Tetrindole

Tetrindole
Clinical data
ATC code	None;
Identifiers
	IUPAC name 2,3,3a,4,5,6-Hexahydro-8-cyclohexyl-1H-pyrazino[3,2,1-j,k]carbazole;
PubChem CID	160020;
ChemSpider	140675 ;
ChEBI	CHEBI:77799 ;
Chemical and physical data
Formula	C20H26N2
Molar mass	294.442 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CCC(CC1)C2=CC3=C(C=C2)N4CCNC5C4=C3CCC5;
	InChI InChI=1S/C20H26N2/c1-2-5-14(6-3-1)15-9-10-19-17(13-15)16-7-4-8-18-20(16)22(19)12-11-21-18/h9-10,13-14,18,21H,1-8,11-12H2 ; Key:AUXCHYJDVJZEPG-UHFFFAOYSA-N ;
	(what is this?) (verify)

Tetrindole was a drug candidate that functions by reversibly inhibiting monoamine oxidase A; it was first synthesized in Moscow in the early 1990s.^[1] Tetrindole is similar in its chemical structure to pirlindole (Pyrazidol), and metralindole.^[2]

Synthesis

The Fischer indole synthesis between 4-Cyclohexylphenylhydrazine [61624-13-3] (1) and 1,2-Cyclohexanedione [765-87-7] (2) gives 6-cyclohexyl-2,3,4,9-tetrahydrocarbazol-1-one [135897-70-0] (3).

There is 2 conceptual ways of continuing the synthesis. In the classical method chloroacetonitrile [107-14-2] (4) is used to alkylate the indole nitrogen to give 5. Reduction to the amine and subsequent imine formation, followed by reduction gives tetrindole. In the other method, ethanolamine is used instead.

References

^ Medvedev AE, Kirkel AA, Kamyshanskaya NS, Moskvitina TA, Axenova LN, Gorkin VZ, et al. (January 1994). "Monoamine oxidase inhibition by novel antidepressant tetrindole". Biochemical Pharmacology. 47 (2): 303–8. doi:10.1016/0006-2952(94)90021-3. PMID 8304974.
^ Ramsay RR, Gravestock MB (March 2003). "Monoamine oxidases: to inhibit or not to inhibit". Mini Reviews in Medicinal Chemistry. 3 (2): 129–36. doi:10.2174/1389557033405287. PMID 12570845.
^ Vasily Ivanovich Shvedov, 18 More », WO 1991007968 (1991 to Vsesojuzny Nauchno-Issledovatelsky Khimiko-Farmatsevtichesky Inst. Imeni Sergo Ordzhonikidze (Vnikhfi)).
^ Vasily Ivanovich Shvedov, et al. SU1694582 (1991).

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[1] Medvedev AE, Kirkel AA, Kamyshanskaya NS, Moskvitina TA, Axenova LN, Gorkin VZ, et al. (January 1994). "Monoamine oxidase inhibition by novel antidepressant tetrindole". Biochemical Pharmacology. 47 (2): 303–8. doi:10.1016/0006-2952(94)90021-3. PMID 8304974.

[2] Ramsay RR, Gravestock MB (March 2003). "Monoamine oxidases: to inhibit or not to inhibit". Mini Reviews in Medicinal Chemistry. 3 (2): 129–36. doi:10.2174/1389557033405287. PMID 12570845.

[3] Vasily Ivanovich Shvedov, 18 More », WO 1991007968 (1991 to Vsesojuzny Nauchno-Issledovatelsky Khimiko-Farmatsevtichesky Inst. Imeni Sergo Ordzhonikidze (Vnikhfi)).

[4] Vasily Ivanovich Shvedov, et al. SU1694582 (1991).

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