GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.
This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
External Descriptors
Not available
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
202.300 g/mol
XLogP3
2.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
3
Exact Mass
202.147 Da
Monoisotopic Mass
202.147 Da
Topological Polar Surface Area
31.000 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
203.000
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
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Application Protocols
No manufacturer-tested biological assay protocols are specified for this item.
General laboratory preparation tips (research use)
Stock solutions: Prepare 10–100 mM stocks in DMSO or ethanol; filter (0.22 µm PTFE) if particulate is present. Record exact concentration by weight/volume.
Aqueous use: If needed in aqueous buffers, convert to a salt (e.g., HCl) or add as DMSO/EtOH cosolvent stock; confirm absence of precipitation upon dilution.
Analytical QC: Verify identity/purity by LC–MS and HPLC prior to screening. Set UV detection around 220–230 nm and ~280 nm to leverage the indole chromophore.
If you require validated protocols (e.g., binding, enzymatic inhibition formats), please contact us; none are provided or claimed for this SKU.
Biological Roles
General biochemical context (literature; no clinical claims)
Structural class: Tryptamines are indole-containing alkylamines structurally related to endogenous metabolites derived from L-tryptophan (e.g., tryptamine, serotonin). N-alkylation modulates basicity, lipophilicity, and receptor-binding profiles.
Research use: N-1-isopropyltryptamine is commonly included in discovery libraries exploring amine-recognizing biomolecular targets (e.g., GPCRs, transporters, and enzymes) in vitro. Substituent sterics at nitrogen (isopropyl vs methyl/ethyl) influence binding and selectivity across target panels, making it a useful SAR node.
Physicochemical drivers: The secondary amine can be protonated at physiological pH, promoting interactions with acidic residues in protein binding sites; the indole ring participates in π–π stacking and hydrogen bonding via the indole NH as a donor.
ADME-relevant properties (qualitative): Increased hydrophobicity from the isopropyl group generally enhances membrane permeability of the free base, while salt forms improve aqueous handling for biochemical assays. Protein binding and metabolic dealkylation pathways (e.g., N-dealkylation, indole oxidation) are typical considerations in probe design (literature trends).
Important note: The above describes general biochemical behavior of N-alkyl tryptamines in research settings. This product is provided strictly for laboratory research use only and is not intended for human or veterinary use.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare biochemical buffer systems.
Practical note: As a secondary amine, it can be protonated to form water-soluble salts (e.g., hydrochloride) for aqueous handling in assays, but it does not provide defined buffering capacity across a controlled pH range like Tris, HEPES, or phosphate.
Recommendation: For buffer preparation, select established buffering agents suited to your target pH. Use this compound as an analyte/substrate/ligand dissolved in the buffer system of choice (often with a co-solvent such as DMSO or ethanol if solubility requires).
Green Alternatives
While N-1-isopropyltryptamine is a substrate/intermediate rather than a solvent, greener choices can be made for its handling, purification, and transformations.
DCM/chloroform → Ethyl acetate, 2-MeTHF, cyclopentyl methyl ether (CPME) for extractions and medium-polarity reactions. These offer lower toxicity and improved sustainability profiles.
Polar aprotic replacements:
DMF/DMAc/NMP → Acetonitrile, propylene carbonate, ethyl lactate, or dimethyl carbonate when compatible with the reaction.
Nonpolar media:
Toluene → p-Cymene or anisole in some electrophilic substitutions on indoles.
Process considerations
Avoid excess nitrosating conditions to mitigate N-nitrosamine risk with secondary amines; use in situ quench strategies and verify absence of nitrosating contaminants in reagents.
Use catalytic hydrogenation or transfer hydrogenation (e.g., HCO2NH4) instead of stoichiometric hydrides when conducting reductive amination, provided selectivity is maintained.
Employ solid-supported acids/bases for Pictet–Spengler or acylation steps to ease separation and reduce aqueous waste.
Purification: Prefer recrystallization of salts (e.g., HCl, fumarate) over extensive silica chromatography; choose greener eluents (heptane/EtOAc or 2-MeTHF/EtOAc).
Trade-offs
Solubility/selectivity may differ in greener solvents; small-scale scouting is recommended.
Some green solvents retain water; dry appropriately if moisture-sensitive steps are planned.
Pharmaceutical Uses
Formulation/CMC context (general; no therapeutic claims)
Role: This material is part of a discovery screening library (Moligand™) and is not an approved excipient or active pharmaceutical ingredient.
