3-Chloromethamphetamine

Substituted amphetamine derivative invented in the 1960s

None

Legal statusLegal 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 dataFormulaC₁₀H₁₄ClNMolar mass183.68 g·mol⁻¹3D 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

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]

References

^ Knoll J, Vizi ES, Ecseri Z (February 1966). "Psychomimetic methylamphetamine derivatives". Archives Internationales de Pharmacodynamie et de Therapie. 159 (2): 442–51. PMID 5916746.
^ Brimblecombe RW, Pinder RM (1975). Hallucinogenic agents. Wright-Scientechnica. pp. 71–74. ISBN 978-0-85608-011-1.
^ 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.