From Wikipedia, the free encyclopedia
Pharmaceutical compound
2-Methoxyphenethylamine (2-MPEA ) is a drug of the phenethylamine family.[ 1] It is one of the methoxyphenethylamine positional isomers .[ 1]
The effects of 2-MPEA in humans have not been reported and are unknown.[ 1]
The drug showed very low affinity for the serotonin receptors in the rat stomach fundus strip (A2 = 3,020 nM).[ 1] [ 2] In another study, it showed no affinity for the serotonin 5-HT2A or 5-HT2C receptors (Ki = >10,000 nM).[ 3] 2-MPEA is a potent full agonist of the human trace amine-associated receptor 1 (TAAR1) (EC50 Tooltip half-maximal effective concentration = 144 nM; Emax Tooltip maximal efficacy = 95%).[ 4]
2-MPEA was first described in the scientific literature by at least 1943.[ 5] [ 6] [ 1] It was included as an entry in 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). "#100. 2-MPEA" . The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley, CA: Transform Press. pp. 241– 243. ISBN 978-0-9630096-3-0 . OCLC 709667010 .
^ 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 .
^ Rangisetty JB, Dukat M, Dowd CS, Herrick-Davis K, DuPre A, Gadepalli S, et al. (September 2001). "1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT(2A) serotonin receptor affinity and antagonist character". Journal of Medicinal Chemistry . 44 (20): 3283– 3291. doi :10.1021/jm0100739 . PMID 11563927 .
^ 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 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 , 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
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 )
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 )