Escaline

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]

Escaline

Clinical data
Other names	E; 3,5-Dimethoxy-4-ethoxyphenethylamine; 4-Ethoxy-3,5-dimethoxyphenethylamine
Routes of administration	Oral[1]
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	8–12 hours[1]
Identifiers
IUPAC name 2-(4-ethoxy-3,5-dimethoxyphenyl)ethan-1-amine
CAS Number	39201-82-6 Y
PubChem CID	38240
ChemSpider	35053 Y
UNII	Q13F1C1N8I
ChEMBL	ChEMBL319415 Y
CompTox Dashboard (EPA)	DTXSID60192455
Chemical and physical data
Formula	C12H19NO3
Molar mass	225.288 g·mol−1
3D model (JSmol)	Interactive image
Melting point	165 to 166 °C (329 to 331 °F) (hydrochloride)
SMILES NCCC1=CC(OC)=C(OCC)C(OC)=C1
InChI InChI=1S/C12H19NO3/c1-4-16-12-10(14-2)7-9(5-6-13)8-11(12)15-3/h7-8H,4-6,13H2,1-3H3 Y Key:RHOGRSKNWDNCDN-UHFFFAOYSA-N Y
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Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose range of escaline as 40 to 60 mg of the hydrochloride salt taken orally.^[1][2] The duration is stated to be 8 to 12 hours, whereas the onset is not described.^[1] Escaline is approximately 5- to 8-fold more potent than mescaline.^[3]

The effects of escaline have been described relatively limitedly but have been reported to include sensory enhancement without an intellectual component, little synthesis of external sensory inputs like music or visual stimuli, easy fantasy, rational thinking and insight, pleasantness, powerful and complex intoxication, pain relief, muscle tension, motor incoordination to the extent of not being able to walk or tie one's shoelaces, body tension that outweighed the desired psychoactive effects, tachycardia, dehydration, nightmares, and next-day hangover symptoms such as tiredness and low energy.^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

The receptor interactions of escaline and analogues have been described.^[4][5]

Escaline produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.^[6][2] It partially substitutes for LSD in rodent drug discrimination tests.^[7]

History

Escaline was first synthesized and reported in the scientific literature by Benington and colleagues in 1954.^[8] 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.^[9][10]

Society and culture

Legal status

Sweden

Escaline is illegal in Sweden as of 26 January 2016.^[11]

United States

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 3,4,5-trimethoxyamphetamine (TMA).^[12]

See also

• Substituted mescaline analogue