic and androgenic activity in rats. [4]


Endocrinology 58, 781 (1956) [4]


“11β-Hydroxy-methyltestosterone is 0.9 times as potent as methyltestosterone as an androgen and 3 times as potent as a myotrophic agent. 9-Fluoro-11β-hydroxy-methyltestosterone is 9.5 times as potent as methyltestosterone as an androgen and 20 times as potent as a myotrophic agent.” [4]

The compound 9α-fluoro 11β-hydroxy 17α-methyltestosterone was subsequently trivialised to fluoxymesterone.

Anabolic/Androgenic Ratio:
◾2000 : 950 vs. 17α-methyl-testosterone by oral administration (Lyster et al, 1956). [4]

The Upjohn researchers found fluoxymesterone had an A:A ratio of 2000:950 vs. methyl testosterone by oral administration. [4]
◾1745 : 757-118 vs. 17α-methyl-testosterone by oral administration (Kincl and Dorfman, 1963). [5]

The Upjohn figures were later supported in 1963 by Syntex researchers Kincl and Dorfman who confirmed LA, SV, and VP figures of 1745%, 757%, and 118% respectively. [5]
◾380 : 140 vs. 17α-methyl-testosterone by oral administration (nitrogen retention:ventral prostate) (Beyler et al, 1963). [6]

When revisited in 1963 by Beyler et al, the anabolic (as measured by nitrogen retention) to androgenic (measured by ventral prostate) ratios of both bolasterone and fluoxymesterone were found to be “considerably less than that reported for certain… heterocyclic steroids of current clinical interest.“, [6] of course their position may have been coloured somewhat by their commercial position; as researchers at Sterling-Winthrop they were responsible for creating the steroid stanozolol – more commonly known as Winstrol. [7]



Stanozolol’s A:A ratio did not appear so favourable in this analysis by Upjohn in 1965.
Adapted from Proc. 1st Int.Congr. Hormonal Steroids, 2, pp119-132, Academic Press, New York [8]

Structure:

Structurally classified as a testosterone derivative, fluoxymesterone possesses a 17α-methyl group common to many oral AAS. This structural modification permits high oral bioavailability through the prevention of 17β-hydroxyl oxidation.
What makes fluoxymesterone particularly distinct from other available anabolic steroids is the substitution of a fluorine atom in the 9α position. While it’s an anomaly in the world of androgens, this is relatively common among synthetic glucocorticoids; it graces the likes of dexamethasone, betamethasone, fludrocortisone, and triamcinolone.
In fact there are some compounds that are substituted at 9α with other halogens. For example, beclometasone has a 9α-chloro function. Schering even tested some 9α,11β-dihalogenated compounds, with limited success, although the dichlorinated dianabol derivative showed some promise with an anabolic:androgenic ratio of 300:60 vs MT by oral admin. [9]


Chemical structure of 9α,11β-dichloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one (“dichloro-dianabol”)

It is not entirely clear why the 9-alpha-fluoro moiety imparts such high anabolic/androgenic activity to fluoxymesterone given orally, but the fluorine atom can potentially change the pharmacokinetics and pharmacodynamics of a drug in several ways:


“(1) Fluorine, because of its small steric size, resembles bioactive hydrogen with respect to steric environment in association with protein receptor regions;
(2) Fluorine, the most electronegative element, alters electronic effects;
(3) Fluorine, which when bonded to carbon has a carbon-fluorine bond energy of 107 kcal/mole, increases the oxidative, thermal, and metabolic stability; and
(4) Perhaps most importantly, carbon-fluorine bonds substantially increase lipid solubility and thereby enhance the rates of bioabsorption and biotransport.” [10]

In accordance with the first property mentioned above, the fluorine atom has a very similar van der Waals radius to the hydrogen atom it replaces. [11] Standard radii for hydrogen lie around 1.1Å-1.2Å and for fluorine around 1.35Å-1.47Å. [11][12][13]

In addition to its unusual 9α-fluoro group, fluoxymesterone also has an 11β-hydroxyl group which is characteristic of many active corticosteroids. A recent study has found that due to this 11β-hydroxyl fluoxymesterone interferes with corticosteroid metabolism.
Cortisol is converted to inactive cortisone by the enzyme 11β-hydroxysteroid dehydrogenase type 2 (11β-HSD2). Since the mineralocorticoid receptor (MR) can be activated by both mineralocorticoids and glucocorticoids, this enzyme is expressed in mineralocorticoid-sensitive tissues to prevent activation of the MR by cortisol. Fluoxymesterone was found to be a potent competitive inhibitor of human 11β-HSD2. [14] This inhibition could cause cortisol-induced MR activation, leading to retention of sodium and excretion of potassium, causing fluid retention and hypertension.

