6-CAT

6-CAT
Clinical data
Routes of; administration	Oral
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 6-Chloro-1,2,3,4-tetrahydronaphtalen-2-amine;
CAS Number	60480-00-4;
PubChem CID	16244336;
ChemSpider	11269876 ;
CompTox Dashboard (EPA)	DTXSID20585667 ;
Chemical and physical data
3D model (JSmol)	Interactive image;
	SMILES C1CC2=C(CC1N)C=CC(=C2)Cl;
	InChI 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 ; Key:CJRJTCMSQLEPFQ-UHFFFAOYSA-N ;
	(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.^[1]^[2] It is a rigid analogue of para-chloroamphetamine (PCA).^[1]

According to Nichols et al.,^[3] 6-CAT is a non-neurotoxic analog of PCA.

Other related compounds that are also credit-worthy of mention include 2-Amino-6,7-dichlorotetralin^[4] & 5,6-Dichloro-2-aminotetralin [57915-89-6].^[4] These compounds were invented by Bryan Molloy (the inventor of Prozac). A positional isomer of the aforementioned two compounds is also known to exist in the literature with a 5,8-dichloro substitution pattern.^[5]^[6] Although more modern discussions on chemical synthesis is possible, Bryan Molloy at least lays out a preliminary drug discovery phase of development.

References

^ ^a ^b 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.
^ 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.
^ 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.
^ ^a ^b Bryan B Molloy, U.S. patent 3,919,316 (1975 to Eli Lilly and Co).
^ https://pubchem.ncbi.nlm.nih.gov/compound/9954388
^ 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.

[pmid4455127-1] 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.

[Molloy-4] Bryan B Molloy, U.S. patent 3,919,316 (1975 to Eli Lilly and Co).

[5] ttps://pubchem.ncbi.nlm.nih.gov/compound/9954388

[6] 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.

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See also

References