3-Methoxyphenethylamine

Last updated

3-Methoxyphenethylamine
3-Methoxyphenethylamine.svg
Clinical data
Other names3-MPEA; meta-Methoxyphenethylamine; m-Methoxyphenethylamine; EA-1302; NSC-124706
ATC code
  • None
Identifiers
  • 2-(3-methoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.016.381 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(=C1)CCN
  • InChI=1S/C9H13NO/c1-11-9-4-2-3-8(7-9)5-6-10/h2-4,7H,5-6,10H2,1H3
  • Key:WJBMRZAHTUFBGE-UHFFFAOYSA-N

3-Methoxyphenethylamine (3-MPEA) is a drug of the phenethylamine family. [1] [2] It is one of the methoxyphenethylamine positional isomers. [1] [2]

Contents

The drug showed very low affinity for the serotonin receptors in the rat stomach fundus strip (A2 = 1,290 nM). [1] [3] 3-MPEA is a low-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] The effects of 3-MPEA in humans have not been reported and are unknown. [1]

3-MPEA was first described in the scientific literature by at least 1943. [5] [6] [1] It was studied at Edgewood Arsenal and received the code name EA-1302. [2] The drug 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). "#101. 3-MPEA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley, CA: Transform Press. pp. 243–245. ISBN   978-0-9630096-3-0. OCLC   709667010.
  2. 1 2 3 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. "A passing bit of charming trivia. A positional isomer of MPEA is 3-methoxyphenethylamine (3-MPEA) and, although there are no reported human trials with this, it has been graced with an Edgewood Arsenal code number, vis., EA-1302."
  3. ↑ 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.
  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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