Psi-DOM
Encyclopedia
Ψ-DOM, or 2,6-dimethoxy-4-methylamphetamine, is a hallucinogenic drug
Psychoactive drug
A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...

 and a structural isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...

 of the better-known hallucinogen DOM
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine...

. Ψ-DOM was first reported by Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...

 in his book PiHKAL (Phenethylamines i Have Known And Loved)
PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...

.

Ψ-DOM has similar effects to DOM, but is only around 1/3 - 1/2 the potency, with an active dose reported to be between 15-25 milligrams. The effects of Ψ-DOM last for around 6–8 hours.

The activity of Ψ-DOM (and Ψ-2C-T-4
2C-T-4
2C-T-4 or 2,5-dimethoxy-4-isopropylthiophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.-Chemistry:...

) demonstrates that the two methoxy groups on the psychedelic phenethylamines are not strictly limited to the 2,5 positions on the phenyl ring. Indeed any of the 2Cx or DOx series of drugs could alternatively be made as the 2,6 isomer and would still be expected to show similar activity, although slightly less potent. In theory this would vastly expand the range of different hallucinogens that could be derived from this family of drugs. The 2,6 isomer of another similar drug 2C-D-FLY (see 2C-B-FLY
2C-B-FLY
2C-B-FLY is a psychedelic phenethylamine of the 2C family. It was first synthesized by Aaron P. Monte.-Chemistry:2C-B-FLY is 8-bromo-2,3,6,7-benzo-dihydro-difuran-ethylamine. The full name of the chemical is 2-ethanamine...

) has also been made by David E. Nichols
David E. Nichols
David E. Nichols is an American pharmacologist and medicinal chemist.Presently the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worked in the field of psychoactive drugs since 1969...

and found to be active, this might by extension be referred to as Ψ-2C-D-FLY.

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