3-Chloromethamphetamine

3-Chloromethamphetamine (3-CMA, MCMA) is a substituted amphetamine derivative invented in the 1960s. In animal studies it was deemed to be a "hallucinogen" rather than a stimulant, though the assays used at the time did not distinguish between the compounds now termed psychedelics and those now termed empathogens.^[1][2][3]

3-Chloromethamphetamine

Clinical data
ATC code	None
Legal status
Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class A
Identifiers
IUPAC name 1-(3-Chlorophenyl)-N-methylpropan-2-amine
CAS Number	77481-92-6 Y
PubChem CID	24257264
ChemSpider	23900073
UNII	57PE8W8UUF
Chemical and physical data
Formula	C10H14ClN
Molar mass	183.68 g·mol−1
3D model (JSmol)	Interactive image
SMILES CNC(Cc1cccc(c1)Cl)C
InChI InChI=1S/C10H14ClN/c1-8(12-2)6-9-4-3-5-10(11)7-9/h3-5,7-8,12H,6H2,1-2H3 Key:QLSSITLVZFHSJT-UHFFFAOYSA-N

See also

• 3-Chloroamphetamine
• 3-Chloromethcathinone
• 4-Chloromethamphetamine
• 3-Fluoromethamphetamine
• 3-Methoxymethamphetamine
• 5-Cl-bk-MPA
• Fenfluramine

References

1. Knoll J, Vizi ES, Ecseri Z (February 1966). "Psychomimetic methylamphetamine derivatives". Archives Internationales de Pharmacodynamie et de Therapie. 159 (2): 442–51. PMID 5916746.
2. Brimblecombe RW, Pinder RM (1975). Hallucinogenic agents. Wright-Scientechnica. pp. 71–74. ISBN 978-0-85608-011-1.
3. Segawa H, T Iwata Y, Yamamuro T, Kuwayama K, Tsujikawa K, Kanamori T, Inoue H (March 2017). "Differentiation of ring-substituted regioisomers of amphetamine and methamphetamine by supercritical fluid chromatography". Drug Testing and Analysis. 9 (3): 389–398. doi:10.1002/dta.2040. PMID 27383263.