5-Methyl-MDA

From Wikipedia, the free encyclopedia
Jump to: navigation, search
5-Methyl-MDA
5-Methyl-MDA.svg
Systematic (IUPAC) name
1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine
Clinical data
Legal status Schedule I (as it is an isomer of MDMA, it is covered under Federal Analogue Act in the United States)
Routes Oral
Identifiers
CAS number 749191-14-8 N
204916-89-2 (HCl)
ATC code None
PubChem CID 10012829
ChemSpider 8188403 YesY
ChEMBL CHEMBL6330 YesY
Chemical data
Formula C11H15NO2 
Mol. mass 193.242 g/mol
 N (what is this?)  (verify)

5-Methyl-3,4-methylenedioxyamphetamine (5-Methyl-MDA) is an entactogen and psychedelic drug of the amphetamine class. It is a ring-methylated derivative of MDA and a structural isomer of MDMA.[1] 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.[2]

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 5x more potent than MDA, with a suitable active dose possibly being around 15–25 mg.[1][2] Subsequent testing, however, has found that it is not as potent as once thought and is active at at least 100mg. 2-Methyl-MDA is also much more potent than MDA, but is not quite as potent as 5-methyl-MDA.[1] Both 6-methyl-MDA and 6-methyl-MDMA (also known as Madam-6) are inactive, likely due to steric hindrance.[1][3]

Recent research has used data on 2-methyl-MDA and 5-methyl-MDA to help guide computer modeling of the serotonin transporter complex.[4]

The synthesis of 5-methyl-MDA can be found online.[2]

See also[edit]

References[edit]

  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. ^ a b c "Synthesis of 5-Methyl-MDA - [www.rhodium.ws]". 
  3. ^ PIHKAL #98
  4. ^ 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.