This compound belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
253.290 g/mol
XLogP3
1.800
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Exact Mass
253.11 Da
Monoisotopic Mass
253.11 Da
Topological Polar Surface Area
52.500 Ų
Heavy Atom Count
19
Formal Charge
0
Complexity
348.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
1
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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No item-specific, vendor-validated protocols are provided for this SKU.
General research-use guidance (adapt as appropriate):
Stock preparation for cell assays: Dissolve in anhydrous DMSO to 10–50 mM. Store aliquots in amber vials at −20°C to limit freeze–thaw (if compatible with your workflow). Thaw quickly and use immediately.
Working solutions: Dilute stock into pre-warmed assay buffer or media with vigorous mixing to a final DMSO content ≤0.1–0.5% v/v (as tolerated by your system). Adjust pH if preparing acid salts in situ.
Light/oxygen control: Prepare just before use; minimize air exposure and protect from light to reduce catechol oxidation. Consider including inert gas overlay on microplates if assay duration is long.
Analytical QC: Verify concentration by UV or LC–MS where possible; monitor for oxidative degradation peaks.
Note: For receptor-binding or functional assays, follow the protocol and controls established in your laboratory. This product is for research use only.
Biological Roles
Context (literature/general biochemistry; no clinical claims):
Norapomorphine is the N-desmethyl analogue of apomorphine and retains the aporphine catecholamine pharmacophore associated with dopaminergic receptor activity. It is used as a research ligand in studies of dopamine receptor signaling pathways (D1-like and D2-like GPCR families), β-arrestin recruitment, and downstream second messenger modulation (e.g., cAMP for D1/D2 coupling contexts).
The catechol motif suggests potential interactions with redox-active cellular environments; autoxidation to quinones may generate reactive oxygen species in vitro, a factor considered in cell-based assay design and interpretation.
Transport/uptake: As a cationic amine at physiological pH, it may interact with organic cation transporters; membrane permeability can be modulated by pH (unionized vs protonated forms) and by O/N-derivatization in analogue studies.
Metabolic considerations in microsomal systems (general): likely pathways include O-methylation (COMT-like activity on catechols), glucuronidation/sulfation of phenols, and N-dealkylation/oxidation where applicable. For norapomorphine specifically (secondary amine), phase II conjugations at phenolic positions are primary.
Usage notes for biological experiments:
Prepare fresh, oxygen-limited solutions to reduce artifactual oxidative stress signals.
Include appropriate receptor-selective controls and antagonists to parse on-target GPCR effects from off-target catechol redox activity.
Determine free (unbound) concentration in protein-containing media, as binding to serum proteins and plastics can be nontrivial for polyaromatic amines.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biochemical buffer systems.
Practical guidance:
If dissolution into aqueous buffers is required for bioassays, dissolve first in a small volume of DMSO or ethanol, or form a dilute acid salt, then dilute into the target buffer while mixing vigorously.
Maintain the final cosolvent content (e.g., DMSO ≤0.1–1% v/v) within assay-compatible limits and verify that pH remains within your assay’s tolerances after addition of acidic stocks.
Green Alternatives
Greener handling considerations focus on solvent choice and minimizing oxidative waste since the compound itself is fixed.
Greener solvent options (general guidance):
Replace DMF with safer high-permittivity solvents where feasible: DMSO (readily biodegradable, low volatility), propylene carbonate (PC), or Cyrene (dihydrolevoglucosenone) for some dissolution/derivatization steps.
Prefer ethanol or isopropanol over methanol for lower toxicity in cleaning and low-strength stock solutions, provided solubility permits.
For aqueous assay work, prepare mildly acidified buffers (acetate/citrate) rather than strong mineral acids when compatible with biology, reducing corrosive hazard and waste-neutralization burden.
Illustrative comparison (general; select per your application):
DMF → DMSO/Cyrene: similar solvency for polar aromatics; DMSO has better EHS profile than DMF; Cyrene is bio-based but viscosity can be limiting.
Methanol → Ethanol: comparable polarity; ethanol is less toxic and often acceptable for screening stocks at ≤1% v/v.
Chlorinated solvents → Ethyl acetate/MEK: for workups/extractions of analogues, choose EtOAc/MEK where partitioning allows.
Operational strategies:
Prepare higher-concentration master stocks to reduce solvent use and shipping volume.
Use amber vials and inert headspace to prolong solution life, reducing frequency of remakes and waste.
Implement micro-scale reactions and LC–MS analytical methods to minimize consumption.
Note: Validate solubility and stability in any alternative solvent before scale-up; catechol oxidation can vary with solvent and dissolved oxygen content.
Pharmaceutical Uses
No excipient or formulation-grade details are provided for this item, and it is sold strictly for research use only.
