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heavyiron
12-23-2010, 09:04 AM
Havoc (methepitiostane)

Androgenic 91
Anabolic 1100
Standard Methyltestosterone (oral)
Chemical Name 2alpha,3alpha-epithio-17alpha-methyl-5alpha-androstan-17beta-ol
Estrogenic Activity none
Progestational Activity none

Description:

Methepitiostane is an oral anabolic steroid derived from dihydrotestosterone. This agent is a c17-alpha alkylated analog of epitiostane (see Thioderon), and like this drug also displays a favorable balance between anabolic and androgenic effect. In this case, however, the separation is considerably more pronounced, with the drug exhibiting an anabolic effect that is roughly 12 times more pronounced than its androgenic effect.That is according to the standard animal assays, which often vary somewhat to experiences in humans. This drug was never clinical tested in humans, so what is known of it is based on a small number of animal experiments, and structural and anecdotal observations. What can be stated with certainty if that methepitiostane is a primarily anabolic steroid with a pronounced level of activity, and is effective for the promotion of lean mass and strength gains. It likely also imparts some anti-estrogenic effect, further strengthening the association between this agent and dieting, cutting, and lean muscle mass phases of training as opposed to bulking.

History:

Methepitiostane was first described in 1966, during investigations into a series of A-ring modified androstane derivatives.571 That same year it was assayed for anabolic and androgenic potency via the standard rat assays, and demonstrated both pronounced anabolic properties and very weak relative androgenicity.572 The assay results were probably most similar to desoxymethyltestosterone (Madol), although methepitiostane is about half as androgenic. Although the results of the early testing were very favorable, this agent never progressed to the point of being a commercial steroid product or even tested on human subjects. Like a great many steroids, it was examined but not actualized as a prescription product. For forty years, the agent would be lost to the public, existing as an item of research interest only.

Methepitiostane would emerge from research obscurity at the end of 2006, when a new company called Recomp Performance Nutrition introduced it to the U.S. market under the trade name Havoc. It would be sold openly as a dietary supplement.This channel of sales does not reflect a weak potency or "non-steroid" classification, however, as methepitiostane is very much a potent drug. It is being sold as such due to the fact that the u.s. dietary supplement market is not tightly regulated, and the drug was never classified (specifically according to the law) as an anabolic steroid. While regulations do exist that would prevent the sale of an unapproved new drug as a food supplement, they do not carry the same weight as the anabolic steroid laws, and have historically not been aggressively enforced. Methepitiostane remains on sale as of December 2006, although the manufacturer has stated that they plan to discontinue the product very shortly.

How Supplied:

Methepitiostane was never approved as a prescription drug preparation. It is being sold in the U.S. supplement market under the trade name Havoc, and is supplied in the form of capsules containing 10 mg of steroid.

Structural Characteristics:

Methepitiostane is a modified form of dihydrotestosterone. It differs by 1) the addition of a 17alpha methyl group, which helps protect the steroid from metabolism during oral administration, and 2) the replacement of 3-keto with 2,3 alpha-epithio, which increases anabolic strength while reducing relative androgenicity.

Side Effects (Estrogenic):

Methepitiostane is not aromatized by the body, and is not measurably estrogenic. Furthermore, its non-methylated analog mepitiostane (Thioderon) is used clinically for its inherent antiestrogenic effect. Some level of antiestrogenic effect is also assumed with methepitiostane. An antiestrogen is, likewise, not necessary when using this AAS, as gynecomastia should not be a concern even among sensitive individuals. Since estrogen is the usual culprit with water retention, this AAS instead produces a lean, quality look to the physique with no fear of excess subcutaneous fluid retention. This makes it a favorable AAS to use during cutting cycles, when water and fat retention are major concerns. Note that some users may notice lethargy with this AAS, which may be due, in part, to its low androgenic or estrogenic component. Stacking it with an aromatizable androgen like testosterone should alleviate this problem.

