N&PD Moderators: Skorpio | thegreenhand
Hey HAMMILTON, I saw your quip about the "two phenethylamines stuck together" and requesting "background on your posts" as well as the query "what does it have to do with anything". Should I assume that this was directed at me and that you're STILL in the dark about it?
The structure depicted is NOT what I had in mind, but I can't get structures to post here. The SMILES depiction of what I was talking about with the primary amine substituted by a tertiary amine or a piperdine is as follows, respectively:
dimethylamine: C1C(C1N(C)C)(C(=O)N(CC)CC)C2=CC=CC=C2
piperidine: C1C(C1N2CCCCC2)(C(=O)N(CC)CC)C3=CC=CC=C3
I hope that this clarifies the manner in which I was "wondering aloud". I'm not a pharmacologist, and I don't even play one on TV. I'm just barely a chemist, but the mystery of structure-activity relationships is the source of considerable fascination for me. If I wandered(OR wondered) too far afield from the topic of this string for the comfort of ANYONE, then I apologize unreservedly.
BTW, thanks DREAD for the input about the cyclopropylmethyl group confering antagonist/partial agonist activity when attached to the amine on phenanthrene based opioids. I wonder if this generalizes to the phenyl-piperidines as well, without making the chemical prone to producing seizures, psychosis, or other intolerable side effects.
cyclopropylmethyl on the amine for morphine (morphinan) skeleton ALWAYS leads to antagonist.
The 14-phenylpropoxy substitution appears to confer potent μ-opioid agonist activity, even when combined with substitutions such as N-cyclopropyl or N-allyl, which normally result in μ-opioid antagonist compounds.