General context (non-clinical, non-therapeutic):
Norapomorphine can serve as a research reference standard for analytical method development (e.g., LC–MS) related to aporphine-class compounds.
In preformulation-type laboratory studies, researchers may examine salt formation (e.g., hydrochloride, sulfate) to modulate solubility and stability for in vitro work. Such studies are strictly for research and are not pharmaceutical manufacturing guidance.
Documentation:
Pharmacopoeial status: Not specified for this item; refer to CoA/Spec Sheet.
Residual solvent limits, elemental impurities, microbiological limits: Not specified for this item; refer to CoA/Spec Sheet.
Note: Aladdin Scientific supplies this material for research use only. It is not an API, not GMP-manufactured, and not intended for human or veterinary use, diagnostics, or clinical applications.
Physical Properties
Item-specific specifications:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Melting point, boiling point, density, refractive index, pKa, logP/logD, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Aporphine catechols typically appear as off-white to tan crystalline solids that may darken on air/light exposure due to catechol oxidation.
Solubility profile: free base forms are generally sparingly soluble in water at neutral pH but soluble in polar aprotic/organic solvents (DMSO, DMF) and in aqueous buffers when protonated (e.g., dilute acids). Phenolic OHs can form strong hydrogen bonds; salt formation (e.g., HCl) markedly increases aqueous solubility.
Chemical stability: catechol functionality is air/light/alkali sensitive and can undergo oxidation to quinonoid species; antioxidants, inert atmosphere, and subdued light improve stability.
Practical notes:
When preparing concentrated stock solutions, prefer anhydrous DMSO or ethanol, protect from light, and minimize headspace oxygen.
If precise physicochemical constants are critical (pKa, logD7.4, solubility), determine experimentally for your matrix or consult the CoA/Spec Sheet for this item.
Quality and Grades
Item-specific grade/purity information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on quality considerations for this compound class:
Reference/Screening grade: For small-molecule library use, materials are commonly provided at high chemical purity (e.g., ≥95% by HPLC/LC–MS) with identity confirmed by NMR/HRMS. Verify actual assay and analytical method on the CoA for this SKU.
UV/LC suitability: Catechol/aporphine chromophores absorb strongly in the UV; if intended for HPLC method development, ensure impurity profile and UV background meet your detection needs.
Stabilizer implications: Catechol-bearing compounds can slowly oxidize. Some vendors include trace antioxidants or package under inert gas. If stabilizers are present, they will be declared on the CoA; absence of declaration generally implies neat compound only.
Batch-to-batch consistency: Review provided chromatograms and NMR spectra for the lot you receive. Minor color variation does not necessarily indicate purity change in catechol-type compounds, which can darken slightly upon air exposure.
Documentation to consult:
CoA/Spec Sheet for this item (assay, residual solvents, water content, ID methods, and any stabilizer used).
SDS for handling and hazard classification.
If regulated analytical use is intended (e.g., internal standards), request any available reference-standard documentation or impurity profile.
Reaction and Applications
This item is primarily a research small molecule (compound library member) rather than a general reagent. Still, its functional groups enable selective transformations and it serves as a valuable reference scaffold.
Applications (general research use):
Receptor pharmacology tool: norapomorphine (the desmethyl apomorphine) is used as a reference agonist/ligand in dopaminergic and related GPCR studies in vitro (binding, signaling). No clinical/therapeutic uses are implied.
Analytical standard: can be employed to validate LC–MS/MS methods for aporphine derivatives, including stability-indicating assays sensitive to catechol oxidation.
Transformations on the molecule (synthetic context):
N-Functionalization: the secondary amine enables controlled N-alkylation (e.g., to access aporphine analogues). Selectivity benefits from protection of phenolic OH groups and use of non-nucleophilic bases.
O-Functionalization: phenolic OHs can be protected (benzyl, silyl) or derivatized (acylation, carbonate formation) to modulate physicochemical properties.
Oxidation chemistry: catechol-to-quinone interconversion provides handles for conjugation (e.g., Michael addition after quinone formation) but requires tight control to avoid overoxidation.
Practical tips:
Work under inert atmosphere and subdued light to limit catechol oxidation.
Use anhydrous solvents and include trace antioxidant (e.g., ascorbate) only if compatible with downstream use; otherwise, prepare fresh solutions.
For bioassays, prepare protonated aqueous stocks immediately before use to limit autoxidation; filter through 0.22 μm if needed.
Reaction Conditions
General literature-guided conditions for typical transformations on aporphine catecholamines (verify and optimize for your substrate):
N-Alkylation (to access apomorphine analogues):
Reagents: alkyl bromide/iodide or mesylate; base such as K2CO3, Cs2CO3, or DIPEA.
