13100-00-0

Basic information

• Product Name: 2-methyltryptoline
• Synonyms: 2-methyltryptoline;N-METHYL-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE;2-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• CAS NO: 13100-00-0
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25
• Mol File: 13100-00-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 216-217 °C
• Boiling Point: 326.4°Cat760mmHg
• Flash Point: 151.2°C
• Appearance: /
• Density: 1.165g/cm³
• Vapor Pressure: 0.000217mmHg at 25°C
• Refractive Index: 1.66
• PKA: 17.28±0.20(Predicted)
• CAS DataBase Reference: 2-methyltryptoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyltryptoline(13100-00-0)
• EPA Substance Registry System: 2-methyltryptoline(13100-00-0)

Safety Data

• Hazardous Substances Data: 13100-00-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H14N2/c1-14-7-6-10-9-4-2-3-5-11(9)13-12(10)8-14/h2-5,13H,6-8H2,1H3

Upstream product

• 61-49-4 [2-(1H-indol-3-yl)-ethyl]-methylamine 
• 16502-01-5 tetrahydrobetacarboline 
• 214834-26-1 2-formyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 5667-11-8 2-methyl-β-carboline-2-ium iodide 
• 81375-36-2 Toluene-4-sulfonate2-methyl-2-methylamino-2,3,4,9-tetrahydro-1H-β-carbolin-2-ium; 
• 59156-98-8 Strychnocarpine 
• 89759-47-7 methyl 1,3,4,9‐tetrahydro‐2H‐pyrido[3,4‐b]indole‐2‐carboxylate 
• 6250-88-0 4,9-Dihydropyrano<3,4-b>indol-1(3H)-on 
• 112585-34-9 α-Phenyl-hydrazono-δ-valerolacton 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 50-00-0 formaldehyd 
• 1147830-51-0 N-(4-chlorophenyl)sulfonyl-2-ethynylaniline 
• 1296770-70-1 4-(2-azidophenyl)pyridine 
• 1296770-95-0 1-methyl-4-(2-azidophenyl)pyridinium triflate 

Downstream Products

• 81375-36-2 Toluene-4-sulfonate2-methyl-2-methylamino-2,3,4,9-tetrahydro-1H-β-carbolin-2-ium; 
• 82820-65-3 Toluene-4-sulfonate2-ethylamino-2-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-2-ium; 
• 1239034-71-9 4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzoic acid methyl ester 
• 1239034-62-8 N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt 

Relevant articles and documents

Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement

Tetrahydro-β-carboline (THBC) is a tricyclic ring system that can be found in a large number of bioactive alkaloids. Herein, we report a simple and efficient method for the synthesis of enantiopure THBCs through a chiral thiosquaramide (11b) catalyzed imine reduction of dihydro-β-carbolines (17a-f). The in situ generated Pd-H employed as hydride source in the reaction of differently substituted chiral THBCs (18a-f) afforded high selectivities (R isomers, up to 96% ee) and good isolated yields (up to 88%). Moreover, the chiral thiosquaramide used also afforded exceptional catalyst activity in the syntheses of (-)-coerulescine (5) and (-)-horsfiline (6) with excellent enantioselectivities up to 98% and 93% ee, respectively, via an enantioselective oxidative rearrangement approach.

RhII2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides

Approaching all isomers: A range of α-, β- and δ-carbolinium ions are readily available from ortho-substituted aryl azides using a rhodium(II) carboxylate catalyst (see scheme). The carbolinium ions are readily reduced to afford tryptolines or deprotonated to access pyridoindoles. This [RhII2]-catalyzed C-H bond amination was used in the synthesis of (±)-horsfiline and neocryptolepine. esp=α,α,α',α'- tetramethyl-1,3-benzenedipropionate. Copyright

HDAC INHIBITORS AND THERAPEUTIC METHODS USING THE SAME

Histone deacetylases inhibitors (HDACIs) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC provides a benefit, like a cancer, a neurodegenerative disorder, a neurological disease, traumatic brain injury, stroke, malaria, an autoimmune disease, autism, and inflammation, also are disclosed.