5-Methyl-MDA

Chemical compound
  • none
Legal statusLegal status
Identifiers
  • 1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number
  • 749191-14-8 ☒N
    204916-89-2 (HCl)
PubChem CID
  • 10012829
ChemSpider
  • 8188403 checkY
UNII
  • 10R3PP3FVM
ChEMBL
  • ChEMBL6330 checkY
Chemical and physical dataFormulaC11H15NO2Molar mass193.246 g·mol−13D model (JSmol)
  • Interactive image
  • O2COc1c2cc(CC(N)C)cc1C
InChI
  • 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 checkY
  • Key:OLENSVFSNAULML-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

5-Methyl-3,4-methylenedioxyamphetamine (5-Methyl-MDA) 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]

Effects and research

Drug discrimination studies showed that 5-methyl-MDA substitutes for MDA, MMAI, and LSD, but not amphetamine, suggesting that it produces a mix of entactogen and hallucinogenic effects without any stimulant effects.[citation needed]

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 efflux.[1] It is over 5 times more potent than MDA in vitro assays, with a suitable active dose possibly in vivo being around 15–25 mg.[1] Subsequent testing in vivo, however, has found that it is not as potent as once thought and is active at at least 100 mg. 2-Methyl-MDA is also much more potent than MDA, but is not quite as potent as 5-methyl-MDA.[1] 6-methyl-MDMA (also known as Madam-6) is mostly inactive, likely due to steric hindrance.[1][2]

Recent research has used data on 2-methyl-MDA and 5-methyl-MDA to help guide computer modeling of the serotonin transporter complex.[3]

Legal status

5-Methyl-MDA is not scheduled by the United Nations' Convention on Psychotropic Substances.[4]

United States

5-Methyl-MDA is not scheduled at the federal level in the United States,[5] but it is possible that 5-Methyl-MDA could legally be considered an analog of MDA, in which case, sales or possession could potentially be prosecuted under the Federal Analogue Act.[6]

References

  1. ^ a b c d e 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. ^ PIHKAL #98
  3. ^ 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.
  4. ^ "Convention on Psychotropic Substances, 1971". Archived from the original on 2022-01-19. Retrieved 2016-06-09.
  5. ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2016-06-09.
  6. ^ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
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