Harmalan , CAS No.525-41-7

CAS: 525-41-7 Cat. No.: H668099 Formula: C₁₂H₁₂N₂ Molecular Weight: 184.24 EC Number: 833-620-2 PubChem CID: 160510

Synonyms

Harmalan|1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole|1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole|1-Methyl-4,9-dihydro-3H-beta-carboline|1-Methyl-3,4-dihydro-beta-carboline|1-methyl-3H,4H,9H-pyrido[3,4-b]indole|Dihydroharman|harman e|3,4-dihydroharman|1-Methyl-3,4-dihydro-2H-.beta.-carboline|3,4-Dihydro-1-methyl-2H-Pyrido[3,4-b]indole|4,9-Dihydro-1-methyl-3H-Pyrido(3,4-b)indole|2H-Pyrido[3,4-b]indole, 3,4-dihydro-1-methyl-|3H-Pyrido(3,4-b)indole, 4,9-dihydro-1-methyl-|4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indole, 9CI

Storage

Room temperature

Specifications

Synonyms

Harmalan | 1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole | 1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole | 1-Methyl-4,9-dihydro-3H-beta-carboline | 1-Methyl-3,4-dihydro-beta-carboline | 1-methyl-3H,4H,9H-pyrido[3,4-b]indole | Dihydroharman | harman e | 3,4-dihydroharman | 1-Methyl-3,4-dihydro-2H-.beta.-carboline | 3,4-Dihydro-1-methyl-2H-Pyri Show more

Storage

Room temperature

Product Properties

ALogP

2.1

Names and Identifiers

Canonical Smiles

CC1=NCCC2=C1NC3=CC=CC=C23

IUPAC Name

1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole

InChIKey

CWOYLIJQLSNRRN-UHFFFAOYSA-N

INCHI

1S/C12H12N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-5,14H,6-7H2,1H3

Isomeric SMILES

CC1=NCCC2=C1NC3=CC=CC=C23

PubChem CID

160510

Molecular Weight

184.24

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Harmala alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Harmala alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Harmala alkaloids
• Alternative Parents: Beta carbolines 3-alkylindoles Benzenoids Pyrroles Heteroaromatic compounds Ketimines Propargyl-type 1,3-dipolar organic compounds Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Harman - Beta-carboline - Pyridoindole - 3-alkylindole - Indole - Indole or derivatives - Benzenoid - Heteroaromatic compound - Pyrrole - Ketimine - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organoheterocyclic compound - Azacycle - Hydrocarbon derivative - Organonitrogen compound - Organic nitrogen compound - Imine - Organopnictogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as harmala alkaloids. These are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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NISCH Tclin Nischarin (2 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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HTR5A Tchem Serotonin 5a (5-HT5a) receptor (1433 Activities)

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HTR6 Tchem Serotonin 6 (5-HT6) receptor (9749 Activities)

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NISCH Tclin Nischarin (304 Activities)

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PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)

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H9 (1832 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)

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RAN Tchem GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 (21853 Activities)

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Associated Targets(non-human)

Htr7 Serotonin 7 (5-HT7) receptor (19 Activities)

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ampC Beta-lactamase AmpC (62480 Activities)

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Plasmodium falciparum (966862 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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FM3A (1296 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Gabrp GABA-A receptor; anion channel (5731 Activities)

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Chrm1 Muscarinic acetylcholine receptor (3770 Activities)

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clpP ATP-dependent Clp protease proteolytic subunit (245 Activities)

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Drd5 Dopamine receptor (1304 Activities)

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Htr3a Serotonin 3 (5-HT3) receptor (1834 Activities)

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Grm5 Metabotropic glutamate receptor (9 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 184.240 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 184.1 Da
• Monoisotopic Mass: 184.1 Da
• Topological Polar Surface Area: 28.200 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 259.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

There are no assay application protocols supplied in the Product Data for this item.

General handling for stock solution preparation (guidance; not product‑specific)

• Prepare a concentrated stock in DMSO (e.g., 10–50 mM) or methanol.
• Filter through a 0.2 µm PTFE syringe filter if particulate is observed.
• For biological assays, dilute into buffer to a final organic content ≤1% v/v; include vehicle controls.
• Protect from strong light during preparation and use to minimize photodegradation of the heteroaromatic chromophore.

