From: eesnyder@boulder.Colorado.EDU (Eric E. Snyder)
Subject: Re: Fentanyl and derivatives
Organization: University of Colorado, Boulder
Date:  6 Jan 93 16:22:02 GMT

aankrom@nyx.cs.du.edu (Anthony Ankrom) writes:

> I still haven't checked my Merck, but after posting this, I wanted to
>pull it back. I realised just how wrong it was...

[Incorrect structure deleted]

>This is _more_ correct, but still not exactly. I'm not sure about the
>methyl group...

Jesus.  If you don't know; don't post.  

Well, I don't have a nice drawing of fentanyl handy but I do have one 
of 3-methylfentanyl, sublimaze's bigger brother.  Below is a PostScript
stereo diagram of 3-methylfentanyl.  I drew this using InsightII, a 
molecular modeling package with a bent towards molecular bioloists.  Thus,
it doesn't handle small molecules very well.  As a result, I am not sure
why the anilino nitrogen is conjugated to the ring.  Perhaps Steve or 
Howard would like to comment as to whether this is an accurate depiction.  
I minimized the structure with the default parameters and obtained the 
following structure.  There has been some discussion as to whether the 
phenethyl group is in the extended conformation (as shown).  Work with
rigid analogs which orient the phenethyl group away from the piperidine
ring are of comparable acivity to the parent compound in binding assays,
supporting the contention that this is the conformation of the ligand 
when bound to the receptor.

---------------------------------------------------------------------------
TTGATTGCTAAACACTGGGCGGCGAATCAGGGTTGGGATCTGAACAAAGACGGTCAGATTCAGTTCGTACTGCTG
Eric E. Snyder                            
Department of MCD Biology              ...making feet for childrens' shoes.
University of Colorado, Boulder   
Boulder, Colorado 80309-0347
LeuIleAlaLysHisTrpAlaAlaAsnGlnGlyTrpAspLeuAsnLysAspGlyGlnIleGlnPheValLeuLeu
---------------------------------------------------------------------------


--------------------------- cut here --------------------------------------
%!PS-Adobe-1.0
%%Creator: RRT.   Copyright (C) 1989 BIOSYM
%%Author: Eric E. Snyder, University of Colorado, MCD Biology
%%CreationDate: Fri May 24 13:14:02 1991 
%%Title: 3-methylfentanyl.ipf 
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Newsgroups: alt.drugs
From: journeyman@spliff.demon.co.uk (Andy Settle)