Metaescaline

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.[1] 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.[2][3][4]

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
InChI
  • InChI=1S/C12H19NO3/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3 Y
    Key: HNBAVLIQFTYMAX-UHFFFAOYSA-N Y
  • InChI=1/C12H19NO3/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3
    Key: HNBAVLIQFTYMAX-UHFFFAOYAZ
SMILES
  • COc1c(cc(cc1OCC)CCN)OC
Properties
Chemical formula
 C12H19NO3
Molar mass 225.288 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

See also

References
  1. Metaescaline entry in PiHKAL
  2. Jacob P 3rd, Shulgin AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues. J Med Chem. 1984 Jul;27(7):881-8. PMID 6737431 doi:10.1021/jm00373a013
  3. Clare BW. Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters. J Med Chem. 1990 Feb;33(2):687-702. PMID 2299636 doi:10.1021/jm00164a036
  4. Clare BW. The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens. J Med Chem. 1998 Sep 24;41(20):3845-56. PMID 9748359 doi:10.1021/jm980144c


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