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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	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

Metaescaline (3,4-dimethoxy-5-ethoxyphenethylamine) is a lesser-known psychedelic drug. It is an analogofmescaline. 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]

References[edit]

^ Metaescaline entry in PiHKAL

^ 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

^ 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

^ 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

v t e Empathogens/entactogens
Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 3-CMA 4-CAB 4-FA 4-MA 4-MMA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA mMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA DMMDA DMMDA-2 EIDA Lys-MDA MDEA MDMA (midomafetamine) MDMOH MDOH MMDA MMDA-2 MMDMA N-t-BOC-MDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MAPBT 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB IBF5MAP Indanes: 5-APDI 5-MAPDI Indoles: 5-IT 6-API Naphthalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI BFAI ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-MMC 4-EMC BK-5-MAPB Brephedrone Butylone Dimethylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

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Retrieved from "https://en.wikipedia.org/w/index.php?title=Metaescaline&oldid=1147950844" Categories: ●Psychedelic phenethylamines ●Mescalines ●Methoxy compounds ●Ethoxy compounds ●Psychoactive drug stubs Hidden categories: ●Articles without KEGG source ●Articles containing unverified chemical infoboxes ●Chembox image size set ●Articles with short description ●Short description matches Wikidata ●All stub articles ●This page was last edited on 3 April 2023, at 06:01 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view