6649-77-0

Basic information

• Product Name: 1-Isobutyl-1,2,3,4-tetrahydro-β-carboline
• Synonyms: 1-Isobutyl-1,2,3,4-tetrahydro-β-carboline;2,3,4,9-Tetrahydro-1-isobutyl-1H-pyrido[3,4-b]indole
• CAS NO: 6649-77-0
• Molecular Formula: C₁₅H₂₀N₂
• Molecular Weight: 228.33
• Mol File: 6649-77-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Isobutyl-1,2,3,4-tetrahydro-β-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Isobutyl-1,2,3,4-tetrahydro-β-carboline(6649-77-0)
• EPA Substance Registry System: 1-Isobutyl-1,2,3,4-tetrahydro-β-carboline(6649-77-0)

Safety Data

• Hazardous Substances Data: 6649-77-0(Hazardous Substances Data)

Upstream product

• 78-77-3 Isobutyl bromide 
• 81535-41-3 (1-Isobutyl-1,2,3,4-tetrahydro-β-carbolin-9-yl)-methanol 
• 128593-36-2 1-isobutyl-4,9-dihydro-3H-β-carboline 
• 16502-01-5 tetrahydrobetacarboline 
• 81535-40-2 1-Isobutyl-9-methoxymethyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 81535-34-4 tert-Butyl-[1-(9-methoxymethyl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-meth-(E)-ylidene]-amine 
• 81535-36-6 tert-Butyl-[1-(1-isobutyl-9-methoxymethyl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-meth-(E)-ylidene]-amine 
• 81535-31-1 2-<(tert-butylimino)methyl>-1,2,3,4-tetrahydro-β-carboline 
• 61-54-1 tryptamine 
• 201230-82-2 carbon monoxide 
• 6335-03-1 2-(2-methyl-allyl)-isoindole-1,3-dione 
• 590-86-3 isovaleraldehyde 
• 343-94-2 tryptamine hydochloride 

Downstream Products

• 335120-82-6 C₂₄H₂₈N₂O 
• 1227626-13-2 benzyl 1-isobutyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate 

Relevant articles and documents

METHOD OF SCREENING FOR AGENTS FOR DIFFERENTIATING STEM CELLS

The present application discloses a method for identifying an agent for the treatment or prevention of cancer or metastatic cancer comprising the steps of contacting stem cell with a potential agent, and identifying an agent that induces differentiation, or inhibits stem cell pluripotency or growth of the stem cell, wherein such agent is determined to be an anti-cancer agent.

Synthesis and Investigation of Tetrahydro-β-carboline Derivatives as Inhibitors of the Breast Cancer Resistance Protein (ABCG2)

The breast cancer resistance protein (ABCG2) transports chemotherapeutic drugs out of cells, which makes it a major player in mediating multidrug resistance (MDR) of cancer cells. To overcome this mechanism, inhibitors of ABCG2 can be used. Only a few potent and selective ABCG2 inhibitors have been discovered, i.e., fumitremorgin C (FTC), Ko143, and the alkaloid harmine, which contain a tetrahydro-β-carboline or β-carboline backbone, respectively. However, toxicity and or instability prevent their use in vivo. Therefore, there is a need for further potent inhibitors. We synthesized and pharmacologically investigated 37 tetrahydro-β-carboline derivatives. The inhibitory activity of two compounds (51, 52) is comparable to that of Ko143, and they are selective for ABCG2 over ABCB1. Furthermore, they are able to reverse the ABCG2-mediated resistance toward SN-38 and inhibit the ATPase activity. The cytotoxicity data show that their inhibitory effect is substantially higher than their toxicity.

Biocatalytic asymmetric formation of tetrahydro-β-carbolines

Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-carbon bond and a new stereogenic center. Strictosidine contains a tetrahydro-β-carboline moiety - an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals. Stereoselective methods to produce tetrahydro-β-carboline enantiomers are greatly valued. We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of simple achiral aldehydes and substituted tryptamines to form highly enantioenriched (ee >98%) tetrahydro-β-carbolines via a Pictet-Spengler reaction. This is the first example of aldehyde substrate promiscuity in the strictosidine synthase family of enzymes and represents a first step toward developing a general biocatalytic strategy to access chiral tetrahydro-β-carbolines.