Side Effects (Androgenic):

Although classified as an anabolic AAS, androgenic side effects are still possible with this substance, especially with higher doses. This may include bouts of oily skin, acne, and body/facial hair growth. Anabolic/androgenic steroids may also aggravate male pattern hair loss. Women are warned of the potential virilizing effects of anabolic/androgenic steroids. These may include a deepening of the voice, menstrual irregularities, changes in skin texture, facial hair growth, and clitoral enlargement. Methepitiostane is a AAS with very low androgenic activity relative to its tissue-building actions, making the threshold for strong androgenic side effects comparably higher than with more androgenic agents such as testosterone, methandrostenolone, or fluoxymesterone. Note that methepitiostane is unaffected by the S-alpha reductase enzyme, so its relative androgenicity is not affected by the concurrent use of finasteride or dutasteride.

Side Effects (Hepatotoxicity):

Methepitiostane is a c17-alpha alkylated compound. This alteration protects the drug from deactivation by the liver, allowing a very high percentage of the drug entry into the bloodstream following oral administration. e17-alpha alkylated anabolic/androgenic steroids can be hepatotoxic. Prolonged or high exposure may result in liver damage. In rare instances life-threatening dysfunction may develop. It is advisable to visit a physician periodically during each cycle to monitor liver function and overall health. Intake of c17-alpha alkylated steroids is commonly limited to 6-8 weeks, in an effort to avoid escalating liver strain.

The use of a liver detoxification supplement such as Liver Stabil, Liv-52, or Essentiale Forte is advised while taking any hepatotoxic anabolic/androgenic steroids.

Side Effects (Cardiovascular):

Anabolic/androgenic steroids can have deleterious effects on serum cholesterol. This includes a tendency to reduce HDL (good) cholesterol values and increase LDL (bad) cholesterol values, which may shift the HDL to LDL balance in a direction that favors greater risk of arteriosclerosis. The relative impact of an anabolic/androgenic AAS on serum lipids is dependant on the dose, route of administration (oral vs. injectable), type of AAS (aromatizable or non-aromatizable), and level of resistance to hepatic metabolism. Methepitiostane has a strong effect on the hepatic management of cholesterol due to its structural resistance to liver breakdown, non-aromatizable nature, and route of administration. Anabolic/androgenic steroids may also adversely affect blood pressure and triglycerides, reduce endothelial relaxation, and support left ventricular hypertrophy, all potentially increasing the risk of cardiovascular disease and myocardial infarction.

To help reduce cardiovascular strain it is advised to maintain an active cardiovascular exercise program and minimize the intake of saturated fats, cholesterol, and simple carbohydrates at all times during active AAS administration. Supplementing with fish oils (4 grams per day) and a natural cholesterollantioxidant formul.a such as Lipid Stabil or a product with comparable ingredients is also recommended.

Side EffectUTestosterone 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 AAS abuse, necessitating medical intervention.

The above side effects are not inclusive. For more detailed discussion ofpotential side effects, see the AAS Side Effects section ofthis book.

Administration (Men):

Methepitiostane was never approved for use in humans., Prescribing guidelines are unavailable. An effective dosage for physique-or performance-enhancing purposes falls in the range of 10-20 mg daily.This is usually taken for no longer than 6-8 weeks, in an effort to avoid significant liver strain. At this level the drug should impart a measurable but moderate lean-mass-building effect, which, depending on dietary and metabolic factors, may be accompanied by measurable fat loss and an increase in! definition. Doses of 30 mg per day are also commonly used, however given the high relative potency of the steroid may present significant hepatotoxicity. When administered, higher doses are usually taken for durations lasting no longer than 4-6 weeks.

Administration (Women):

Methepitiostane was never approved for use in humans. Prescribing guidelines are unavailable. An effective dosage for physique-or performance-enhancing purposes would be around 5 mg per day. This would be taken for no longer than 4-6 weeks, in an effort to avoid significant liver strain or virilizing side effects. Given that complete separation of anabolic and androgenic effect has not been achieved with any steroid, this agent is still capable of producing virilizing activity given the right dose or individual sensitivity.


