This compound belongs to the class of organic compounds known as n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
327.500 g/mol
XLogP3
4.100
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
7
Exact Mass
327.22 Da
Monoisotopic Mass
327.22 Da
Topological Polar Surface Area
42.200 Ų
Heavy Atom Count
24
Formal Charge
0
Complexity
456.000
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
Lösungsrechner
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Bewertungen
Kundenbewertungen
Application Protocols
No application protocols are provided in the Product Data for SKU U669149.
General guidance for analytical workflows
Prepare a primary stock in DMSO or methanol under subdued light. Store aliquots to minimize freeze–thaw.
LC–MS/MS: Develop multiple reaction monitoring (MRM) transitions based on molecular ion and characteristic indole fragment ions. Optimize source conditions to balance desolvation without thermal decomposition.
Calibration: Use serial dilutions in matched matrix or solvent with internal standards where applicable; verify linearity and carryover.
For any bioassay protocols, adhere to institutional approvals and consult the literature for assay-specific conditions.
Biological Roles
No endogenous biological role is assigned to UR-144 N-5-hydroxypentyl; it is a laboratory research chemical.
Research context (general, non-clinical)
Synthetic cannabinoid analogs based on indole/TMCP scaffolds are commonly studied as ligands for cannabinoid receptors in vitro. The N-alkyl chain’s oxidation state (e.g., terminal –OH) is frequently investigated for its effect on binding potency and efficacy.
Hydroxylated side chains are also examined as putative Phase I metabolites or metabolite surrogates of parent compounds in metabolic fate and toxicokinetic studies undertaken in cell-free or cellular systems.
Biochemical interactions (literature context)
The indole carbonyl and hydrophobic TMCP group drive lipophilic interactions; the terminal alcohol can introduce hydrogen-bonding and altered membrane permeability relative to non-hydroxylated analogs.
Note: This product is for research use only. No claims are made regarding therapeutic, diagnostic, or clinical use.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare pH buffer systems.
Practical guidance
If introducing into aqueous buffers for assays, dissolve first in a compatible co-solvent (e.g., DMSO or ethanol) and add slowly with vigorous mixing to avoid precipitation.
Maintain final organic solvent concentrations at levels compatible with your biological/analytical system (commonly ≤1–2% v/v), validating for your specific assay.
Green Alternatives
Green chemistry considerations for handling and analyzing indole synthetic cannabinoids focus primarily on solvent choice and minimizing hazardous reagents.
Ethyl acetate over dichloromethane for extractions and workups.
2-Methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME) as alternatives to THF/DCM for certain reactions and preparative chromatography eluents.
Acetonitrile or ethanol/water mobile phases for LC in place of chlorinated solvents.
Trade-offs
DCM/chloroform often provide superior solubility for hydrophobic indoles; switching to EtOAc or MeTHF may require longer elution times or modified gradients.
Aqueous ethanol can reduce environmental impact but may compromise solubility; consider co-solvent systems with modest DMSO fractions.
Small comparison (general)
DCM vs EtOAc: DCM has higher density and broader solvency but greater toxicity; EtOAc is biodegradable with lower toxicity—use if resolution and solubility are adequate.
THF vs 2-MeTHF: 2-MeTHF offers improved stability to peroxides and renewable sourcing; verify selectivity in your chromatographic or synthetic step.
Process recommendations
Scale procedures with solvent recovery in mind; employ rotovap recovery of ACN/EtOH.
Favor catalytic conditions and avoid stoichiometric halogenating/oxidizing agents when derivatizing the alcohol.
Pharmaceutical Uses
No pharmacopeial status or excipient role is assigned for this material.
Appropriate uses in a pharmaceutical R&D context (non-clinical)
Analytical reference or impurity/degradation surrogate in method development for drug-substance screening programs involving indole-based cannabinoids.
Tool compound for in vitro receptor-binding or functional assay development in discovery laboratories.
