6-CAT

6-CAT
Clinical data
Routes of
administration		Oral
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 6-Chloro-1,2,3,4-tetrahydronaphtalen-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
3D model (JSmol)
  • C1CC2=C(CC1N)C=CC(=C2)Cl
  • InChI=1S/C10H12ClN/c11-9-3-1-8-6-10(12)4-2-7(8)5-9/h1,3,5,10H,2,4,6,12H2 checkY
  • Key:CJRJTCMSQLEPFQ-UHFFFAOYSA-N checkY
  (verify)

6-Chloro-2-aminotetralin (6-CAT) is a drug which acts as a selective serotonin releasing agent (SSRA) and is a putative entactogen in humans. It is a rigid analogue of para-chloroamphetamine (PCA).

According to Nichols et al., 6-CAT is a non-neurotoxic analog of PCA.

Other related compounds that are creditworthy of mention include 6,7-DCAT & 5,6-DCAT [57915-89-6]. These compounds were invented by Bryan Molloy (the inventor of Prozac). These can be thought to be rigid analogs of 3,4-Dichloroamphetamine and might be predicted to be similarly non-neurotoxic. A positional isomer of the aforementioned two compounds is also known to exist in the literature with a 5,8-dichloro substitution pattern (PC9954388). The compound depicted in the latter case is with the spirodecanone pharmacophore.

It is worth pointing out that the precursor used in the synthesis of 6-CAT is called 6-Chloro-2-tetralone [17556-18-2]. This compound is actually the starting material in the synthesis of Bexlosteride.

See also

References

  1. 1 2 Fuller RW, Perry KW, Baker JC, Molloy BB (November 1974). "6-Chloro-2-aminotetralin, a rigid Conformational analog of 4-chloroamphetamine: pharmacologic properties of it and related compounds in rats". Archives Internationales de Pharmacodynamie et de Therapie. 212 (1): 141–53. PMID 4455127.
  2. ↑ Fuller RW, Wong DT, Snoddy HD, Bymaster FP (1977). "Comparison of the effects of 6-chloro-2-aminotetralin and of ORG 6582, a related chloroamphetamine analog, on brain serotonin metabolism in rats". Biochemical Pharmacology. 26 (1): 1, 333–1, 337. doi:10.1016/0006-2952(77)90094-6.
  3. ↑ Johnson MP, Frescas SP, Oberlender R, Nichols DE (May 1991). "Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)". Journal of Medicinal Chemistry. 34 (5): 1662–8. doi:10.1021/jm00109a020. PMID 1674539.
  4. 1 2 Bryan B Molloy, U.S. patent 3,919,316 (1975 to Eli Lilly and Co).
  5. ↑ Röver, S., Adam, G., Cesura, A. M., Galley, G., Jenck, F., Monsma, F. J., Wichmann, J., Dautzenberg, F. M. (6 April 2000). "High-Affinity, Non-Peptide Agonists for the ORL1 (Orphanin FQ/Nociceptin) Receptor". Journal of Medicinal Chemistry. 43 (7): 1329–1338. doi:10.1021/jm991129q.