Table 3.

MAO inhibitory activity of β-substituted AMPH derivatives.

									MAOI Activity IC50 a (µM)
Compoundb	Rβ	R2	R3	R4	R5	R6	Rα1	Rα2	MAO-A	MAO-B
Cathinone	=O	H	H	H	H	H	HCH3		NE	NE
4-MetOCat	=O	H	H	OCH3	H	H	HCH3		77.0	NE
4-EtOCat	=O	H	H	OCH2CH3	H	H	HCH3		37.0	> 100
4-PropOCat	=O	H	H	O(CH2)2CH3	H	H	HCH3		7.2	8.9
4-ButOCat	=O	H	H	O(CH2)3CH3	H	H	HCH3		14.4	6.0
(+)4-ButOCat	=O	H	H	O(CH2)3CH3	H	H	CH3	H	29.5	5.6
(-)4-ButOCat	=O	H	H	O(CH2)3CH3	H	H	H	CH3	6.8	6.4
4-MetSCat	=O	H	H	SCH3	H	H	HCH3		45.0	> 100
(+)4-MetSCat	=O	H	H	SCH3	H	H	CH3	H	44.5	> 100
(-)4-MetSCat	=O	H	H	SCH3	H	H	H	CH3	38.9	NT
4-EtSCat	=O	H	H	S CH2CH3	H	H	HCH3		15.1	> 100
(+)4-EtSCat	=O	H	H	S CH2CH3	H	H	CH3	H	12.9	> 100
(-)4-EtSCat	=O	H	H	S CH2CH3	H	H	H	CH3	38.0	NT
4-MetONEPhe	OH	H	H	OCH3	H	H	HCH3		9.8	NE
4-EtONEPhe	OH	H	H	O CH2CH3	H	H	HCH3		7.0	NE
4-PropONEPhe	OH	H	H	O (CH2)2CH3	H	H	HCH3		2.8	100
4-ButONEPhe	OH	H	H	O (CH2)3CH3	H	H	HCH3		4.7	65
4-OHNEPhe	OH	H	H	OH	H	H	HCH3		220.0c	NEc
4-MetSNEPhe	OH	H	H	SCH3	H	H	HCH3		7.3	NE
4-EtSNEPhe	OH	H	H	S CH2CH3	H	H	HCH3		1.9	> 100
4-PropSNEPhe	OH	H	H	S (CH2)2CH3	H	H	HCH3		1.7	> 100
BMetOA	OCH3	H	H	H	H	H	HCH3		> 100	> 100
B,4DMetOA	OCH3	H	H	OCH3	H	H	HCH3		77.5	> 100
BMetSA	OCH3	H	H	SCH3	H	H	HCH3		50.6	> 100

^aUnless stated, IC₅₀ values are from Osorio-Olivares et al., 2004. ^bChemical name and/or common acronym and/or common name is given. When not indicated the compound is the racemic mixture. ^c Arai et al., 1990. NE, No effect at 100 µM; NT, Not tested.