Not for human or veterinary use. Not a drug substance, API, or excipient. Any handling within regulated environments should follow institution and jurisdictional controls for synthetic cannabinoid analogs.
Physical Properties
Item-specific values are not provided in the Product Data. Do not treat the following as specifications; consult the CoA/Spec Sheet for certified values.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting/boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Hydroxylated UR-144 analogs are commonly solids with high bp; literature values vary by salt/form.)
Density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Organic: Expected to be soluble in polar aprotic solvents (DMSO, DMF, acetonitrile), moderately soluble in alcohols (MeOH, EtOH), and in chlorinated solvents (DCM, CHCl3). Limited solubility in alkanes compared with non-hydroxylated analogs due to the –OH.
Aqueous: Poorly soluble in pure water; solubility can be improved using co-solvents, cyclodextrins, or surfactants.
LogP/logD (literature expectation)
The terminal –OH reduces lipophilicity versus UR-144; overall remains lipophilic. Exact values: Not specified for this item; refer to CoA/Spec Sheet.
pKa
Phenolic/indolic N is weakly acidic; primary alcohol pKa not relevant to protonation under neutral conditions. Exact pKa values: Not specified for this item; refer to CoA/Spec Sheet.
Note: Where precise numeric values are required for design or QC, use the lot-specific CoA.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Research Use Note (from Product Data): For research use only.
Interpretation and implications:
Research-grade materials are intended for laboratory R&D, method development, and reference studies. They are not for human or veterinary use, diagnostic use, or in vivo administration.
Without an explicit grade (e.g., Analytical Standard, HPLC Grade, USP/EP), purity profile, stabilizers, residual solvents, and elemental impurities are controlled per internal specifications documented on the CoA.
If used as a reference material (e.g., for analytical calibration, metabolic profiling, or structural elucidation), verify:
Identity: NMR, HRMS/ESI, and chromatographic purity per CoA.
Impurities: Review related substances thresholds and residual solvent limits.
Stability: Check re-test/expiry dating and storage instructions.
If your application requires a defined grade (e.g., certified reference material with traceability), contact us with SKU U669149 for current lot documentation and availability.
Reaction and Applications
This compound is typically used as a research standard and as a chemical probe in SAR, metabolism, and analytical method development rather than as a reagent. Common research applications include:
Analytical reference and standards
LC–MS/MS method development and validation for synthetic cannabinoid screening; assessment of ionization efficiency vs UR-144 due to the terminal –OH.
Internal/secondary standards in stability and forced-degradation studies of UR-144 analog series.
Metabolism and biotransformation studies
Serves as a Phase I-like oxidation analog to probe metabolic soft spots of the N-alkyl chain; comparisons with microsomal/hepatocyte-generated hydroxylated metabolites.
Structure–Activity Relationship (SAR)
Evaluates the impact of N-alkyl hydroxylation on receptor binding affinity and functional assays (binding/β-arrestin/cAMP) in heterologous systems. Note: for research use only; ensure compliance with institutional approvals.
Derivatization chemistry
The primary alcohol enables formation of esters, carbonates, carbamates, or conversion to halides/azides for further analog generation while retaining the UR-144 core.
Practical tips
Use dry, oxygen-free conditions when necessary to prevent side reactions during derivatizations (e.g., with acid chlorides or sulfonyl chlorides).
Protect the indole N (if needed) and/or the alcohol selectively with standard protecting groups (e.g., TBDMS, MOM) depending on the transformation.
Reaction Conditions
General, literature-style guidance for common transformations of the terminal alcohol (not item specifications):
Esterification
Conditions: Carboxylic acid (1.2–2.0 eq), DCC or EDCI/DMAP, solvent CH2Cl2 or DMF, 0–25°C, 2–16 h. Monitor by TLC/LC–MS. Typical isolated yields for similar substrates: 60–90%.
