Sorry, I should have posted this with my original comments...
Methoxy
I know I'm going to get a lot of hot water for badmouthing this one. But fact remains this is the shadiest stuff on the market. The most recent tests I found were dated 1981, and all of them conducted under suspect circumstances in the country of origin, Hungary. All of the information on Methoxy isoflavone and Ipriflavone , the two most common forms of methoxy, is based on US patent information dating back to 1977. Even with the patent locked up, there should have been evidence of use in the sports world throughout the past 24 years. After all, they claim this stuff is better than steroids. I've heard some pretty bold remarks by companies claiming their supplements are almost as good as steroids and not be able to uphold it, but this is ludicrous. I don't think anyone could really fall for something better than steroids but with no side-effects. What really worries me is that I haven't heard even a single testimonial from someone who gained a pound of lean mass that couldn't be accredited to something else. I mean, even with the worst supplements you always hear someone that experiences some minor gains, but not a one with methoxy. The body protects itself against exogenous substances, which is why steroids are so popular, because they trick the body into thinking they're endogenous substances. But with flavonoids, they would be broken down before exerting these effects. If any of these test-results are for real, I guarantee you the stuff was injected.
And is it common in this industry to go by test material supplied by the manufacturing company (Chinoin), tests done in-house and with a world of flaws in them ? In the medical community people laugh at practices like these, but praying on the believing nature of intermediate bodybuilders they just smell money. When Twinlabs or Universal comes out with a methoxy supplement, I may just decide to give methoxy the benefit of doubt, but as long as the major, quality companies shy away from it, It remains hard to accept the supplement as a steady factor. Which is why it is so hard to find quality Nor-diol as well...
(Update! Universal has two new Methoxy products: Natural Sterol Extreme and IsoStak. Twinlab does not yet have a Methoxy product.)
A recent attempt has been undertaken to do tests to prove methoxy worked. They showed it did. Why does this not surprise me you ask? Well, looking at the study you'll notice that the study contains a few flaws both in the way testing was performed (the gains were not shown to be conclusive, nor shown to be accredited to the product) and the test-subjects. Last time I tried to explain this to someone I was said to be prejudiced. But if you look at the top of the study you'll also notice that the study was sponsored (and we're not talking peanuts so I think some of that money may compromise the integrity of the researcher) by one of the companies that manufactures methoxy and has a great stake in that market. I'm not going to name the company, but if you go back through some of the message boards of the past few weeks and months you can find it.
As far as I'm concerned, buying methoxy is wasted money. I wrote to some people in the industry who have their ears to the grapevine where new supplements are concerned. All of them agreed that there is no basis for the power of methoxy, and I believe Will Brink gave me the best answer "There is no proof this stuff works, and for me that's all I need to know."
3'-prenyl-4'-methoxy-isoflavone-7-O-beta-D-(2''-O-p-coumaroyl) glucopyranoside, a novel phytoestrogen from Sopubia delphinifolia.
Saxena VK, Bhadoria BK.
Department of Chemistry, Dr. H.S. Gour University, Sagar, Madhya Pradesh, India.
A novel phytoestrogen compound, 3'-prenyl-4'-methoxy-isoflavone-7-O- beta-D-(2''-O-p-coumaroyl)glucopyranoside, has been isolated from the EtOAc-soluble fraction of the stems of Sopubia delphinifolia and has been identified by chemical and spectral analysis. Pharmacological examination of the compound showed it to have estrogenic activity.
Howz it Work?:
Ipriflavone/Methoxyflavone
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by Bryan Haycock MSc., CSCS
First came Ipriflavone, sold as an anabolic isoflavone. It was preceded by hype and mystery, both tantalizing and frustrating to anybody "in the know" and not on drugs. A lot of people bought it, including me. A lot of people stopped buying it a short time after. A short time after they didn�t notice any new muscle growth, that is. Then came 5-methyl-7-methoxy-isoflavone, a slightly tweaked version of Ipriflavone. It was also preceded by a lot of hype and mystery. As you might expect, a lot of people bought it (not me). It appears people are still buying it.
