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Escaline

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Escaline
Clinical data
Other namesE; 3,5-Dimethoxy-4-ethoxyphenethylamine; 4-Ethoxy-3,5-dimethoxyphenethylamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
Pharmacokinetic data
Duration of action8–12 hours[1]
Identifiers
  • 2-(4-ethoxy-3,5-dimethoxyphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO3
Molar mass225.288 g·mol−1
3D model (JSmol)
Melting point165 to 166 °C (329 to 331 °F) (hydrochloride)
  • NCCC1=CC(OC)=C(OCC)C(OC)=C1
  • InChI=1S/C12H19NO3/c1-4-16-12-10(14-2)7-9(5-6-13)8-11(12)15-3/h7-8H,4-6,13H2,1-3H3 checkY
  • Key:RHOGRSKNWDNCDN-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Escaline (E), also known as 3,5-dimethoxy-4-ethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1] It is the 4-ethoxy analogue of mescaline (3,4,5-trimethoxyphenethylamine) and the phenethylamine (non-α-methyl) analogue of 3C-E (3,5-dimethoxy-4-ethoxyamphetamine).[1]

Effects

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The effects of escaline and related mescaline analogues in humans were first described by Alexander Shulgin.[1] In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin lists the dosage range as 40 to 60 mg of the hydrochloride salt taken orally.[1][2] The duration of action was stated to be 8 to 12 hours.[1] Escaline is approximately 5- to 8-fold more potent than mescaline in humans.[3]

Pharmacology

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The receptor interactions of escaline and analogues have been described.[4]

Escaline produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[5][2] It partially substitutes for LSD in rodent drug discrimination tests.[6]

History

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Escaline was first synthesized and reported in the scientific literature by Benington and colleagues in 1954.[7] It was later re-examined in the laboratory of David E. Nichols, who prepared a series of mescaline analogues that included escaline, proscaline, and isoproscaline and published their work in 1977.[8][9]

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Sweden

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Escaline is illegal in Sweden as of 26 January 2016.[10]

United States

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Escaline is a Schedule I controlled substance (DEA #7930) in the United States with the reason cited being that it is a positional isomer of TMA (3,4,5-trimethoxyamphetamine).[11]

See also

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References

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  1. ^ a b c d e f g "Erowid Online Books : "PIHKAL" - #72 E". www.erowid.org. Archived from the original on 2023-05-06. Retrieved 2024-02-02.
  2. ^ a b Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167: 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152.
  3. ^ Blaazer AR, Smid P, Kruse CG (September 2008). "Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors" (PDF). ChemMedChem. 3 (9): 1299–1309. doi:10.1002/cmdc.200800133. PMID 18666267.
  4. ^ Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines" (PDF). Front Pharmacol. 12: 794254. doi:10.3389/fphar.2021.794254. PMC 8865417. PMID 35222010.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  5. ^ Halberstadt AL, Chatha M, Chapman SJ, Brandt SD (March 2019). "Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice" (PDF). J Psychopharmacol. 33 (3): 406–414. doi:10.1177/0269881119826610. PMC 6848748. PMID 30789291.
  6. ^ Cassels BK, Sáez-Briones P (October 2018). "Dark Classics in Chemical Neuroscience: Mescaline" (PDF). ACS Chem Neurosci. 9 (10): 2448–2458. doi:10.1021/acschemneuro.8b00215. PMID 29847089. In the case of the 3,4,5- trioxygenated compounds, binding studies at 5-HT2A and 5- HT2C receptors revealed somewhat higher affinities than mescaline but, in phosphoinositide hydrolysis assays (only for 5-HT2A), lower efficacies relative to serotonin and the full agonist mescaline (60 and 45%, respectively). More striking, however, was the observation that the new compounds did not fully substitute for LSD in LSD-trained rats, and at doses well above the mescaline EC50, only 50 and 29% appropriate responding was recorded. In view of this unexpected result, 3,5- dimethoxy-4-ethoxyphenethylamine (escaline), which is considerably more potent than mescaline in humans,128 was also tested. It was found to have about twice the affinity of mescaline for 5-HT2A receptors and was a complete agonist with very similar functional potency, but again it failed to substitute completely for LSD in the drug discrimination experiments.
  7. ^ Benington, F.; Morin, R. D.; Clarke, Leland C. (1954). "Synthesis of 4-Hydroxy- and 4-Ethoxy-3,5-dimethoxy-β-phenethylamines 1". Journal of the American Chemical Society. 76 (21): 5555–5556. doi:10.1021/ja01650a084. ISSN 0002-7863.
  8. ^ Nichols DE, Dyer DC (February 1977). "Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues". J Med Chem. 20 (2): 299–301. doi:10.1021/jm00212a022. PMID 836502.
  9. ^ Nichols DE, Shulgin AT, Dyer DC (August 1977). "Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives". Life Sci. 21 (4): 569–575. doi:10.1016/0024-3205(77)90099-6. PMID 904435.
  10. ^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015. Archived from the original on 2017-08-05. Retrieved 2024-02-02.
  11. ^ "Archived copy" (PDF). Archived (PDF) from the original on 2021-04-21. Retrieved 2024-02-02.{{cite web}}: CS1 maint: archived copy as title (link)
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