Will the real methoxyestratetraenone please stand up? - the problem with common pheromone names
  • Earlier this week I posted on PheroTruth to ask if anyone had any information on what pheromone molecule is actually referred to by the name methoxyestratetraenone. There was some early speculation regarding this in an old thread on PheroTalk, which I'll elaborate on more in the MEO-EST thread in the Pheromone Molecules forum.

    Today I found a listing for what True Pheromones is selling as MEO-EST on the website of the manufacturer, Molcan. So what is currently on the market as MEO-EST, and used in the True Love product, is:
    • 3-METHOXY-ESTRA-1,3,5(10),8-TETRAEN-17-ONE
    • CAS: 6030-83-7

    If you do some searching on the CAS number you'll find that it is typically referred to as equilin methyl ether.

    Unfortunately, we have no way of know whether that is the same molecule previous sold by Androtics under the same name! Furthermore, because there has been no detailed reporting on the molecule's pheromone effects, we have no way of knowing if it behaves the same as the molecule previously sold by Androtics, for which there was a great deal of individual field reports (summarized here on the wiki.) The good news is that the effects of True Love, which was based on a mix originally developed using the MEO-EST sold by Androtics, seems to be pretty similar to the original mix. So it is a good bet that the pheromone effects, if not identical, are at least similar.

    Up until now, everyone seems to have just assumed that anything called methoxyestratetraenone would be the same stuff. But there are a couple of other viable candidates for that name, at least one of which seems to be present in humans. And it is extremely unlikely that Androtics will ever reveal the identity of the molecule they used to sell, since they seem to be solidly opposed to advancing the general knowledge of pheromones molecules.

    Really, all of the common names we use for pheromone molecules are misleading. There are tons of stereoisomers, enantiomers, and functional isomers for most of these molecules, and probably some other types of similar arrangements that I don't know the names of since I'm not a chemist.

    A great example is what we call androstenone. It's 5α-androst-16-en-3-one.

    But what we now call 4-androstenone could be termed simply androstenone with just as much validity. It is 5α-androst-4-en-3-one.

    The fact that one was recognized as a plausible human pheromone first and sold in products was basically by chance, and that's the principle which has guided all of the common knowledge of pheromones to this point. Chance.

    Are there more of these androstenone molecules that we still don't know about? A quick search turns up at least one: 5α-Androst-2-ene-17-one. And it's already known to be active as a pheromone in boars and elephants. I'd say there's a very good chance of human pheromone activity there. And judging by the major difference in effects between 4-androstenone and 16-androstenone, it is anybody's guess what this new 2-androstenone molecule might do in humans. There's only one way to find out, and that is rigorous testing. Of course, before we can test something, we have to recognize that it exists.

    This is one of the major reasons why I attempted to develop a coding system for these molecules in the past. To get around the problems with ambiguous and misleading common names.

    There's no perfect way to code pheromone molecules, so I just used an alphabetic character to signify the primary functional group (e.g. androstanes) and then an arbitrary sequential numerical code indicating when it was added to the list.

    I still think the pheromone codex was a huge advance, but stupid politics held it back from gaining acceptance. Specifically, Chris from Alpha Dream decided that his blind molecule tests needed to use molecule codes that interfered with the codes already in place in the fledgling codex. Since the blind tests were ongoing at that time and a topic of immediate interest, those codes took precedence and destroyed the codex. For now, I'm just using molecule names, but as you can see from the discussion above, there is a lot of ambiguity that can create a serious problem for a shadowy and splintered market like pheromones. With something like MEO-EST, we can hardly ever know what we're really using, or how much estrogenic effect it might have on us.

    In the future, I think we as a community should talk about how we can refer to molecules in ways that give us more clarity and certainty.

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