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ZK-93426

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ZK-93426
Names

Preferred IUPAC name Ethyl 4-methyl-5-[(propan-2-yl)oxy]-9H-pyrido[3,4-b]indole-3-carboxylate
Other names ZK-93426 Ethyl 5-isopropoxy-4-methyl-9H-β-carboline-3-carboxylate
Identifiers
CAS Number	89592-45-0^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1271047^N
ChemSpider	103086^N
IUPHAR/BPS	4347
PubChem CID	115210
CompTox Dashboard(EPA)	DTXSID401008889
InChI InChI=1S/C18H20N2O3/c1-5-22-18(21)17-11(4)15-13(9-19-17)20-12-7-6-8-14(16(12)15)23-10(2)3/h6-10,20H,5H2,1-4H3^N Key: VMDUABMKBUKKPG-UHFFFAOYSA-N^N InChI=1/C18H20N2O3/c1-5-22-18(21)17-11(4)15-13(9-19-17)20-12-7-6-8-14(16(12)15)23-10(2)3/h6-10,20H,5H2,1-4H3 Key: VMDUABMKBUKKPG-UHFFFAOYAG
SMILES CCOC(=O)C1=NC=C2C(=C1C)C3=C(N2)C=CC=C3OC(C)C
Properties
Chemical formula	C₁₈H₂₀N₂O₃
Molar mass	312.369 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

ZK-93426 (ethyl-5-isopropoxy-4-methyl-beta-carboline-3-carboxylate) is a drug from thebeta-carboline family. It acts as a weak partialinverse agonist ofbenzodiazepine receptors,^[1] meaning that it causes the opposite effects to thebenzodiazepine class of drugs and hasanxiogenic properties,^[2] although unlike most benzodiazepine antagonists it is not aconvulsant and actually has weak anticonvulsant effects.^[3] In human tests it produced alertness, restlessness and feelings ofapprehension,^{[clarification needed]} and reversed the effect of the benzodiazepinelormetazepam.^[4]^[5] It was also shown to producenootropic effects^[6]^[7] and increased release ofacetylcholine.^[8]^[9]

References

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^Camerman, A; Mastropaolo, D; Hempel, A; Camerman, N (2005). "Ethyl 5-isopropoxy-4-methyl-beta-carboline-3-carboxylate: structural determinants of benzodiazepine-receptor antagonism".Acta Crystallographica C.61 (Pt 4): o265–6.Bibcode:2005AcCrC..61O.265C.doi:10.1107/S0108270105005457.PMID 15805647.
^File, SE; Pellow, S; Jensen, LH (1986). "Actions of the beta-carboline ZK 93426 in an animal test of anxiety and the holeboard: interactions with Ro 15-1788".Journal of Neural Transmission.65 (2):103–14.doi:10.1007/BF01256486.PMID 3009709.S2CID 7230560.
^Jensen, LH; Petersen, EN; Braestrup, C; Honoré, T; Kehr, W; Stephens, DN; Schneider, H; Seidelmann, D; Schmiechen, R (1984). "Evaluation of the beta-carboline ZK 93 426 as a benzodiazepine receptor antagonist".Psychopharmacology.83 (3):249–56.doi:10.1007/BF00464789.PMID 6089247.S2CID 37990146.
^Dorow, R; Duka, T; Höller, L; Sauerbrey, N (1987). "Clinical perspectives of beta-carbolines from first studies in humans".Brain Research Bulletin.19 (3):319–26.doi:10.1016/0361-9230(87)90100-6.PMID 2890423.S2CID 54287050.
^Duka, T; Goerke, D; Dorow, R; Höller, L; Fichte, K (1988). "Human studies on the benzodiazepine receptor antagonist beta-carboline ZK 93 426: antagonism of lormetazepam's psychotropic effects".Psychopharmacology.95 (4):463–71.doi:10.1007/bf00172956.PMID 2905500.S2CID 25383323.
^Duka, T; Edelmann, V; Schütt, B; Dorow, R (1988). "β-Carbolines as Tools in Memory Research: Human Data with the β-Carboline ZK 93426".Benzodiazepine Receptor Ligands, Memory and Information Processing. Psychopharmacology Series. Vol. 6. pp. 246–60.doi:10.1007/978-3-642-73288-1_18.ISBN 978-3-642-73290-4.PMID 3064085.
^Duka, T; Ott, H; Rohloff, A; Voet, B (1996). "The effects of a benzodiazepine receptor antagonist beta-carboline ZK-93426 on scopolamine-induced impairment on attention, memory and psychomotor skills".Psychopharmacology.123 (4):361–73.doi:10.1007/BF02246647.PMID 8867876.S2CID 36950692.
^Moore, H; Sarter, M; Bruno, JP (1992). "Age-dependent modulation of in vivo cortical acetylcholine release by benzodiazepine receptor ligands".Brain Research.596 (1–2):17–29.doi:10.1016/0006-8993(92)91527-L.PMID 1334777.S2CID 39356368.
^Moore, H; Sarter, M; Bruno, JP (1993). "Bidirectional modulation of stimulated cortical acetylcholine release by benzodiazepine receptor ligands".Brain Research.627 (2):267–74.doi:10.1016/0006-8993(93)90330-P.PMID 8298971.S2CID 29549067.