Reference:
Llewellyn's W. (2009). Anabolics (9th ed), Havoc methepitiostane (pp. 267-269): Jupiter, FL: Molecular Nutrition

heavyiron
12-23-2010, 09:06 AM
Methylepitiostanol (Epistane)


Characteristics

Methylepitiostanol is a methylated version of the steroid Epitiostanol. It is readily active and does not require conversion. Under the influence of heat methylepitiostanol readily breaks down to 17a-Methyl-androstan-2-en-17b-ol (DMT), a now illegal anabolic steroid.

It does not aromatize, however it is possible that methylepitiostanol may offset estrogen and testosterone from SHBG thus increase the risk of gyno for certain individuals with high SHBG levels. Gyno symptoms from this compound may also be a result of this compounds inability to form a potent androgen such as DHT (to antagonize the effects of estrogen). However, in other cases methylepitiostanol can be used to prevent or reduce gynecomastia from an estrogenic steroid by acting as an aromatase inhibitor to keep estrogen down.

It is a DHT derivative with a fairly moderate androgenic value so the chances of hair loss may be increased in certain sensitive users. Swelling of the prostate may also become an issue. The powerful estrogen suppressing action of this steroid and its 17aa stucture will cause it to negatively influence the cholesterol profile by lowering HDL and increasing LDL. It has also been reported to cause stiff joints, possibly related to its suppressive effect on estrogen levels.

Anecdotal reports of appetite suppression and general fatigue would lead one to believe that the liver stress from this 17aa compound is rather severe. For this reason it is recommended to use a liver protecting supplement prior to and during the use of this steroid.

Methylepitiostanol has a strong anabolic action that will lead to quick gains in lean muscle mass and strength with very little bloat. The gains will appear with minimal fat gain and increased vascularity.

Because methylepitiostanol can negatively affect joint comfort it is recommended to be stacked with an aromatizing or progestational compound. However, it is not recommended to stack this steroid with another 17aa oral.

Common Clones:

Epistane by Innovative Body Enhancement (IBE)
Havoc by Primaforce
Havoc by Recomp Performance Nutrition (RPN)
Epi-MAX by Anabolic Formulations
M14-E by Purus Labs
Methyl-E by Engineered Sports Technology (EST)
E-Max by Juggernaut Nutrition
E-Stane by Competitive Edge Labs (CEL)
Hemaguno by Spectra Force Research
Hemapolin by Starmark Labs
Epi-Mass by Armour Nutrition
Epidrol by Genera Labs
Methyl Freak by Rockhard Formulations
Epistrong by Mrsupps

References

“2,3-Epithio-5-androstan-17ß-yl 1-Methoxycyclopentyl Ether in the Treatment of Advanced Breast Cancer —A Preliminary Clinical Trial”
SOICHI KUMAOKA, M.D., OSAMU TAKATANI, M.D., MINORU YOSHIDA, M.D., SHIGETO MIURA, M.D., TETSUTO TAKAO, M.D., YÜJI HAMANAKA, M.D., MASARU IZUO, M.D. and TADAKAZU OKADA, M.D.
Japanese Journal of Clinical Oncology 4:65-68 (1974)
“Inhibited growth in vivo of a mouse pregnancy-dependent mammary tumor (TPDMT-4) by an antiestrogen, 2alpha, 3alpha-epithio-5alpha-androstan-17beta-ol (10275-S).”
Matsuzawa A, Yamamoto T.Cancer Res. 1976 May;36(5):1598-606.
“Antitumor Effect of Two Oral Steroids, Mepitiostane and Fluoxymesterone, on a Pregnancy-dependent Mouse Mammary Tumor (TPDMT-4)1”
Akio Matsuzawa and Tadashi Yamamoto
Cancer Research 37, 4408-4415, December 1, 1977

By Jason Rowland

Chemical Name(s):

