thatpersonthatiam - 25-7-2006 at 22:19
Hey,
Would anyone here know where I could find data on clomipramine (anafranil), namely a chemical synthesis, and NMR (both 13C and 1H), IR and raman
spectra?
I've tried the major databases and have found a fair bit of information (as well as a synthesis in the 1988 edition of the Pharmaceutical
Manufacturing Encyclopaedia volume 1), however the synthesis mentioned has some (well non existant or badly misspelt) chemicals used in it, and the
only other source of this data that I learnt of was an article published in the Journal of Radioanalytical Chemistry in 1976 that I do not have access
to.
Any help would be greatly appreciated.
sparkgap - 26-7-2006 at 00:10
Have you checked the patents filed by Ciba-Geigy (now Novartis) for Anafranil? That may have useful info. 
I don't have my Merck Index with me, but I know there are references on preparation there. 
As for spectra, the chances of finding those seem murky to me unless you have access to a huge spectral database, and offhand, I don't know of any
online for the public.
sparky (~_~)
ziqquratu - 26-7-2006 at 05:47
Two decent sites for obtaining spectra (dont know if the ones you want will be there!) are (in order of usefulness):
www.sigmaaldrich.com
www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=...
Check out Aldrich first, they have the best database of spectra that I know of. Try SDBS if that fails you. Dont know if you need to be registered
to access the data on the Aldrich site, but even if you do need to be, it's free to do.
One other thing you can try is to obtain a copy of ChemDraw and use the "predict NMR spectrum" feature. It's actually surprisingly accurate a lot of
the time. But, of course, it's only a model, so DO NOT BLINDLY TRUST IT TO BE ACCURATE! If your compound has any unusual groups (including
organosulfur compounds, for example) you may find it has some problems with them. But for general organics, as I said, it's reasonable, and a good
starting point if you can't find a real spectrum anywhere.
EDIT: Something else that I've just thought of - since you're looking for a synthetic procedure anyway, that SHOULD give you the details of the NMR
spectra, at the least, anyway! The databases above actually have images, but the original syntheses should have the data they used to confirm the
identities of their products.
[Edited on 26-7-2006 by ziqquratu]
PainKilla - 26-7-2006 at 11:25
Here is a synthesis and some other info from Pharmaceutical Substances:
thatpersonthatiam - 27-7-2006 at 16:56
wow.
i didn't expect so many helpful replies. thanks everyone.
PainKilla: That synthesis is very helpful. Thanks. Would you have the full name, edition and publisher of the 'Pharmaceutical Substances' that you
obtained that from, by any chance? (I need to provide citations).
ziqqurtu: I've tried the second site there and can't find it, though SigmaAldrich does have an entry, however I think I need to be registered to view
more specific details (ie; i need to remember my username&pword!). As for ChemDraw, I have used this to generate some NMR predictions and GAMESS
to generate an IR prediction, however as you said they are only computer models and therefore not completely accurate.
sparkgap: i've contacted by local Novartis Pharmaceuticals firm and they said they'd email me what they had on file, though the weren't sure if they
kept the actual synthesis on file.
PainKilla - 27-7-2006 at 19:28
http://www.amazon.com/gp/product/3135584046/ref=sr_11_1/104-...
Enjoy!
(Note: This book wasn't scanned by me.)
http://rapidshare.de/files/27283698/Pharmaceutical_Substance...
[Edited on 28-7-2006 by PainKilla]
Ritter - 3-7-2008 at 12:36
Years ago I was dating a lady physician who gave me a copy of this reference on the unusual side-effect associated with clomipramine: yawning caused
both male & female patients to orgasm as well as experience intense sexual urges.
See http://www.baillement.com/clomipramine.html
I filed this in my 'Better Things for Better Living Through Chemistry' folder.