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1-Ethyl-β-carboline

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1-Ethyl-β-carboline
Clinical data
Other names1-Ethyl-BC; 1-Ethyl-βC; 1-Et-BC; 1-Et-βC; 1-Ethylnorharman; 1-Ethyl-norharmane; 1-Ethyl-9H-β-carboline
Drug classMonoamine oxidase inhibitor (MAOI); Reversible inhibitor of MAO-A (RIMA); Dopamine reuptake inhibitor; Dopamine releasing agent
ATC code
  • None
Identifiers
  • 1-ethyl-9H-pyrido[3,4-b]indole
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H12N2
Molar mass196.253 g·mol−1
3D model (JSmol)
  • CCC1=NC=CC2=C1NC3=CC=CC=C23
  • InChI=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
  • Key:YTQRHYCHEIXUIU-UHFFFAOYSA-N

1-Ethyl-β-carboline is an alkaloid of the β-carboline family found in tobacco smoke.[1][2] It is the 1-ethyl derivative of β-carboline (norharmane).[1][2]

The drug is an antagonist of serotonin, histamine, acetylcholine, and barium chloride in guinea pig ileum tissue.[2] In addition, it is an antagonist of the effects of catecholamines.[2] 1-Ethyl-β-carboline produces central depression or hypolocomotion and hypotension in rodents.[2] It is a weak reversible inhibitor of monoamine oxidase A (RIMA) (IC50Tooltip half-maximal inhibitory concentration = 1,690 nM), with similar potency as β-carboline but 28- to 85-fold lower potency than harmaline and harmane (1-methyl-β-carboline).[1][3] In addition, the drug is a lower-potency dopamine reuptake inhibitor (DRI), with an IC50 at the dopamine transporter (DAT) of 660 nM.[1] It has also been found to induce dopamine release in rat striatal synaptosomes.[1] It has been hypothesized that 1-ethyl-β-carboline might contribute to the rewarding effects of tobacco smoking.[1]

The chemical synthesis of 1-ethyl-β-carboline has been described.[2]

1-Ethyl-β-carboline was first described in the scientific literature by 1968.[3][2][1]

See also

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References

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  1. 1 2 3 4 5 6 7 Saro G, Johne S, Latino DA, Moine F, van der Toorn M, Mathis C, Veljkovic E (March 2025). "Monoamine Oxidase Inhibitors Present in Tobacco Modulate Dopamine Balance Via the Dopamine Transporter". ACS Chem Neurosci. 16 (6): 1117–1131. doi:10.1021/acschemneuro.4c00789. PMC 11926787. PMID 40033845.
  2. 1 2 3 4 5 6 7 Bamgbose SO, Dramane KL, Okogun JI (February 1977). "Synthesis and preliminary pharmacological studies of 1-ethyl-beta-carboline". Planta Med. 31 (2): 193–200. doi:10.1055/s-0028-1097513. PMID 854548.
  3. 1 2 Ho BT, McIsaac WM, Walker KE, Estevez V (February 1968). "Inhibitors of monoamine oxidase. Influence of methyl substitution on the inhibitory activity of beta-carbolines". J Pharm Sci. 57 (2): 269–274. doi:10.1002/jps.2600570205. PMID 5641670.
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1-Ethyl-β-carboline
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