Pharmacopeial status: No monograph is indicated. Any compendial compliance (USP/EP/JP) is not specified for this item; refer to CoA/Spec Sheet if needed.
Potential formulation-relevant considerations in research
Salt selection: Converting the free base to a salt (e.g., HCl, mesylate, fumarate) can enhance aqueous solubility and crystallinity, aiding in assay stock preparation and solid-form studies.
Stability: Secondary amines may undergo oxidative degradation; antioxidants, inert atmosphere packaging, or light-protective containers can be considered during formulation studies (research scale).
Vehicle choices for in vitro use: DMSO or ethanol stock solutions with subsequent dilution into buffered media are common; verify absence of precipitation and keep final organic cosolvent fraction low (e.g., ≤1–2%).
Regulatory disclaimer
Supplied strictly for research use only. Not for use in humans or in diagnostic procedures. For any translational work, appropriate toxicology and regulatory pathways would be required.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values for the free base (for context only; not product specifications)
Physical state: Often encountered as an oil or low-melting solid for the free base; crystalline salts (e.g., HCl) are common (literature).
Basicity: Secondary amine pKaH typically ~9–11 for dialkyltryptamines; indole NH is much less basic/weakly acidic (pKa ~16–17 in DMSO) (literature).
Lipophilicity: logP for N-alkyl tryptamines commonly in the 1.5–3 range; N-isopropyl substitution tends to increase logP vs tryptamine (literature trend).
UV characteristics: Indole chromophore; strong absorbance near 220–230 nm and 270–290 nm (ε high), useful for UV detection in HPLC (literature).
Solubility profile (qualitative, literature):
Free base: Soluble in many organic solvents (DCM, chloroform, EtOAc, MeOH, EtOH, acetone, acetonitrile). Limited solubility in water.
Protonated salts (e.g., HCl): Freely soluble in water, alcohols; lower solubility in nonpolar solvents.
Volatility/thermal behavior: Tertiary/secondary tryptamines may darken on prolonged exposure to air/light due to oxidation/polymerization pathways (literature observation).
Practical note: For precise BP/MP, density, refractive index, and UV cutoff of this specific lot, consult the CoA/Spec Sheet; they are not specified for this item.
Quality and Grades
Item-specific grade: Moligand™
Description: Moligand™ designates Aladdin’s small-molecule screening collection suitable for discovery chemistry, chemical biology, and ligand-profiling workflows. Compounds in this line are curated for structural diversity and functional-group coverage to support SAR and target-profiling studies.
Implication for users: Material is intended for research use, including assay development, hit-finding, fragment/add-on screening, and probe synthesis. It is not intended for clinical or diagnostic use.
Purity/assay
Specific purity percentage, residual solvents, and elemental limits: Not specified for this item; refer to CoA/Spec Sheet.
Typical analytical controls for Moligand™ line (general): Identity confirmation by NMR/MS, and purity by HPLC/UPLC or GC where applicable (literature/generic program description). Exact release tests for this SKU should be verified on the CoA.
Stabilizers/additives
Any stabilizers or inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Documentation and traceability
Recommended: Request and review the batch CoA and, where available, analytical spectra (1H/13C NMR, MS, HPLC trace). These documents provide the definitive specifications for the lot shipped.
Suitability notes
Moligand™ compounds are typically supplied to support medicinal chemistry and screening; if you require specialized grades (e.g., anhydrous, low-peroxide, LC/MS-grade), inquire about custom preparation to align with your analytical or synthetic constraints.
Reaction and Applications
This compound is a functionalized indole (tryptamine) bearing a secondary amine, making it a versatile substrate, intermediate, or ligand in discovery chemistry and probe synthesis.
Representative application areas (research use)
Chemical biology and screening: Member of small-molecule libraries probing amine-binding proteins, GPCR-ligand recognition, transporter interactions, or enzyme active sites (general context; no clinical claims).
Derivatization platform: Amenable to acylation, sulfonylation, carbamate formation, and quaternization to access cationic probes or handle-tagged derivatives (e.g., biotinylation via linkers).
Electrophilic substitution: Indole C-3 is normally the most nucleophilic position; here it is substituted by the side chain, steering substitution to C-2 under certain conditions (e.g., directed lithiation with s-BuLi/TMP bases at low temperature).
Pictet–Spengler cyclization: With aldehydes or ketones under acidic conditions to form tetrahydro-β-carbolines; N-isopropyl substitution can influence rate and diastereoselectivity.
Reductive amination/N-derivatization: Secondary amine allows formation of tertiary analogs via reductive amination (NaBH3CN/BH(OAc)3) or alkyl halide alkylation (careful to avoid overalkylation).