Analytical method development tips (general)

• LC–UV/FLD: exploit UV absorption (near‑UV) or intrinsic fluorescence; perform wavelength/excitation–emission scans to optimize sensitivity.
• LC–MS: positive ESI typically gives strong [M+H]+ for β‑carbolines; add 0.1% formic acid to mobile phase to enhance ionization. Validate retention with a CAS‑matched reference.

Biological Roles

General literature context for β‑carbolines like Harmalan (not product‑specific, no clinical claims)

• Natural product lineage: β‑Carbolines occur in plants and animals as tryptophan/tryptamine‑derived alkaloids. They often function as secondary metabolites with roles in chemical defense and signaling.
• Enzymatic interactions: many β‑carbolines interact with oxidoreductases and neurotransmitter‑related proteins in vitro. Notably, several congeners modulate monoamine oxidase (MAO) activity in biochemical assays (literature). The extent and direction (inhibition/activation) depend on oxidation state and substitution.
• Photophysics: strong UV absorption and environment‑sensitive fluorescence enable use as intrinsic fluorophores in binding/uptake studies and as reporters of microenvironment polarity and protonation.
• Redox/ROS: some β‑carbolines undergo photoinduced electron transfer and can generate reactive intermediates under irradiation (literature), which is relevant to photobiology assays but warrants careful control of light exposure.
• Transport/metabolism: protonatable nitrogen(s) confer pH‑dependent membrane permeability; in metabolic studies, oxidative dealkylation, aromatic hydroxylation, and N‑oxidation are common biotransformations (literature).

Note

• Specific biochemical potency, off‑targets, or ADME parameters for this exact catalog item are not provided in the Product Data. For any in vitro use, determine activity empirically under your assay conditions and consult primary literature for the exact CAS‑matched compound.

Buffer Applications

Not typically applicable. Harmalan is a small‑molecule heteroaromatic, not a buffering reagent. It does not define a conventional buffer system.

Practical guidance (general)

• Stock preparation for assays: dissolve in DMSO or ethanol to prepare a concentrated stock; dilute into biological buffers (e.g., PBS, HEPES, Tris) keeping final organic cosolvent ≤1% v/v to minimize assay perturbation.
• pH considerations: solubility can increase under mildly acidic conditions due to protonation of ring nitrogen(s); if aqueous dosing is needed, dissolve first in minimal DMSO, then titrate into buffer, or prepare a dilute acid solution (e.g., 0.1 N HCl) and neutralize after dilution if compatible with the assay.

No recipe‑style buffer formulations are provided for this item.

Green Alternatives

Assessment context: This section discusses greener choices for solvents and processes used with β‑carbolines like Harmalan; it does not change the identity of the compound itself.

Greener solvent choices (general guidance)

• Replace DMF/DMAc with safer polar aprotics when feasible:
  • 2‑MeTHF or CPME for extractions and some reactions (reduced toxicity, bio‑based 2‑MeTHF).
  • Propylene carbonate or Cyrene (dihydrolevoglucosenone) as high‑bp polar aprotics for certain substitutions (tradeoff: viscosity, solute solubility).
• Alcohols over chlorinated solvents:
  • Use EtOH/i‑PrOH for recrystallization or workup in place of CH2Cl2/CHCl3 where solubility permits.
• Aqueous media and micellar catalysis:
  • For cross‑couplings on halogenated β‑carbolines, consider aqueous micellar systems (e.g., TPGS‑750‑M) to reduce organic solvent use.

Small comparison (typical; not product‑specific)

• DMF vs Cyrene: similar polarity and solvating power; Cyrene is biodegradable but more viscous and may require temperature elevation.
• CH2Cl2 vs 2‑MeTHF: 2‑MeTHF is less toxic and from renewable feedstocks; however, it has peroxide‑forming risk and different polarity, affecting separations.

Process considerations

• Minimize light/air exposure to reduce degradation and waste.
• Employ catalytic over stoichiometric oxidants/reductants where possible (e.g., catalytic DDQ alternatives, hydrogenation over transfer hydrogenation with safer donors).

Always validate reaction performance and impurity profiles when implementing greener substitutions.

Pharmaceutical Uses

Scope of use

• For research use only (per Product Data). Not for human or veterinary use.

