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Methyldiazirinol

Table of contents

Other Names

(5alpha,17beta)-17-Methylspiro[androstane-3,3'-[3H]diazirin]-17-ol3,3-azo-17-alpha-methyl-5-alpha-androstan-17-beta-ol3,3-azo-17a-methyl-5a-androstan-17b-ol3,3-azo-17α-methyl-5α-androstan-17β-ol3,3-azo-17α-methyl-5α-dihydrotestosterone3-Azi-17-Methyl-5a-Androstan-17b-ol3-azi-17α-methyl-DHTMethyl-diazMethyldiazinol

Synopsis

Methyldiazirinol: An Encyclopedic Reference

1. Identity: Chemical Name, Structure, and Forms

Methyldiazirinol is a synthetic anabolic-androgenic steroid (AAS) that is marketed under the guise of a dietary supplement ingredient. In 2013, the compound appeared on the market, and chemists prefer to call it 3,3-azo-17-alpha-methyl-5-alpha-androstan-17-beta-ol. It is also referred to by the synonym Methyldiazinol, and in product marketing by names such as Triumphalis and Methyl-diaz.

According to Wikidata and PubChem (CID 112500385), methyldiazirinol is classified as a subclass of steroid, with the molecular formula C₂₀H₃₂N₂O. Its IUPAC name is (5alpha,17beta)-17-Methylspiro[androstane-3,3'-[3H]diazirin]-17-ol, CAS number 2429-17-6, with a molar mass of 316.48, density of 1.33 g/cm³, and a melting point of 156–157°C.

The compound belongs to the class of diazirine-containing steroids. Compared to other anabolic agents, methyldiazirinol features a nucleophilic heteroatom in place of the standard 3-ketone group, and the additional nitrogen atom is reported to influence receptor binding and assimilation. The 17-alpha alkylation of the C-17α position allows oral administration by inhibiting metabolic deactivation in the liver.

Common forms and preparations: Methyldiazirinol has been sold almost exclusively as oral capsules. One commercially documented formulation, Primobol Dex, contained Methyldiazirinol (3,3-azo-17a-methyl-5a-androstan-17b-ol) at 20 mg per capsule, combined with other compounds including Epistane (20 mg), Trenavar (20 mg), and TUDCA (100 mg). Another product, Xtreme Shed, was documented as containing 3,3-azo-17a-methyl-5a-androstan-17b-ol at 20 mg per serving; both methyldiazirinol and co-ingredient hexadrone were characterized as prohormones or designer steroids.

Methyldiazirinol is classified as an anabolic steroid and is converted in the body to testosterone and other sex hormones.

2. Origin and History of Development

Methyldiazirinol has no botanical or natural plant-based origin. It is an entirely synthetic compound with no traditional use in herbal medicine, folk medicine, or any documented ethnomedical tradition. Claims by some supplement-marketing websites attributing traditional use of methyldiazirinol to historical herbal systems are not supported by any historical, ethnobotanical, pharmacopeial, or scholarly sources and should be disregarded.

In 1965, chemists from the American Lederle Laboratories, part of the American Cyanamid Company, published an article in the Journal of the American Chemical Society in which they introduced a group of diaziridine and diazirine steroids that they made and studied in their laboratory. In animal studies, preliminary diazirine steroids were found to be either androgenic but not very anabolic, or anabolic but not very androgenic; when the researchers modified the second type, they synthesized 3,3-azo-17-alpha-methyl-5-alpha-androstan-17-beta-ol, i.e., methyldiazirinol.

Methyldiazirinol was first researched by the pharmaceutical entity Lederle Labs, which published results of their testing in 1965 and obtained a patent for use of methyldiazirinol as a steroid for therapy in 1966. However, according to one secondary analysis, the researchers at Lederle reportedly obtained a patent on methyldiazirinol, but independent verification of that patent literature could not be confirmed.

Methyldiazirinol was never commercialized as a pharmaceutical drug, though Lederle continued to explore the possibilities of the diazirine group in other non-steroidal molecules. It was first released onto the dietary supplement market as Iron Legion Triumphalis in 2013.