Carbamate formation
Conditions: Chloroformates (e.g., Boc2O with catalytic DMAP or p-nitrophenyl chloroformate), solvent CH2Cl2/ACN, 0–25°C. Alternative: CDI activation followed by amine coupling.
Halide/azide via sulfonate
Conditions: MsCl (1.2 eq), Et3N, CH2Cl2, 0°C→rt, then displacement with NaI (acetone) or NaN3 (DMF) at 50–80°C. Work under inert atmosphere to protect indole.
Carbonate/urethanes for pro-moieties
Conditions: Triphosgene or carbonyldiimidazole (CDI) mediated coupling at 0–25°C in dry ACN/THF.
Analytical sample preparation
Stock solutions: 1–10 mg/mL in DMSO or MeOH. For LC–MS, 50:50 ACN:H2O (0.1% FA) often provides stable signals for indole cannabinoids; avoid high pH to prevent indole degradation.
These conditions are representative for hydroxylated indole cannabinoids; optimize for your specific substrate and scale.
Safety and Handling
GHS information (Product Data)
Signal word: Not specified for this item; refer to SDS.
Hazard statements: Not specified for this item; refer to SDS.
Classification and pictograms: Not specified for this item; refer to SDS.
General laboratory precautions (best practice; consult SDS for authoritative guidance)
Handle in a chemical fume hood; avoid inhalation and skin contact. Synthetic cannabinoid analogs can be biologically active at low concentrations.
PPE: lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid aerosol generation and use closed-transfer techniques where possible.
Incompatibilities: Strong oxidizers may react with the indole/aryl ketone framework; strong bases/acids can cause side-chain transformations (e.g., dehydration/esterification of the alcohol in certain conditions).
First aid (general): If on skin, wash with soap and water. If in eyes, rinse cautiously with water for several minutes and remove contact lenses if present. If inhaled, move to fresh air. If swallowed, rinse mouth. Seek medical attention as needed and provide the SDS.
Waste: Collect organics in halogenated or non-halogenated waste per solvent system; label with constituents.
Regulatory note
Jurisdictional controls may apply to certain synthetic cannabinoid analogs. Ensure all possession, use, and disposal comply with local laws and institutional policies.
Always consult the product SDS and institutional EHS guidance before use.
Solvent Selection
UR-144 N-5-hydroxypentyl combines a hydrophobic indole/TMCP core with a terminal primary alcohol, yielding modest amphiphilicity.
Less suitable: Alkanes (hexanes, heptane) due to the –OH increasing polarity; toluene may dissolve it moderately.
Aqueous media: Typically requires co-solvent (e.g., 1–10% DMSO or ethanol) or formulation aids (cyclodextrins, micelles) for clear solutions.
Practical recommendations
Prepare concentrated DMSO stock solutions (e.g., 10–50 mM) and dilute into assay buffers with rapid mixing to avoid precipitation.
For chromatographic workflows, acetonitrile/water (with 0.1% formic acid) or methanol/water gradients are commonly used for indole cannabinoids; the hydroxyl group improves peak shape relative to fully apolar analogs.
Comparison to alternatives
Versus non-hydroxylated UR-144: Slightly better solubility in polar solvents and stronger retention modulation in reversed-phase LC due to H-bonding interactions.
Versus more polar analogs (e.g., diol-bearing): Retains higher organic solubility and better compatibility with low-water systems.
Storage and Reconstitution
Storage (from Product Data): Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Best-practice handling
Protect from light and moisture. Store in a tightly sealed container within a desiccator or with desiccant to limit hydrolysis/oxidation of sensitive motifs.
For long-term stability, consider refrigerated storage (2–8°C) if compatible with institutional controls; verify lot-specific guidance on the CoA.
Reconstitution
Prepare concentrated stocks in anhydrous DMSO or methanol (e.g., 10–50 mM). Vortex and, if needed, gently warm (≤40°C) to aid dissolution; avoid prolonged heating.
