Escaline
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| Other names | E; 3,5-Dimethoxy-4-ethoxyphenethylamine; 4-Ethoxy-3,5-dimethoxyphenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonergic psychedelic; Hallucinogen |
| Pharmacokinetic data | |
| Duration of action | 8–12 hours[1] |
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| Chemical and physical data | |
| Formula | C12H19NO3 |
| Molar mass | 225.288 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 165 to 166 °C (329 to 331 °F) (hydrochloride) |
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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
[edit]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
[edit]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
[edit]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]
Legal status
[edit]Sweden
[edit]Escaline is illegal in Sweden as of 26 January 2016.[10]
United States
[edit]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
[edit]References
[edit]- ^ 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.
- ^ 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.
- ^ 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. Archived from the original (PDF) on 21 July 2019.
- ^ 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). Frontiers in Pharmacology. 12: 794254. doi:10.3389/fphar.2021.794254. PMC 8865417. PMID 35222010.
- ^ 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". Journal of Psychopharmacology. 33 (3): 406–414. doi:10.1177/0269881119826610. PMC 6848748. PMID 30789291.
- ^ Cassels BK, Sáez-Briones P (October 2018). "Dark Classics in Chemical Neuroscience: Mescaline" (PDF). ACS Chemical Neuroscience. 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.
- ^ Benington F, Morin RD, Clarke LC (1954). "Synthesis of 4-Hydroxy- and 4-Ethoxy-3,5-dimethoxy-β-phenethylamines 1". Journal of the American Chemical Society. 76 (21): 5555–5556. Bibcode:1954JAChS..76.5555B. doi:10.1021/ja01650a084. ISSN 0002-7863.
- ^ Nichols DE, Dyer DC (February 1977). "Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues". Journal of Medicinal Chemistry. 20 (2): 299–301. doi:10.1021/jm00212a022. PMID 836502.
- ^ Nichols DE, Shulgin AT, Dyer DC (August 1977). "Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives". Life Sciences. 21 (4): 569–575. doi:10.1016/0024-3205(77)90099-6. PMID 904435.
- ^ "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.
- ^ "Controlled Substances - Alphabetical Order" (PDF). Diversion Control Division, Drug Enforcement Administration. U.S. Department of Justice. December 2024. Archived (PDF) from the original on 2021-04-21. Retrieved 2024-02-02.