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2-(benzo[d][1,3]dioxol-5-yl)-N,N-diethylacetamide

Hey, related question: I know there was/is a program, or website, where you can type in a molecule name, and it will try and guess at all the receptors it might hit, and gave numbers etc.. like it would list every (or almost) receptor, all the 5ht's, D1-D4 (or more) etc. I know I used it before but i lost the link or download.

Like you can type in amphetamine and it would list all the receptors it hits, or put the IUPAC name etc.. anyone know what i'm talking about? You could type in the above IUPAC and it would try to guess and list all receptors and the level it may hit at etc...

Oh and are there any comparable programs to Chemdraw/office available for Mac/OSX? or is chemoffice just the King of all chem programs? (probably)
 
You're probably thinking of the PDSP database. Predicting affinity/efficacy is a very "hard" problem that requires either experimental testing or accurate 3d models of both the protien and ligand as well as astronomical amounts of computer time. As of my knowledge there are no programs where you can just build a structure and have the computer say "This binds to XYZ-1,2, and 3a receptors".

ChemDraw is pretty much the MS Office of chemistry applications, run it in VMWare or something. Theres lots of comparable programs too.

As for the parent compound, this belongs in the "fruitless chemical masturbation" thread because it's not active nor "fun". I think it would just be degraded in the body to to safrolic acid (methylenedioxyphenylacetate ?) and a few ethyl groups. My advice: Don't start "practicing" with SAR until you get a really strong grasp on organic chemistry, functional groups etc.
 
The N,N-diethyl substitutions on that molecule would most likely make the compound completely void of activity. I have a paper that would elucidate this effect for you, but I'm not at my computer. I'll post a reference when I get a chance.
 
Check out these papers, they are a little older but may still be able to give you some useful info.

Indoleamine and Phenylalkylamine Hallucinogens: Effect of alpha-methyl and n-methyl substituents on behavioral activity.
RICHARD A. GLENNON. RICHARD YOUNG and JOHN M. Jacyno

Influence of Amine Substituents on 5-HT2A versus 5-HT2C Binding of Phenylalkyl- and Indolylalkylamines
Richard A. Glennon, J Malgorzata Dukat, Mohamed El-Bermawy, Ho Law, Joseph De Loa Angeles, Milt Teitler, Allison King, and Katharine Herrick-Davis

The latter may be of less help to you, because they only discuss activity of the compounds in regards to 5-HT2A and 5-HT2C receptors, but it is interesting nonetheless.
 
i'm pretty sure Chemdraw works just fine on OS X; before i repartitioned for Lion I had a a copy that I used.
Avagadro was useful too, and free/open source. It was nice for its molecular dynamics system that you could use for predicting/optimizing the geometry of a molecule. You can't assume its 100% right but it gives you a starting point at least
 
On a horrifically unrelated and noob subject.. what does N,N- mean in chem names? Been wondering for a while :P
 
^^ for example, in the molecule described above, the N,N states that both ethyl groups are positioned on the nitrogen atom of the molecule. If you want to learn more you can probably just read about organic nomenclature on Wikipedia.
 
^ N-methyl means that the methyl group is attached to the nitrogen. N,N-diwhatever means that you have two identical groups attached to the same nitrogen.
 
/navarone/ said:
Also I wanted to remind or inform, you than when speaking of amphetaines turning the amine into an amide eliminates its basicity which seems central for activity.
Click to expand...

I understand that the electron delocalization across the amide group and the electron-withdrawing nature of oxygen lead to decreased basicity, but how does that decrease activity? Is it because without a lone pair on the nitrogen group, the amide cannot be a hydrogen-bond acceptor?
 
I guess so, and it makes sense. Hydrogen bonding with receptor proteins is almost always present AFAIK.
I was told about this in another pharmacology forum though, I'm no researcher yet, I'm still a uni student.
 
JiminiPimini said:
hey guys, i just wanted to see what the experts would say about my novice attempt at making an new chemical, im kind of a novice when it comes to structural activeness relatvity, so ya. any pointers and criticisms would be epic. thanks.

2-(benzo[d][1,3]dioxol-5-yl)-N,N-diethylacetamide

http://i105.photobucket.com/albums/m220/llsdetroit/2-benzod13dioxol-5-yl-NN-diethylacetamide.png
Click to expand...

could you explain to us a bit more what your reasoning was behind this structure? in particular i'm especially not sure why the Keto isn't attached to the carbon closer to the phenyl ring.

also there's already a thread for this type of question :) http://www.bluelight.ru/vb/threads/582708-I-like-to-draw-pictures-of-random-molecules


/navarone/ said:
Hydrogen bonding with receptor proteins is almost always present AFAIK.
Click to expand...

http://en.wikipedia.org/wiki/JWH-171 only exception i can think of, i'm a total noob though =p
 
Indole said:
I understand that the electron delocalization across the amide group and the electron-withdrawing nature of oxygen lead to decreased basicity, but how does that decrease activity? Is it because without a lone pair on the nitrogen group, the amide cannot be a hydrogen-bond acceptor?
Click to expand...
While an amide still has the lone pair, it ain't basic anymore and thus can not form salt bridges (eg. with aspartate or glutamate). IIRC, /navarone/ is quite right with suggesting a basic moiety. I don't recall the proposed binding mode (if there were any) for amphetamines and its derivatives, but yes, an amide abolishes activity.
 
Acylating a simple amphetamine does abolish stimulant activity, but IIRC some of the amides show depressant properties. Some sympathetic amine derivatives traditionally thought to be similar to amphetamine, e.g., pemoline (a weak central stimulant), contain the amido function. It's also interesting to note the the high activity of aminorex, considering the analogous nitrogen isn't basic.
 
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