Formulation/analytical roles (general; not product‑specific)

• Reference standard: β‑Carbolines are frequently used as system suitability standards or reference markers in natural product QC, impurity profiling, and LC–MS method validation.
• Impurity/isomer tracking: where β‑carboline congeners are present in botanical extracts, defined standards support identity/purity testing per pharmacopeial general chapters (e.g., chromatography, spectroscopy). This listing does not claim pharmacopeial compliance.
• Excipient status: none. This compound is not described as an excipient.

Regulatory note

• No pharmacopeial monograph, lot‑specific residual solvents, or elemental impurity limits are provided in the Product Data; consult the CoA if your workflow requires these details.

Formulation considerations

• Prepare analytical stocks in MeOH, ACN, or DMSO for LC–UV/LC–MS; protect from strong light to maintain integrity of chromophore. Use amber vials when possible.

Physical Properties

Item-specific (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Literature/General (for β‑carboline/“harmalan”-type scaffolds; not product specifications)

• Physical state: typically crystalline solids for neutral/aromatic β‑carbolines; partially reduced tetrahydro analogs can also be low-melting solids.
• Solubility: many β‑carbolines show limited solubility in water at neutral pH but dissolve in polar organics (DMSO, DMF, MeOH, EtOH) and in dilute aqueous acid due to protonation of the ring nitrogen(s).
• Ionization: basic ring nitrogen (pKb corresponds to conjugate acid pKa commonly in the ~6–9 range for related β‑carbolines; literature) leading to pH‑dependent solubility.
• Partitioning: planar aromatic cores often exhibit moderate hydrophobicity (positive logP; literature) balanced by a ring nitrogen that can be protonated.
• Spectroscopy: strong UV absorption typical of indole/β‑carboline chromophores with multiple bands in the near‑UV (literature). Fluorescence is commonly observed, sensitive to protonation state and substitution (literature).

Not provided for this specific item

• Melting point, boiling point, density, refractive index, water/peroxide/metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Quality & Grades

Item-specific (from Product Data)

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting grade (general; not product‑specific)

• Research‑grade small molecules are typically suited for discovery chemistry, in vitro assays, and method development. When “HPLC grade” or “LC–MS grade” is indicated for solvents/standards, this typically refers to low UV background and low non‑volatile residue suitable for trace analysis; for solids like β‑carbolines, a stated chemical purity (e.g., ≥98%) is common.
• CoA indicators to review for heteroaromatics: assay/purity by HPLC or qNMR; identity by 1H NMR/HRMS; residual solvents; water (KF); and limits on related substances/isomers.
• UV/fluorescence background: due to strong chromophores, low‑level fluorescent impurities may influence bioassays/spectroscopy—CoA chromatograms and impurity profiling are useful.

Recommendation

• Request the current CoA to confirm assay, spectral identity, residual solvent content, and any stabilizer or salt form information prior to regulated or quantitative applications.

Reaction & Applications

Scope for β‑carboline scaffolds such as Harmalan (general/literature; not item‑specific)

• Scaffold role: β‑carbolines serve as privileged cores in heterocyclic chemistry, enabling derivatization at the C‑1, C‑3, and C‑9 positions and at ring nitrogen(s).
• Named reactions and strategies:
  • Pictet–Spengler cyclization: assembly of tetrahydro‑β‑carbolines from tryptamine derivatives and carbonyl partners; subsequent oxidation affords aromatic β‑carbolines (e.g., harman‑type).
  • Electrophilic substitution on the indole ring (e.g., Vilsmeier–Haack formylation, halogenation at activated positions) followed by cross‑coupling (Suzuki, Buchwald–Hartwig) for diversification.
  • N‑alkylation/acylation: quaternization or selective N‑functionalization to tune basicity and solubility.
  • Oxidation/reduction: control over ring saturation state (tetrahydro ↔ dihydro ↔ fully aromatic) to access libraries of analogs.
• Applications in research workflows:
  • Chemical biology probes: fluorescent β‑carboline cores for binding/uptake studies (intrinsic fluorescence; literature).
  • Reference standards: used to benchmark extraction, LC–MS method development, and impurity profiling in natural product studies.
  • SAR studies: systematic substitution on the β‑carboline core to modulate electronics and binding to enzyme/receptor targets in biochemical assays.

Practical tips

• Sensitivity to strong oxidants and light suggests handling under subdued light and inert atmosphere for extended reactions.
• For N‑alkylations, moderate bases (K2CO3, Cs2CO3) in polar aprotics reduce over‑alkylation.
• For cross‑couplings, pre‑install aryl halides via regioselective halogenation; Pd(0) catalysts with dialkylbiaryl phosphines often outperform standard systems on indole‑like substrates.

