Rilmenidine - ≥95% , CAS No.54187-04-1

CAS: 54187-04-1 Cat. No.: R769888 Formula: C₁₀H₁₆N₂O·0.5C₄H₄O₄ Molecular Weight: 238.28 EC Number: 259-021-0 PubChem CID: 68712

GRADE & PURITY ≥95%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Specifications & Purity

≥95%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Product Properties

alogp

1.2

Names and Identifiers

Canonical Smiles

C1CC1C(C2CC2)NC3=NCCO3

IUPAC Name

N-(dicyclopropylmethyl)-4,5-dihydro-1,3-oxazol-2-amine

InChIKey

CQXADFVORZEARL-UHFFFAOYSA-N

INCHI

1S/C10H16N2O/c1-2-7(1)9(8-3-4-8)12-10-11-5-6-13-10/h7-9H,1-6H2,(H,11,12)

Isomeric SMILES

C1CC1C(C2CC2)NC3=NCCO3

WGK Germany

3

RTECS

RP7207400

PubChem CID

68712

Molecular Weight

238.28

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Azolines
      • Subclass Oxazolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azolines
• Subclass: Oxazolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Oxazolines
• Alternative Parents: Isoureas Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Carboximidamides Azacyclic compounds Organopnictogen compounds Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Oxazoline - Isourea - Oxacycle - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as oxazolines. These are organic compounds containing 1,3-oxazoline, a five-membered ring with a nitrogen and an oxygen atoms at the 1- and 3-position, respectively. Additionally, it contains two double bonds.
• External Descriptors: isourea

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

Chemical and Physical Properties

• Molecular Weight: 180.250 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 180.126 Da
• Monoisotopic Mass: 180.126 Da
• Topological Polar Surface Area: 33.600 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 219.000
• 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

No tested application protocols are provided in the Product Data. The following are general, literature-informed suggestions for small-molecule tool compounds like rilmenidine; adapt to your assay and validate in-house.

• Stock solution preparation:
  • Dissolve in anhydrous DMSO to 10–50 mM. Vortex and sonicate if needed. Store aliquots at −20°C protected from light and moisture.
  • For aqueous use, adjust pH with dilute HCl or prepare a salt form to enhance solubility; filter through 0.22 µm for cell-based assays.
• Receptor binding assay (membrane prep):
  • Prepare serial dilutions (10-point, 1:3) in assay buffer (e.g., 50 mM HEPES, 1 mM EDTA, 0.1% BSA, pH 7.4).
  • Incubate with membrane protein and radioligand/fluorescent probe at 25–37°C for 60–120 min; separate bound/free by filtration or SPA beads; fit Ki/IC50 via nonlinear regression.
• Cell-based functional assay:
  • Treat cells expressing target receptors with rilmenidine across 7–8 log concentration range.
  • Measure downstream readouts (cAMP, Ca2+ flux, reporter gene) with appropriate controls (vehicle, positive control agonist/antagonist).
• LC–MS quantitation (bioanalytical):
  • Protein precipitate plasma with acetonitrile containing internal standard; centrifuge and inject supernatant onto C18 column.
  • Use ESI+ MRM transitions optimized from authentic standard; validate linearity, accuracy, precision, recovery, and matrix effects.

These are starting frameworks; tailor parameters to your system.

Biological Roles

General, literature-based overview (no clinical claims):

• Rilmenidine is widely used in research as a small-molecule ligand interacting with imidazoline receptors (notably I1) and demonstrating cross-reactivity with certain alpha-2 adrenergic receptor subtypes at varying concentrations. These interactions are typically explored to dissect signaling pathways in neuronal, cardiovascular, and metabolic contexts in vitro and ex vivo.
• Mechanistic points of interest: imidazoline receptor engagement can modulate G-protein–coupled signaling cascades, influence ion channel activity, and affect second messengers (e.g., cAMP), often studied via binding assays, reporter gene assays, and electrophysiology (literature).
• Cellular disposition: as a basic, heterocycle-rich compound, rilmenidine is expected to partition according to protonation state; lysosomal trapping and pH-dependent uptake can be relevant in cell-based experiments (general for cationic amphiphiles; verify experimentally for your system).
• Metabolic considerations: oxidative dealkylation and heterocycle transformations are common routes in related scaffolds; microsomal stability assays and metabolite identification by LC–HRMS are standard for mechanistic ADME research (literature, general).

Experimental tips (general):

• Establish concentration–response curves across several logs to capture both high- and lower-affinity target interactions.
• Confirm target engagement with orthogonal assays (binding vs. functional readouts) and include counter-screens to distinguish imidazoline vs. adrenergic effects.
• Report salt form, solvent, and final vehicle concentration to ensure reproducibility.

Note: For research use only.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare buffer systems. However, buffers are central to its biological and analytical use:

• Assay buffers (general): physiological salt solutions (e.g., HBSS, PBS, HEPES-buffered media) at pH 7.2–7.4 are commonly used for receptor binding or functional assays. Include carrier protein (e.g., 0.1% BSA) if nonspecific binding is observed.
• Solubilization: when preparing aqueous working solutions, adjust pH below the compound’s conjugate-acid pKa to enhance solubility for the free base, or use preformed salt. Filter-sterilize (0.22 µm) if using in cell-based assays.
• LC–MS sample prep: use volatile buffers (ammonium formate/acetate at pH 3–6) for ESI compatibility; avoid non-volatile phosphate in LC–MS workflows unless using orthogonal detection.