Methyldiazirinol was one of many steroids listed in Julius Vida's reference text Androgens and Anabolic Agents. In a section detailing "Compounds displaying decreased androgenic activity coupled with increased anabolic activity," the 3,3-azo steroid was listed alongside steroids such as oxandrolone (Anavar), methenolone (Primobolan), stanozolol (Winstrol), and norbolethone.

3. Key Constituents and Active Compound

As a single synthetic molecule, methyldiazirinol is itself the active entity — it contains no multiple botanical constituents. Its defining structural features are:

  • 17-alpha methyl group: Alkylation at the C-17α position allows oral administration by inhibiting metabolic deactivation in the liver and often alters the relative anabolic potency in relation to the masculinizing effects.
  • 3,3-azo (diazirine) ring: Instead of having a 3-ketone, methyldiazirinol contains a stronger nucleophilic heteroatom, which reportedly improves receptor bonding.
  • 17-beta hydroxyl group: Characteristic of many anabolic steroids and important for receptor interaction. Reduction of a 17β hydroxy group to a 17-keto metabolite is important for urinary elimination of inactive metabolites.
  • 5-alpha reduction: The compound is a 5-alpha reduced androstane derivative, with structural similarities to epistane, stanozolol, and furazabol.

4. Reported Mechanisms of Action

Methyldiazirinol exerts its effects through androgen receptor (AR) agonism. It is a type of anabolic steroid and is converted in the body to testosterone and other sex hormones. For the purposes of anti-doping regulation, anabolic steroids of this class activate testosterone and epitestosterone receptors, thereby improving muscle strength and endurance.

Julius Vida drew from the animal studies described in the Lederle Laboratories publication; methyldiazirinol was found to have 20 percent of the androgenic effect of methyltestosterone and 300 percent of its anabolic effect. According to the Lederle Laboratories researchers, methyldiazirinol has an oral anabolic:androgenic ratio of 300:20 when compared to methyltestosterone, giving it a "Q factor" of 15; this provides anabolic-to-androgenic effects similar to methasterone (Superdrol), which was reported to have an anabolic:androgenic ratio of 400:20.

Methyldiazirinol does not aromatize, and neither the parent compound nor its metabolites are estrogenic or progestinic. Numerous chemical modifications to testosterone's structure have been made to improve oral bioavailability by inhibiting hepatic first-pass metabolism; however, complete dissociation of the desirable anabolic effects from the undesirable androgenic effects has not been achieved.

Methyldiazirinol has a reported half-life of approximately 6 hours.

5. Scientific Evidence by Area of Use

5.1 Evidence Overview: Critical Assessment

The scientific evidence base for methyldiazirinol is extremely limited. Methyldiazirinol has never been tested on humans. The Lederle study — published in the Journal of the American Chemical Society (1965, 87(12): 2665–71) — is the only study in which researchers have examined this steroid. That study was an animal study conducted in the 1960s by the compound's pharmaceutical inventors. There are no published randomized controlled trials, no cohort studies, no systematic reviews, and no human pharmacokinetic data specifically for methyldiazirinol in the peer-reviewed literature.

Methyldiazinol is used for weight loss, to improve athletic performance, to reduce sexual problems, and for many other uses, but there is no good scientific evidence to support its use.

5.2 Muscle Mass and Athletic Performance

The only documented data on anabolic efficacy derive from the Lederle animal studies of the 1960s. In those animal studies, methyldiazirinol demonstrated 20 percent of the androgenic effect and 300 percent of the anabolic effect of methyltestosterone. This does not mean that methyldiazirinol is therefore a safer anabolic than methyltestosterone. No human clinical trial data on muscle mass, strength, body composition, or athletic performance exist for this compound.

The American College of Sports Medicine acknowledges that anabolic-androgenic steroids, in the presence of adequate diet, can contribute to increases in body weight, often as lean mass increases, and that gains in muscular strength achieved through high-intensity exercise and proper diet can be additionally increased by AAS in some individuals. This general finding for the AAS class cannot be extrapolated specifically to methyldiazirinol in the absence of human trials.

