Escaline
| Summary sheet: Escaline |
| Escaline | |||||||||||||||||||||||||||
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| Chemical Nomenclature | |||||||||||||||||||||||||||
| Common names | Escaline | ||||||||||||||||||||||||||
| Substitutive name | 3,5-methoxy-4-ethoxyphenethylamine | ||||||||||||||||||||||||||
| Systematic name | 2-(4-Ethoxy-3,5-dimethoxy-phenyl)-ethylamine | ||||||||||||||||||||||||||
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| Psychoactive class | Psychedelic | ||||||||||||||||||||||||||
| Chemical class | Phenethylamine | ||||||||||||||||||||||||||
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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.[1] 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.”[2]
Contents
Chemistry
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.
Pharmacology
Escaline's agonist activity at the serotonin 5-HT2A receptor is known to be 5-8 times greater than that of mescaline. [3][4] 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.
Subjective effects
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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 which relies on collected anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be taken 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 (common+) are more likely to induce the full spectrum of reported effects. Likewise, adverse effects become much more likely with higher doses and may include serious injury or death.
Physical effects 
- The negative physical side effects are more intense in comparison to mescaline, resulting in a more synthetic and unnatural feel.
Visual effects 
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Enhancements
Distortions
- Drifting (melting, flowing, breathing and morphing)
- Tracers
- After images
- Symmetrical texture repetition
- Colour shifting
- Scenery slicing
Geometry
Hallucinatory states
Cognitive effects 
- 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.
Auditory effects 
Experience reports
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.
Dangerous interactions
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.
- Tramadol - Tramadol lowers the seizure threshold[5] and psychedelics may act as triggers for seizures, particularly in those who are predisposed to them.[citation needed]
- Stimulants - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable anxiety, panic, thought loops and paranoia. This interaction may cause elevated risk of psychosis.[citation needed]
- Lithium - Lithium is often used as treatment for bipolar disorder. It may possibly cause elevated risk of seizures and psychosis due to its glutaminergic and GABAergic effects.[citation needed]
Legality
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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.[6][7] Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.[8]
- Switzerland: Escaline is a controlled substance specifically named under Verzeichnis E.[9]
- 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.[10]
- United States: Escaline is unscheduled in the U.S. but may be illegal via the Federal Analogue Act.[citation needed]
See also
External links
References
- ↑ www.erowid.org/library/books_online/pihkal/pihkal072.shtml | #72 E; ESCALINE
- ↑ https://www.erowid.org/archive/rhodium/chemistry/shulgin.pea.sar.hop.html | Psychotomimetic Drugs: Structure-Activity Relationships
- ↑ http://www.ncbi.nlm.nih.gov/pubmed/18666267 | Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors.
- ↑ https://www.erowid.org/archive/rhodium/chemistry/shulgin.pea.sar.hop.html | Psychotomimetic Drugs: Structure-Activity Relationships
- ↑ 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
- ↑ "Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 10, 2019.
- ↑ "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
- ↑ "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
- ↑ "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 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted