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Metaescaline

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Metaescaline
Names
Preferred IUPAC name 2-(3-Ethoxy-4,5-dimethoxyphenyl)ethan-1-amine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H19NO3/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3Key: HNBAVLIQFTYMAX-UHFFFAOYSA-N
  • InChI=1/C12H19NO3/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3Key: HNBAVLIQFTYMAX-UHFFFAOYAZ
SMILES
  • COc1c(cc(cc1OCC)CCN)OC
Properties
Chemical formula C12H19NO3
Molar mass 225.288 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Metaescaline (3,4-dimethoxy-5-ethoxyphenethylamine) is a lesser-known psychedelic drug. It is an analog of mescaline. Metaescaline was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 200–350 mg, and the duration listed as 8–12 hours. Metaescaline produces mental insights, entactogenic, MDMA-like effects, and TOMSO-like activation. Little data exists about the pharmacological properties, metabolism, and toxicity of metaescaline, though it has been studied to a limited extent in comparison with other related compounds.

See also

References

  1. Metaescaline entry in PiHKAL
  2. Jacob, Peyton; Shulgin, Alexander T. (1984). "Sulfur analogs of psychotomimetic agents. 30. Ethyl homologs of mescaline and their monothioanalogs". Journal of Medicinal Chemistry. 27 (7): 881–888. doi:10.1021/jm00373a013. PMID 6737431.
  3. Clare, Brian W. (1990). "Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: Electronic, volume, and hydrophobicity parameters". Journal of Medicinal Chemistry. 33 (2): 687–702. doi:10.1021/jm00164a036. PMID 2299636.
  4. Clare, Brian W. (1998). "The Frontier Orbital Phase Angles: Novel QSAR Descriptors for Benzene Derivatives, Applied to Phenylalkylamine Hallucinogens". Journal of Medicinal Chemistry. 41 (20): 3845–3856. doi:10.1021/jm980144c. PMID 9748359.
Empathogens/entactogens
Phenylalkyl-
amines
(other than
cathinones)
Cyclized phenyl-
alkylamines
Cathinones
Tryptamines
Chemical classes
Categories: