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
E number{{#property:P628}}
CompTox Dashboard (EPA)
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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
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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 Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). ψ-DOM Entry
  2. ^ a b c d e Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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  4. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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  6. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  7. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  8. ^ US 3547999, Shulgin AT, "Phenethylamines and their pharmacologically-acceptable salts", issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Dow Chemical Co. 
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