Hormone Behavior has a special issue devoted to chemosignals. I thought this particular line was interesting;

Quote: systemic injection of tritiated estradiol (3H-E2) into a male mouse or bat has been shown to produce significant levels of radioactivity in the reproductive tissues and brain of cohabiting female conspecifics.

http://www.ncbi.nlm.nih.gov/pubmed/25125222

So inject a male mouse with a particular molecule and the exact same molecule winds up in the genitalia of the female mouse.

Good luck reproducing this with humans...

From the full text of the publication:

Quote:In recorded interval samples of their behavior, males increasingly directed urine at the females' adjacent compartments over the days of exposure, and urinated more frequently when exposed to a female than when not. Male water consumption during this time increased by 20 to 30%, and creatinine values fell in urine of female-exposed males, indicating greater dilution of urine.

(10-10-2014 9:40 PM)wiserd Wrote:  Hormone Behavior has a special issue devoted to chemosignals. I thought this particular line was interesting;
http://www.ncbi.nlm.nih.gov/pubmed/25125222

So inject a male mouse with a particular molecule and the exact same molecule winds up in the genitalia of the female mouse.

(10-10-2014 9:40 PM)wiserd Wrote:  Hormone Behavior has a special issue devoted to chemosignals. I thought this particular line was interesting;
http://www.ncbi.nlm.nih.gov/pubmed/25125222

So inject a male mouse with a particular molecule and the exact same molecule winds up in the genitalia of the female mouse.

Super interesting! I would like to test Estradiol. Where can I get some?

Again, I'm not a chemist or doctor.

What is the difference between Estradiol and the Estratetraenol that is in many formulas?

Estradiol is the main estrogen found in humans. You definitely don't want to mess around with any estrogen derivatives if they have a polar group on carbon 16 (the D ring). The reason most pheromones have a double bond there is that the steroid D ring features are often part of the pharmacophore which activates the steroid nuclear receptor. The lack of the polar group deactivates the molecule as a steroid, and is most likely what bind to pheromone receptors. This is the case for androstadienol, androstenol & androstenone as well.

This is estradiol and the estrogen receptor binding site:


Here's a few compounds that also bind the estrogen receptor:


The compounds form hydrogen bonds with residues on opposite sides of the receptor active site.


Both of the polar groups are necessary to activate the receptor, and they must be within a certain distance of each other.


This shows diethylstilbestrol (a synthetic estrogen and "endocrine disruptor") fitting the estrogen receptor active site.

These are estrogen receptor ligands (estradiol, DES, and BPA):


This (estratetraenol) is not:


Seriously, don't mess around with estrogens.

(04-10-2015 10:05 AM)Paradox Wrote:  Super interesting! I would like to test Estradiol. Where can I get some?

Again, I'm not a chemist or doctor.

What is the difference between Estradiol and the Estratetraenol that is in many formulas?

(04-13-2015 8:17 AM)DrHorrible Wrote:  Seriously, don't mess around with estrogens.

Thanks for taking the time to reply with pictures. It made understanding what Estrogens are doing easier to follow.

I agree with you that they have no place in male formulas.

Are Beta isomers the feminine version of the Alpha isomer. I hope you understand.

I'm not a scientist or chemist but you can get as technical as you want.

(04-13-2015 10:25 AM)Paradox Wrote:  Are Beta isomers the feminine version of the Alpha isomer. I hope you understand.

No, though beta Androsterone does seem more feminine than alpha androsterone. The prefixes just refer to stereo-isomers. Stereo-isomers are like left and right handed gloves. Same number of fingers and such, almost identical. but they're non-superimpostable mirror images. You can't make a left handed glove fit comfortably on your right hand. Living things will interact very differently with molecules of different 'handedness.'

(04-13-2015 8:17 AM)DrHorrible Wrote:  Estradiol is The reason most pheromones have a double bond there is that the steroid D ring features are often part of the pharmacophore which activates the steroid nuclear receptor. The lack of the polar group deactivates the molecule as a steroid, and is most likely what bind to pheromone receptors.

Thanks Dr. H. Is there any software you'd recommend for matching receptors and ligands?

If you know the pharmacophore for a certain ligand/receptor interaction, or even if you don't, you can search pubchem by structural similarity.

Ideally to design or match a ligand to a certain receptor you'd want the crystal structure of the receptor protein. I don't think these have been discovered for any of the VN receptors yet.
You could check protein databases like http://www.rcsb.org/pdb/

With the crystal structure and knowledge of the binding interaction you could use software (UCSF Chimera?) or a 3d printer to analyze the active site. I don't have any real experience with this.

Even assuming all this is accomplished, one should keep in mind that receptor proteins are not entirely rigid structures, that they exist in a variety of active and inactive conformations. There is significant evidence that GPCR receptors (like the vomeronasal receptors in humans) can couple to different g-proteins based which ligand binds and the conformation it induces in the receptor. There may also be allosteric sites that increase or decrease binding affinity or induce further conformational changes.

In short, we may have the amino acid sequence of the receptor, but if we don't know the specifics of how it folds (crystal structure), it's not possible to match a ligand to its active site (which is yet unknown). However, knowing the general structural similarities of certain ligands will certainly help point to whether another structure would be a suitable ligand or not.

(04-13-2015 11:42 AM)wiserd Wrote:  Thanks Dr. H. Is there any software you'd recommend for matching receptors and ligands?

(04-13-2015 11:30 AM)wiserd Wrote:  No, though beta Androsterone does seem more feminine than alpha androsterone. The prefixes just refer to stereo-isomers. Stereo-isomers are like left and right handed gloves. Same number of fingers and such, almost identical. but they're non-superimpostable mirror images. You can't make a left handed glove fit comfortably on your right hand. Living things will interact very differently with molecules of different 'handedness.'

Thanks Wiserd for the explanation. Even though you say that the Beta Isomers are just the other hand of the glove, I have noted that many Beta isomers have feminine/feminizing properties like Beta Androstenol, Beta Androsterone and Beta Androstanol.

My theory is that perhaps Beta isomers do not belong in male formulas either.

(04-13-2015 1:21 PM)Paradox Wrote:  Thanks Wiserd for the explanation. Even though you say that the Beta Isomers are just the other hand of the glove, I have noted that many Beta isomers have feminine/feminizing properties like Beta Androstenol, Beta Androsterone and Beta Androstanol.

My theory is that perhaps Beta isomers do not belong in male formulas either.

While none of this stuff exists in a vaccum but only in relation to other mones, it's worth noting that beta androstenol is found in higher concentrations in men than women.

http://www.pheromonetalk.com/beta-andros...28769.html

I'm curious what you mean by 'feminine' or 'feminizing.' Could you give a more objective and neutral definition of the term?