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

Table 4.

MAO inhibitory activity of AMPH derivatives polysubstituted 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
2,4-DMA	OCH₃	H	OCH₃	H	H	HCH₃			H	H	0.6^c	NE^c
3,4-DMA	H	OCH₃	OCH₃	H	H	HCH₃			H	H	20^c	NE^c
2,5-DMA	OCH₃	H	H	OCH₃	H	HCH₃			H	H	> 100^f	NE^f
3,4,5-TMA	H	OCH₃	OCH₃	OCH₃	H	HCH₃			H	H	NE^c;NI^d	NE^c;NI^d
2,4,5-TMA	OCH₃	H	OCH₃	OCH₃	H	HCH₃			H	H	NE^c	NE^c
2,4,6-TMA	OCH₃	H	OCH₃	H	OCH₃	HCH₃			H	H	0.4^e	NE^e
2-Br-DMA	Br	H	OCH₃	OCH₃	H	HCH₃			H	H	9.3^c	NE^c
5-Br-DMA	OCH₃	H	OCH₃	Br	H	HCH₃			H	H	13.0^c	NE^c
2-NO₂-DMA	NO₂	H	OCH₃	OCH₃	H	HCH₃			H	H	NE^c	NE^c
6-Cl-DMA	OCH₃	H	OCH₃	H	Cl	HCH₃			H	H	0.07^e	NE^e
ALEPH-1	OCH₃	H	SCH₃	OCH₃	OCH₃	HCH₃			H	H	5.1^c	NE^c
ALEPH-2	OCH₃	H	SCH₂CH₃	OCH₃	H	HCH₃			H	H	3.2^c	NE^c
4-PrS-DMA	OCH₃	H	S(CH₂)₂CH₃	OCH₃	H	HCH₃			H	H	2.4^e	NE^e
4-BuS-DMA	OCH₃	H	S(CH₂)₃CH₃	OCH₃	H	HCH₃			H	H	2.9^e	NE^e
4-PentS-DMA	OCH₃	H	S(CH₂)₄CH₃	OCH₃	H	HCH₃			H	H	14.3^e	NE^e
2,5-DM-MTAB	OCH₃	H	SCH₃	OCH₃	H	HCH₂CH₃			H	H	30.9^e	NE^e
2,5-DM-ETAB	OCH₃	H	SCH₂CH₃	OCH₃	H	HCH₂CH₃			H	H	11.8^e	NE^e
2,6-DM-MTA	OCH₃	H	SCH₃	H	OCH₃	HCH₃			H	H	0.30^e	NE^e
2,6-DM-ETA	OCH₃	H	SCH₂CH₃	H	OCH₃	HCH₃			H	H	0.08^e	NE^e
4-ESO-2,5-DMA	OCH₃	H	SOCH₃	OCH₃	H	HCH₃			H	H	> 100^f	NT
4-ESO2-2,5-DMA	OCH₃	H	SO₂CH₃	OCH₃	H	HCH₃			H	H	NE^f	NT
DOM	OCH₃	H	CH₃	OCH₃	H	HCH₃			H	H	24.0^c	NE^c
DOI	OCH₃	H	I	OCH₃	H	HCH₃			H	H	24^c;37^d	NE^c
DOB	OCH₃	H	Br	OCH₃	H	HCH₃			H	H	100^c	NE^c
DON	OCH₃	H	NO₂	OCH₃	H	HCH₃			H	H	NE^c	NE^c
DOTFM	OCH₃	H	CF₃	OCH₃	H	HCH₃			H	H	NE^c	NE^c
MDA	H	CH₂-O-CH₂		H	H	HCH₃			H	H	9.3^c(8.5^g)	NE^c
2Br-MDA	Br	H	CH₂-O-CH₂		H	HCH₃			H	H	13.0^c	64.0^c
2Cl-MDA	Cl	H	CH₂-O-CH₂		H	HCH₃			H	H	6.3^c	38.0^c
2NO₂-MDA	NO₂	H	CH₂-O-CH₂		H	HCH₃			H	H	NE^c	NE^c
MDMA	H	CH₂-O-CH₂		H	H	HCH₃			CH₃	H	30^c(24.7^g)	NE^c
(+)-MDMA	H	CH₂-O-CH₂		H	H	CH₃		H	CH₃	H	44^h(22^h)	370^h
(-)-MDMA	H	CH₂-O-CH₂		H	H	H		CH₃	CH₃	H	56^h(28.3^h)	378^h

^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 Gallardo-Godoy et al., 2005. ^f Vallejos et al., 2002. ^g Steuer et al., 2016. ^h Leonardi and Azmitia, 1994. NE, No effect at 100 µM; NI, No inhibition at 200 µM; NT, Not tested.