6-Chloro-MDA

Last updated
6-Chloro-MDA
6-Cl-MDA.svg
Clinical data
Other names6-Cl-MDA; 6-Chloro-3,4-methylenedioxyamphetamine; 2-Chloro-4,5-methylenedioxyamphetamine; 2-Chloro-4,5-MDA; 2-Cl-4,5-MDA; C-MDA; 6CL-MDA
Routes of
administration 		Oral [1]
Drug class Psychoactive drug
ATC code
  • None
Identifiers
  • 1-(6-chloro-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C10H12ClNO2
Molar mass 213.66 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1Cl)OCO2)N
  • InChI=1S/C10H12ClNO2/c1-6(12)2-7-3-9-10(4-8(7)11)14-5-13-9/h3-4,6H,2,5,12H2,1H3
  • Key:RLXSVYSNRAKQGZ-UHFFFAOYSA-N

6-Chloro-MDA, also known as 6-chloro-3,4-methylenedioxyamphetamine or as 2-chloro-4,5-methylenedioxyamphetamine (2-Cl-4,5-MDA), is a psychoactive drug of the phenethylamine, amphetamine, and MDxx families related to 3,4-methylenedioxyamphetamine (MDA). [1] [2] It is the 6-chloro derivative of MDA. [1] The drug has an active dose of 160 mg orally and a duration of approximately 8 hours. [1] It is a weak monoamine oxidase inhibitor (MAOI). [3] [4] [5] 6-Chloro-MDA was first described in the scientific literature by 1970. [2] [6] The properties of 6-chloro-MDA in humans were described by Daniel Trachsel and colleagues in 2013 via personal communication with P. Rausch in 2009. [1]

See also

References

  1. 1 2 3 4 5 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 830, 878. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025. Die halogenierten Verbindungen 6F-MDA (294), 6CL-MDA (295) und 6BR-MDA (296; 2-BR-4,5-MDA) sind bekannte Verbindungen. [...] Das Chloroanalogon 6CL-MDA (295) war in ersten Tests im Menschen vergleichbar aktiv Wie 2Me-MDA (292) (160mg, rund 8h Dauer) [140], und 6BR-MDA (296; 2-BR-4,5-MDA) erwies sich bei Dosierungen von bis zu 350mg als inaktiv [8, 134]. [...] 295; 6CL-MDA; 160mg; 8h. [...] [140] P. Rausch. Persönliche Mitteilung, 2009.
  2. 1 2 Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. pp. 347–347. ISBN   978-0-9630096-3-0. 2-Cl-4,5-MDA [27164-29-0] (2,3) [...] (2) Synthesized as a potential psychedelic drug (Hellot et al., 1970a). (3) MDA, and three analogues with a chloro, bromo, or a nitro group in the 6-position, were experimentally oxidized by differential pulse voltammetry (Squella et al., 1993).
  3. ↑ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi:10.3389/fphar.2019.01590. PMC   6989591 . PMID   32038257.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  4. ↑ Scorza MC, Carrau C, Silveira R, Zapata-Torres G, Cassels BK, Reyes-Parada M (December 1997). "Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships". Biochem Pharmacol. 54 (12): 1361–1369. doi:10.1016/s0006-2952(97)00405-x. PMID   9393679.
  5. ↑ Vallejos G, Rezende MC, Cassels BK (February 2002). "Charge-transfer interactions in the inhibition of MAO-A by phenylisopropylamines--a QSAR study". J Comput Aided Mol Des. 16 (2): 95–103. doi:10.1023/a:1016344030772. PMID   12188024.
  6. ↑ Hellot, J; Violland-Duperret, N; Pacheco, H. (1970). Psychotropes potentiels VI. Synthèse de nouveaux mescalinoïdes. Chimie Therapeutique5(1), 55–64. https://isomerdesign.com/bitnest/external/ChimieTherapeutique/5.1.55
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