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Table of Contents

1. Overview of 3,5-Dimethoxy-4-ethoxyphenethylamine (Escaline)
   • Introduction
   • Historical Background
   • Effects and Dosage
2. Chemistry
   • Molecular Structure
3. Pharmacology
   • Mechanism of Action
4. Physical Effects
   • Overview of Physical Effects
     • Physical Sensations
5. Visual Effects
   • Enhancements
   • Distortions
   • Geometry and Hallucinatory States
6. Cognitive Effects
   • Comparison to Other Psychedelics
     • Cognitive Enhancements
7. Auditory Effects
   • Enhancements
8. Transpersonal Effects
   • Overview
9. Experience Reports
10. Toxicity and Harm Potential
    • Research and Evidence
    • Harm Reduction
11. Tolerance and Addiction Potential
    • Tolerance
12. Dangerous Interactions
    • Known Interactions
    • Conducting Research
13. Legal Status
    • Germany
    • Japan
    • Switzerland
    • United Kingdom
    • United States

Overview of 3,5-Dimethoxy-4-ethoxyphenethylamine (Escaline)

Introduction

3,5-Dimethoxy-4-ethoxyphenethylamine, commonly known as Escaline, is a synthetic psychedelic substance belonging to the phenethylamine chemical class. It produces psychedelic effects when administered and is structurally similar to mescaline, sharing many of its properties.

Historical Background

Escaline was first synthesized and reported in scientific literature by Benington and colleagues in 1954. Later, it was re-examined in the laboratory of David E. Nichols, who prepared a series of mescaline analogues, including proscaline, jimscaline, isoproscaline, among others.

Effects and Dosage

The effects of Escaline were first described by Alexander Shulgin in his book "PiHKAL: A Chemical Love Story." According to Shulgin, the dosage range for Escaline is between 40 mg and 60 mg when taken orally. He notes that the duration of action ranges from 8 to 12 hours. Shulgin describes Escaline as having a quicker onset of action compared to mescaline, with effects beginning within the first hour and no nausea reported. He also states that the overall time course and qualitative experience are quite similar to those of mescaline.

Chemistry

Molecular Structure

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-) attached to the carbons at positions R3 and R5 of the phenyl ring, as well as an additional ethoxy group at position R4. Structurally, Escaline is the 4-ethoxy analog of mescaline.

Pharmacology

Mechanism of Action

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 stem from its efficacy as a partial agonist at the 5-HT2A receptor. However, the exact role of these interactions and their contribution to the psychedelic experience remain elusive.

Subjective Effects

Comparison to Mescaline

In comparison to mescaline, Escaline has significantly more negative physical side effects, less insightful cognitive effects, and less complex visual effects. The following details are derived from the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. These should be viewed with a healthy degree of skepticism.

Predictability and Risks

The effects of Escaline do not occur in a predictable or reliable manner. However, higher doses are more likely to induce the full spectrum of effects. Adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death.

Dosage

Threshold

• Threshold: 20 mg

Light

• Light: 30 - 50 mg

Common

• Common: 50 - 100 mg

Strong

• Strong: 100 - 150 mg

Heavy

• Heavy: 150 mg +

Physical Effects

Overview of Physical Effects

Compared to mescaline, Escaline is associated with more intense negative physical side effects, resulting in a more synthetic and unnatural feel.

Physical Sensations

• Stimulation
• Spontaneous physical sensations
• Tactile enhancement
• Bodily control enhancement
• Stamina enhancement
• Increased heart rate
• Nausea
• Pupil dilation
• Muscle contractions

Visual Effects

Enhancements

• Acuity enhancement
• Color enhancement
• Pattern recognition enhancement

Distortions

• Drifting (melting, flowing, breathing, and morphing)
• Tracers
• After images
• Symmetrical texture repetition
• Color shifting
• Scenery slicing

Geometry and Hallucinatory States

• Transformations
• Internal hallucination (autonomous entities, settings, sceneries, landscapes, perspective hallucinations, scenarios, and plots)
• External hallucination (autonomous entities, settings, sceneries, landscapes, perspective hallucinations, scenarios, and plots)

Cognitive Effects

Comparison to Other Psychedelics

Although Escaline exhibits typical psychedelic cognitive effects, they are less insightful and shorter-lasting compared to those of classical psychedelics like mescaline, magic mushrooms, or LSD.

Cognitive Enhancements

• Increased music appreciation
• Thought acceleration
• Thought connectivity
• Novelty enhancement
• Time distortion
• Déjà vu
• Personal bias suppression
• Conceptual thinking
• Immersion enhancement
• Memory suppression
• Ego death
• Delusion
• Suggestibility enhancement
• Increased sense of humor
• Laughter fits
• Mindfulness
• Wakefulness

Auditory Effects

Enhancements

• Distortions
• Hallucinations

Transpersonal Effects

Overview

• Existential self-realization
• Unity and interconnectedness

Experience Reports

There are currently no anecdotal reports describing the effects of this compound within the PsychonautWiki experience index. Additional experience reports can be found on Erowid Experience Vaults: Escaline.