I have always been one to do my homework on any new supplement I was interested in trying. Not that I�m more savvy than other people, it�s just that I�ve always had a fairly limited supplement budget and couldn�t afford to waste my money. When doing your homework on supplements, you have to ask yourself a couple of questions. First, what is being claimed about a particular supplement? Second, do the claims make sense given the mechanism of action? In trying to answer these two questions you will be lead to the right information to help you make savvy supplement purchases.
So what about Ipriflavone and/or 5-methyl-7-methoxy-isoflavone? What are the claims? What is the mechanism of action?
The claims made by those selling the stuff are as follows:
"� the ultimate, "perfect" anabolic agent. You may be saying to yourself, "I've heard this story before." Well, you may have, but this time the story has a different ending � it's true!"
"It [5-methyl-7-methoxy-isoflavone] was originally designed to increase lean mass on animals and humans, without the negatives associated with steroids."
"�potent anabolic�"
"it's [5-methyl-7-methoxy-isoflavone] not only anabolic, it's healthy!"
"it [5-methyl-7-methoxy-isoflavone] significantly increases calcium, phosphorous, potassium, and nitrogen retention, which clearly shows its anabolic horsepower."
"so powerful it�s guaranteed to help you pack on up to 10 pounds of rock-hard mass in just 30 days!"
"it [5-methyl-7-methoxy-isoflavone] works."
"�5-methyl-7-methoxy isoflavone (methoxivone), the strongest Nutrient partitioning isoflavone. Potent for gaining muscle, losing fat, and increasing vitality, well-being and endurance. Also useful in suppor[t]ing strong, healthy bones, and maintaining low cholesterol levels"
I could go on and on, but I�ll spare you. The point I�m trying to make is that the people making and selling this stuff are telling us it is the "perfect anabolic." That�s a pretty hefty claim!
Our second step in determining the value of ipriflavone/methoxyflavone is to figure out the mechanism of action. The mechanism of action refers to what and how it changes the chemistry of the body. Let�s review the relevant research. Keep in mind that ipriflavone and 5-methyl-7-methoxy-isoflavone (methoxyflavone) are assumed to have the same mechanism of action, so I will use Ipriflavone and methoxyflavone interchangeably.
Ipriflavone inhibits bone resorption:
Most people familiar with Ipriflavone know that it has been extensively studied with respect to bone metabolism, or more specifically, osteoporosis. For instance, one representative animal study found ipriflavone inhibited parathyroid hormone-, vitamin D-, PGE2-, and interleukin 1�-stimulated bone resorption (1). The effects of Ipriflavone on bone loss have also been demonstrated in humans. The same protocol was used throughout most of these studies (i.e. 200 mg ipriflavone or placebo three times daily). Several two-year studies looked at women immediately postmenopause (age 50-65) and found bone mass was maintained or improved slightly in the ipriflavone groups while those in the placebo groups experienced significant bone loss (2,3,4,5).
This research on bone metabolism doesn�t really back up "the perfect anabolic" claims made by the supplement companies. There still may be hope however, as other research has been done looking at slightly different physiological effects.
Ipriflavone acts as an estrogen "sensitizer" in several tissues:
Before you shriek at the thought of enhancing estrogen�s effects, read on to see exactly how this happens. While Ipriflavone does not have any significant direct estrogenic effects, it does enhance the effects of estrogen, particularly in bone, the thyroid gland, and the gastrointestinal tract (6,7). In bone, ipriflavone makes estrogen�s bone sparing effect more potent. Ipriflavone, like the soy flavone genistein, has decent affinity for the estrogen receptor-beta (8).
OK, so this still doesn�t exactly sound like the "perfect anabolic." Ipriflavone and methoxy do have other effects.
Ipriflavone�s effects on Ca2+:
In the heart, ipriflavone has been shown to prevent Ca2+ ions from building up in the mitochondria (9). Ca2+ builds up in mitochondria when there is insufficient oxygen. Ipriflavone actually enables heart muscle tissue to survive longer without oxygen. This means less damage due to hypoxia (lack of oxygen). No studies have been performed looking at skeletal muscle function during ipriflavone supplementation however, it is not unreasonable to assume a similar function in skeletal muscle. More research is needed in this area.
OK, I will let you in on a little secret. All of the claims about the "anabolic" properties of ipriflavone and methoxyflavone are based on the claims made in their respective patents. Here is an excerpt from one of the patents on Ipriflavone United States patent number 3,949,085.