Amide/sulfonamide synthesis: With acyl/sulfonyl chlorides in the presence of base (e.g., Et3N/DIPEA) to tune basicity and solubility.
Practical tips
Protecting groups: Indole NH can be protected (Boc, SEM) to modulate reactivity and improve chromatographic behavior.
Workup strategy: Toggle between free base and protonated salt to simplify separations and crystallization.
Analysis: Monitor by LC–MS using ESI+; indole UV absorbance at 220–230 and ~280 nm provides sensitive detection.
Reaction Conditions
General conditions reported in the literature for related tryptamine chemistry (for guidance only; not specifications for this item)
Reductive amination to form tertiary amines
Solvent: MeOH, EtOH, or MeCN
Carbonyl partner: aldehyde or ketone (1.0–1.5 equiv)
Reductant: NaBH3CN (pH 6–7 with AcOH) or NaBH(OAc)3 (AcOH, DCE/MeCN)
Temperature/time: 0–25°C, 2–16 h
Notes: Control stoichiometry to avoid bis-alkylation; monitor by LC–MS (ESI+).
Acylation/sulfonylation (to amides/sulfonamides)
Base: Et3N or DIPEA (2–3 equiv)
Electrophile: acyl chloride, anhydride, or sulfonyl chloride (1.1–1.5 equiv)
Solvent: DCM, THF, or MeCN
Temperature: 0°C to rt; 1–4 h
Notes: Protect indole NH (Boc/SEM) if competitive acylation is observed.
Solvent: DCM, MeOH, or toluene; sometimes aqueous media
Temperature: 0–50°C; 2–24 h
Notes: N-substituent sterics (isopropyl) can affect rate; chiral acids may induce asymmetry.
C-2 functionalization via directed lithiation
Base: s-BuLi or LDA with TMP-type directing conditions
Solvent: THF
Temperature: −78 to −40°C; minutes to 1 h, then electrophile quench
Notes: Protect indole NH to improve regioselectivity and stability.
Workup/purification
Toggle salt/free-base forms to aid separations; recrystallize salts or purify by silica gel using heptane/EtOAc or DCM/MeOH gradients.
All conditions should be scouted on small scale and optimized for this specific substrate.
Safety and Handling
GHS information (item-specific)
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations for indole alkylamines (literature/good practice)
Hazards: Secondary amines can be irritants to skin, eyes, and mucosa. Indole derivatives may be harmful if swallowed or inhaled. Avoid dust/aerosol generation; handle in a fume hood.
PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). For scale-up or aerosol risk, use splash goggles and respiratory protection per institutional SOPs.
Incompatibilities: Strong oxidizers, nitrosating agents (amines can form N-nitrosamines), acylating and sulfonylating reagents without control, and strong acids/bases that may cause exothermic neutralization.
Stability: Protect from prolonged exposure to air, light, and elevated temperature to minimize oxidative discoloration. Store tightly closed; purge headspace with inert gas if long-term storage is anticipated.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
Ingestion: Rinse mouth; seek medical advice. Do not induce vomiting unless directed by medical personnel.
Spill response: Absorb with inert material, collect for disposal. Prevent entry into drains. Decontaminate area with suitable solvent/detergent.
Always consult the product SDS for authoritative and complete safety guidance.
Solvent Selection
Compound class considerations (secondary amine, indole)
Polarity/ionization: The free base is moderately lipophilic and neutral; the conjugate acid (as HCl or other salts) is cationic and water-soluble. Choice of solvent depends strongly on protonation state.
Practical solvent choices (general guidance)
Free base handling and synthesis: DCM, chloroform, THF, EtOAc, acetone, acetonitrile, methanol, ethanol. These provide good solubility for chromatographic loading or reaction media.
Analytical HPLC: Reversed-phase with water/acetonitrile or water/methanol (0.1% formic acid or ammonium formate can improve peak shape by suppressing secondary amine tailing).
Aqueous workup: Convert to a water-soluble ammonium salt by adding dilute HCl; back-extract to the free base with NaHCO3/Na2CO3 and an immiscible organic solvent (e.g., DCM or MTBE) as needed.
Comparison and tips
Alcohols (MeOH/EtOH) vs aprotic (ACN/THF): Alcohols can facilitate salt formation and may participate in hydrogen bonding, occasionally affecting reaction selectivity; ACN/THF are frequently preferred for base-sensitive steps.