5.3 Body Weight and Composition

No human clinical data exist. Anabolic steroids are synthetic derivatives of testosterone that have both medical applications and a high potential for misuse; they play a clinical role in managing conditions such as hypogonadism and delayed male puberty, but when misused for muscle enhancement they can lead to significant adverse effects and long-term health risks. None of these clinical indications have been studied specifically for methyldiazirinol.

5.4 Endocrine and Hormonal Effects

Methyldiazirinol is classified as an anabolic steroid and is converted in the body to testosterone and other sex hormones. Based on its structural class, it would be expected to suppress endogenous testosterone production through hypothalamic-pituitary-gonadal axis feedback — a known consequence of exogenous androgen use. No human studies have examined this directly for methyldiazirinol.

6. Body Systems and Health Areas Associated With Methyldiazirinol

Based on its classification as a 17-alpha-alkylated anabolic-androgenic steroid, the systems most implicated — whether as desired effects or adverse effects — include:

  • Musculoskeletal system: Protein synthesis, nitrogen retention, and muscle accretion (effects claimed from animal data only; no human trials).
  • Endocrine system: Converted in the body to testosterone and other sex hormones. Potential suppression of the hypothalamic-pituitary-gonadal axis is a class effect of exogenous androgens.
  • Hepatic system: Use of 17-alpha-alkylated androgenic steroids has long been associated with a distinctive form of liver injury marked by intense and prolonged jaundice.
  • Cardiovascular system: Harmful changes in cholesterol levels (increased LDL, decreased HDL), acne, high blood pressure, liver damage (mainly with oral steroids), and dangerous changes in the structure of the left ventricle of the heart are health risks associated with anabolic steroids.
  • Reproductive system: Side effects of methyldiazirinol include infertility, behavioral changes, hair loss, and breast development (gynecomastia) in men.

7. Dosage Forms and Reported Dosages

Methyldiazirinol has been marketed exclusively in oral capsule form. The following dosages are documented in product labeling and supplement-focused discussions (not from clinical trials):

  • In the Primobol Dex formulation, each capsule contained Methyldiazirinol at 20 mg, with the product supplying 60 capsules per container.
  • A daily amount of 20–40 mg has been referenced in supplement marketing materials.
  • Product producers recommend that methyldiazirinol should not be used for more than 5 consecutive weeks.
  • Like most orally administered designer steroids in this class, a four-to-six week cycle has been suggested as a typical duration in supplement forum discussions.

Important caveat: None of these dosages derive from clinical pharmacology or human safety studies. They represent commercially marketed or user-reported figures only, and there is no established safe or effective dose for humans.

8. Regulatory Status

In the United States, it is illegal to include anabolic steroids in dietary supplement products. These chemicals are also banned by the World Anti-Doping Agency (WADA).

All anabolic agents, including anabolic-androgenic steroids such as exogenously administered testosterone, nandrolone, stanozolol, and methandienone, are permanently banned by WADA due to their muscle growth and strength effects. Sport drug-testing programs globally reference the WADA Prohibited List as the definitive resource for identifying substances and methods banned in sport; WADA maintains and updates this document annually to address emerging threats to the integrity of athletic competition.

Methyldiazirinol has been characterized by anti-doping researchers as a prohormone or designer steroid. Although products containing substances of this type are generally marketed as dietary supplements, they are not lawful dietary supplements; instead, they are unapproved drugs that the FDA has not reviewed for safety and effectiveness.

The Designer Anabolic Steroid Control Act of 2014 (Public Law No. 113-260) broadened the scope of controlled substances to include many designer steroids not previously scheduled.

The NIH's Dietary Supplement Label Database (DSLD), developed by the Office of Dietary Supplements, catalogs information printed on labels of dietary supplement products sold in the United States — and methyldiazirinol appears in this database as an ingredient in labeled supplement products, reflecting its documented presence in marketed products.