Following the successful clinical use of fluoxymesterone, some 16α-methylated variations were synthesized and tested by Merck, though they were found to be disappointingly inactive by comparison. [15]



The 11-keto analogue of fluoxymesterone is marginally more anabolic and slightly less androgenic than fluoxymesterone.
J. Am. Chem. Soc., 1956, 78 (2), pp 500–501 [16]

Metabolism:
Despite the 9α-fluoro and 11β-hydroxyl group modifications, fluoxymesterone undergoes both 5α-reduction and 5β-reduction in humans. [17] 3-keto reduced metabolites have also been detected in man. [17][18]

Although 9a-fluoro-testosterone aromatizes at around half the rate of testosterone, the 11β-hydroxyl group of fluoxymesterone will prevent aromatization. [19][20]


“The presence of axial substituents at carbon 11 interferes with ring A aromatization.” [19]

As with all 17α-alkyl-17β-hydroxy steroids, 17-keto metabolites of fluoxymesterone are impossible. 17-epimerization of fluoxymesterone has been reported and is a common (though minor) metabolic pathway among 17α-methyl-17β-hydroxy steroids. [21]

The presence of several hydroxylated, dihydroxylated, 11,12 and 13,14 unsaturated, and 11-keto metabolites have also been identified (post-administration) in humans, according to a recent study. [17]



Fluoxymesterone (F1) and its metabolites in humans (F2-F13)
Steroids. 2012 Jul;77(8-9):871-877. [17]
It is also worth noting that fluoxymesterone is metabolized to its corresponding 11-keto analogue “11-oxofluoxymesterone” by human 11β-HSD2 (though not extensively), as demonstrated by a contemporary in vitro experiment.


Metabolism of fluoxymesterone via 11β-HSD2
Toxicological Sciences. 2012 Apr;126(2):353-61. [14]


“Biological data showed that fluoxymesterone is a substrate of 11β-HSD2, but with a lower conversion rate than cortisol.” [14]



References:
[1] Steroids 57, Issue 12, 593-616
[2] Hormonal Steroids 2, Academic Press 1965, 59-67
[3] J. Am. Chem. Soc., 1953, 75 (9), pp 2273–2274
[4] Endocrinology 58, 781 (1956)
[5] Endocrinology. 1963 Jan 2;72(2):259–66.
[6] J Endocrinol 1963 28 87-92
[7] Endocrinology 1961 vol. 68 no. 6 987-995
[8] Proc. 1st Int.Congr. Hormonal Steroids, 2, pp119-132, Academic Press, New York (1965)
[9] J Am Chem Soc 82, 4611 (1960)
[10] J. Chem. Educ., 1979, 56 (4), p 228
[11] Androgens and Anabolic Agents. 1969. Academic Press. p. 63
[12] J. Phys. Chem., 1964 Mar;68 (3):441-551
[13] J. Phys. Chem., 1996 May;100 (18), pp 7384–7391
[14] Toxicological Sciences. 2012 Apr;126(2):353-61.
[15] J Org Chem 27, 682 (1962)
[16] J. Am. Chem. Soc., 1956, 78 (2), pp 500–501
[17] Steroids. 2012 Jul;77(8-9):871-877.
[18] J. Steroid Biochem. 1990 Aug;36(6):659-666.
[19] Endocrinology. 1962 Dec;71:920–925.
[20] Endocrinology. 1980 Feb;106(2):440-3.
[21] Steroids. 1992 Nov;57(11):537-50.

 

[jbryand101b]

Re: Designer steroid profiles by henryv

the read would be a bit more entertaining if images could be posted. lol. 🙁

 

[jbryand101b]

SUPERDROL

Superdrol/Methyldrostanolone/Methasteron

Androgenic Rating = 20

Anabolic Rating = 400

Chemical Name = 2a,17a-dimethyl-5a-androstane-17b-ol-3-one

Estrogenic Activity = none

Progestational Activity = no data available

Methyldrostanolone, also known as methasteron, is a potent oral anabolic steroid that was never sold as a prescription drug. In structure, this steroid is a close derivative of drostanolone (Masteron). The only difference in this case is the addition of a c-17 alpha methyl group, a modification that gives this steroid high oral bioavailability. The two agents remain very comparable, however. Both methyldrostanolone and drostanolone are non-aromatizable, so there is no difference in the estrogenicity of these two steroids, and both steroids retain favorable anabolic to androgenic ratios. Lab assays do put Superdrol ahead here, however, showing it to possess 4 times the anabolic potency of oral methyltestosterone while displaying only 20% of the androgenicity (a 20:1 ratio, compared to 3:1). The exact real-world relevance of these figures remains to be seen, however. Methyldrostanolone is favored by athletes for its moderate anabolic properties, which are usually accompanied by fat loss and minimal androgenic side effects.