Toxicity and Harm Potential

Research and Evidence

The toxicity and long-term health effects of recreational Escaline use have not been studied in any scientific context, and the exact toxic dose is unknown due to its status as a research chemical with limited human usage history. Anecdotal evidence suggests no significant negative health effects at low to moderate doses when used sparingly. However, this cannot be guaranteed, and independent research is essential to ensure safety when combining substances.

Harm Reduction

It is strongly recommended to employ harm reduction practices when using Escaline.

Tolerance and Addiction Potential

Tolerance

Escaline is not habit-forming, and the desire to use it typically decreases with use. Tolerance to Escaline's effects builds almost immediately after ingestion, taking about three days to reduce by half and seven days to return to baseline without further consumption. Escaline presents cross-tolerance with all psychedelics, meaning all psychedelics will have a reduced effect after consuming Escaline.

Dangerous Interactions

Known Interactions

Certain combinations with Escaline can be dangerous and even life-threatening:

• Lithium: Increased risk of psychosis and seizures.
• Cannabis: Strong and unpredictable synergy, increasing the risk of adverse psychological reactions.
• Stimulants: Increased risk of anxiety, paranoia, panic attacks, thought loops, mania, and psychosis.
• Tramadol: Lower seizure threshold, increasing the risk of seizures.

Conducting Research

Always conduct independent research to ensure that a combination of substances is safe to consume.

Legal Status

Germany

Escaline is controlled under the New Psychoactive Substances Act (NpSG) as of November 26, 2016. Production, import, and trading with the intent to place on the market are punishable. Possession is illegal but not punishable.

Japan

Escaline became a controlled substance on December 21, 2016.

Switzerland

Escaline is specifically named as a controlled substance under Verzeichnis E.

United Kingdom

It is illegal to produce, supply, or import Escaline under the Psychoactive Substance Act, effective May 26, 2016.

United States

Escaline is unscheduled but may be considered illegal under the Federal Analogue Act.

FAQ

What is Escaline?

Escaline, or 3,5-Dimethoxy-4-ethoxyphenethylamine, is a synthetic psychedelic substance in the phenethylamine chemical class that produces psychedelic effects when administered.

How was Escaline discovered?

Escaline was first synthesized and reported by Benington and colleagues in 1954 and later re-examined by David E. Nichols.

What are the effects of Escaline?

Escaline produces psychedelic effects, including visual and cognitive enhancements, similar to mescaline but with more intense negative physical side effects.

What is the recommended dosage for Escaline?

• Threshold: 20 mg
• Light: 30 - 50 mg
• Common: 50 - 100 mg
• Strong: 100 - 150 mg
• Heavy: 150 mg +

How long do the effects of Escaline last?

The effects of Escaline typically last between 8 to 12 hours.

What is the chemical structure of Escaline?

Escaline is a substituted phenethylamine with a phenyl ring bound to an amino -NH2 group through an ethyl chain, containing two methoxy functional groups at R3 and R5, and an ethoxy group at R4.

How does Escaline work?

Escaline acts as a partial agonist at the serotonin 5-HT2A receptor, with its agonist activity being 5-8 times greater than that of mescaline.

What are the physical effects of Escaline?

Physical effects include stimulation, tactile enhancement, increased heart rate, nausea, pupil dilation, and muscle contractions.

What are the visual effects of Escaline?

Visual effects include acuity enhancement, color enhancement, pattern recognition, drifting, tracers, after images, and hallucinatory states.

Are there any cognitive effects?

Cognitive effects include thought acceleration, novelty enhancement, time distortion, ego death, delusion, and increased sense of humor.

Are there any auditory effects?

Auditory effects include enhancements, distortions, and hallucinations.

What are the transpersonal effects of Escaline?

Transpersonal effects include existential self-realization and feelings of unity and interconnectedness.

Is Escaline safe?

The toxicity and long-term health effects of Escaline have not been thoroughly studied. Harm reduction practices are strongly recommended.

Can tolerance develop with Escaline use?

Yes, tolerance to Escaline builds quickly and takes about a week to return to baseline without further consumption. Cross-tolerance with other psychedelics is also noted.

Are there any dangerous interactions?

Yes, combining Escaline with substances like lithium, cannabis, stimulants, or tramadol can be dangerous and even life-threatening.

What is the legal status of Escaline?

• Germany: Controlled under the New Psychoactive Substances Act (NpSG).
• Japan: Controlled substance since December 21, 2016.
• Switzerland: Specifically named under Verzeichnis E.
• United Kingdom: Illegal under the Psychoactive Substance Act since May 26, 2016.
• United States: Unscheduled but may be considered illegal under the Federal Analogue Act.