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
PubChemCID	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, orpsi-DOM, also known as2,6-dimethoxy-4-methylamphetamine or asZ-7, is apsychedelic drug of thephenethylamine,amphetamine, andΨ-PEA families related toDOM.^[1][3][2] It is apositional isomer of DOM in which themethoxy group at the 5 position has been relocated to the 6 position.^[1][3][2] The drug is takenorally.^[1][3][2]

In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin lists ψ-DOM's dose as 15 to 25 mgorally and itsduration as 6 to 8 hours.^[1][3] The effects of ψ-DOM were reported to include feeling weird or strange,closed-eyeimagery, somevisuals,introspection, feelingstoned, spaciness,lightheadedness,muscle tremors,palpitations, anddiarrhea.^[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 aspotent as DOM.^[1][3]

ψ-DOM showsaffinity for theserotonin5-HT_2A and5-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 ofDOM.^[4][5] The drug acts as anagonist of the serotonin 5-HT_2A receptor similarly to DOM.^[5]

ψ-DOM has been found to substitute forLSD and5-MeO-DMT in rodentdrug discrimination tests.^[6][7] Conversely, it did not substitute for the serotonin5-HT_1A receptor agonistLY-293284 in such tests.^[6]

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

Analogues of ψ-DOM include otherψ-PEAderivatives likeTMA-6 (ψ-TMA-2),Ψ-2C-T-4, andΨ-DODFMO, among others.^[1][3]

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

Ψ-DOM is acontrolled substance inCanada under phenethylamine blanket-ban language.^[9]

Ψ-DOM is not an explicitlycontrolled substance in theUnited States.^[10] However, it could be considered a controlled substance under theFederal Analogue Act if intended for human consumption. In addition, it may be considered scheduled as apositional isomer ofDOM.^[10][11]

• Ψ-PEA (psychedelics)

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

• Drugs not assigned an ATC code
• Ψ-PEA (psychedelics)
• 5-HT2A agonists
• Methyl compounds
• PiHKAL
• Psychedelic phenethylamines
• Serotonin receptor modulators
• Substituted amphetamines

• Articles with short description
• Short description is different from Wikidata
• Drugs with non-standard legal status
• Chemical pages without DrugBank identifier
• Articles without KEGG source
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