Ψ-DOM

---

title: "Ψ-DOM" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["ψ-pea-(psychedelics)", "5-ht2a-agonists", "methyl-compounds", "pihkal", "psychedelic-phenethylamines", "serotonin-receptor-modulators", "substituted-amphetamines"] description: "Psychedelic drug" topic_path: "general/ps-pea-psychedelics" source: "https://en.wikipedia.org/wiki/Ψ-DOM" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Psychedelic drug ::

::data[format=table title="Infobox drug"]

Field	Value
Verifiedfields	changed
verifiedrevid	464375917
image	Psi-DOM chemical structure.svg
image_class	skin-invert-image
width	200px
routes_of_administration	Oral
class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC_prefix	None
legal_US	Schedule I (isomer of DOM)
duration_of_action	6–8 hours
CAS_number_Ref
CAS_number	80888-36-4
UNII	JW946TWT6M
PubChem	13753734
ChemSpiderID_Ref
ChemSpiderID	21106372
ChEMBL_Ref
ChEMBL	293399
synonyms	Psi-DOM; Pseudo-DOM; Z-7; Z7; 2,6-Dimethoxy-4-methylamphetamine; 4-Methyl-2,6-dimethoxyamphetamine
IUPAC_name	1-(2,6-dimethoxy-4-methylphenyl)-2-aminopropane
C	12
SMILES	CC1=CC(=C(C(=C1)OC)CC(C)N)OC
StdInChI_Ref
StdInChI	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
StdInChIKey_Ref
StdInChIKey	CFFJUEYUTHKVMQ-UHFFFAOYSA-N
melting_point	203
::

| Verifiedfields = changed | verifiedrevid = 464375917 | image = Psi-DOM chemical structure.svg | image_class = skin-invert-image | width = 200px

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | routes_of_administration = Oral | class = Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist | ATC_prefix = None | ATC_suffix =

| legal_AU = | legal_CA = | legal_UK = | legal_US = Schedule I (isomer of DOM) | legal_US_comment = | legal_status =

| bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = 6–8 hours | excretion =

| CAS_number_Ref = | CAS_number = 80888-36-4 | UNII = JW946TWT6M | PubChem = 13753734 | ChemSpiderID_Ref = | ChemSpiderID = 21106372 | ChEMBL_Ref = | ChEMBL = 293399 | synonyms = Psi-DOM; Pseudo-DOM; Z-7; Z7; 2,6-Dimethoxy-4-methylamphetamine; 4-Methyl-2,6-dimethoxyamphetamine

| IUPAC_name = 1-(2,6-dimethoxy-4-methylphenyl)-2-aminopropane | C=12 | H=19 | N=1 | O=2 | SMILES = CC1=CC(=C(C(=C1)OC)CC(C)N)OC | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = CFFJUEYUTHKVMQ-UHFFFAOYSA-N

| melting_point = 203 | melting_high =

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. It is a positional isomer of DOM in which the methoxy group at the 5 position has been relocated to the 6 position. The drug is taken orally.

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists ψ-DOM's dose as 15 to 25mg orally and its duration as 6 to 8hours. 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. The visuals were said to have been less than expected based on the intensity of its effects. The drug is about one-third as potent as DOM.

Interactions

Pharmacology

Pharmacodynamics

ψ-DOM shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 49–351nM and 50nM, respectively). Its affinity for the serotonin 5-HT2A receptor was about 2.6- to 3.5-fold lower than that of DOM. The drug acts as an agonist of the serotonin 5-HT2A receptor similarly to DOM.

ψ-DOM has been found to substitute for LSD and 5-MeO-DMT in rodent drug discrimination tests. Conversely, it did not substitute for the serotonin 5-HT1A receptor agonist LY-293284 in such tests.

Chemistry

Synthesis

The chemical synthesis of ψ-DOM has been described.

Analogues

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

History

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

Society and culture

Legal status

Canada

Ψ-DOM is a controlled substance in Canada under phenethylamine blanket-ban language.

United States

Ψ-DOM is not an explicitly controlled substance in the United States. 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.

References

References

1. {{CitePiHKAL [http://www.erowid.org/library/books_online/pihkal/pihkal069.shtml ψ-DOM Entry]
2. (20 November 2025). "Receptor interaction profiles of 4-alkoxy-2,6-dimethoxyphenethylamines (Ψ derivatives) and related amphetamines". Frontiers in Pharmacology.
3. (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis.
4. (August 2002). "Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT(2A/2C) receptor affinity". Bioorganic & Medicinal Chemistry Letters.
5. (April 2008). "The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands". Bioorganic & Medicinal Chemistry.
6. (2002). "Use of conformationally-restricted analogues and homology modeling to provide insight into the nature of the 5-HT2A receptor agonist binding site". Purdue University.
7. (December 1981). "Behavioral properties of psychoactive phenylisopropylamines in rats". European Journal of Pharmacology.
8. "Phenethylamines and their pharmacologically-acceptable salts".
9. "Controlled Drugs and Substances Act".
10. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
11. [[Drug Enforcement Administration]]. (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances".

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