2,3-Methylenedioxymethamphetamine

Last updated
2,3-Methylenedioxymethamphetamine
2,3-MDMA.svg
Clinical data
Other names2,3-MDMA; 2,3-Methylenedioxy-N-methylamphetamine; ORTHO-MDMA
ATC code
  • None
Identifiers
  • 1-(1,3-Benzodioxol-4-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C11H15NO2
Molar mass 193.246 g·mol−1
3D model (JSmol)
  • CC(CC1=C2C(=CC=C1)OCO2)NC
  • InChI=1S/C11H15NO2/c1-8(12-2)6-9-4-3-5-10-11(9)14-7-13-10/h3-5,8,12H,6-7H2,1-2H3/t8-/m0/s1 Yes check.svgY
  • Key:RTZIIFGBTSUSEL-QMMMGPOBSA-N Yes check.svgY

2,3-Methylenedioxymethamphetamine, also known as 2,3-MDMA or ORTHO-MDMA, is a positional isomer of the recreational drug 3,4-MDMA (commonly known as Ecstasy or Molly). [1] It is a monoamine transporter (MAT) substrate and inhibitor similarly to 3,4-MDMA. [2] However, while showing similar potency at the norepinephrine transporter (NET), 2,3-MDMA is less potent at the serotonin transporter (SERT). [2] 2,3-MDMA has not been encountered as a recreational or designer drug. [2]

Contents

See also

References

  1. ↑ Cody JT, Valtier S (2002). "Differentiation of the 2,3-methylenedioxy regioisomer of 3,4-MDMA (ecstasy) by gas chromatography-mass spectrometry". J. Anal. Toxicol. 26 (7): 537–539. doi: 10.1093/jat/26.7.537 . PMID   12423014.
  2. 1 2 3 Montgomery T, Buon C, Eibauer S, Guiry PJ, Keenan AK, McBean GJ (December 2007). "Comparative potencies of 3,4-methylenedioxymethamphetamine (MDMA) analogues as inhibitors of [3H]noradrenaline and [3H]5-HT transport in mammalian cell lines". Br J Pharmacol. 152 (7): 1121–1130. doi:10.1038/sj.bjp.0707473. PMC   2095113 . PMID   17891159.



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