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Metaescaline
Names
Preferred IUPAC name
2-(3-Ethoxy-4,5-dimethoxyphenyl)ethan-1-amine
Identifiers
ChEMBL
ChemSpider
UNII
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
Properties
C 12 H 19 N O 3
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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 [ 1] 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 entry in PiHKAL ^ 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 . ^ 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 . ^ 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 .
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs.
2,N ,N -TMT 4,N ,N -TMT 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-N ,N -TMT 7,N ,N -TMT 5-MeO-2,N ,N -TMT 5-MeO-4,N ,N -TMT 6-Fluoro-DMT Bretisilocin (GM-2505; 5-fluoro-MET) α-Alkyltryptamines
5-Methoxy-α-alkyltryptamines: 5-MeO-AET α,N ,N -TMT (α-Me-DMT; Alpha-N) 5-MeO-AMT (α,O -DMS; Alpha-O) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) Others
Ergolines /lysergamides (e.g., LSD )β-Carbolines and Harmala alkaloidsharmine , harmaline , 6-methoxyharmalan )Iboga alkaloids18-MAC , 18-MC , coronaridine , ibogaine , ibogamine , ME-18-MC , noribogaine , tabernanthine , voacangine )Ibogalogs (e.g., ibogainalog )O -MethylnordehydrobufoteninePartial ergolines (e.g., NDTDI , RU-28306 , CT-5252 )Piperidinylethylindoles (e.g., pip-T )Pyrrolidinylethylindoles (e.g., pyr-T , 5-MeO-pyr-T )Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5-MeO-MPMI )Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI) , NEtPhOH-THPI )
Benzofurans (e.g., 5-MeO-DiBF , dimemebfe (5-MeO-BFE) , mebfap )Benzothiophenes (e.g., 3-APBT )Indazolethylamines (e.g., AL-38022A , O -methyl-AL-34662Indenylethylamines (e.g., C-DMT )Isotryptamines (e.g., 6-MeO-isoDMT , Ro60-0175 )MYCO-005 Quinolinylethylamines (e.g., mefloquine )
Others: 2C-B-AN 2C-DB 2C-G-x (e.g., 2C-G-3 , 2C-G-5 )β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOB , BOD , BOH-2C-B )HOT-2 , HOT-7 , HOT-17 )N -Ethyl-2C-B2CD-2-ETO , 2CD-5-ETO , 2CE-5-ETO , 2CE-5iPrO , 2CT2-5-ETO , ASR-2001 (2CB-5PrO) ) Others
2-TOET 2-TOM 25B-NAcPip 4-HA 5-TOET 5-TOM Benzofurans (e.g., 5-APB , 5-APDB , 6-APB , 6-APDB , F , F-2 , F-22 )Benzothiophenes (e.g., 5-APBT , 6-APBT )CT-5172 DMAs (e.g., 2,4-DMA , 3,4-DMA )Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine 25D-NM-NDEAOP , DOB-NDEPA , DOI-NDEPA , DOM-NDEPA , DOTFM-NDEPA , M-NDEPA , TMA-2-NDEPA )PMA (4-MA) TMA-3 , TMA-4 , TMA-5 )TOMSO ZDCM-04
1-Aminomethylindanes (e.g., 2CB-Ind , jimscaline )2-Aminoindanes (e.g., DOM-AI )3-Benzazepines (e.g., lorcaserin )3-Phenylpiperidines (e.g., LPH-5 , LPH-48 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )DMBMPP (juncosamine) Ergolines /lysergamides (e.g., LSD )Glaucine Partial ergolines (e.g., NDTDI , DEIMDHPCA , DEMPDHPCA , DEMTMPDHPCA , DEMNDHPCA )Phenylcyclopropylamines (e.g., DMCPA , TMT )Phenyloxazolamines (aminorexes ) (e.g., 2C-B-aminorex )Pyridopyrroloquinoxalines (e.g., IHCH-7113 )Z3517967757 ZC-B
Others
Arylpiperazines (e.g., 2C-B-PP , 2-NP , mCPP , MK-212 , ORG-12962 , pCPP , pFPP , quipazine , TFMPP )Dihydrobenzoxazines (e.g., efavirenz )Phenoxyethylamines (e.g., CT-4719 , ORG-37684 )Pyridopyrroloquinoxalines (e.g., IHCH-7113 )Quinazolinylethylamines (e.g., RH-34 ) Natural sources
Tryptamines: Acacia spp.Acacia acuminata Acacia confusa Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna)Dipolopterys cabrerana (chaliponga, chacruna)Mimosa tenuiflora (Mimosa hostilis ; jurema)Brosimum Brosimum acutifolium (takini)Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene)Anadenanthera colubrina (vilca, cebil)Incilius alvarius (Bufo alvarius ; Colorado River toad, Sonoran Desert toad; bufo)Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis Psilocybe mexicana (teonanacatl)Lysergamides: Achnatherum robustum (sleepy grass)Epichloë spp.Ergot (Claviceps ) (e.g., Claviceps purpurea Claviceps paspali Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea )Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa , Turbina Corymbosa )Argyreia nervosa (Hawaiian baby woodrose; HBWR)Periglandula spp.Periglandula ipomoeae Periglandula clandestina
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted
1-Aminomethylindanes (e.g., 2CB-Ind , AMMI , bromojimscaline , jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g., fenoldopam , lorcaserin , 7-chlorolorcaserin , SCHEMBL5334361 )3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine , 3-PPP , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 , Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g., adrenochrome , adrenolutin )Benzocyclobutenes (e.g., 2CBCB-NBOMe , bromotomscaline , S33005 , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g., LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g., NDTDI , RU-27849 , DEIMDHPCA , DEMPDHPCA , DEMPDHPCA-2C-D , RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g., DMCPA , TMT , tranylcypromine )Phenylpiracetams (e.g., phenylpiracetam , MRZ-9547 , RGPU-95 )Pyridopyrroloquinoxalines (e.g., lumateperone , deulumateperone , IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )Tetrahydrobenzopyranylamines (e.g., CT-5126 )Tolazoline Tricyclics (e.g., AMDA , AMDH , benzoctamine , dizocilpine , SpAMDA )ZC-B
Related compounds
2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 1,4-dimethylamylamine , heptaminol , iproheptine , isometheptene , methylhexanamine/1,3-DMAA , octodrine , oenethyl , tuaminoheptane )Benzylamines (e.g., benzylamine , α-methylbenzylamine , MDM1EA , ALPHA , M-ALPHA , pargyline )Benzylpiperazines (e.g., benzylpiperazine , MDBZP , fipexide )Cyclohexylaminopropanes (e.g., propylhexedrine , norpropylhexedrine )Cyclopentylaminopropanes (e.g., isocyclamine , cyclopentamine )Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine , CT-4719 , ORG-37684 )Phenylalkenylamines (e.g., phenylbutenamine )Phenylalkynylamines (e.g., phenylbutynamine )Phenylpiperazines (e.g., 1-phenylpiperazine , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )
