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Tonquil / Clofenciclan

Hammilton

Hammilton

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Is anyone familiar with anything on this drug? This 'abstract' is all I can find that's relevant:

W POELDINGER
Praxis 1962 Jan 18
PMID: 14487367
abstract
citation
W POELDINGER. Therapeutic experiences with thiopropazate and with a combination of thiopropazate and chlorphencyclan (Vesitan) in psychiatry. Praxis. 1962 Jan 18;51:73-8

200px-Clofenciclan.svg.png

2-[1-(4-chlorophenyl)cyclohexyl]oxy-N,N-diethyl-ethanamine

Wiki says it's a stimulant, though it doesn't look like one to me, that's not exactly surprising. I'm guessing this whole class has been looked at carefully, right? This was an American drug, I guess, so it has been approved; I'm guessing it's been discontinued completely though, correct?
 
The INN-name is/was chlorphencyclan (german) resp. chlofenciclan (US).
In Germany produced by the (now not any more existent) "C.F. Boehringer & Söhne GmbH", Mannheim (now part of "Roche Diagnostics").
It was used in combination with thiopropazate in form of dragées (10 mg Thio~-HCl + 15 mg Chlor~-HCl) or in ampules with 60 resp 90 mg of the 2 substances. Field of application were psychosis with fear and anxiety, in particular stupor.

Hard to get more info without a sophisticated database. I'll keep on looking!

Peace! Murphy

Edit: And yes, completely discontinued.
Edit 2: And the patent that is cited as a reference @Wiki is completely useless. US 6.340.476 describes just a pharmaceutical dosage form of methylphenidate and not at all chlorphencyclan.
 
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Actually looks like it could be a dopamine reuptake inhibitor... it's got a p-halo substituent on the phenyl ring, and N,N diethyl substitution... (compare to dimethocaine...)
 
I've been using ChemBioDraw to draw out dozens of very different substances that could compare well to dimethocaine. By chance, I drew this out and found that it compares very well with cocaine. It's practically dimethocaine's twin, though. Well, para-chloro-dimethocaine, which following the pattern with these sorts of things is also most likely more potent.

Compare great, in 3D, anyway.
 
http://img300.imageshack.us/my.php?image=tonquiltoclomethocaine.jpg

Here's the comparison to 4-chloro-dimethocaine aka clomethocaine (my own name, but it makes sense).

I would imagine that, following the rest of em, 3,4 dichloro would be most potent for both of these.

It's a PCP derivative; I haven't compared to BTCP, but will. It should be cheap to make.




.3A by the amines is the distance between lone pairs. .2 is the nitrogen atoms.

This is probably the closest comparison I've found. If anyone is interested, though, I have about a dozen various chems that fit very closely, but are not analogues. AFAIK, they're untested but might not be.
 
I suspected that would be the case. I bet it lacks the cardiotoxic and local anaesthetic effects of dimethocaine/cocaine as well, since there is no ester link.
 
Practice your reading and you won't have to make such pointless posts, and neither will I.
 
I know this is a rather old post, but I was fascinated by just how close the aromatic & basic nitrogen overlay. I also note that the medical dose-regime makes this compound quite potent.

Has anyone got refs?
 
I hate to resurrect.... but all this talk about Clofenciclan and the equivalent 4-cl-dimethocaine is reminding me of 4-fluoro-dimethocaine, which I've seen pop up recently at a vendor or two.... but which is also said to be essentially inert material....

I can't think of a reason why this would be the case? I'm leaning towards bunk synthesis or bad reports, but would be very interested in such a quirk in the SAR actually exists.
 
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