9. Safety Considerations

9.1 Hepatotoxicity

Hepatic adverse effects are classically associated with 17α-alkylated AAS due to their ability to bypass first-pass hepatic metabolism. As a 17-alpha-methylated compound, methyldiazirinol carries this class risk. Anabolic steroids marketed as bodybuilding supplements typically induce a prolonged cholestatic, but ultimately self-limiting liver injury that has a distinctive serum biochemical as well as histological phenotype.

Although cholestasis is unlikely with parenterally administered unmodified testosterone, 17α-alkyl-substituted steroids, which are designed to decrease hepatic metabolism, directly contribute to a highly characteristic form of acute cholestasis, ranging from very mild to severe; clinical manifestations include nausea, pruritus, fatigue, jaundice, and dark urine with elevated bilirubin and ALP.

HDS-induced liver injury now accounts for 20% of cases of hepatotoxicity in the United States based on research data, and the major implicated agents include anabolic steroids, green tea extract, and multi-ingredient nutritional supplements.

Methyldiazirinol can also lead to liver damage and heart disease.

9.2 Endocrine and Reproductive Adverse Effects

Methyldiazirinol is possibly unsafe for most people when taken by mouth; side effects include infertility, behavioral changes, hair loss, and breast development in men.

9.3 Cardiovascular Risks

Anabolic steroids of this class can cause serious liver injury and life-threatening reactions such as heart attack, stroke, pulmonary embolism, deep vein thrombosis, and kidney damage. Documented class risks include harmful changes in cholesterol levels (increased low-density lipoprotein and decreased high-density lipoprotein), acne, high blood pressure, liver damage, and dangerous changes in the structure of the left ventricle of the heart.

9.4 Absence of Human Safety Data

Methyldiazirinol has never been tested on humans. The Lederle study, published in the Journal of the American Chemical Society (1965, 87(12): 2665–71), is the only study in which researchers have examined this steroid. A high anabolic-to-androgenic ratio in animal models does not mean that methyldiazirinol is therefore a safer anabolic than methyltestosterone.

9.5 User-Reported Adverse Effects

Based on anecdotal reports, methyldiazirinol appears to be an active oral anabolic steroid, but many users experience serious side effects — which is consistent with expectations for a 17-alpha-methylated substance.

9.6 Potential Drug Interactions

No pharmacokinetic drug-interaction studies have been conducted for methyldiazirinol. Based on its structural class, interactions expected for 17-alpha-alkylated anabolic-androgenic steroids are relevant. Some compounds are 17-alpha alkylated to improve the oral bioavailability of androgens, but this modification increases the toxicity of the androgen. Co-administration with other hepatotoxic agents (including alcohol, acetaminophen, and other oral AAS) would be expected to increase hepatotoxic risk. Anticoagulants (notably warfarin) may have their effects potentiated by anabolic steroids as a class.

9.7 Stability Concerns

The formula of methyldiazirinol is a derivative of diazirinol and may be slightly unstable under heat or over periods of time.

10. Evidence Summary and Characterization

Methyldiazirinol is a fully synthetic, 17-alpha-methylated anabolic-androgenic steroid with no botanical origin, no traditional use history, and no published human clinical trial data. Its entire scientific basis rests on a single animal study from 1965 by Lederle Laboratories and secondary reporting in Julius Vida's pharmacological reference text. It entered the dietary supplement market in 2013 as a designer steroid under branding such as Iron Legion Triumphalis and various prohormone "stack" products.

Its classification by the Natural Medicines database (Therapeutic Research Center) as an anabolic steroid, its inclusion on the WADA Prohibited List as a banned anabolic agent, and the FDA's position that such compounds are unapproved drugs rather than lawful dietary supplements all reflect the regulatory and scientific consensus that methyldiazirinol is not an appropriate or legal dietary supplement ingredient. The evidence for any health benefit is absent at the human level, while the potential for harm — particularly hepatotoxicity, cardiovascular injury, and endocrine disruption — is well-documented for its pharmacological class.

References

Health Conditions

Health conditions that Methyldiazirinol may help support.

  • No conditions available.

Body Systems

Body systems that Methyldiazirinol may help support.

  • No body systems available.
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