2a,3a-epithio-17a-methyl-etioallocholan-17b-ol
2a,3a-epithio-17a-methyl-5a-androstan-17b-ol
Chemical Formula: C20H30OS
Molecular Weight: 320.5
CAS: NA
Q Qatio: 12
Anabolic #: 1,100
Androgenic #: 91
Oral Bioavailability: Estimated at 40%
AR Binding Affinity: NA
SHBG Binding Affinity: NA
Half Life: ~6 hours
Legal Status (US): Not listed as a controlled substance
Average Dose:
40-50mg/day standalone
10-20mg/day when stacked
Average Cycle Length: 4-6 weeks

heavyiron
12-24-2010, 07:24 PM
2α 3α-Epithio-5α-androstan-17β-ol in Treatment of Gynecomastia


OSAHIKO ABE (http://jjco.oxfordjournals.org/search?author1=OSAHIKO+ABE&sortspec=date&submit=Submit), M.D.1 (http://jjco.oxfordjournals.org/content/3/2/99.short#aff-1),
SOICHI KUMAOKA (http://jjco.oxfordjournals.org/search?author1=SOICHI+KUMAOKA&sortspec=date&submit=Submit), M.D.2 (http://jjco.oxfordjournals.org/content/3/2/99.short#aff-2) and
HIROSHI YAMAMOTO (http://jjco.oxfordjournals.org/search?author1=HIROSHI+YAMAMOTO&sortspec=date&submit=Submit), M.D.3 (http://jjco.oxfordjournals.org/content/3/2/99.short#aff-3)
+ (http://jjco.oxfordjournals.org/content/3/2/99.short#) Author Affiliations

1Department of Surgery, National Cancer Center Hospital Tokyo, Japan
2Endocrinology Division, National Cancer Center Research Institute Tokyo, Japan
33Department of Surgery, National Cancer Center Hospital Tokyo, Japan


Received November 19, 1973.
Abstract




1. The clinical effect of epitiostanol, a new anti-estrogen agent (2α,3α-epithio-5a-androstan-17β-ol) against gynecomastia was studied in comparison with dromostanolone propionate in fifty-four patients ranging from twenty to fifty years in age without previous history of hormone therapy and with normal liver function. The experiment was performed for eight weeks by double blind methods in three dosage groups, epithiostanol 10 mg, and 20 mg and dromostanolone propionate 50 mg.
2. Epithiostanol 20 mg was most effective with regards to effect on mass size and tenderness, (effective in 96%, 20/21), followed by 10 mg epitiostanol (effective in 89%, 16/18) and dromostanolone propionate 50 mg (effective in 89%, 16/18) in descending order. No side effects were observed in any of the three groups.
3. Based on the results of the present study, epitiostanol is concluded to be at least as effective as dromostanolone propionate against gynecomastia and to be safe from the viewpoint of side effects. A satisfactory therapeutical effect on gynecomastia can be expected with a weekly dosage of 20 mg of epitiostanol for an administration period of between five to eight weeks.


© 1973 JAPANESE JOURNAL OF CLINICAL ONCOLOGY

heavyiron
12-24-2010, 07:24 PM
Gan To Kagaku Ryoho. (http://javascript<b></b>:AL_get(this, 'jour', 'Gan To Kagaku Ryoho.');) 1988 Jul;15(7):2163-7.

[A case of advanced breast cancer successfully treated with combined tamoxifen and epitiostanol]

[Article in Japanese]
Konishi Y (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Konishi%20Y%22%5BAuthor%5D), Morimoto T (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Morimoto%20T%22%5BAuthor%5D), Komaki K (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Komaki%20K%22%5BAuthor%5D), Yamakawa T (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Yamakawa%20T%22%5BAuthor%5D), Mituyama N (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Mituyama%20N%22%5BAuthor%5D), Tanaka T (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Tanaka%20T%22%5BAuthor%5D), Oomine Y (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Oomine%20Y%22%5BAuthor%5D), Monden Y (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Monden%20Y%22%5BAuthor%5D).
2nd Dept. of Surgery, School of Medicine, University of Tokushima.