History:

Methyldrostanolone was first described in 1959. This steroid was developed by the international pharmaceuticals giant Syntex, alongside such other well known anabolic agents as drostanolone propionate and Oxymetholone. Unlike drostanolone and oxymetholone, however, this steroid (at least in its basic form) was never released as a medicinal product. It was only sold for a brief period of time as a modified hormone called dimethazine. Dimethazine is made from two molecules of Methyldrostanolone that are bonded together, which are later metabolically separated to yield free Methyldrostanolone.

So while technically Methyldrostanolone itself was never sold as a prescription agent, we can say that the drug was one utilized medicinally.OtherWise, the methyldrostanolone molecule Methyldrostanolone remained an obscure research steroid only, and was never itself approved for use in humans. Methyldrostanolone was released in early 2005 as an over the counter "grey market" anabolic steroid in the United States.

The drug was being sold without restrictions as a nutritional supplement product, barring some minimum age disclaimers by the manufacturer. No State or Federal laws identify this drug as an anabolic steroid, which remove the legalities associated with being a Class III controlled substance like other steroids. This is simply due to the fact that methyldrostanolone was not in commerce at the time such laws were written, and was unknown to lawmakers. It was never legal to sell as a dietary supplement, however, and in late 2005 the FDA angrily acknowledged methyldrostanolone was being sold on the sports supplement market. In early 2006, the FDA sent letters to the manufacturer and a distributor demanding it be pulled from commerce. Superdrol has since been discontinued.

Structural Characteristics:

Methyldrostanolone is a modified form of dihydrotestosterone. It differs by: 1) the addition of a methyl group at carbon 17-alpha, which helps protect the hormone during oral administration, and 2) the introduction of a methyl group at carbon-2 (alpha), which considerably increases the anabolic strength of the steroid by heightening its resistance to metabolism by the 3-hydroxysteroid dehydrogenase enzyme in skeletal muscle tissue.

Side Effects (Estrogenic):

Methyldrostanolone is not aromatized by the body, and is not measurably estrogenic. An anti-estrogen is not necessary when using this steroid, as gynecomastia should not be a concern even among sensitive individuals. Since estrogen is the usual culprit with water retention, methyldrostanolone instead produces a lean, quality look to the physique with no fear of excess subcutaneous fluid retention. This makes it a favorable steroid to use during cutting cycles, when water and fat retention are major concerns.

Administration (Men):

Methydrostanolone was never approved for use in humans. Prescribing guidelines are unavailable. An effective dosage of methyldrostanolone for physique or performance-enhancing purposes seems to begin in the range of 10-20 mg per day, taken for no longer than 6 or 8 weeks. At this level it seems to impart a measurable muscle-building effect, which is usually accompanied by fat loss and increased definition. Don't expect to gain 30 pounds on this agent (its name, which is short for "Super Anadrol" is more marketing than reality), but many do walk away with more than 10 pounds of solid muscle gain when using this agent alone. In determining an optimal daily dosage, some do find the drug to be measurably more effective when venturing up to the 30 mg range. Potential hepatotoxicity should definitely be taken into account with such use, however.

To avoid further escalating liver strain, 20 mg daily of daily of methyldrostanolone is sometimes stacked with a non-toxic injectable steroid, such as testosterone for mass-building phases of training, or nandrolone or boldenone for more lean tissue gain and definition, instead of simply increasing the dosage.The drug also works well in cutting cycles,where its lack of estrogenicity is highly favored. Often it is combined here with a non-aromatizable Injectable steroid like Primobolan or Parabolan.

Administration (Women):

Methyldrostanolone was never approved for use in humans. Prescribing guidelines are unavailable. In the athletic arena, an effective oral daily dosage would fall around 2.5 mg per day, taken in cycles lasting no more fhan 4-6 weeks to minimize the chance for virilization. The main point of contention with females is probably going to be the 10 mg per capsule dosage, which is far too high to use. Application would require opening each capsule and splitting the powdered contents up into 4 separate doses. As with all steroids, virilization is still possible.