Filter solutions (0.22 μm PTFE) if particulate is present. For aqueous use, dilute into buffer with rapid mixing; final organic content typically ≤1–2% v/v unless otherwise validated.
Avoid repeated freeze–thaw of solutions; aliquot and store at −20°C for organic stocks when extended storage is required. Inspect for precipitation or discoloration before use.
Always consult the lot-specific CoA/SDS for definitive storage and stability instructions.
Structure and Identity
UR-144 N-5-hydroxypentyl is a hydroxylated side-chain analog within the indole-class synthetic cannabinoid family, based on the UR-144 scaffold.
Item-specific identifiers (from Product Data)
CAS: 895155-95-0
CID: 11515395
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists a truncated value)
SMILES: 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.
Structural features (general, literature-based description of the chemotype)
Core: 1H-indole ring substituted at C3 by a carbonyl bearing a 2,2,3,3-tetramethylcyclopropyl (TMCP) group (the hallmark UR-144 carbonyl motif).
N1 side chain: 5-hydroxypentyl substituent on the indole nitrogen (–(CH2)5–OH), increasing polarity vs the parent pentyl chain.
Stereochemistry: TMCP ring carbons are quaternary; no specified stereocenters on the side chain alcohol in the IUPAC name; overall typically handled as achiral/racemate unless otherwise specified.
2D description in words
Indole N1 connected to a linear five-carbon chain terminating in –OH; indole C3 carbonyl linked to a neopentyl-like tetramethylcyclopropyl group. The molecule is amphiphilic relative to UR-144 due to the terminal alcohol, yet remains predominantly hydrophobic from the indole and TMCP motifs.
Synthetic Utility
Although primarily a target/analyte, UR-144 N-5-hydroxypentyl can function as a versatile intermediate for analogue synthesis due to its terminal alcohol.
Functional group leverage
Alcohol: Convert to mesylate/tosylate for SN2 diversification (to halides, azides, amines). Form esters/carbamates/carbonates to modulate polarity and potency for SAR.
Indole core: Electrophilic substitutions or protection at the indole N (if deprotected during synthesis) can be used strategically; however, the N is already substituted by the hydroxypentyl chain in this scaffold.
Carbonyl: The aryl ketone adjacent to the indole can undergo typical carbonyl chemistry (e.g., oxime/hydrazone formation) for derivatization or analytical tagging.
Retrosynthetic perspective
Disconnection at the N-alkyl C–N bond suggests late-stage alkylation of an indole precursor with a protected 5-hydroxypentyl halide followed by acylation at C3 with the TMCP acid chloride or equivalent.
Purification considerations
Hydroxyl functionality can broaden spots in normal-phase TLC; reversed-phase chromatography often provides cleaner separations. Use minimal protic additives to maintain indole integrity.
Target Specificity
No target specificity, antibody clone, or biological target validation is provided for this item in the Product Data.
Item-specific note: Not specified for this item; refer to CoA/Spec Sheet.
General research context: Indole synthetic cannabinoids are often evaluated against cannabinoid receptors in vitro; any potency/affinity values for this specific analog must be sourced from peer-reviewed literature or the CoA if available.
Häufig gestellte Fragen
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 895155-95-0, the molecular formula is C21H29NO2, and the molecular weight is 327.5 g/mol. InChIKey AFWBYMXUEMOBRP-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
Wir verwenden Cookies, um die ordnungsgemäße Funktion der Website sicherzustellen und, soweit zulässig, Ihr Nutzererlebnis zu verbessern. Sie können Ihre Einstellungen jederzeit unter „Einstellungen“ verwalten. Weitere Informationen finden Sie in unserer Cookie-Richtlinie.
Dürfen wir Sie über Rabattaktionen informieren?
Später erinnern
Vielen Dank! Bitte überprüfen Sie Ihren E-Mail-Posteingang, um zu bestätigen.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
