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

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=11863...

http://www.chemspider.com/Chemical-Structure.45149...

Update:

Similar in that they both caused an allergic reaction in a patient, particularly chronic months long hives outbreak and in the case of Lisinopril, also shortness of breath (patient passed out - unconcious) and nausea.

1 Answer

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  • Dr W
    Lv 7
    8 years ago
    Favourite 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)-Pseudoephe...

    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...

    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!

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