. 2020 Jan 23;10:1590. doi: 10.3389/fphar.2019.01590

Table 2.

MAO inhibitory activity of AMPH derivatives monosubstituted in the aromatic ring.


										MAOI Activity IC₅₀(Ki)^a (µM)
Compound^b	R2	R3	R4	R5	R6	R^α1	R^α2	R^N1	R^N2	MAO-A	MAO-B
PMA/4-MeOA	H	H	OCH₃	H	H	HCH₃		H	H	0.3^c;0.6^d(0.2^e)	45^d(530^e)
2-MeOA	OCH₃	H	H	H	H	HCH₃		H	H	9.0^e	350^e
3-MeOA	H	OCH₃	H	H	H	HCH₃		H	H	23^e	1940^e
PMMA	H	H	OCH₃	H	H	HCH₃		CH₃	H	1.7^d	58^d
4-EtOA	H	H	OCH₂CH₃	H	H	HCH₃		H	H	0.22^f	> 100^f
4-PrOA	H	H	O(CH₂)₂CH₃	H	H	HCH₃		H	H	0.13^f	> 100^f
4-BuOA	H	H	O(CH₂)₃CH₃	H	H	HCH₃		H	H	0.32^f	> 100^f
4-BzOA	H	H	OCH₂Phe	H	H	HCH₃		H	H	3.42^f	0.71^f
MTA	H	H	SCH₃	H	H	HCH₃		H	H	0.25^g	NE^g
(+)-MTA	H	H	SCH₃	H	H	CH₃	H	H	H	0.13^h	NE^h
(-)-MTA	H	H	SCH₃	H	H	H	CH₃	H	H	2.04^g	NE^g
NMMTA	H	H	SCH₃	H	H	HCH₃		CH₃	H	0.89^g	NE^g
DMMTA	H	H	SCH₃	H	H	HCH₃		CH₃	CH₃	2.10^g	NE^g
NEMTA	H	H	SCH₃	H	H	HCH₃		CH₂CH₃	H	1.80^g	NE^g
DEMTA	H	H	SCH₃	H	H	HCH₃		CH₂CH₃	CH₂CH₃	6.45^g	NE^g
NPMTA	H	H	SCH₃	H	H	HCH₃		(CH₂)₂CH₃	H	2.41^g	> 10^g
DPMTA	H	H	SCH₃	H	H	HCH₃		(CH₂)₂CH₃	(CH₂)₂CH₃	> 10^g	NE^g
NBzMTA	H	H	SCH₃	H	H	HCH₃		CH₂Phe	H	> 100^f	> 100^f
MTAB	H	H	SCH₃	H	H	HCH₂CH₃		H	H	0.84^g	NE^g
ETA	H	H	SCH₂CH₃	H	H	HCH₂CH₃		H	H	0.10^c	29^c
(+)-ETA	H	H	SCH₂CH₃	H	H	CH₃	H	H	H	0.075^h	> 100^h
(+)-PTA	H	H	S(CH₂)₂CH₃	H	H	CH₃	H	H	H	0.030^h	14.0^h
ITA	H	H	SCH(CH₃)₂	H	H	HCH₃		H	H	0.40^c	8.1^c
(+)-BTA	H	H	S(CH₂)₃CH₃	H	H	HCH₃		H	H	0.022^h	4.6^h
MSOA	H	H	SOCH₃	H	H	HCH₃		H	H	> 100ⁱ	NT
MSO2A	H	H	SO₂CH₃	H	H	HCH₃		H	H	> 100ⁱ	NT
PCA/p-Chloroamphetamine	H	H	Cl	H	H	HCH₃		H	H	4.0^c;1.9^j	NE^c
PBA/p-Bromoamphetamine	H	H	Br	H	H	HCH₃		H	H	1.5^j	NT
PFA/p-Fluoroamphetamine	H	H	F	H	H	HCH₃		H	H	16^j	NT
POHA	H	H	OH	H	H	HCH₃		H	H	24.0^k	NE^k
(+)-Fenfluramine	H	CF₃	H	H	H	CH₃	H	CH₂CH₃	H	256^l	800^l
Fenfluramine	H	CF₃	H	H	H	HCH₃		CH₂CH₃	H	440^m	720^m
(-)-Fenfluramine	H	CF₃	H	H	H	H	CH₃	CH₂CH₃	H	115^l	685^l
(+)-Norfenfluramine	H	CF₃	H	H	H	CH₃	H	H	H	36^l	160^l

^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 Scorza et al., 1997. ^d Matsumoto et al., 2014. ^e Green and el Hait, 1980. ^f Vilches-Herrera et al., 2009. ^g Hurtado-Guzmán et al., 2003. ^h Fierro et al., 2007. ⁱ Vallejos et al., 2002. ^j Fuller et al., 1975. ^k Arai et al., 1990. ^l Kilpatrick et al., 2001. ^m Leonardi and Azmitia, 1994. NE, No effect at 100 µM; NT, Not tested.