Availability:

Superdrol is no longer commercially produced, although some clone products may still be located, and in 2012 is now a controlled substance, but can be easily obtained from a ug lab.

William Llewellyn Anabolics 2009.

 

[Hanzo]

I posted an article about the dude who designed SDrol, last week. You can search for it. He's designed some innovative products, and he even sold a "diet" pill that contained DNP. Hah!

He owns DS and, of course, invented Craze.

 

[jbryand101b]

Re: Designer steroid profiles

EPISTANE/HAVOC

written by henryv



Nomenclature: 2a,3a-epithio-17a-methyl-5a-androstan-17b-ol or 2a,3a-epithio-17a-methyl-etioallocholan-17b-ol

Anabolic/Androgenic Ratio:

1100:91 vs. methyl test by oral administration [1]

Synonyms: Epistane, Havoc, Epi, E-Stane, Epi-Strong, Methylepithiostanol

Etymology:

Methylepithiostanol: Methyl indicates the 17a-methyl group, epi means above, indicating the bridge, thio indicating sulphur, stan is short for the androstane skeleton, and ol points out the hydroxyl at 17b.

History:

One of a number of steroidal compounds researched in the 60s by Searle Laboratories, while it was never used clinically in the West, the unmethylated analog epitiostanol has been used to treat breast cancer and gynecomastia in Japan. [2][3]

The two first "prohormone" products containing this compound, IBE's Epistane and RPN's Havoc, are still the two best-selling "epi" products on the market.

Structure and Function:

Resembling methyl DHT, but with a sulphur atom spanning C2 and C3, methylepitiostanol is an orally active compound that lacks the 3-ketone common to most anabolic steroids. Some of it's activity will be due to metabolism in vivo to other active compounds - including desoxymethyltestosterone (pheraplex). [4]

It will undergo dethionylation (loss of the sulphur atom) both in vivo or via pyrolysis (administration of high temperatures) to produce phera, as illustrated in this diagram. [5]



Effects:

Greatly increased protein synthesis and accrual of lean muscle mass with attendant strength gains. Some fat loss may be experienced, though this is dependent on diet and training.

Side Effects:

Side-effects may include (but are not limited to): loss of or heightened libido, elevated liver enzymes and potential temporary liver function impairment, HPTA disruption, adverse shifts in lipoprotein subfractions (lowered HDL, increased LDL cholesterol), acne, hair growth or loss, and an increase in blood pressure. This product should not be used by women or teens.

Gains are very lean and dry with many users complaining of sore joints (so a joint supp like Joint Force would be recommended to those experiencing pain or discomfort).

Recommended Dosages and Cycle Durations:

Cycles are typically 30 - 40mg daily for four to six weeks, followed by a SERM PCT protocol to avoid "rebound gyno".

References:
[1] Anabolic agents. 2,3-Epithioandrostane derivatives. J. Med. Chem., 1966, 9 (5), pp 693?697
[2] Gan To Kagaku Ryoho. 1988 Jul;15(7):2163-7.
[3] Jpn. J. Clin. Oncol. (1973) 3 (2): 99-104.
[4] Xenobiotica. 1991 Jul;21(7):865-72.
[5] Drug Test Anal. 2009 Nov;1(11-12):518-25.

 

[jbryand101b]

I posted an article about the dude who designed SDrol, last week. You can search for it. He's designed some innovative products, and he even sold a "diet" pill that contained DNP. Hah!

He owns DS and, of course, invented Craze.

yes, I watched the news program on it. it's sad. and a bunch of bull shit. mat cahill has been around for a while.

designer supplements brought a lot of potent oral anabolic steroids to the market.

 

[jbryand101b]

DYMETHAZINE
Roxilon, mebolazine Dimethazine (DMZ)
Androgenic 96
Anabolic 210
Standard Methyltestosterone (oraI)
Chemical Name 17beta-hydroxy-2alpha,17alpha-dimethyl-androstan-3-one azine
Estrogenic Activity none
Progestational Activity none

Description:
Dimethazine, also known as mebolazine, is a potent oral anabolic steroid derived from dihydrotestosterone. The dimethazine molecule is fairly unique in structure, being made from two methyldrostanolone molecules bonded together with an azine bridge. The body breaks this bond, however, so that the drug actually provides free methyldrostanolone (Superdrol) to the user. Dimethazine is strongly anabolic, moderately androgenic, and not appreciably estrogenic or progestational. Although presently unavailable, this drug was once highly favored by athletes for its ability to promote solid gains in lean muscle tissue without excess water retention or fat gain. Qualitatively, the drug behaves in a very similar manner to drostanolone propionate (Masteron), although as an oral c17alpha alkylated .steroid it presents considerably more toxicity.

