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	90132-31-3 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL126963 Y
ChemSpider	21106344 Y
PubChem CID	44350068
UNII	M4HNS35MM2 Y
CompTox Dashboard (EPA)	DTXSID30658376
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

• Substituted phenethylamine
• Phenethylamine
• Psychedelics, dissociatives and deliriants

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.