Chemistry:Ψ-DOM

From HandWiki

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][2][3] It is a positional isomer of DOM in which the methoxy group at the 5 position has been relocated to the 6 position.[1][2][3] The drug is taken orally.[1][2][3]

Use and effects

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][2] 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][2]

Interactions

Pharmacology

Pharmacodynamics

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

Synthesis

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

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.[1][2]

History

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]

Society and culture

Canada

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

United States

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]

See also

  • Ψ-PEA (psychedelics)

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml.  ψ-DOM Entry
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis 4 (7–8): 577–590. 2012. doi:10.1002/dta.413. PMID 22374819. 
  3. ↑ 3.0 3.1 3.2 "Receptor interaction profiles of 4-alkoxy-2,6-dimethoxyphenethylamines (Ψ derivatives) and related amphetamines". Frontiers in Pharmacology 16. 20 November 2025. doi:10.3389/fphar.2025.1703480. ISSN 1663-9812. 
  4. ↑ 4.0 4.1 "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. August 2002. doi:10.1016/s0960-894x(02)00306-2. PMID 12113827. 
  5. ↑ 5.0 5.1 5.2 "The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands". Bioorganic & Medicinal Chemistry 16 (8): 4661–4669. April 2008. doi:10.1016/j.bmc.2008.02.033. PMID 18296055. 
  6. ↑ 6.0 6.1 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. ↑ "Behavioral properties of psychoactive phenylisopropylamines in rats". European Journal of Pharmacology 76 (4): 353–360. December 1981. doi:10.1016/0014-2999(81)90106-0. PMID 7327208. 
  8. ↑ Shulgin AT, "Phenethylamines and their pharmacologically-acceptable salts", US patent 3547999, issued 15 December 1970
  9. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  10. ↑ 10.0 10.1 Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 
  11. ↑ Drug Enforcement Administration (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances". https://www.federalregister.gov/documents/2007/12/03/E7-23413/definition-of-positional-isomer-as-it-pertains-to-the-control-of-schedule-i-controlled-substances. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Ψ-DOM&oldid=4243196"