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Pharmaceutical compound
3-Methoxyphenethylamine (3-MPEA ) is a drug of the phenethylamine family.[ 1] [ 2] methoxyphenethylamine positional isomers .[ 1] [ 2]
The drug showed very low affinity for the serotonin receptors in the rat stomach fundus strip (A2 = 1,290 nM).[ 1] [ 3] potency partial agonist of the human trace amine-associated receptor 1 (TAAR1) (EC50 Tooltip half-maximal effective concentration = 1,444 nM; Emax Tooltip maximal efficacy = 73%).[ 4] [ 1]
3-MPEA was first described in the scientific literature by at least 1943.[ 5] [ 6] [ 1] Edgewood Arsenal and received the code name EA-1302 .[ 2] Alexander Shulgin 's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds [ 1]
^ a b c d e f Shulgin A, Manning T, Daley PF (2011). "#101. 3-MPEA" . The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds 243– 245. ISBN 978-0-9630096-3-0 OCLC 709667010 . ^ a b c Shulgin A , Shulgin A (September 1991). PiHKAL: A Chemical Love Story Berkeley, California : Transform Press . ISBN 0-9630096-0-5 OCLC 25627628 .^ Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". Journal of Medicinal Chemistry . 23 (3): 294– 299. doi :10.1021/jm00177a017 . PMID 7365744 . ^ Lewin AH, Navarro HA, Mascarella SW (August 2008). "Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1" . Bioorganic & Medicinal Chemistry . 16 (15): 7415– 7423. doi :10.1016/j.bmc.2008.06.009 . PMC 2601700 PMID 18602830 . ^ Alles GA, Heegaard EV (1943). "Substrate specificity of amine oxidase" . Journal of Biological Chemistry . 147 (3): 487– 503. doi :10.1016/S0021-9258(18)72344-2 ^ 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 .
TAAR1 Tooltip Trace amine-associated receptor 1
TAAR5 Tooltip Trace amine-associated receptor 5
Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the
List of trace amines ,
TAAR , and
TAAR1 pages.
See also: Receptor/signaling modulators
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 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 )Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )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 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 )Phenylpiracetams (e.g., phenylpiracetam , MRZ-9547 , RGPU-95 )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 )
