Escaline

Escaline (3,5-methoxy-4-ethoxyphenethylamine) is a psychedelic drug and entheogen of the phenethylamine class of compounds. 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 that included escaline, proscaline, and isoproscaline. The effects of this and related mescaline analogues in humans were first described by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin lists the dosage range as 40 to 60 mg of hydrochloride salt, consumed orally. The duration of action was stated to be 8–12 hours.

Escaline

Names
Preferred IUPAC name 2-(4-Ethoxy-3,5-dimethoxyphenyl)ethan-1-amine
Other names 3,5-Dimethoxy-4-ethoxy-phenethylamine
Identifiers
CAS Number	39201-82-6 Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL319415 Y
ChemSpider	35053 Y
PubChem CID	38240
UNII	Q13F1C1N8I N
CompTox Dashboard (EPA)	DTXSID60192455
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 InChI=1/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 Key: RHOGRSKNWDNCDN-UHFFFAOYAR
SMILES NCCC1=CC(OC)=C(OCC)C(OC)=C1 O(c1c(OC)cc(cc1OC)CCN)CC
Properties
Chemical formula	C12H19NO3
Molar mass	225.28 g/mol
Melting point	165 to 166 °C (329 to 331 °F; 438 to 439 K) (hydrochloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Escaline is the phenethylamine analog of 3C-E and the 4-ethoxy analog of mescaline.

Legal status

Escaline is illegal in Sweden as of 26 January 2016.

Escaline is a Schedule I controlled substance (DEA #7930) in the United States as it is a positional isomer of TMA (3,4,5-trimethoxyamphetamine).

See also

• Functional analog (chemistry)