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Psi-DOM



Psi-DOM
Systematic (IUPAC) name
1-(2,6-dimethoxy-4-methylphenyl)-2-aminopropane
Identifiers
CAS number 80888-36-4
ATC code  ?
PubChem  ?
Chemical data
Formula C12H19NO2 
Mol. mass 209.29 g/mol
Physical data
Melt. point 203 °C (397 °F)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

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Legal status

Controlled in the US via the Federal Analog Act.

Routes  ?

Ψ-DOM, or 2,6-dimethoxy-4-methylamphetamine, is a hallucinogenic drug and a structural isomer of the better-known hallucinogen DOM. Ψ-DOM was first reported by Alexander Shulgin in his book PIHKAL.

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) 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,[1] this might by extension be referred to as Ψ-2C-D-FLY.


References

  1. ^ Chambers JJ, Kurrasch-Orbaugh DM, Nichols DE. Translocation of the 5-Alkoxy Substituent of 2,5-Dialkoxyarylalkylamines to the 6-Position: Effects on 5-HT2A/2C Receptor Affinity. Bioorganic & Medicinal Chemistry Letters (2002); (12):1997–1999

Ψ-DOM Entry in PIHKAL

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Psi-DOM". A list of authors is available in Wikipedia.
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