Solvent: DMF or MeCN; DMSO as alternative. Dry conditions; protect phenols to minimize O-alkylation.
Temperature/time: 20–60°C, 2–16 h. Monitor by LC–MS. Quench and deprotect as required.
O-Acylation/O-alkylation (phenols):
Reagents: acyl chlorides/anhydrides with pyridine/DMAP; for O-alkyl, alkyl halides with K2CO3.
Solvent: DCM, THF, or acetone (anhydrous). 0–25°C for acylations; 25–50°C for alkylations.
Notes: Regioselectivity can be tuned with protecting groups and steric control.
Catechol protection:
Benzylation: BnBr, NaH or K2CO3, DMF, 0–25°C. Debenzylate by hydrogenolysis (H2/Pd-C) under mild conditions to avoid hydrogenolysis at other sites.
Silylation: TBSCl, imidazole, DMF; deprotect with TBAF.
Controlled oxidation to quinone:
Reagents: Ag2O, Fremy’s salt, or ceric ammonium nitrate (CAN) in MeCN/MeOH at 0–25°C.
Notes: Perform under inert atmosphere and monitor closely to prevent overoxidation and ring cleavage.
Yields: Highly substrate- and condition-dependent; typical isolated yields range 50–85% for clean N/O-functionalizations when phenols are appropriately protected (literature, general guidance).
Always validate on small scale; aporphine frameworks can undergo rearrangements/oxidations if overheated or exposed to air/alkali for extended periods.
Safety and Handling
Item-specific hazard details (from Product Data):
Signal word: Not specified for this item; refer to SDS.
H-Statements / GHS classification / Pictograms: Not specified for this item; refer to SDS.
General safety guidance (professional laboratory practice; defer to SDS for authoritative information):
Likely hazards: phenolic/catecholamine-type alkaloids may cause skin/eye irritation and are harmful if swallowed or inhaled. Secondary amine and phenolic groups suggest potential sensitization/irritation.
PPE: wear lab coat, nitrile gloves, and safety glasses. Use in a chemical fume hood to avoid inhalation of dust or solvent vapors.
Handling: minimize exposure to air and light to limit oxidative degradation. Avoid strong bases/oxidants that can promote catechol oxidation. Use amber glassware when feasible.
Incompatibilities: strong oxidizing agents; strong bases (which accelerate autoxidation of catechols); iron/copper salts that can catalyze redox cycling. Store away from peroxides and oxidants.
First aid (overview):
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Ingestion/inhalation: move to fresh air; rinse mouth; seek medical attention. Provide SDS to responders.
Spill response: avoid dust formation; absorb solutions with inert material; collect for disposal according to institutional and local regulations.
Waste: segregate from oxidizers; dispose as halogen-free organic waste unless solution matrix dictates otherwise.
Always consult the item-specific SDS provided with your shipment for detailed classification and response procedures.
Solvent Selection
Applicability: As a polyfunctional aromatic amine with phenolic groups, norapomorphine is typically handled in polar organic solvents or as acidic aqueous salts for biological assays.
General solvent behavior (literature/general chemistry knowledge):
Polarity class: polar, protic functionality; overall molecule dissolves best in polar aprotic solvents when unprotonated.
Typical solvents for stock solutions: DMSO (preferred), DMF, ethanol, methanol. For aqueous work, dissolve first in a small volume of DMSO/EtOH, then dilute into buffer; or prepare as a dilute acid salt.
Aqueous solubility: increases markedly upon protonation (e.g., 0.1 M HCl or acetate/citrate buffers). Free base shows limited solubility at neutral pH.
Dielectric considerations: DMSO (ε ≈ 47) and DMF (ε ≈ 37) support dissolution of aromatic amines and phenols; alcohols (MeOH/EtOH) can also be effective but may promote acetal/ester formation under harsh conditions if protecting groups are present.
When to choose what:
DMSO: best for high-concentration assay stocks (e.g., 10–50 mM). Low volatility, excellent solvency; watch hygroscopicity.
Ethanol/methanol: for lower-to-moderate concentrations and when DMSO is incompatible with the assay. Faster evaporation for film formation.
Acidified water/buffers: for immediate use in biological assays; adjust pH last to avoid localized precipitation.
Small comparison (general):
DMSO: highest solubility, assay-compatible up to 0.1–1% v/v in many systems.
2-propanol/acetone: moderate solubility; use for quick rinses, not long-term stocks.
Nonpolar solvents (hexanes, toluene): generally poor for the free base; not recommended.
