1-Ethyl-β-carboline

1-Ethyl-β-carboline.svg skin-invert-image 200px Monoamine oxidase inhibitor (MAOI); Reversible inhibitor of MAO-A (RIMA); Dopamine reuptake inhibitor; Dopamine releasing agent None 20127-61-1 5324325 4481858 K98LP3Z6TC 182548 441986 1-Ethyl-BC; 1-Ethyl-βC; 1-Et-BC; 1-Et-βC; 1-Ethylnorharman; 1-Ethyl-norharmane; 1-Ethyl-9H-β-carboline 1-ethyl-9H-pyrido[3,4-b]indole 13 12 2 CCC1=NC=CC2=C1NC3=CC=CC=C23 1S/C13H12N2/c1-2-11-13-10(7-8-14-11)9-5-3-4-6-12(9)15-13/h3-8,15H,2H2,1H3 YTQRHYCHEIXUIU-UHFFFAOYSA-N 1-Ethyl-β-carboline is an alkaloid of the β-carboline family found in tobacco smoke. Saro G, Johne S, Latino DA, Moine F, van der Toorn M, Mathis C, Veljkovic E Monoamine Oxidase Inhibitors Present in Tobacco Modulate Dopamine Balance Via the Dopamine Transporter ACS Chem Neurosci 16 6 1117–1131 March 2025 40033845 11926787 10.1021/acschemneuro.4c00789 Bamgbose SO, Dramane KL, Okogun JI Synthesis and preliminary pharmacological studies of 1-ethyl-beta-carboline Planta Med 31 2 193–200 February 1977 854548 10.1055/s-0028-1097513 It is the 1-ethyl derivative of β-carboline (norharmane). The drug is an antagonist of serotonin, histamine, acetylcholine, and barium chloride in guinea pig ileum tissue. In addition, it is an antagonist of the effects of catecholamines. 1-Ethyl-β-carboline produces central depression or hypolocomotion and hypotension in rodents. It is a weak reversible inhibitor of monoamine oxidase A (RIMA) (IC50 half-maximal inhibitory concentration = 1,690nM), with similar potency as β-carboline but 28- to 85-fold lower potency than harmaline and harmane (1-methyl-β-carboline). In addition, the drug is a lower-potency dopamine reuptake inhibitor (DRI), with an IC50 half-maximal inhibitory concentration at the dopamine transporter (DAT) of 660nM. It has also been found to induce dopamine release in rat striatal synaptosomes. It has been hypothesized that 1-ethyl-β-carboline might contribute to the rewarding effects of tobacco smoking. The chemical synthesis of 1-ethyl-β-carboline has been described. 1-Ethyl-β-carboline was first described in the scientific literature by 1968. Ho BT, McIsaac WM, Walker KE, Estevez V Inhibitors of monoamine oxidase. Influence of methyl substitution on the inhibitory activity of beta-carbolines J Pharm Sci 57 2 269–274 February 1968 5641670 10.1002/jps.2600570205 See also Substituted β-carboline 1-Ethyl-6-hydroxytryptoline References Category:Alkaloids Category:Beta-Carbolines Category:Dopamine releasing agents Category:Dopamine reuptake inhibitors Category:Ethyl compounds Category:Monoamine oxidase inhibitors Category:Smoking Category:Tobacco