3-Chloroamphetamine

3-Chloroamphetamine
Clinical data
Other names3-CA; meta-Chloroamphetamine; m-Chloroamphetamine
Drug classPsychostimulant; Serotonergic neurotoxin
Identifiers
  • 1-(3-chlorophenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC9H12ClN
Molar mass169.65 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=CC=C1)Cl)N
  • InChI=1S/C9H12ClN/c1-7(11)5-8-3-2-4-9(10)6-8/h2-4,6-7H,5,11H2,1H3
  • Key:ORWQJKNRYUIFJU-UHFFFAOYSA-N

3-Chloroamphetamine (3-CA), also known as meta-chloroamphetamine, is a psychostimulant of the amphetamine family and a potent serotonergic neurotoxin related to para-chloroamphetamine (PCA).[1][2][3][4] It is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA).[5][6][7]

  1. ^ Biel JH, Bopp BA (1978). "Amphetamines: Structure-Activity Relationships". Stimulants. Boston, MA: Springer US. p. 1–39. doi:10.1007/978-1-4757-0510-2_1. ISBN 978-1-4757-0512-6.
  2. ^ Coppola M, Mondola R (December 2013). "4-methylamphetamine (4-MA): chemistry, pharmacology and toxicology of a new potential recreational drug". Mini Reviews in Medicinal Chemistry. 13 (14): 2097–2101. doi:10.2174/13895575113136660106. PMID 24195663. [...] was less potent than amphetamine, 3-chloroamphetamine and 4-chloroamphetamine in inducing motor stimulation [31]. [...]
  3. ^ Lapoint J, Welker KL (2022). "Synthetic amphetamine derivatives, benzofurans, and benzodifurans". In Dargan P, Wood D (eds.). Novel Psychoactive Substances. Elsevier. pp. 247–278. doi:10.1016/b978-0-12-818788-3.00007-3. ISBN 978-0-12-818788-3. [...] amphetamine analogue required to increase motor activity by 200 percent was 38 μmol/kg for 4-MA, 16 μmol/kg for amphetamine and 24 μmol/kg for both 2- and 3-chloroamphetamine.
  4. ^ Fuller RW, Baker JC (November 1974). "Long-lasting reduction of brain 5-hydroxytryptamine concentration by 3-chloramphetamine and 4-chloroamphetamine in iprindole-treated rats". The Journal of Pharmacy and Pharmacology. 26 (11): 912–914. doi:10.1111/j.2042-7158.1974.tb09206.x. PMID 4156568.
  5. ^ Forsyth AN (22 May 2012). "Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines". ScholarWorks@UNO. Retrieved 4 November 2024.
  6. ^ Blough B (July 2008). "Dopamine-releasing agents". Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN 978-0-470-11790-3. Archived from the original on 3 November 2024. TABLE 11-2 Comparison of the DAT- and NET-Releasing Activity of a Series of Amphetamines [...]
  7. ^ Ross SB, Ogren SO, Renyi AL (October 1977). "Substituted amphetamine derivatives. I. Effect on uptake and release of biogenic monoamines and on monoamine oxidase in the mouse brain". Acta Pharmacol Toxicol (Copenh). 41 (4): 337–352. doi:10.1111/j.1600-0773.1977.tb02673.x. PMID 579062.