Storage and Reconstitution
Item-specific storage/shipping:
Storage Conditions: Room temperature (from Product Data).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General best practices for this compound class (catechol-bearing aporphines):
Solid storage: Keep tightly closed in the original amber container at room temperature, dry environment, away from light and oxidants. Consider using desiccant. If long-term storage is planned, an inert gas blanket (N2/Ar) in the vial headspace is beneficial.
Solution stability: Prepare solutions fresh when possible. Catechols can oxidize in solution, especially in basic or neutral aqueous media. If storing solutions, use amber vials, fill to minimize headspace, and refrigerate or freeze according to your lab’s stability data. Documented, item-specific solution stability is not provided.
Reconstitution guidance (research use):
For analytical/screening stocks: Dissolve the solid in anhydrous DMSO (typical 10–50 mM), vortex, and, if needed, gently warm (<40°C) briefly to aid dissolution. Filter (0.22 μm PTFE) if particulate remains.
For aqueous use: Either form an acidified aqueous solution (e.g., dilute HCl or acetate buffer) or predissolve in DMSO/ethanol before dilution into buffer. Check pH after dilution and use immediately.
Always consult the CoA/Spec Sheet for any lot-specific stability or reconstitution notes. Research use only.
Structure and Identity
Brief overview: Norapomorphine is the N-desmethyl analogue of apomorphine, an aporphine-type catecholamine scaffold. The core is a tetracyclic aporphine framework bearing a secondary amine and phenolic hydroxyls (catechol-like) on the aromatic ring system.
Item-specific identifiers (from Product Data):
SKU: N667883
CAS: 478-76-2
InChIKey: 219323 (as provided)
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 class: aporphine (benzyltetrahydroisoquinoline-derived) alkaloid framework fused into a tetracyclic system.
Functional groups: secondary benzylic amine (desmethyl relative to apomorphine), two adjacent phenolic OH groups (catechol motif), multiple aromatic rings.
Stereochemistry: aporphines commonly possess a chiral center at C10 (numbering by aporphine convention); commercial material may be racemic unless otherwise specified. Configuration for this item is not specified.
2D description in words: a polycyclic, partially saturated isoquinoline fused to a benzodioxole/catechol-like ring, with a bridgehead secondary amine and vicinal phenolic hydroxyls on one aromatic ring.
Notes:
Exact structural identifiers (canonical SMILES, full InChI/InChIKey) should be verified on the CoA/Spec Sheet for this specific lot.
The “nor-” prefix indicates removal of an N-methyl from apomorphine, yielding a secondary amine amenable to further N-alkylation.
Synthetic Utility
Norapomorphine is a versatile aporphine scaffold with multiple orthogonal handles for analogue synthesis and SAR exploration.
Key reactive sites (general chemistry knowledge):
Secondary amine (bridgehead): amenable to N-alkylation (e.g., Mitsunobu-free alkylation via alkyl halides under mild base), reductive amination (after transient deprotection/oxidation), or carbamate/amide formation.
Phenolic OHs (catechol): selective O-protection (Bn, MOM, SEM, silyl) enables stepwise derivatization; O-acylation/alkylation tunes lipophilicity and metabolic stability.
Aromatic ring: electrophilic substitution can be directed once phenols are protected; late-stage C–H functionalization (e.g., Pd-catalyzed arylation/oxygenation) is reported for aporphine frameworks in the literature.
Retrosynthetic value:
Serves as a parent nucleus for constructing aporphine libraries; N-alkylation affords apomorphine analogues, while O-modifications probe hydrogen-bonding and redox properties.
Quinone formation from the catechol (under controlled oxidation) opens routes to conjugate additions or cycloadditions, enabling bioconjugation strategies.
Practical strategy notes:
Protect phenols prior to N-alkylation to avoid competitive O-alkylation; employ non-nucleophilic bases (e.g., DIPEA, Cs2CO3) and polar aprotic solvents.
For selective mono-O-acylation, use sterically biased acyl donors or transient silyl protection of one phenol.
Monitor reactions by LC–MS in positive ESI mode; aporphines ionize efficiently as [M+H]+, aiding rapid optimization.
Target Specificity
Item-specific, experimentally verified target data are not provided for this catalog entry.
From literature (general research context; not a specification of this item):
Norapomorphine is commonly used as a dopaminergic receptor agonist in vitro. Reported activities vary by receptor subtype and assay conditions. Do not assume potency/selectivity for your application without direct testing.
For this item:
Tested targets, binding constants (Ki/EC50), and selectivity panels: Not specified for this item; refer to CoA/Spec Sheet or primary literature.
Domande frequenti
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 478-76-2, the molecular formula is C16H15NO2, and the molecular weight is 253.29 g/mol. InChIKey MHPQCGZBAVXCGA-GFCCVEGCSA-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.
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