2-Methoxyphenethylamine

Last updated

2-Methoxyphenethylamine
2-Methoxyphenethylamine.svg
Clinical data
Other names2-MPEA; ortho-Methoxyphenethylamine; o-Methoxyphenethylamine
Drug class Trace amine-associated receptor 1 (TAAR1) agonist
ATC code
  • None
Identifiers
  • 2-(2-methoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.016.425 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H13NO
Molar mass 151.209 g·mol−1
3D model (JSmol)
  • COC1=CC=CC=C1CCN
  • 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]

Contents

Use and effects

The effects of 2-MPEA in humans have not been reported and are unknown. [1]

Pharmacology

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]

History

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]

See also

References

  1. 1 2 3 4 5 6 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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 .
  6. ↑ 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.


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