PEDs: Oral Anabolics (part 2)

I recently wrote about PEDs here, focusing on testosterone and its effects. In this post I’ll focus on prohormones, which are oral androgenic anabolic steroids (AAS). These are taken like any other pill. Hence, they may seem safer since there are no needles involved. Interestingly, first time steroid users will usually choose an oral compound for convenience.

Prohormones were created to mimic the effects of testosterone without the detriments. This equates to increased muscle mass and reduced fat mass without the possible androgenic side effects. A perfect anabolic compound would theoretically allow people to only receive the beneficial effects regardless of dosage. Ultimately scientists couldn’t produce the perfect analog of testosterone but before they gave up they created over 50 synthetic AAS.

In order to develop a testosterone analog they first needed to solve a key problem. This problem was that the liver can break down the basic steroids (nandrolone, testosterone and DHT) when taken orally. Therefore, a change of structure was needed to avoid first pass removal by the liver. They also focused on the problems of excess estrogen build-up and aimed to increase the half-life.

One of the first breakthroughs came when chemists replaced a hydrogen atom at the 17-alpha position with a methyl group on the testosterone molecule. This addition made the structure resistant to breakdown by the liver. However, this change increased the tendency of estrogenic side effects. The modification also lowered the affinity in which it binds to the androgen receptor. Interestingly, it prolonged the half-life of the compound which created a more potent anabolic agent. Importantly, the key problem with this type of prohormone was liver toxicity. In order to solve the liver toxicity seen with the C17-alpha compounds, scientists tried a number of alterations. They included  adding a methyl group at the C1 position (Primobolan & Proviron) and/or adding a 17beta carboxylic acid ester (Andriol). These modifications placed less stress on the liver, but are also less potent. Examples of methylated prohoromones include Winstrol, Dianabol, Anavar, and Anadrol. Each of these have compounds have a slightly different effect on the body.

Other prohormones are based around nandrolone. This is done by modifying 1, 2, 9, or 11 carbon of the ring structure in testosterone which increases its anabolic effect. These compounds are often in the structure of 19-nor-testosterone. In combination with the previously mentioned methylation, this can combine for a very anabolic drug. Examples of these drugs are Norethandrolone, Ethylesternol, and Trenbolone.

Now that I’ve gone over the chemistry let’s take a look at a more practical approach. Prohormones are often used in a cycle. A cycle can last 6-12 weeks with either a sustained or increasing dosage. Users often see significant weight gain during this period, but it may not all be due to an increase in muscle mass. A side effect of these compounds is often water retention. Frequently, people take prohormones by stacking them, which means they take two or more at a time. This is done to increase effectiveness. Essentially it increases the amount of testosterone that gets into the body. However it also increases toxicity.

Prohormones are mostly found on the black market or the internet. They are sometimes smuggled into the United States from other countries where they have been manufactured. The black market forms are dangerous because the quality may be compromised and/or diluted. Interestingly, some dietary supplements sold here in the US may contain trace amounts of steroids. For example, one in five supplements are contaminated – whether accidental or deliberate – with products that are not on the label. Prohormones can have numerous side effects. These include jaundice, hepatosis, hypertension, left ventricular hypertrophy, and increased risk for acute myocardial infarction.

Examples of prohormones:

Anadrol
Anavar/Oxandrolone
Deca-Durabolin/Nandrolone decanoate
Dianabol/Methandrostenolone
Equipoise/Boldenone undecylenate
Trenbolone/Finaplix
Winstrol/Stanozolol

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References

      Broeder, Craig E. “Oral Andro-Related Prohormone Supplementation: Do the Potential Risks Outweigh the Benefits?” Canadian Journal of Applied Physiology = Revue Canadienne De Physiologie Appliquée 28, no. 1 (February 2003): 102–16.
     Cohen PA, Maller G, DeSouza R, and Neal-Kababick J. “Presence of Banned Drugs in Dietary Supplements Following Fda Recalls.” JAMA 312, no. 16 (October 22, 2014): 1691–93. doi:10.1001/jama.2014.10308.
      Dimick, D. F., M. Heron, E. E. Baulieu, and M. F. Jayle. “A Comparative Study of the Metabolic Fate of Testosterone, 17 Alpha-Methyl-Testosterone. 19-nor-Testosterone. 17 Alpha-Methyl-19-nor-Testosterone and 17 Alpha-Methylestr-5(10)-Ene-17 Beta-Ol-3-One in Normal Males.” Clinica Chimica Acta; International Journal of Clinical Chemistry 6 (January 1961): 63–71.
      Dotson, Jennifer L., and Robert T. Brown. “The History of the Development of Anabolic-Androgenic Steroids.” Pediatric Clinics of North America 54, no. 4 (August 2007): 761–69, xi. doi:10.1016/j.pcl.2007.04.003.
      Souza, Jeanderson Pereira, Eneida de Moraes Marcílio Cerqueira, and José Roberto Cardoso Meireles. “Chromosome Damage, Apoptosis, and Necrosis in Exfoliated Cells of Oral Mucosa from Androgenic Anabolic Steroids Users.” Journal of Toxicology and Environmental Health. Part A 78, no. 2 (2015): 67–77. doi:10.1080/15287394.2014.941126.
      Ziegenfuss, Tim N., John M. Berardi, and Lonnie M. Lowery. “Effects of Prohormone Supplementation in Humans: A Review.” Canadian Journal of Applied Physiology = Revue Canadienne De Physiologie Appliquée 27, no. 6 (December 2002): 628–46.
     Álvarez-Ginarte, Yoanna María, Luis Alberto Montero-Cabrera, José Manuel García de la Vega, Pedro Noheda-Marín, Yovani Marrero-Ponce, and José Alberto Ruíz-García. “Anabolic and Androgenic Activities of 19-nor-Testosterone Steroids: QSAR Study Using Quantum and Physicochemical Molecular Descriptors.” The Journal of Steroid Biochemistry and Molecular Biology 126, no. 1–2 (August 2011): 35–45. doi:10.1016/j.jsbmb.2011.04.003.

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