dormouse
(Member)
04-19-00 06:43
No 122779
      alpha-cyclohexyl amphetamine analogue -Lilienthal
(Rated as: good read)
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Author  Topic:   alpha-cyclohexyl amphetamine analogue 
Lilienthal
Member   posted 12-18-98 04:25 PM          
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Chem. Pharm. Bull. 34, 2071 1986 H. Takahashi e.a.:"Interestingly, S-isomers such as (S)-alpha-cyclohexyl-beta-phenylethylamine and it's N-methyl analogue showed an exciting effect in mice, and appeared to have a potent amphetamine-like activity" along with non-morphin and morphin-like analgesic activities. The enantiselective syntheses are given.
Arzneimittelforschung 28, 1561 1978 P. Ghosh e.a.: Synthesis of (R,S)-alpha-cyclohexyl-beta-phenylethylamine, pharmacological activity of related substances.
Chem. Ber. 67, 1617 1934: Another route.
Lil. Drms. 12, 18 1989 O. Lilienthal: Synthesis from benzaldehyde and nitromethyl-cyclohexane, excellent yields!.
 
Beagle
Member   posted 12-19-98 01:15 AM          
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Very interesting. Is there any receptor binding data in that Chem. Pharm. Bull. article? Or is the amphetamine-like activity seen in some pharmacological assay (grooming behavior, increased locomotor activity, etc)? Looking at the structure, seems like it could be acting at PCP or other receptors.
 
drone 342
Member   posted 12-19-98 03:44 PM          
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You're getting into some amazing stuff here. THere's a double-phenylated ring compound with a potency 10 times that of d-meth. Interested? I'll post ref's if anyones cares for them.
-drone #342


Osmium
Member   posted 12-21-98 04:12 AM          
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Drone: "I'll post ref's if anyones cares for them."
Of course we do. You know that. Want me to say PLEEZE again? 


Lilienthal
Member   posted 12-21-98 05:30 AM          
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Takahashi (Chem. Pharm. Bull. 34, 2071 1986) only gave this short remark and analgesic activities (acid writhing, mice).
Ghosh (Arzneim.-Forschg. / Drug. Res. 28, 1561 1978) found a decrease in motor activity (d-amphetamine gave a strong increase, it's the classical stimulants test). But they used the racemate at 1/10 lethal dose. Maybe it's the opioid (or another, who knows?) activity which dominates at higher doses or with the stereoisomers.
 
drone 342
Member   posted 12-21-98 01:06 PM          
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I don't have my ref's with me, but a few of them for 2-benzhydryl-1-methyl-piperidine are:
Helv.Chim.Acta; 37; 1954; 2133,2142,2143;
JACS; 117; 45; 1995; 11124-11133;
CA 57; 2197d; 1962;
JACS; 118; 16; 1996; 3862-3868;

These are some potent analogs, but I know there are ones out there that leave even these ones in the dust. When I remember to bring them, I'll send y'all thei page nubmers, etc. Still from this you should be able get enough info to keep you plenty busy.

-drone #342


I ca


drone 342
Member   posted 12-21-98 01:08 PM          
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I think the following ref should also be of interest: JMC; 11; 4; 1968; 792-796
 
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