Reaction Conditions

General literature conditions for transformations on β‑carboline scaffolds (not product‑specific; typical examples)

• Pictet–Spengler cyclization (to tetrahydro‑β‑carbolines):
  • Conditions: tryptamine + aldehyde/ketone, Brønsted/Lewis acid (TFA, HCl, BF3·Et2O) in toluene, MeOH, or AcOH, 0–60 °C, 1–24 h.
  • Notes: control diastereoselectivity with chiral acids/catalysts; subsequent oxidation affords aromatic cores.
• Aromatization/oxidation:
  • DDQ (1–2 eq) in toluene/CH2Cl2 at rt–reflux; or MnO2 in CH2Cl2/THF; or Pd/C (5–10 wt%) with air/O2 in EtOH under reflux.
  • Caution: over‑oxidation can occur; monitor by TLC/LC–MS.
• N‑alkylation:
  • Base (K2CO3, Cs2CO3) in DMF/MeCN, RX (1.2–2.0 eq), rt–60 °C, 2–16 h.
  • For selective quaternization, use more reactive alkyl halides (MeI) and polar aprotic solvents.
• Electrophilic halogenation (for cross‑coupling handles):
  • NBS/NCS (1.0–1.2 eq) in DMF/AcOH at 0–25 °C to target activated positions; regioselectivity must be verified.
• Cross‑coupling (on aryl halides):
  • Suzuki–Miyaura: Pd(dppf)Cl2 (1–3 mol%), K2CO3, dioxane/H2O 80–100 °C, 4–16 h.
  • Buchwald–Hartwig amination: Pd2(dba)3 (1–2 mol%), BrettPhos ligand, NaOtBu, toluene 80–110 °C.

Yields vary widely with substitution/oxidation state; consult primary literature for the exact CAS‑matched “Harmalan” derivative.

Safety & Handling

Item-specific (from Product Data)

• Storage conditions: Room temperature.
• GHS classification, signal word, pictograms, H‑statements: Not specified for this item; refer to SDS.

General safety guidance for β‑carboline alkaloids (literature/typical; not product‑specific)

• Hazards: many β‑carbolines are bioactive heteroaromatics; avoid inhalation, ingestion, and skin contact. Treat as harmful if swallowed and irritating to eyes/skin. Some members may affect the central nervous system or enzyme activity in vitro.
• PPE: lab coat, safety glasses, and appropriate chemical‑resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation.
• Incompatibilities: strong oxidizers (may over‑oxidize the heteroaromatic core), strong bases/acids can alter protonation state and solubility; photosensitivity possible for aromatic chromophores—store protected from intense light.
• First aid (overview): if inhaled—move to fresh air; if on skin—wash with soap/water; if in eyes—rinse cautiously for several minutes; if ingested—rinse mouth. Seek medical attention if symptoms occur. Always defer to the SDS for authoritative instructions.
• Waste: collect organic‑nitrogen heteroaromatic waste in halogen‑free organic waste streams unless your local procedures specify otherwise.

Note: Always consult the product SDS and institutional EHS guidance for definitive hazard and handling procedures.

Solvent Selection

Applicability: Harmalan is a heteroaromatic/indole‑derived small molecule. Solvent choice primarily impacts dissolution for weighing/stock solutions and governs reactivity in synthesis.

General solubility/miscibility guidance (literature/typical for β‑carbolines)

• Preferred stock solvents: DMSO (excellent), DMF, methanol, ethanol, acetonitrile.
• Aqueous systems: poor water solubility at neutral pH; solubility increases under mildly acidic conditions (e.g., dilute HCl) via protonation of ring nitrogen(s).
• Nonpolar solvents: limited solubility in hexanes; moderate in chlorinated solvents (CH2Cl2, CHCl3) depending on substitution/oxidation state.

Selection considerations

• Bioassays: prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into assay buffer to ≤1% DMSO final to avoid cosolvent artifacts.
• Spectroscopy/analytical: methanol, acetonitrile, or buffered aqueous mixtures for HPLC/UV; verify retention and fluorescence to avoid detector saturation.
• Synthesis: polar aprotic solvents (DMF/DMAc/DMSO) favor nucleophilic substitutions or cross‑couplings on the aryl ring; protic alcohols support Pictet–Spengler/acid‑catalyzed steps when building β‑carbolines.

