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Pharmaceutical compound
3,4,5-Trimethylphenethylamine Other names TMePEA; 3,4,5-tris-Desoxymescaline; 2-(3,4,5-Trimethylphenyl)ethanamine
2-(3,4,5-trimethylphenyl)ethanamine
CAS Number PubChem CID ChemSpider CompTox Dashboard (EPA ) Formula C 11 H 17 N Molar mass −1 3D model (JSmol )
InChI=1S/C11H17N/c1-8-6-11(4-5-12)7-9(2)10(8)3/h6-7H,4-5,12H2,1-3H3
Key:KAUIOBNOAIVCQQ-UHFFFAOYSA-N
3,4,5-Trimethylphenethylamine (also known as TMePEA and 3,4,5-tris-desoxymescaline ) is a chemical compound of the phenethylamine family.[ 1] analogue of mescaline (3,4,5-trimethoxyphenethylamine) in which all three methoxy groups on the phenyl ring have been replaced with methyl groups .[ 1] [ 1] [ 2] [ 3] [ 2] psychoactivity of TMePEA is unknown.[ 1] Alexander Shulgin 's The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds [ 1]
^ a b c d e Shulgin A, Manning T, Daley PF (2011). "#123. TMePEA" . The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds 305– 307. ISBN 978-0-9630096-3-0 OCLC 709667010 . ^ a b Patel AR (1968). "Mescaline and related compounds". Fortschr Arzneimittelforsch . 11 : 11– 47. doi :10.1007/978-3-0348-7062-7_1 . PMID 4873202 . BENINGTON and coworkers [34-36, 66, 71, 355, 357] have synthesized several mescaline analogs and their deoxy congeners. CLARK et al. [157, 158, 171, 172] reported results of in vitro biochemical studies and behavioral studies of these compounds in cats. Substitution of 4-OCH3 group in mescaline with CH3 imparted rage producing properties to the compound, whereas mescaline itself did not induce rage [355]. Other compounds with similar effects were: 3,5-dimethyl-4-methoxy- and 3,4,5-trimethylphenethyl-amines [66, 158]. Amines which produced rage response in cats also caused hyperthermia and were readily deaminated by rabbit liver amine oxidase. Pretreatment with MAO inhibitors increased the rage response. Increasing the aliphatic side chain decreased or abolished the rage reaction [158]. ^ Clark LC, Benington F, Morin RD (October 1964). "The Enzymatic Oxidative Deamination and Effect on Cat Behavior Mescaline and Structurally-Related Beta-Phenethylamines". The Alabama Journal of Medical Sciences . 1 : 417– 429. PMID 14230671 .
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 , jimscaline )2-ADN 2-Benzhydrylpyrrolidine 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 )6-AB AL-1095 Aminochromes (e.g., adrenochrome , adrenolutin )Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , S33005 , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )Butyltolylquinuclidine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g., LSD )GYKI-52895 HDMP-29 Ivabradine Lumateperone and analogues (e.g., IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )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 )Tetrahydrobenzopyranylamines (e.g., CT-5126 )Tricyclics (e.g., benzoctamine , dizocilpine )Z3517967757 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 )