Abstract

A patient with stage IV advanced breast cancer with multiple metastasis (bones of the whole body, lungs) were treated by ovariectomy, administration of an non-steroidal antiestrogen (tamoxifen) and mild chemotherapeutic drugs, with favorable results. After four years, however, the patient had a relapse of the cancer. A steroidal antiestrogen (epitiostanol) was then administered with satisfactory results. When a breast cancer relapse occurs in patients once treated successfully with endocrinotherapy, a different form of endocrinotherapy should be tried. There is a possibility that the mechanism of action of Epitiostanol, which is regarded as a steroidal antiestrogen, is different from that of tamoxifen in which an estrogen receptor (ER) system is included.


PMID: 3395140 [PubMed - indexed for MEDLINE]

heavyiron
12-24-2010, 07:25 PM
"Effects of 2alpha, 3alpha-epithio-5alpha-androstan-17beta-ol (epitiostanol) on hypothalamo-pituitary-gonadal axis in humans."

Effective on treating gyno in 12 of 12 patients, only 2 cases of side effects, 1 libido increase and 1 acne (out of acne, hoarseness, hirsutism, pigmentation, clitoris enlargement (some of the patients were female), libido increase, liver function change, other).

"...results seems to suggest that epitiostanol has clinical effects at the target organ level rather than via the suppression of gonadotropin secretion."

heavyiron
12-24-2010, 07:25 PM
Drug Test Anal. (http://javascript%3cb%3e%3c/b%3E:AL_get(this,%20'jour',%20'Drug%20Test%20Anal. ');) 2009 Nov;1(11-12):518-25.

Analysis of non-ketoic steroids 17alpha-methylepithiostanol and desoxymethyl- testosterone in dietary supplements.

Okano M (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Okano%20M%22%5BAuthor%5D), Sato M (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Sato%20M%22%5BAuthor%5D), Ikekita A (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Ikekita%20A%22%5BAuthor%5D), Kageyama S (http://www.ncbi.nlm.nih.gov/pubmed?term=%22Kageyama%20S%22%5BAuthor%5D).
Anti-Doping Centre, Mitsubishi Chemical Medience Corporation, 3-30-1 Shimura, Itabashi-ku, Tokyo, Japan. Okano.Masato@mk.medience.co.jp (Okano.Masato@mk.medience.co.jp)

Abstract

Dietary supplements containing 17alpha-methyl-2,3-epithio-5alpha-androstane-17beta-ol (17alpha-methylepithiostanol), which is a 17-methylated analogue of epithiostanol or a prodrug of desoxymethyltestosterone (17alpha-methyl-5alpha-androst-2-en-17beta-ol), have recently appeared on the Internet. 17alpha-Methylepithiostanol and desoxymethyltestosterone are classified as prohibited substances on the World Anti-Doping Agency (WADA) list. Two preparations, EPISTANE and P-PLEX, were obtained from the Internet so that their contents could be investigated. This study involved gas chromatography/mass spectrometry (GC/MS) analysis after trimethylsilyl (TMS) derivatization, liquid chromatography/mass spectrometry (LC/MS) in atmospheric pressure photoionization (APPI) mode and nuclear magnetic resonance (NMR) spectroscopy. Analysis using LC/MS in APPI mode would be a useful tool for detecting heat-labile and non-polar steroids.Although the labelling of EPISTANE indicates that it contains 17alpha-methyl-2alpha, 3alpha-epithio-5alpha-androstane-17beta-ol only, 17alpha-methyl-2beta,3beta-epithio-5alpha-androstane-17beta-ol and desoxymethyltestosterone were identified in the supplement. The results showed that P-PLEX contained desoxymethyltestosterone and its isomer 17alpha-methyl-5alpha-androst-3-en-17beta-ol. Urine samples can be screened after EPISTANE or P-PLEX administration using the normal screening procedure for anabolic steroids with GC/MS.

Copyright (c) 2009 John Wiley & Sons, Ltd.

PMID: 20355167 [PubMed - indexed for MEDLINE]