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4-Substituted-2,5-dimethoxyamphetamines (DO''x'') is a chemical class of substituted amphetamine derivatives featuring
methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...
groups at the 2- and 5- positions of the
phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...
ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor
partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonis ...
s. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.


DOx derivatives

The DO''x'' family includes the following members:


Related compounds

A number of additional compounds are known with alternative substitutions:


See also

* 2Cs, 25-NB * Substituted amphetamines * Substituted benzofurans * Substituted cathinones *
Substituted methylenedioxyphenethylamine Substitution reaction, Substituted methylenedioxy- phenethylamines (MDxx) are a large chemical class of derivative (chemistry), derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelic drug, ...
s *
Substituted phenethylamine Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by ...
s * Substituted tryptamines


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) {{DEFAULTSORT:Dox Chemical classes of psychoactive drugs 2,5-Dimethoxyphenethylamines