Author Topic: trans-4-methylaminorex vs. cis-4-mar  (Read 3349 times)

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trans-4-methylaminorex vs. cis-4-mar
« on: February 14, 2003, 01:33:00 PM »

Some time ago when the "4-mar w/o cyanogenbromide" thread was discussed it was stated that: "
It does not seem to be possible to create the less active cis-4-MAR using the cyanate route.".

This has haunted me for some time, as most(all actually) references i have read, says that the cis-isomer is the active one. Could it be that the wonder product that has been "theoretically" made is actually the less active isomer?

According to:

the trans isomer would actually be legal? This is great news for us european bees if it hold here aswell :) Thoughts?



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4-MAR isomer potency
« Reply #1 on: February 14, 2003, 05:48:00 PM »
Stimulus properties of a new designer drug: 4-methylaminorex ("U4Euh")
Richard A. Glennon and Bryan Misenheimer
Pharmacol. Biochem. Behav. 35(3), 517-521 (1990)



Like other phenylisopropylamine derivatives, 4-methylaminorex is a central stimulant. The cis isomer of 4-methylaminorex ("U4Euh"; "ICE") has appeared on the clandestine market as a novel designer drug and was recently classified as a Schedule I substance. In the present investigation, the stimulus properties of racemic cis, racemic trans, and all four individual optical isomers of 4-methylaminorex were examined in rats trained to discriminate 1 mg/kg of S(+)amphetamine sulfate from saline. The S(+)amphetamine stimulus generalized to all of the agents investigated and the relative potencies of the optical isomers (followed by ED50 values) were as follows:trans(4S,5S) (0.25 mg/kg) > cis(4S,5R) (1.2 mg/kg) = cis(4R,5S) (1.5 mg/kg) > trans(4R, 5R). The trans(4R,5R) isomer did not completely substitute for S(+)amphetamine unless a longer (i.e., 60-min) presession injection interval was used, suggesting that it has a longer duration of onset that the other isomers of 4-methylaminorex. The results, which are consistent with established structure-activity relationships, suggest that the trans(4S,5S) isomer (which has not been scheduled) is similar in potency to (+)amphetamine (ED50=0.4 mg/kg) and is more potent than either of the cis isomers.