Ψ-DOM

ψ-DOM, or 2,6-dimethoxy-4-methylamphetamine, is a hallucinogenic, psychedelic drug and a structural isomer of the better-known hallucinogen DOM. ψ-DOM was first reported by Alexander Shulgin in his book PiHKAL.^[1]

Ψ-DOM

Legal status
Legal status	US: Schedule I (isomer of DOM)
Identifiers
IUPAC name 1-(2,6-Dimethoxy-4-methylphenyl)-2-aminopropane
CAS Number	80888-36-4 N
ChemSpider	21106372 Y
UNII	JW946TWT6M
ChEMBL	ChEMBL293399 Y
CompTox Dashboard (EPA)	DTXSID20548454
Chemical and physical data
Formula	C12H19NO2
Molar mass	209.289 g·mol−1
3D model (JSmol)	Interactive image
Melting point	203 °C (397 °F)
SMILES COc1cc(C)cc(OC)c1CC(C)N
InChI InChI=1S/C12H19NO2/c1-8-5-11(14-3)10(7-9(2)13)12(6-8)15-4/h5-6,9H,7,13H2,1-4H3 Y Key:CFFJUEYUTHKVMQ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

ψ-DOM has similar effects to DOM, but is only around one third to one half the potency, with an active dose reported to be between 15 and 25 milligrams.^[1] The effects of ψ-DOM last for around six to eight hours.^[1]

The activity of ψ-DOM (and ψ-2C-T-4) 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) has also been made by David E. Nichols and found to be active,^[2] this might by extension be referred to as ψ-2C-D-FLY.

ψ-2C-D-FLY