Cathinone analogues

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New cathinone analogues or ketones are becoming available. The most famous is, of
course, methylone. In this article methylone and the MDA analogue are
discussed. Dose anyone know more about cathinone analogues/ ketones?



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Cathinone: An Investigation of Several N-Alkyland Methylenedioxy-Substituted Analogs </span>



TERRY A. DAL CASON,* RICHARD YOUNGâ€* AND RICHARD A. GLENNONâ€*

*North Central Laboratory, Drug Enforcement Administration, 500 U. S.
Customhouse, Chicago, IL 60607, andâ€*Department of Medicinal Chemistry,
School of Pharmacy, Medical College of Virginia/ Virginia Commonwealth University, Richmond, VA 23298-0540



Received 24 October 1996; Revised 21 March 1997; Accepted 2 April 1997


PHARMACOL BIOCHEM BEHAV </span>5 (4) 1109–1116, 1997.



Structurally, methcathinone is to cathinone what methamphetamine is to
amphetamine. Due to increased interest in the abuse of such agents we
wished to determine if certain derivatives of cathinone would behave in
a manner consistent with what is known about their amphetamine
counterparts; that is, can amphetamine structure–activity relationships
be extrapolated to cathinone analogs? As expected on the basis of known
structure–activity relationships for amphetaminergic agents, both N
-monoethylcathinone and N -monon

-propylcathinone (N-Et CAT and N-Pr CAT; ED 50 5 0.77 and 2.03 mg/kg,
respectively) produced amphetaminelike stimulus effects in rats trained
to discriminate 1 mg/kg of ( 1)amphetamine from vehicle and were
somewhat less potent than racemic methcathinone. In contrast, (
2)N,N-dimethylcathinone or (2)Di Me CAT (ED50 5 0.44 mg/kg) was more
potent than expected; although (1)N,N-dimethylamphetamine is sevenfold
less potent than
(1)methamphetamine, (2)Di MeCAT is only about 1.6-fold less potent than
(2)methcathinone, and is essentially equipotent with (2)cathinone. In
addition,although it has been previously demonstrated that
1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDA) results in stimulus
generalization in rats trained to discriminate (1 )amphetamine or DOM
from vehicle, the cathinone counterpart of MDA
(i.e., MDC) resulted in partial (maximum: 58%) generalization in (1
)amphetamine-trained animals, and failed to produce.



7% DOM-appropriate responding in rats trained to discriminate DOM from
vehicle. On the other hand, the N-methyl analog of MDC (i.e., MDMC)
behaved in a manner similar to that of the N -methyl analog of MDA
(i.e., MDMA); that is, a (1)amphetamine stimulus (MDMC: ED

50 5 2.36 mg/kg) but not a DOM stimulus generalized to MDMC. In
MDMA-trained rats, stimulus generalization occured both to MDC and MDMC
(ED 50 5 1.64 and 1.60 mg/kg, respectively). Although this

and previous studies have demonstrated that significant parallelisms
exist between the structure–activity relationships of amphetamine

analogs and cathinone analogs, we now report several unexpected
qualitative and/or quantitative differences. It is suggested that
caution be used in attempting to draw conclusions or make predictions
about the activity and potency of novel cathinone analogs by analogy to
the structure–activity relationships derived from amphetamine-related
agents; it would appear that each new cathinone analog will require
individual investigation.

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