Nonpolar solvents (toluene/hexanes): Limited solubility for the free base unless warmed; more suitable when the compound is converted to a less polar derivative.
Greener alternatives: Where feasible, replace DCM with EtOAc or 2-MeTHF; replace DMF/DMAc with MeCN or propylene carbonate for certain transformations (see Green Alternatives tab).
Drying: For moisture-sensitive reactions, thoroughly dry solvents and glassware; amines can absorb CO2 to form carbamates, which can affect stoichiometry in highly basic, anhydrous media.
Storage and Reconstitution
Item-specific storage
Storage Conditions: Room temperature (as provided in Product Data).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling and stability guidance (literature/practice)
Container: Store in a tightly closed, chemically compatible container. For extended storage, consider amber vials to limit light exposure. Optionally blanket with inert gas to mitigate oxidative discoloration.
Environment: Dry, well-ventilated area away from strong oxidizers and nitrosating agents.
Reconstitution/preparation
Solid or neat oil: If provided as a solid or viscous oil, warm gently to room temperature to ensure homogeneity before sampling. For analytical or biological assays, prepare concentrated stocks in dry DMSO or ethanol (e.g., 10–100 mM).
Aqueous solutions: Prepare as a water-soluble salt (e.g., HCl) for aqueous applications, or dilute organic stocks into buffer while keeping final organic content low (≤1–2%).
Filtration: If needed, sterile-filter through a 0.22 µm PTFE membrane for cell-free assays. Avoid repeated freeze–thaw of solutions; aliquot stocks.
Shelf-life and specifications
Specific shelf-life, water/peroxide/metal limits, and UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Research use notice: For research use only.
Structure and Identity
Brief description: N-1-isopropyltryptamine (often abbreviated iPT) is a secondary tryptamine featuring an indole core and an isopropyl-substituted terminal amine.
Item-specific (from Product Data)
SKU: N611077
Product Name: N-1-isopropyltryptamine
CAS: N611077 (catalog placeholder)
CID: 5115445
InChIKey: 12909 (as provided)
Grade: Moligand™
Storage: Room temperature
Literature identity (general reference; not item specification)
2D description in words: An indole ring bears at its 3-position a two-carbon linker terminating in a secondary amine; that amine is further substituted by an isopropyl group, creating a branched, hydrophobic appendage adjacent to a basic nitrogen.
Notes: Literature identifiers/formula are provided for chemical context only. For definitive identity and release criteria of this catalog item, refer to the product’s CoA/Spec Sheet.
Synthetic Utility
Key functional elements
Secondary aliphatic amine (N–H) with an isopropyl substituent: nucleophilic, readily acylated/sulfonylated; can be oxidized to N-oxide (less common for secondary amines) or converted to tertiary amines.
Indole nucleus: π-rich heteroaromatic with a hydrogen-bond donor (indole NH); electrophilic substitution typically favors C-3, but here C-3 bears the side chain, enabling alternative strategies (C-2 functionalization, N1 functionalization, or benzylic derivatization).
Transformations (literature examples)
Reductive amination on the secondary amine to prepare tertiary analogs; careful stoichiometry limits overalkylation.
Carbamate/amide/sulfonamide libraries via reaction with chloroformates, acyl chlorides, or sulfonyl chlorides (DIPEA/Et3N base), enabling tuning of pKa and permeability.
Pictet–Spengler cyclizations with aldehydes/ketones under Brønsted acid catalysis to access tetrahydro-β-carbolines; diastereocontrol influenced by N-substituent sterics.
Benzylic (side-chain) oxidation or halogenation to access further derivatives; protection of indole NH (Boc/SEM) often improves selectivity.
Directed metalation (e.g., LDA/TMP bases) at C-2 followed by quench with electrophiles to diversify the indole ring when C-3 is blocked.
Retrosynthetic value
Serves as a branch point in SAR campaigns on tryptamine-derived scaffolds; N-substituent variation (iPr → Me, Et, iBu, cyclic amines) and ring substitutions allow systematic mapping of property–activity relationships.
Practical notes
Manage acid–base toggling for isolation: protonate to form crystalline salts for purification, then regenerate the free base as required.
Indole protection reduces streaking on silica and suppresses undesired electrophilic substitution during multi-step sequences.
Target Specificity
Not applicable for this product.
This SKU is a small-molecule chemical and not an antibody, enzyme, or biologic with defined antigen/epitope specificity. No clone, isotype, or species reactivity is relevant.
For biochemical target engagement studies, users may generate their own binding data or profiling results; none are specified for this item.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
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