Ψ-DOM

Ψ-DOM

Clinical data
Other names	Psi-DOM; Pseudo-DOM; Z-7; Z7; 2,6-Dimethoxy-4-methylamphetamine; 4-Methyl-2,6-dimethoxyamphetamine
Routes of administration	Oral[1][2]
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code	None
Legal status
Legal status	US: Schedule I (isomer of DOM)
Pharmacokinetic data
Duration of action	6–8 hours[1][3][2]
Identifiers
IUPAC name 1-(2,6-dimethoxy-4-methylphenyl)-2-aminopropane
CAS Number	80888-36-4 Y
PubChem CID	13753734
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 CC1=CC(=C(C(=C1)OC)CC(C)N)OC
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, or psi-DOM, also known as 2,6-dimethoxy-4-methylamphetamine or as Z-7, is a psychedelic drug of the phenethylamine, amphetamine, and Ψ-PEA families related to DOM.^[1][3][2] It is a positional isomer of DOM in which the methoxy group at the 5 position has been relocated to the 6 position.^[1][3][2] The drug is taken orally.^[1][3][2]

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists ψ-DOM's dose as 15 to 25 mg orally and its duration as 6 to 8 hours.^[1][3] The effects of ψ-DOM were reported to include feeling weird or strange, closed-eye imagery, some visuals, introspection, feeling stoned, spaciness, lightheadedness, muscle tremors, palpitations, and diarrhea.^[1] The visuals were said to have been less than expected based on the intensity of its effects.^[1] The drug is about one-third as potent as DOM.^[1][3]

ψ-DOM shows affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = 49–351 nM and 50 nM, respectively).^[4][5] Its affinity for the serotonin 5-HT_2A receptor was about 2.6- to 3.5-fold lower than that of DOM.^[4][5] The drug acts as an agonist of the serotonin 5-HT_2A receptor similarly to DOM.^[5]

ψ-DOM has been found to substitute for LSD and 5-MeO-DMT in rodent drug discrimination tests.^[6][7] Conversely, it did not substitute for the serotonin 5-HT_1A receptor agonist LY-293284 in such tests.^[6]

The chemical synthesis of ψ-DOM has been described.^[1]

Analogues of ψ-DOM include other ψ-PEA derivatives like TMA-6 (ψ-TMA-2), Ψ-2C-T-4, and Ψ-DODFMO, among others.^[1][3]

Ψ-DOM was first described in the literature by Alexander Shulgin in 1970.^[8] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I have Known and Loved).^[1]

Ψ-DOM is a controlled substance in Canada under phenethylamine blanket-ban language.^[9]

Ψ-DOM is not an explicitly controlled substance in the United States.^[10] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption. In addition, it may be considered scheduled as a positional isomer of DOM.^[10][11]

• Ψ-PEA (psychedelics)

• ψ-DOM - Isomer Design
• ψ-DOM - PiHKAL - Erowid
• ψ-DOM - PiHKAL - Isomer Design