5-Methyl-MDA

Last updated
5-Methyl-MDA
5-methyl-MDA.svg
Clinical data
Routes of
administration 		Oral
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H15NO2
Molar mass 193.246 g·mol−1
3D model (JSmol)
  • O2COc1c2cc(CC(N)C)cc1C
  • InChI=1S/C11H15NO2/c1-7-3-9(4-8(2)12)5-10-11(7)14-6-13-10/h3,5,8H,4,6,12H2,1-2H3 Yes check.svgY
  • Key:OLENSVFSNAULML-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

5-Methyl-MDA, also known as 5-methyl-3,4-methylenedioxyamphetamine, is an entactogen and psychedelic designer drug of the amphetamine class. It is a ring-methylated homologue of MDA and a structural isomer of MDMA. [1]

Contents

Pharmacology

5-Methyl-MDA acts as a selective serotonin releasing agent (SSRA) with IC50 values of 107nM, 11,600nM, and 1,494nM for serotonin, dopamine, and norepinephrine release, respectively. [1]

2-methyl-MDA and 5-methyl-MDA have been used to help guide computer modelling of the serotonin transporter complex. [2]

Society and culture

International

5-Methyl-MDA is not scheduled by the United Nations' Convention on Psychotropic Substances. [3]

United States

5-Methyl-MDA is not explicitly scheduled at the federal level in the United States, [4] however 5-Methyl-MDA is a structural isomer of MDMA, and so sales or possession could potentially be prosecuted under the Federal Analogue Act. [5]

Canada

As per the Safe Streets and Communities Act, 5-Methyl-MDA, along with all other amphetamines, is a Schedule I controlled substance under the Controlled Drugs and Substances Act.

See also

References

  1. 1 2 Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE (March 1998). "Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry. 41 (6): 1001–5. doi:10.1021/jm9705925. PMID   9526575.
  2. ↑ Walline CC, Nichols DE, Carroll FI, Barker EL (June 2008). "Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition". The Journal of Pharmacology and Experimental Therapeutics. 325 (3): 791–800. doi:10.1124/jpet.108.136200. PMC   2637348 . PMID   18354055.
  3. ↑ "Convention on Psychotropic Substances, 1971". Archived from the original on 2022-01-19. Retrieved 2016-06-09.
  4. ↑ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2016-06-09.
  5. ↑ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
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