Non‑product‑specific comparison (typical)

• DMSO: highest solvating power; high bp, hygroscopic.
• MeOH/EtOH: volatile, assay‑friendly; may participate in acid‑catalyzed steps.
• MeCN: LC‑MS compatible; lower proticity.

Note: Verify solubility and stability for this specific lot using small‑scale trials; consult CoA for any salt form that may alter solvent choice.

Storage & Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature.

Additional guidance (general; not product‑specific)

• Protection: store in a dry, well‑closed container, protected from strong light. Desiccation recommended to limit moisture uptake and potential hydrolysis/oxidation.
• Stock solutions: prepare aliquots in dry DMSO, MeOH, or ACN; store in amber vials. For sensitive β‑carbolines, refrigeration (2–8 °C) of solutions can improve stability, though the solid is listed as room‑temperature stable.
• Freeze–thaw: avoid repeated freeze–thaw of solutions; aliquot to single‑use vials.
• Reconstitution: if the material is poorly soluble at neutral pH, dissolve first in a minimal volume of DMSO or methanol, or in dilute acid (e.g., 0.1 N HCl), then dilute with the desired solvent or buffer.

Not specified for this item

• Exact solvent recommendation, stability window after opening, and solution shelf life: Not specified for this item; refer to CoA/Spec Sheet.

Structure & Identity

Item-specific (from Product Data)

• Product name: Harmalan (SKU: H668099)
• CAS: 525-41-7
• InChIKey: 55610 (as provided in listing)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/General information for “Harmalan” (CAS 525-41-7)

• Compound class: beta‑carboline alkaloid (indole-fused pyridine framework).
• Core structural features: bicyclic indole (benzopyrrole) fused to a pyridine/tetrahydropyridine ring (β‑carboline scaffold). Some members of this name family are partially reduced (“dihydro” or “tetrahydro”) variants of the fully aromatic β‑carboline (harman) core and may be N‑methylated at the ring junction nitrogen.
• 2D structure description: an indole ring (benzene fused to a five-membered pyrrole bearing a 2-position side annulation) fused along the 2,3-positions to a six‑membered aza ring. Substitution patterns (e.g., N‑methyl, O‑methoxy) vary among β‑carbolines and determine oxidation state and electronics.

Notes

• Exact stereochemistry or substitution pattern for this specific catalog item is not provided in the Product Data; consult the CoA/SDS for the definitive structural identifiers of the supplied material.

Synthetic Utility

General synthetic value of β‑carbolines (applies to Harmalan scaffold; literature, not product‑specific)

• Privileged heterocycle: the β‑carboline core enables rapid SAR through modular modifications at multiple positions (C‑1, C‑3, C‑9) and at the ring nitrogen(s).
• Functional group handles:
  • Indole C‑3 reactivity: electrophilic substitutions (acylation/formylation), radical additions, and cross‑couplings after halogenation.
  • Ring nitrogen: controllable basicity; N‑alkylation/acylation to tune solubility and binding.
  • Oxidation state editing: hydrogenation/dehydrogenation between tetrahydro/dihydro/aromatic states to adjust planarity and electronics.
• Convergent routes:
  • Pictet–Spengler assembly from tryptamine + aldehyde/ketone → tetrahydro‑β‑carboline; oxidation (e.g., DDQ, MnO2, Pd/C–air) to aromatic β‑carboline.
  • Fischer indolization on suitable precursors followed by annulation strategies.
• Late‑stage diversification: C–H activation/functionalization on the indole or pyridine ring using Pd/Ir/Ru catalysis for rapid library generation.
• Utility in materials/photophysics: intrinsic fluorescence can be leveraged for tagging or as internal standards in reaction monitoring (literature).

Practical notes

• Protect the indole NH (if present) when harsh conditions are used; Boc or SEM protections are common.
• Control regioselectivity via directing groups or electronics before cross‑coupling to avoid mixtures of positional isomers.

Target Specificity

Not applicable to this product type. Harmalan is a small molecule, not an antibody or affinity reagent. No antigen/epitope/clone/isotype information is relevant.

Product Data provides no target-binding specificity metrics; any biochemical interactions discussed elsewhere are general literature context for β‑carbolines and not validated for this specific catalog item.