Can someone tell me if there is more than one type of Alpha Androstenol? I thought A-nol was only one of several names for Alpha Androstenol (i.e 5a-Androst-16-en-3a-ol). Someone asked about the difference between 5a-Androstenol & Androstenol and I got a bit confuddled... I thought they were just different names for the same molecule...

It they aren't the same, how do they differ?

(11-08-2009 1:04 PM)Xiphoid Wrote:  Can someone tell me if there is more than one type of Alpha Androstenol? I thought A-nol was only one of several names for Alpha Androstenol (i.e 5a-Androst-16-en-3a-ol). Someone asked about the difference between 5a-Androstenol & Androstenol and I got a bit confuddled... I thought they were just different names for the same molecule...

It they aren't the same, how do they differ?

Technically any androgen steroid isomer with a single A-ring hydroxyl group and one D-ring double bond is an Androstenol.

But the two isomers that occur naturally in humans and other mammals is 16,(5a)-androsten-3a-ol, and 16,(5a)-androsten-3b-ol. Both are 5a-androstenols, with the 3 position hydroxyl being the difference in conformation.

Below Alpha Androstenol is on the left and Beta Androstenol is on the right.

       

The binding affinities of these to receptors depends on both the 3-hydroxyl and the 5-hydrogen conformation, which determines if these will be positive allosteric modulators of GABA-A or if they will be partially inhibitory on GABA-A.

From the research it is clear that the 3-alpha-hydroxyl (5-alpha) conformation of steroids is a positive allosteric modulator of GABA-A. And a 3-beta (5-beta) conformation of steroids is inhibitory, and all 3-beta/5-beta steroids are inhibitory to one degree or another.

What is not clear is whether a 3-alpha, 5-beta is also a positive modulator on GABA A or not.

Diane

Here is a really good research article on Alpha Androstenol as a pheromone. It is very long, though so just a heads up.

https://jpet.aspetjournals.org/cgi/repri...8319v1.pdf

Diane