History:
Dimethazine was first described in 1962.714 It was
developed into a medicine by Ormonoterapia Richter in
Milan, Italy. The firm sold it under the Roxilon brand name
in Italy, and as Dostalon in Mexico. The Roxilon brand was
also reportedly sold under license by Lepetit. Dimethazine
has been evaluated clinically for a number of treatments,
often including use with women, the elderly, and children.
Such applications have included the promotion of growth
in underweight children and adolescents, the retention of
lean body mass with chronic pulmonary tuberculosis, the treatment of osteoporosis, and as a general anabolic in conditions necessitating the use of such an agent. In spite of a favorable record of efficacy and safety, dimethazine was ultimately a drug that saw only limited success as a prescription agent. It was discontinued many years ago, and has been unavailable worldwide for so long that few even recognize the active ingredient as a once-marketed commercial steroid.

Structural Characteristics:
Methyldrostanolone is a modified form of dihydrotestosterone. It differs by: 1) the addition of methyl group at carbon 17-alpha, which helps protect th hormone during oral administration, and 2) th\ introduction of a methyl group at carbon-2 (alpha), whicl considerably increases the anabolic strength of the steroi< by heightening its resistance to metabolism by the 3 hydroxysteroid dehydrogenase enzyme in skeletal muscl. tissue. Dimethazine consists of two methyldrostanolone molecules bonded together with an azine bridge. These molecules are metabolically separated, yielding free methyldrostanolone.

side Effects (Hepatotoxicity):
Dimethazine is a c17-alpha alkylated compound. This 31teration protects the drug from deactivation by the liver, 3110wing a very high percentage of the drug entry into the bloodstream following oral administration. e17-alpha 31kylated anabolic/androgenic steroids can be ~epatotoxic. Prolonged or high exposure may result in liver damage. In rare instances life-threatening ;jysfunction may develop. It is advisable to visit a :Jhysician periodically during each cycle to monitor liver runction and overall health. Intake of c17-alpha alkylated jsteroids is commonly limited to 6-8 weeks, in an effort to ~void escalating liver strain. Note that in studies administering 20 mg per day to patients for 45-95 days, dimethazine was shown to induce modest to moderate bilirubinemia (excess bilirubin in the blood, indicative of hepatic stress) in close to 50% of patients.?16
Approximately 25% of the patients noticed substantial increases in serum transaminases. These results suggest this steroid has a significant level of hepatotoxicity.

Side Effects (Testosterone Suppression):
All anabolic/androgenic steroids when taken in doses sufficient to promote muscle gain are expected to suppress endogenous testosterone production. Without the intervention of testosterone-stimulating substances, testosterone levels should return to normal within 1-4 months of drug secession. Note that prolonged hypogonadotrophic hypogonadism can develop secondary to steroid abuse, necessitating m'edical intervention.
The above side effects are not inclusive. For more detailed discussion ofpotential side effects, see the Steroid Side Effects section ofthis book.
Administration (Men):
An effective dosage of dimethazine for physique-or performance-enhancing purposes begins in the range of 10-20 mg per day, taken for no longer than 6 or 8 weeks. At this level it seems to impart a measurable musclebuilding effect, which is usually accompanied by fat loss and increased definition. Higher doses are usually avoided due to potential hepatotoxicity.

SOURCE: William Llewellyns anabolics 9th edition.

typical real world dosage seems to be 30-45mg e/d

 

[GRIM]

Re: Designer steroid profiles by henryv

the read would be a bit more entertaining if images could be posted. lol. 🙁

images can be posted

 

[R2D2]

I hope you had Henry V's prior consent before posting that. ;D

 

[jbryand101b]

I hope you had Henry V's prior consent before posting that. ;D

lol, of course. 😉

 

[jbryand101b]

Re: Designer steroid profiles by henryv

images can be posted

 

[Hanzo]

We love William's Llewellyn's writings. I have the latest edition.

 

[goodfella]

Re: Designer steroid profiles by henryv

Triumphalis

This is one thats suppose to be pretty clean and dry. Would like to try this later.

 

[TSizemore]

I may have to clean this up and sticky it..... 😉

 

[Hanzo]

I may have to clean this up and sticky it..... 😉

Clean it up? Commie. That will make it lose it's ambience.

 

[TSizemore]

Clean it up? Commie. That will make it lose it's ambience.

Need to isolate them per compound