2-Methoxyphenethylamine

2-Methoxyphenethylamine
Clinical data
Other names	2-MPEA; ortho-Methoxyphenethylamine; o-Methoxyphenethylamine
Drug class	Trace amine-associated receptor 1 (TAAR1) agonist
ATC code	None;
Identifiers
	IUPAC name 2-(2-methoxyphenyl)ethanamine;
CAS Number	2045-79-6;
PubChem CID	74896;
ChemSpider	67459;
UNII	A87YWS9XM3;
ChEMBL	ChEMBL100635;
CompTox Dashboard (EPA)	DTXSID00174412 ;
ECHA InfoCard	100.016.425
Chemical and physical data
Formula	C9H13NO
Molar mass	151.209 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC=CC=C1CCN;
	InChI InChI=1S/C9H13NO/c1-11-9-5-3-2-4-8(9)6-7-10/h2-5H,6-7,10H2,1H3; Key:WSWPCNMLEVZGSM-UHFFFAOYSA-N;

2-Methoxyphenethylamine (2-MPEA) is a drug of the phenethylamine family.^[1] It is one of the methoxyphenethylamine positional isomers.^[1]

Use and effects

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-HT_2A or 5-HT_2C receptors (K_i = >10,000 nM).^[3] 2-MPEA is a potent full agonist of the human trace amine-associated receptor 1 (TAAR1) (EC₅₀Tooltip half-maximal effective concentration = 144 nM; E_maxTooltip maximal efficacy = 95%).^[4]

^ ^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.