|Summary sheet: Escaline|
|Routes of Administration|
3,5-Dimethoxy-4-ethoxyphenethylamine (commonly known as Escaline) is a synthetic psychedelic substance of the phenethylamine chemical class that produces psychedelic effects when administered. It is a closely related structural analog of mescaline with which it shares many common properties.
Escaline was first synthesized and reported in the scientific literature by Benington, et al., in 1954, but was later re-examined in the laboratory of David E. Nichols who prepared a series of mescaline analogues, including proscaline, jimscaline, isoproscaline, and others.
The effects of escaline were first described by Alexander Shulgin in his book PiHKAL: A Chemical Love Story. He lists the dosage range as 40 mg to 60 mg orally and describes the duration of action to be 8–12 hours. Shulgin states that escaline “differs from mescaline in that the onset of action is quicker (within the first hour) and there is no nausea noted, but otherwise the time course, and much of the qualitative content, is quite similar.”</ref>
- 1 Chemistry
- 2 Pharmacology
- 3 Subjective effects
- 4 Toxicity and harm potential
- 5 Legal status
- 6 See also
- 7 External links
- 8 References
Escaline, or 3,5-dimethoxy-4-ethoxyphenethylamine, is a substituted phenethylamine featuring a phenyl ring bound to an amino -NH2 group through an ethyl chain. Escaline contains two methoxy functional groups CH3O- which are attached to carbons R3 and R5 as well as an additional ethoxy group at carbon R4 of the phenyl ring. Escaline is the 4-ethoxy analog of mescaline.
Escaline's agonist activity at the serotonin 5-HT2A receptor is known to be 5-8 times greater than that of mescaline.  The effects of this compound are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.
|This subjective effects section is a stub.|
As such, it is still in progress and may contain incomplete or wrong information.
You can help by expanding or correcting it.
In comparison to mescaline, this compound has significantly more negative physical side effects, less insightful cognitive effects and less complex visual effects. Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), a literature based on anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be treated with a healthy amount of skepticism. It is worth noting that these effects will not necessarily occur in a consistent or reliable manner, although higher doses are more likely to induce the full spectrum of effects. Likewise, adverse effects become much more likely with higher doses and may include serious injury or death.
- The negative physical side effects are more intense in comparison to mescaline, resulting in a more synthetic and unnatural feel.
- Drifting (melting, flowing, breathing and morphing)
- After images
- Symmetrical texture repetition
- Colour shifting
- Scenery slicing
Although typical psychedelic cognitive effects are apparent on escaline, they are less insightful and shorter lasting when compared to those found on other classical psychedelics like mescaline, magic mushrooms or LSD.
- Increased music appreciation
- Thought acceleration
- Thought connectivity
- Novelty enhancement
- Time distortion
- Déjà vu
- Personal bias suppression
- Conceptual thinking
- Immersion enhancement
- Memory suppression
- Suggestibility enhancement
- Increased sense of humor
There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:
Toxicity and harm potential
The toxicity and long-term health effects of recreational escaline use do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because escaline is a research chemical with a very brief history of human usage. Anecdotal evidence from people within the community who have tried escaline suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
It is strongly recommended that one use harm reduction practices when using this substance.
Tolerance and addiction potential
Escaline is not habit-forming, and the desire to use it can actually decrease with use. It is most often self-regulating.
Tolerance to the effects of escaline is built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). Escaline presents cross-tolerance with all psychedelics, meaning that after the consumption of escaline all psychedelics will have a reduced effect.
Although many psychoactive substances are reasonably safe to use on their own, they can quickly become dangerous or even life-threatening when combined with other substances. The list below includes some known dangerous combinations (although it cannot be guaranteed to include all of them). Independent research (e.g. Google, DuckDuckGo) should always be conducted to ensure that a combination of two or more substances is safe to consume. Some interactions listed have been sourced from TripSit.
- Lithium - Lithium is commonly prescribed for the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
- Cannabis - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of Escaline. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid unintentional overdose.
- Stimulants - Stimulants like amphetamine, cocaine or methylphenidate affect many parts of the brain and alter dopaminergic function. This combination can increase the risk of anxiety, paranoia, panic attacks, and thought loops. This interaction may also result in an elevated risk of mania and psychosis.
- Tramadol - Tramadol is well-documented to lower the seizure threshold and psychedelics may act to trigger seizures in susceptible individuals.
This legality section is a stub.
As such, it may contain incomplete or wrong information. You can help by expanding it.
- Germany: Escaline is controlled under the NpSG (New Psychoactive Substances Act) as of November 26, 2016. Production and import with the aim to place it on the market, administration to another person, placing it on the market and trading is punishable. Possession is illegal but not punishable. The legislator considers it possible that orders of escaline are punishable as an incitement to place it on the market.
- Switzerland: Escaline is a controlled substance specifically named under Verzeichnis E.
- United Kingdom: It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.
- United States: Escaline is unscheduled in the U.S. but may be illegal via the Federal Analogue Act.
- Alexander Shulgin; Ann Shulgin (1991). "#72. E; Escaline". PiHKAL: A Chemical Love Story. United States: Transform Press. ISBN 0963009605. OCLC 1166889264.
- A. T. Shulgin (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In L. L. Iversen; S. D. Iversen; S. H. Snyder. Handbook of Psychopharmacology. Stimulants. Plenum Press. ISBN 1475705107. OCLC 853263370.
- Blaazer, A. R.; Smid, P.; Kruse, C. G. (2008). "Structure–Activity Relationships of Phenylalkylamines as Agonist Ligands for 5‐HT2A Receptors". ChemMedChem. 3 (9): 1299–1309. doi:10.1002/cmdc.200800133. eISSN 1860-7187. ISSN 1860-7179. PMID 18666267.
- Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. ISSN 1556-9039.
- "Anlage NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019.
- "Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF). Bundesgesetzblatt Jahrgang 2016 Teil I Nr. 55 (in German). Bundesanzeiger Verlag (published November 25, 2016). November 21, 2016. pp. 2615–2622. ISSN 0341-1095. OCLC 1004462279.
- "§ 4 NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019.
- "§ 3 NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019.
- "Gesetzentwurf der Bundesregierung: Entwurf eines Gesetzes zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Deutscher Bundestag. May 30, 2016. p. 20. Drucksache 18/8579.
- "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.
- "Psychoactive Substances Act 2016". UK Government. Retrieved January 1, 2020.