Is there any Chemical similarity between Aspartame (C14H18N2O5) and Lisinopril (C21H31N3O5)?

Question

I am no chemist, but I am wondering how to tell if these two substances have any chemical similarities. Aspartame is a sweetner and Lisinopril is a Blood pressure medication.
http://www.chemspider.com/RecordView.aspx?id=118630
http://www.chemspider.com/Chemical-Structure.4514933.html

Dr W · Accepted Answer

define "similarities"

both are organic molecules
both have a benzene ring.
both have a carboxylic acid group
both have an amine group.

but.... if you're asking about pharmacological properties, the answer is no.  Even tiny differences in structure can cause drastic differences in biological functions.

consider this.
http://en.wikipedia.org/wiki/File:(%2B)-Pseudoephedrin.svg
a common nasal decongestant

Now remove the OH group and you have d-methamphetamine.  Crystal meth if prepared properly.  here's a ball and stick model
http://upload.wikimedia.org/wikipedia/commons/9/90/Methamphetamine2.png

the gray balls are carbon
the white ones are hydrogen
the blue is nitrogen

now locate this carbon on that model
... .. .. .. .. . .H... .this one
... .. .. .. .. .. .|..↙
C6H5CH2 - C - NHCH3
... .. .. .. .. .. .|
...  .. .. .. .. . .CH3

now swap the positions of the H anc NHCH3 group and you have the other enantiomer L-methamphetamine.  This is the drug found in vicks sinus inhalers.  another decongestant.

now move that NH-CH3 from the back to the front

****
tiny changes in the chemical structure or chemical composition of organic molecules create HUGE differences in chemical and biological properties.

****
unrelated allergic response!

Is there any Chemical similarity between Aspartame (C14H18N2O5) and Lisinopril (C21H31N3O5)?

1 Answer