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Escaline

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Psychedelic phenthylamine drug
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
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H19NO3/c1-4-16-12-10(14-2)7-9(5-6-13)8-11(12)15-3/h7-8H,4-6,13H2,1-3H3Key: RHOGRSKNWDNCDN-UHFFFAOYSA-N
  • InChI=1/C12H19NO3/c1-4-16-12-10(14-2)7-9(5-6-13)8-11(12)15-3/h7-8H,4-6,13H2,1-3H3Key: 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 , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

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 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).

References

  1. "Erowid Online Books : "PIHKAL" - #72 E". www.erowid.org. Archived from the original on 2023-05-06. Retrieved 2024-02-02.
  2. "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015. Archived from the original on 2017-08-05. Retrieved 2024-02-02.
  3. "Archived copy" (PDF). Archived (PDF) from the original on 2021-04-21. Retrieved 2024-02-02.{{cite web}}: CS1 maint: archived copy as title (link)

See also

Hallucinogens
Psychedelics
(5-HT2A
agonists)
Benzofurans
Lyserg‐
amides
Phenethyl‐
amines
2C-x
25x-NBx
25x-NB
25x-NB3OMe
25x-NB4OMe
25x-NBF
25x-NBMD
25x-NBOH
25x-NBOMe
Atypical structures
25x-NMx
N-(2C)-fentanyl
3C-x
4C-x
DOx
HOT-x
MDxx
Mescaline (subst.)
TMAs
  • TMA
  • TMA-2
  • TMA-3
  • TMA-4
  • TMA-5
  • TMA-6
Others
Piperazines
Tryptamines
alpha-alkyltryptamines
x-DALT
x-DET
x-DiPT
x-DMT
x-DPT
Ibogaine-related
x-MET
x-MiPT
Others
Others
Dissociatives
(NMDAR
antagonists)
Arylcyclo‐
hexylamines
Ketamine-related
PCP-related
Others
Adamantanes
Diarylethylamines
Morphinans
Others
Deliriants
(mAChR
antagonists)
Others
Cannabinoids
(CB1 agonists)
Natural
Synthetic
AM-x
CP x
HU-x
JWH-x
Misc. designer cannabinoids
D2 agonists
GABAA
enhancers
Inhalants
(Mixed MOA)
κOR agonists
Oneirogens
Others


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