Table 1.

MAO inhibitory activity of AMPH derivatives and amiflamine analogues.

										MAOI Activity IC50(Ki)a (µM)
Compoundb	R2	R3	R4	R5	R6	Rα1	Rα2	RN1	RN2	MAO-A	MAO-B
(+)-Amphetamine	H	H	H	H	H	CH3	H	H	H	20.0c;4.9d;33.8e	770c;118d;161e
Amphetamine	H	H	H	H	H	HCH3		H	H	11.0f(5.3g)	236g
(-)-Amphetamine	H	H	H	H	H	H	CH3	H	H	70.0c;203e	600c;180e
Methamphetamine	H	H	H	H	H	HCH3		CH3	H	41h(17.2g)	> 200h(297)g
Phentermine	H	H	H	H	H	CH3	CH3	H	H	143i(88d;196g)	285i(310d;138g)
AEPEA	H	H	H	H	H	HCH2CH3		H	H	14.0g	234g
N,α-DEPEA	H	H	H	H	H	HCH2CH3		CH2CH3	H	251g	159g
Amiflamine/(+)-FLA336	CH3	H	N(CH3)2	H	H	CH3	H	H	H	0.8j;2.0f	> 1000j
FLA336	CH3	H	N(CH3)2	H	H	HCH3		H	H	2.7k	440k
(-)-FLA336	CH3	H	N(CH3)2	H	H	H	CH3	H	H	3.0j	125l
FLA289	H	H	N(CH3)2	H	H	HCH3		H	H	3.7l;2.0m	400l
FLA727	H	H	NHCH3	H	H	HCH3		H	H	0.55l-1.2m	1500l
(+)-FLA788	CH3	H	NHCH3	H	H	CH3	H	H	H	0.13j	> 1000j
FLA558	F	H	N(CH3)2	H	H	HCH3		H	H	1.2k	120k
FLA314	Cl	H	N(CH3)2	H	H	HCH3		H	H	0.21k	80k
FLA405	Br	H	N(CH3)2	H	H	HCH3		H	H	0.22k	100k
FLA365	Cl	H	N(CH3)2	H	Cl	HCH3		H	H	0.013l	180l
FLA450	Cl	H	N(CH3)2	H	H	HCH2CH3		H	H	0.38k	75k
FLA463	Cl	H	N(CH3)2	H	H	CH3	CH3	H	H	1.2k	700k
FLA717	CH3	H	N(CH3)2	H	H	CH3	CH3	H	H	12.0k	2100k
FLA384	H	CH3	N(CH3)2	H	H	HCH3		H	H	8.0l	650l
(+)NBF003	CH3	H	N(CH3)2	Br	H	CH3	H	H	H	1.1l	480l

^aIC₅₀ and/or Ki are reported, depending on the reference considered. ^bChemical name and/or common acronym and/or common name is given. When not indicated, the compound is the racemic mixture. ^c Mantle et al., 1976. ^d Ulus et al., 2000. ^e Robinson, 1985. ^f Scorza et al., 1997.^g Santillo, 2014. ^h Matsumoto et al., 2014. ⁱ Kilpatrick et al., 2001. ^j Ask et al., 1982b. ^k Ask et al., 1982a. ^l Ask et al., 1985. ^m Reyes-Parada et al., 1994a.