From Wikipedia, the free encyclopedia
Pharmaceutical compound
2,3,5,6-Tetramethoxyphenethylamine Other names 2,3,5,6-TeMPEA; TeMPEA-3
2-(2,3,5,6-tetramethoxyphenyl)ethanamine
PubChem CID ChemSpider Formula C 12 H 19 N O 4 Molar mass 241.287 g·mol−1 3D model (JSmol )
COC1=CC(=C(C(=C1OC)CCN)OC)OC
InChI=1S/C12H19NO4/c1-14-9-7-10(15-2)12(17-4)8(5-6-13)11(9)16-3/h7H,5-6,13H2,1-4H3
Key:MRCWRNATBFUERI-UHFFFAOYSA-N
2,3,5,6-Tetramethoxyphenethylamine (2,3,5,6-TeMPEA ), also known as TeMPEA-3 , is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine).[ 1] It is one of the possible positional isomers of tetramethoxyphenethylamine (TeMPEA).[ 1]
The in-vitro metabolism and effects of TeMPEA-3 on behavior in animals have been studied.[ 1] [ 2] [ 3] Unlike mescaline, TeMPEA-3 was inactive in the conditioned avoidance response test in rats.[ 1] [ 4] The effects of TeMPEA-3 in humans have not been reported and are unknown.[ 1]
The drug was first described in the scientific literature by 1955.[ 1] [ 5] TeMPEA-3 was included as an entry in Alexander Shulgin 's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds .[ 1]
Substituted methoxyphenethylamine
Tetramethoxyphenethylamine (TeMPEA)
2,3,4,5-Tetramethoxyphenethylamine (TeMPEA, TeMPEA-1)
2,3,4,6-Tetramethoxyphenethylamine (TeMPEA-2)
2,3,4,5-Tetramethoxyamphetamine (TeMA)
Pentamethoxyphenethylamine (PeMPEA)
Trimethoxyphenethylamine (TMPEA)
^ a b c d e f g Shulgin A, Manning T, Daley PF (2011). "#115. TeMPEA-3" . The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley, CA: Transform Press. pp. 282– 283. ISBN 978-0-9630096-3-0 . OCLC 709667010 .
^ Clark LC, Benington F, Morin RD (October 1964). "The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related β-phenethylamines". The Alabama Journal of Medical Sciences . 1 : 417– 429. PMID 14230671 .
^ Clark LC, Benington F, Morin RD (May 1965). "The effects of ring-methoxyl groups on biological deamination of phenethylamines". Journal of Medicinal Chemistry . 8 (3): 353– 355. doi :10.1021/jm00327a016 . PMID 14323146 .
^ Smythies JR, Bradley RJ, Johnston VS, Benington F, Morin RD, Clark LC (1967). "Structure-activity relationship studies on mescaline. 3. The influence of the methoxy groups". Psychopharmacologia . 10 (5): 379– 387. doi :10.1007/BF00403978 . PMID 5588333 .
^ Benington F, Morin RD, Clark LC (1955). "Mescaline Analogs. II. Tetra- and Penta-Methoxy-β-Phenethylamines". The Journal of Organic Chemistry . 20 (1): 102– 108. doi :10.1021/jo01119a017 . ISSN 0022-3263 .
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized phenethylamines
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)
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 , bromotomscaline , 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 )