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ψ-DOM

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Ψ-DOM
Clinical data
Other namesPsi-DOM; Pseudo-DOM; Z-7; Z7; 2,6-Dimethoxy-4-methylamphetamine; 4-Methyl-2,6-dimethoxyamphetamine
Routes of
administration		Oral[1][2]
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action6–8 hours[1][3][2]
Identifiers
  • 1-(2,6-dimethoxy-4-methylphenyl)-2-aminopropane
CAS Number
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO2
Molar mass209.289 g·mol−1
3D model (JSmol)
Melting point203 °C (397 °F)
  • COc1cc(C)cc(OC)c1CC(C)N
  • 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 checkY
  • Key:CFFJUEYUTHKVMQ-UHFFFAOYSA-N checkY
 ☒NcheckY (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]

Use and effects

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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]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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ψ-DOM shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 49–351 nM and 50 nM, respectively).[4][5] Its affinity for the serotonin 5-HT2A 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-HT2A 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-HT1A receptor agonist LY-293284 in such tests.[6]

Chemistry

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Synthesis

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

History

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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]

See also

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References

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  1. ^ a b c d e f g h i j k Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. ψ-DOM Entry
  2. ^ a b c d e Kolaczynska KE, Trachsel D, Hoener MC, Liechti ME, Luethi D (20 November 2025). "Receptor interaction profiles of 4-alkoxy-2,6-dimethoxyphenethylamines (Ψ derivatives) and related amphetamines". Frontiers in Pharmacology. 16. doi:10.3389/fphar.2025.1703480. ISSN 1663-9812.
  3. ^ a b c d e f Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
  4. ^ a b Chambers JJ, Kurrasch-Orbaugh DM, Nichols DE (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. 12 (15): 1997–1999. doi:10.1016/s0960-894x(02)00306-2. PMID 12113827.
  5. ^ a b c Parker MA, Kurrasch DM, Nichols DE (April 2008). "The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands". Bioorganic & Medicinal Chemistry. 16 (8): 4661–4669. doi:10.1016/j.bmc.2008.02.033. PMC 2442558. PMID 18296055.
  6. ^ a b Chambers JJ (2002). Use of conformationally-restricted analogues and homology modeling to provide insight into the nature of the 5-HT2A receptor agonist binding site (Thesis). Purdue University. Table 2. Results of radioligand competition binding studies at cloned receptors. [...] Table 3. Results of the IP3 accumulation studies at cloned rat 5-HT2A receptors. [...]
  7. ^ Glennon RA, Rosecrans JA, Young R (December 1981). "Behavioral properties of psychoactive phenylisopropylamines in rats". European Journal of Pharmacology. 76 (4): 353–360. doi:10.1016/0014-2999(81)90106-0. PMID 7327208.
  8. ^ US 3547999, Shulgin AT, "Phenethylamines and their pharmacologically-acceptable salts", issued 15 December 1970, assigned to Dow Chemical Co. 
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