"Test of anabolic effect: The investigation was carried out with castrated rats by means of the musculus levator ani test and vesicula seminalis test. The preparations were administered orally for a period of three weeks. The tests were performed by the method of Eisenberg and Gordan (Eisenberg, E., Gordan, G. S. J.: J. Pharmacol. 99, 38, 1950). In addition to that, also the weight of the prepared diaphragm of the animals was established. According to these tests, the weight of musculus levator ani rose by a Student significance of p 0.01, the weight of vesicula seminalis did not increase while the weight of the prepared diaphragm of the animals increased by a Student significance of p 0.05. On the basis of these results the preparations proved to possess the anabolic activity free from androgen effect."
The patent goes on to relate�
"The weight yield increasing effect induced by doses of 2 g/100 kg of feed was in the various animal species as follows:
8 to 15% in calves
7 to 10% in cattle
7 to 10% in hogs
8 to 20% in poultry
10 to 20% in rabbits
8 to 12% in guinea pigs"
The amount of feed given to these animals did not increase, only their body weights increased. They did test their new compound on ill humans as well:
"The anabolic effect of the composition was tested on thinned (asthenic), reconvalescent, dystrophic patients suffering from pathological thinness. It has been found that as a result of a treatment lasting for some weeks the patients have gained 2-3 kg of weight. According to our experiments the physical condition of the patients has also improved."
In the patent on 5-methyl-7-methoxy-isoflavone (U.S. patent 4,163,746), the details on increasing ipriflavone�s effectiveness are outlined. Several compounds are mentioned, namely 5-methyl-7-methoxy-isoflavone; 5-methyl-7-ethoxy-isoflavone; 5-methyl-7-(2-hydroxy-ethoxy)-isoflavone; and 5-methyl-7-isopropoxy-isoflavone. The same guys filed the 5-methyl-7-methoxy-isoflavone patent some 3 years after they filed the ipriflavone patent. Basically, all this patent does is show that when you methylate the isoflavone, you make it nearly twice as anabolic compared to ipriflavone. The claims are the same except that I noticed the claim that the "compounds are useful as anorexigenic agents. A significant advantage of these compounds over known catabolic agents is that they do not exhibit a central stimulating effect." Now this is quite a claim to add to the fact that they profess that it is an anabolic, as well. So not only does it cause a shift towards more muscle, it also decreases appetite at the same time. Thus far, no manufacturers that I have seen make the claim that ipriflavone or 5-mthyl-7-methoxy-isoflavone is a good appetite suppressants. But if they wanted to I guess they could, based on this patent.
One note about patents; just because an individual or company gets a patent, does not mean that their claims are accurate about their invention. It only means that whoever was assigned their file at the US patent and trademark office approved their file for a patent. It would certainly be nice to see someone do a little research on these flavones to see if in fact there are measurable anabolic effects when given to humans at reasonable doses.
Still, I do feel that ipriflavone/methoxyflavone is a valuable supplement to anybody who trains regularly. It "should" help to strengthen bones and tendons and even enhance cellular metabolism. If the patents are true, it may even increase muscle mass and decrease fat mass if used long enough. Keep in mind that we only answered the first question completely. There is still NO good explanation of how ipriflavone or its methylated derivatives could produce non-hormonal, or hormonal for that matter, anabolic effects.
Methoxyisoflavone: The Truth
by Paul Cribb, B.H.Sci HMS
AST Director of Research
reatine was probably the best and worst thing to happen to the sports supplement industry.
Several hundred studies now validate creatine's remarkable muscle building, performance enhancing abilities in a variety of sports. Extensive research shows creatine to be safe, side effect-free and, best of all, economical to use. To some extent, the Holy Grail had been found. Creatine single handedly bolstered the credibility of an industry filled with unscrupulous companies.
Now creatine's success has caused a gold-rush among sports supplement companies. They are all eager to cash in on the restored faith of the consumer and discover the next creatine. Creatine was the perfect example of how science and the supplement industry could work together. And while I suspect there will never be another creatine, this has not stopped many supplement companies desperately attempting to find something better. One of the recent, and perhaps most fraudulent, examples is methoxyisoflavone (5-methyl-7-methoxy-isoflavone). This isoflavone has been marketed as a "powerful anabolic", a "scientifically-proven lean mass stimulator" and an "alternative to anabolic steroids".
