fbpx
Wikipedia

5-Methyl-MDA

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]

5-Methyl-MDA
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
  • 749191-14-8 N
    204916-89-2 (HCl)
PubChem CID
  • 10012829
ChemSpider
  • 8188403 Y
UNII
  • 10R3PP3FVM
ChEMBL
  • ChEMBL6330 Y
Chemical and physical data
FormulaC11H15NO2
Molar mass193.246 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 Y
  • Key:OLENSVFSNAULML-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Effects and research edit

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 edit

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

United States edit

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 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. ^ 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. ^ . Archived from the original on 2022-01-19. Retrieved 2016-06-09.
  5. ^ Archived from the original on 2009-08-27. Retrieved 2016-06-09.
  6. ^ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary

methyl, methyl, methylenedioxyamphetamine, entactogen, psychedelic, designer, drug, amphetamine, class, ring, methylated, homologue, structural, isomer, mdma, clinical, dataroutes, ofadministrationoralatc, codenonelegal, statuslegal, statusca, schedule, npsg, . 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 5 Methyl MDAClinical dataRoutes ofadministrationOralATC codenoneLegal statusLegal statusCA Schedule I DE NpSG Industrial and scientific use only UK Class A US Analogue to a Schedule I II drug possibly if human consumption intent can be proven IdentifiersIUPAC name 1 7 methyl 1 3 benzodioxol 5 yl propan 2 amineCAS Number749191 14 8 N 204916 89 2 HCl PubChem CID10012829ChemSpider8188403 YUNII10R3PP3FVMChEMBLChEMBL6330 YChemical and physical dataFormulaC 11H 15N O 2Molar mass193 246 g mol 13D model JSmol Interactive imageSMILES O2COc1c2cc CC N C cc1CInChI 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 YKey OLENSVFSNAULML UHFFFAOYSA N Y N Y what is this verify Contents 1 Effects and research 2 Legal status 2 1 United States 3 ReferencesEffects and research editThis section appears to contradict itself Please see the talk page for more information June 2016 This section relies excessively on references to primary sources Please improve this section by adding secondary or tertiary sources Find sources 5 Methyl MDA news newspapers books scholar JSTOR June 2016 Learn how and when to remove this template message 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 edit5 Methyl MDA is not scheduled by the United Nations Convention on Psychotropic Substances 4 United States edit 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 edit 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 PIHKAL 98 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 Convention on Psychotropic Substances 1971 Archived from the original on 2022 01 19 Retrieved 2016 06 09 1308 11 Schedule I Archived from the original on 2009 08 27 Retrieved 2016 06 09 Erowid Analog Law Vault Federal Controlled Substance Analogue Act Summary Retrieved from https en wikipedia org w index php title 5 Methyl MDA amp oldid 1172538314, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.