Chemistry:1-Ethyl-β-carboline
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) (IC50 = 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
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Monoamine Oxidase Inhibitors Present in Tobacco Modulate Dopamine Balance Via the Dopamine Transporter". ACS Chem Neurosci 16 (6): 1117–1131. March 2025. doi:10.1021/acschemneuro.4c00789. PMID 40033845.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 "Synthesis and preliminary pharmacological studies of 1-ethyl-beta-carboline". Planta Med 31 (2): 193–200. February 1977. doi:10.1055/s-0028-1097513. PMID 854548.
- ↑ 3.0 3.1 "Inhibitors of monoamine oxidase. Influence of methyl substitution on the inhibitory activity of beta-carbolines". J Pharm Sci 57 (2): 269–274. February 1968. doi:10.1002/jps.2600570205. PMID 5641670.
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