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

The effects of escaline and related mescaline analogues in humans were first described by Alexander Shulgin.^[1] In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin lists the dosage range as 40 to 60 mg of the hydrochloride salt taken orally.^[1][2] The duration of action was stated to be 8 to 12 hours.^[1] Escaline is approximately 5- to 8-fold more potent than mescaline in humans.^[3]

Interactions

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

Pharmacology

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

See also

• Substituted mescaline analogue