DOx

2,5-Dimethoxyamphetamine (2,5-DMA), the base structure of the DOx family.

DOx is a term used to refer to a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. The compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor partial agonists.

The DOx family includes the following members:

Structure	Name	Abbreviation
	2,5-Dimethoxy-4-amylamphetamine	DOAM
	2,5-Dimethoxy-4-bromoamphetamine	DOB
	2,5-Dimethoxy-4-butylamphetamine	DOBU
	2,5-Dimethoxy-4-chloroamphetamine	DOC
	2,5-Dimethoxy-4-ethoxyamphetamine	MEM
	2,5-Dimethoxy-4-ethylamphetamine	DOET
	2,5-Dimethoxy-4-ethylthioamphetamine	Aleph-2
	2,5-Dimethoxy-4-fluoroamphetamine	DOF
	2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine	DOEF
	2,5-Dimethoxy-4-iodoamphetamine	DOI
	2,5-Dimethoxy-4-isopropylthioamphetamine	Aleph-4
	2,4,5-Trimethoxyamphetamine	TMA-2
	2,5-Dimethoxy-4-methylamphetamine	DOM
	2,5-Dimethoxy-4-methylthioamphetamine	Aleph-1
	2,5-Dimethoxy-4-nitroamphetamine	DON
	2,5-Dimethoxy-4-phenylthioamphetamine	Aleph-6
	2,5-Dimethoxy-4-propylamphetamine	DOPR
	2,5-Dimethoxy-4-propylthioamphetamine	Aleph-7
	2,5-Dimethoxy-4-trifluoromethylamphetamine	DOTFM

As well as the following members with additional substitutions:

• 2,5-Dimethoxy-4-methyl-α-ethylphenethylamine (Ariadne)
• 2,5-Dimethoxy-4,N-dimethylamphetamine (Beatrice)
• 2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA)
• 2,5-Dimethoxy-3,4-dimethylamphetamine (Ganesha)
• 2,5-Dimethoxy-3,4-trimethylenylamphetamine (G-3)
• 2,5-Dimethoxy-3,4-tetramethylenylamphetamine (G-4)
• 2,5-Dimethoxy-3,4-norbornylamphetamine (G-5)
• 2,5-Dimethoxy-4-iodo-N,N-dimethylamphetamine (IDNNA)
• 2,5-dimethoxy-4-bromo-N-methylamphetamine (Methyl-DOB)
• 2,3,4,5-Tetramethoxyamphetamine (TA, TeMA)

See also

References

External links

• PiHKAL ("Phenethylamines i Have Known And Loved") by Alexander "Sasha" Shulgin (1991)
• Psychotomimetic Drugs: Structure-Activity Relationships by Alexander "Sasha" Shulgin (1978)