View source for Chemistry:ZK-93426

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 445991871
| ImageFile = ZK-93426_structure.png
| ImageSize = 
| PIN = Ethyl 4-methyl-5-[(propan-2-yl)oxy]-9''H''-pyrido[3,4-''b'']indole-3-carboxylate
| OtherNames = ZK-93426<br/>Ethyl 5-isopropoxy-4-methyl-9''H''-β-carboline-3-carboxylate
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 4347
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 89592-45-0
| PubChem = 115210
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1271047
| SMILES = CCOC(=O)C1=NC=C2C(=C1C)C3=C(N2)C=CC=C3OC(C)C
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 103086
| 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
| InChIKey = VMDUABMKBUKKPG-UHFFFAOYAG
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = VMDUABMKBUKKPG-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula = C<sub>18</sub>H<sub>20</sub>N<sub>2</sub>O<sub>3</sub>
| MolarMass = 314.336 g/mol
| Appearance = 
| Density = 
| MeltingPtC = 
| BoilingPt = 
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = }}
}}

'''ZK-93426''' (ethyl-5-isopropoxy-4-methyl-beta-carboline-3-carboxylate) is a drug from the beta-carboline family. It acts as a weak partial [[Chemistry:Inverse agonist|inverse agonist]] of benzodiazepine receptors,<ref>{{cite journal | last1 = Camerman | first1 = A | last2 = Mastropaolo | first2 = D | last3 = Hempel | first3 = A | last4 = Camerman | first4 = N | title = Ethyl 5-isopropoxy-4-methyl-beta-carboline-3-carboxylate: structural determinants of benzodiazepine-receptor antagonism | journal = Acta Crystallographica C | volume = 61 | issue = Pt 4 | pages = o265–6 | year = 2005 | pmid = 15805647 | doi = 10.1107/S0108270105005457 }}</ref> meaning that it causes the opposite effects to the [[Chemistry:Benzodiazepine|benzodiazepine]] class of drugs and has [[Chemistry:Anxiogenic|anxiogenic]] properties,<ref>{{cite journal | last1 = File | first1 = SE | last2 = Pellow | first2 = S | last3 = Jensen | first3 = LH | title = Actions of the beta-carboline ZK 93426 in an animal test of anxiety and the holeboard: interactions with Ro 15-1788 | journal = Journal of Neural Transmission | volume = 65 | issue = 2 | pages = 103–14 | year = 1986 | pmid = 3009709 | doi = 10.1007/BF01256486 | s2cid = 7230560 }}</ref> although unlike most benzodiazepine antagonists it is not a [[Chemistry:Convulsant|convulsant]] and actually has weak anticonvulsant effects.<ref>{{cite journal | last1 = Jensen | first1 = LH | last2 = Petersen | first2 = EN | last3 = Braestrup | first3 = C | last4 = Honoré | first4 = T | last5 = Kehr | first5 = W | last6 = Stephens | first6 = DN | last7 = Schneider | first7 = H | last8 = Seidelmann | first8 = D | last9 = Schmiechen | first9 = R | title = Evaluation of the beta-carboline ZK 93 426 as a benzodiazepine receptor antagonist | journal = Psychopharmacology | volume = 83 | issue = 3 | pages = 249–56 | year = 1984 | pmid = 6089247 | doi=10.1007/BF00464789 | s2cid = 37990146 }}</ref> In human tests it produced alertness, restlessness and feelings of [[Philosophy:Fear|apprehension]]{{clarify|date=July 2012}}, and reversed the effect of the benzodiazepine [[Chemistry:Lormetazepam|lormetazepam]].<ref>{{cite journal | last1 = Dorow | first1 = R | last2 = Duka | first2 = T | last3 = Höller | first3 = L | last4 = Sauerbrey | first4 = N | title = Clinical perspectives of beta-carbolines from first studies in humans | journal = Brain Research Bulletin | volume = 19 | issue = 3 | pages = 319–26 | year = 1987 | pmid = 2890423 | doi=10.1016/0361-9230(87)90100-6| s2cid = 54287050 }}</ref><ref>{{cite journal | last1 = Duka | first1 = T | last2 = Goerke | first2 = D | last3 = Dorow | first3 = R | last4 = Höller | first4 = L | last5 = Fichte | first5 = K | title = Human studies on the benzodiazepine receptor antagonist beta-carboline ZK 93 426: antagonism of lormetazepam's psychotropic effects | journal = Psychopharmacology | volume = 95 | issue = 4 | pages = 463–71 | year = 1988 | pmid = 2905500 | doi=10.1007/bf00172956| s2cid = 25383323 }}</ref> It was also shown to produce [[Chemistry:Nootropic|nootropic]] effects<ref>{{cite book | last1 = Duka | first1 = T | last2 = Edelmann | first2 = V | last3 = Schütt | first3 = B | last4 = Dorow | first4 = R | title = Benzodiazepine Receptor Ligands, Memory and Information Processing | chapter = β-Carbolines as Tools in Memory Research: Human Data with the β-Carboline ZK 93426 | journal = Psychopharmacology Series | volume = 6 | pages = 246–60 | year = 1988 | pmid = 3064085 | doi=10.1007/978-3-642-73288-1_18| isbn = 978-3-642-73290-4 }}</ref><ref>{{cite journal | last1 = Duka | first1 = T | last2 = Ott | first2 = H | last3 = Rohloff | first3 = A | last4 = Voet | first4 = B | title = The effects of a benzodiazepine receptor antagonist beta-carboline ZK-93426 on scopolamine-induced impairment on attention, memory and psychomotor skills | journal = Psychopharmacology | volume = 123 | issue = 4 | pages = 361–73 | year = 1996 | pmid = 8867876 | doi=10.1007/BF02246647| s2cid = 36950692 }}</ref> and increased release of [[Chemistry:Acetylcholine|acetylcholine]].<ref>{{cite journal | last1 = Moore | first1 = H | last2 = Sarter | first2 = M | last3 = Bruno | first3 = JP | title = Age-dependent modulation of in vivo cortical acetylcholine release by benzodiazepine receptor ligands | journal = Brain Research | volume = 596 | issue = 1–2 | pages = 17–29 | year = 1992 | pmid = 1334777 | doi=10.1016/0006-8993(92)91527-L| s2cid = 39356368 }}</ref><ref>{{cite journal | last1 = Moore | first1 = H | last2 = Sarter | first2 = M | last3 = Bruno | first3 = JP | title = Bidirectional modulation of stimulated cortical acetylcholine release by benzodiazepine receptor ligands | journal = Brain Research | volume = 627 | issue = 2 | pages = 267–74 | year = 1993 | pmid = 8298971 | doi=10.1016/0006-8993(93)90330-P| s2cid = 29549067 }}</ref>

==See also==
* [[Chemistry:ZK-93423|ZK-93423]]

==References==
<references/>

{{GABAergics}}

[[Category:Anxiogenics]]
[[Category:GABAA receptor negative allosteric modulators]]
[[Category:Nootropics]]
[[Category:Phenol ethers]]
[[Category:Carboxylate esters]]
[[Category:Ethyl esters]]
[[Category:Isopropyl compounds]]



{{Sourceattribution|ZK-93426}}