What are isoflavones?
Isoflavones are compounds found in soy beans or soy-containing foods.[1] They are naturally occurring, non-steroidal phytoestrogens that bind to estrogen receptors and possess weak estrogenic properties.[2] Some of the research that is sited in the marketing of "anabolic" isoflavones shows that compounds such as ipriflavone may hold promise in the treatment of osteoporosis, and soy isoflavone extracts to treat estrogen-deficient conditions, but this research has nothing to do with building muscle.[2-4]
So, exactly what is the scientific literature behind methoxyisoflavone, ipriflavone and the other "highly anabolic" isoflavones? None. I have performed numerous literature scans on these compounds and can find absolutely nothing to do with building muscle, in fish, birds, chickens or any other animal.
What's in a patent?
According to many of the companies that market methoxyisoflavone, this "mysterious" compound remained "buried" in the US Patent Office until 1997 when the rights expired. Some researchers in Hungary filed patents on these compounds over 30-years ago.[5,6] They believed these isoflavone compounds possessed non-estrogenic properties. The patents contain some descriptions of animal research and recommendations of how these compounds may be of use to humans. However, that is about it. That is all the evidence there is to support the amazing anabolic properties of methoxyisoflavone and its related compounds!
Some supplement marketers will attempt to impress you in their advertising with the sighting of patent numbers claiming that the US Patent Office would not award a patent to something that was not effective. This is simply not true. Patent officials do not judge the validity of the information presented to support the patent. A patent is not, in any way, a certification of the effectiveness of a product. A patent is not a verification of the science behind a product. A patent is merely a copyright, concerned only with the novelty of product.
Latest Research?
To successfully complete controlled research involving human subjects consuming sports supplements is a formidable undertaking and the costs are substantial. Funding this type of research at an independent academic facility is something that most supplement companies are not interested in. So when the first ever study involving humans supplementing with methoxyisoflavone was presented at the 2001 American College of Sports Medicine annual conference, [7] I was very interested.
The study examined 14-college men supplementing with methoxyisoflavone during resistance training. However, the research was poorly controlled and yielded insignificant results. The training program and dietary intake were not carefully monitored and the control group showed an increase in body fat, which suggests that many of the subjects did not comply with the procedures required of them during the eight-week period. Disappointingly, no conclusions can be drawn from this kind of research.
There is a lot of hype surrounding methoxy supplements, but there is one thing missing - the science. At this point I would have to say there is absolutely no research at all showing methoxy isoflavone helps build muscle. My personal suspicion is that as an anabolic agent, this supplement's value is non-existent.
You have to understand this industry to understand why products like methoxy isoflavone ever make it to the market. You see, most companies' philosophy is to continually offer the consumer something new. And there is nothing wrong with this, providing the "new" product has science to support its use as an effective nutritional supplement. Methoxyisoflavone does not. Methoxy isoflavone is a perfect example of a supplement that is completely backed by marketing and not by science.
References:
1. Messina M, Messina V. Soyfoods, soybean isoflavones, and bone health: a brief overview. J.Ren Nutr. 10:63-8, 2000.
2. Scheiber MD, Rebar RW. Isoflavones and post menopausal bone health: a viable alternative to estrogen therapy? Menopause. 6:233-41,1999.
3. Carusi D. Pytoestrogens as hormone replacement therapy: an evidence-based approach. Prim Care Update Observ Gyn. 7:253-259, 2000.
4. Ohta H. et al., Effects of 1-year of ipriflavone treatment on lumbar bone mineral density and bone metabolic markers in postmenopausal women with low bone mass. Horm Res. 51:178-83, 1999.
5. US Patent 3949085: Anabolic-weight-gain promoting compositions containing isoflavone deriviatives and method using the same.
6. US Patent 4163746: Metabolic5-methyl-isoflavone-derivatives, process for preparation thereof and compositions containing the same.
7. Incledon T, Van Gammeren D, Antonio J. The effects of 5-methyl-7-methoxyisoflavone on body composition and performance in college men. Med. Sci. Sports Exercise