2506-10-7

Basic information

• Product Name: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole
• Synonyms: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole;1-Methyltetrahydro-b-carboline;tetrahydroharmane;1,2,3,4-Tetrahydroharman;Eleagnine;Methtryptoline;1,2,3,4-Tetrahydroharmane;1H-Pyrido[3,4-B]indole, 2,3,4,9-tetrahydro-1-methyl-
• CAS NO: 2506-10-7
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25296
• EINECS: 219-711-4
• Mol File: 2506-10-7.mol
• Article Data: 59

Chemical Properties

• Melting Point: 179-180 °C
• Boiling Point: 362.6°Cat760mmHg
• Flash Point: 173.1°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 1.91E-05mmHg at 25°C
• Refractive Index: 1.632
• PKA: 17.81±0.40(Predicted)
• CAS DataBase Reference: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole(2506-10-7)
• EPA Substance Registry System: 2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole(2506-10-7)

Safety Data

• Hazardous Substances Data: 2506-10-7(Hazardous Substances Data)

Usage

General Description

2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole, also known as norharmane, is a chemical compound belonging to the indole alkaloid class. It is a derivative of beta-carboline and is commonly found in processed food, tobacco smoke, and coffee. Norharmane has been identified as a potential neurotoxin and has been studied for its role in neurodegenerative diseases such as Parkinson's and Alzheimer's. It interacts with neurotransmitter receptors in the brain and has been shown to have psychoactive effects, including sedative and hallucinogenic properties. Research on norharmane's pharmacological properties is ongoing, and it is being investigated for its potential therapeutic applications in various medical conditions.

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

Upstream product

• 16250-73-0 2,3-dimethyl-1,3-oxalidine 
• 61-54-1 tryptamine 
• 16250-89-8 2-methyl-3-phenyloxazolidine 
• 4894-26-2 3,4-dihydro-β-carboline 
• 917-54-4 methyllithium 
• 75-16-1 methylmagnesium bromide 
• 525-41-7 1-methyl-4,9-dihydro-3H-β-carboline 
• 6543-83-5 1-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-carboxylic acid 
• 116965-61-8 2,9-bis-(trimethylsilyl)-3,4-dihydropyrido<3,4-b>indolium trifluoromethane sulphonate 
• 771-51-7 indole-3-acetonitrile 
• 75-05-8 acetonitrile 
• 64-17-5 ethanol 
• 343-94-2 tryptamine hydochloride 
• 75-07-0 acetaldehyde 

Downstream Products

• 486-84-0 harmane 
• 5159-20-6 1-methyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 525-40-6 (R)-1-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 
• 23844-21-5 (S)-(-)-tetrahydroharman 
• 20069-02-7 (S)-brevicolline 
• 18813-71-3 6-bromo-1-methyl-9H-pyrido[3,4-b]indole 
• 144434-73-1 8-bromo-1-methyl-9H-pyrido[3,4-b]indole 
• 102207-02-3 8-nitro-1-methyl-9H-pyrido[3,4-b]indole 
• 38314-91-9 6-nitro-1-methyl-9H-pyrido[3,4-b]indole 
• 128879-67-4 1-(1-Methyl-3-phenyl-propylamino)-3-(1-methyl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-propan-2-ol 
• 128857-28-3 1-(1-Methyl-2-phenyl-ethylamino)-3-(1-methyl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-propan-2-ol 

Relevant articles and documents

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Formation of tetrahydroharman (1-methyl-1,2,3,4-tetrahydro-beta-carboline) by Helicobacter pylori in the presence of ethanol and tryptamine

Helicobacter pylori contains alcohol dehydrogenase which oxidizes ethanol to acetaldehyde. In the present study, H. pylori cytosol was incubated in a buffered media at pH 6.0 and 7.4 in the presence of ethanol and tryptamine. Under these conditions, tetrahydroharman (1-methyl-tetrahydro-β-carboline) was produced as a condensation product of tryptamine and acetaldehyde. At pH 6.0, 20.60 ± 5.00% of the added tryptamine was converted to tetrahydroharman, while 27.00 ± 4.80% (mean ± SD) was converted at pH 7.4. Similar reactions between acetaldehyde and other dietary amines seem likely. Such biogenic alkaloids, if formed in vivo, might contribute to the dysphoric effects of alcohol.

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Tandem cleavage of hydrogenated β- and γ-carbolines - New practical synthesis of tetrahydroazocino[4,5-b]indoles and tetrahydroazocino[5, 4-b]indoles showing acetylcholinesterase inhibitory activity

Hydrogenated γ-carbolines underwent tandem piperidine ring cleavage on treatment with dimethyl acetylenedicarboxylate (DMAD) or ethyl propiolate (EP) in the presence of alcohols, producing 3-alkoxymethyl-substituted indoles in high yields. These compounds were cyclized to tetrahydroazocino[4,5-b]indoles in the presence of AlCl3. Hydrogenated β-carbolines produced tetrahydroazocino [5,4-b]indoles directly upon treatment with EP in ethanol. The resulting azocinoindole derivatives were subjected to a preliminary evaluation of their in vitro acetylcholinesterase (AChE) inhibitory activities. Most of them were found to inhibit AChE with IC50 values in the micromolar range, compound 17 being the most potent (IC50 = 8.7 μm). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Crossing the Border: From Keto- to Imine Reduction in Short-Chain Dehydrogenases/Reductases

The family of NAD(P)H-dependent short-chain dehydrogenases/reductases (SDRs) comprises numerous biocatalysts capable of C=O or C=C reduction. The highly homologous noroxomaritidine reductase (NR) from Narcissus sp. aff. pseudonarcissus and Zt_SDR from Zephyranthes treatiae, however, are SDRs with an extended imine substrate scope. Comparison with a similar SDR from Asparagus officinalis (Ao_SDR) exhibiting keto-reducing activity, yet negligible imine-reducing capability, and mining the Short-Chain Dehydrogenase/Reductase Engineering Database indicated that NR and Zt_SDR possess a unique active-site composition among SDRs. Adapting the active site of Ao_SDR accordingly improved its imine-reducing capability. By applying the same strategy, an unrelated SDR from Methylobacterium sp. 77 (M77_SDR) with distinct keto-reducing activity was engineered into a promiscuous enzyme with imine-reducing activity, thereby confirming that the ability to reduce imines can be rationally introduced into members of the “classical” SDR enzyme family. Thus, members of the SDR family could be a promising starting point for protein approaches to generate new imine-reducing enzymes.

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.