Escaline (E), also known as 3,5-dimethoxy-4-ethoxyphenethylamine, is a

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluc ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

and scaline families related to

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

. It is the 4- ethoxy analogue of mescaline (3,4,5-trimethoxyphenethylamine) and the phenethylamine (non-α-methyl) analogue of

3C-E 3C-E (3,5-Dimethoxy-4-ethoxyamphetamine) is a psychedelic of the amphetamine class. It was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', Shulgin lists the dosage range as 30 to 60 mg, consumed orally. The duration of act ...

(3,5-dimethoxy-4-ethoxyamphetamine).

Effects

The effects of escaline and related

analogues in humans were first described by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', Shulgin lists the dosage range as 40 to 60mg of the

hydrochloride In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (e.g. an amine). An alternative name is chlorhydrate, which comes from French. An archaic alternati ...

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

taken orally. The duration of action was stated to be 8 to 12hours. Escaline is approximately 5- to 8-fold more potent than mescaline in humans.

Pharmacology

The

receptor Receptor may refer to: * Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and respond ...

interactions of escaline analogues have been described. Escaline produces the

head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...

, a behavioral proxy of psychedelic-like effects, in rodents. It partially substitutes for

LSD Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...

in rodent drug discrimination tests.

History

Escaline was first synthesized and reported in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

by Benington and colleagues in 1954. It was later re-examined in the laboratory of David E. Nichols, who prepared a series of

analogues that included escaline,

proscaline Proscaline (4-propoxy-3,5-dimethoxyphenethylamine or 4-propoxy-3,5-DMPEA) is a Psychedelic drug, psychedelic and hallucinogenic drug. It has structural properties similar to the drugs mescaline, isoproscaline, and escaline. In ''PiHKAL'', Alexan ...

, and isoproscaline and published their work in 1977.

Legal status

Sweden

Escaline is illegal in

Sweden Sweden, formally the Kingdom of Sweden, is a Nordic countries, Nordic country located on the Scandinavian Peninsula in Northern Europe. It borders Norway to the west and north, and Finland to the east. At , Sweden is the largest Nordic count ...

as of 26 January 2016.

United States

Escaline is a Schedule I controlled substance (DEA #7930) in the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

with the reason cited being that it is a positional isomer of TMA (3,4,5-trimethoxyamphetamine).

References

External links

Escaline - Isomer Design

Escaline - PsychonautWiki

The Small & Handy Escaline Thread - Bluelight

Escaline - PiHKAL - Erowid

Escaline - PiHKAL - Isomer Design
{{Phenethylamines 5-HT2A agonists Designer drugs Ethoxy compounds O-methylated phenols Phenol ethers Psychedelic phenethylamines Scalines