Because rilmenidine does not provide buffering capacity, select buffer systems based on assay biology and analytical detection requirements.

Green Alternatives

As a solid, nitrogen-rich small molecule used primarily as a research tool compound, rilmenidine itself is not readily replaced by a “green alternative” without altering biological activity. However, greener choices can be made for solvents and workflows surrounding its use.

Greener solvent choices (general guidance):

• Prefer ethanol or isopropanol over methanol when feasible for cleaning or preparative steps (lower toxicity, renewable sourcing potential).
• In analytical LC, consider water–ethanol systems or supercritical CO2 (SFC) where method performance allows; otherwise, acetonitrile has a higher EHS burden than methanol but offers lower UV background—balance performance vs. impact.
• For stock solutions, minimize DMSO volumes and consider aqueous buffers adjusted to pH < pKa to enhance solubility when compatible with assays, reducing reliance on high-boiling aprotic solvents.

Process and waste minimization:

• Use microscale assay formats (96-/384-well plates) to reduce solvent consumption.
• Adopt closed-transfer systems for DMSO to limit exposure and reduce loss.
• Consolidate waste streams (halogen-free organics vs. aqueous) to facilitate proper disposal and potential solvent recycling.

Comparison snapshot (general):

• DMSO vs. ethanol: DMSO offers superior solvency for basic heterocycles but is higher boiling and harder to remove; ethanol is greener but may not dissolve as effectively. Choose based on solubility and assay tolerance.

Note: The core compound has no “green” substitute without changing its research function; focus sustainability efforts on solvents, scale, and waste.

Pharmaceutical Uses

No clinical or therapeutic claims are made. The notes below address formulation and analytical roles in a research/manufacturing context (literature, general):

• Reference standard: may be used as a system suitability or calibration standard in QC methods for related imidazoline-class compounds, pending verification of purity and identity.
• Formulation studies (research): salt screening (e.g., hydrochloride, mesylate, tartrate) to evaluate solubility and stability; preformulation studies examining pH solubility profiles, hygroscopicity, and polymorphism of the free base vs. salts.
• Excipient compatibility: stress-test with common excipients (microcrystalline cellulose, lactose, PVP, magnesium stearate) under ICH conditions to identify potential interactions (e.g., Maillard reaction risk with reducing sugars if primary/secondary amines are present—general consideration).
• Stability indicating methods: develop LC methods with gradient elution (water–acetonitrile, acidic modifier) and diode-array/MS detection to resolve degradants from oxidative or hydrolytic stress.

Any GMP/GLP or pharmacopoeial use requires grade confirmation, validated methods, and full documentation. For this catalog item, Grade/Purity is not specified; consult the CoA/Spec Sheet before regulated applications.

Physical Properties

Item-specific specifications were not provided in the Product Data. Do not treat the following as specifications; they are general/literature guidance to assist method development. Always verify against the lot-specific CoA/Spec Sheet.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Literature values vary depending on free base vs. salt form.)
• Boiling point: Not applicable for many solid heterocycles; decomposition may occur before boiling (literature, general).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable for solids; Not specified for this item; refer to CoA/Spec Sheet.
• pKa: Basic nitrogen(s) typical of imidazoline-class compounds; reported pKa values for related scaffolds are in the ~7–9 range for conjugate acids (literature, general). Exact value for rilmenidine should be confirmed from primary sources.
• LogP/LogD: Imidazoline ligands often show moderate polarity (literature, general). Confirm exact value from primary sources.
• Solubility (general guidance):
  • Polar organics (DMSO, methanol, ethanol): typically soluble (literature, general for small basic heterocycles).
  • Water: the free base may be sparingly to moderately soluble; salt forms (e.g., HCl) are usually more water-soluble (literature, general). Verify form and solubility on CoA.

Note: If you require precise physicochemical constants for modeling or assay development, consult the lot CoA/SDS or peer-reviewed databases.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet. In the absence of an explicit grade, users should verify assay, residual solvents, and related-substance limits on the lot CoA prior to regulated use.

Understanding common grades (general guidance):

• Research grade: suitable for exploratory synthesis or in vitro studies; assay typically ≥95% by HPLC/GC; impurity profile adequate for general research.
• Analytical/Reference grade: tighter impurity limits and documented identity/purity assessments (e.g., quantitative NMR, mass balance).
• Pharmacopoeial grade (e.g., Ph. Eur./USP): conforms to monograph specifications when available; includes identification, impurity classes, and residual solvent limits.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Many imidazoline derivatives do not require stabilizers; however, salts may include defined hydration levels.

Documentation and testing suggestions:

• Verify identity by orthogonal methods (HPLC-UV/ELSD, HRMS, 1H/13C NMR). For bioassay consistency, confirm salt form and water content (KF) where relevant.
• For LC applications, ensure low non-volatile residue and acceptable UV baseline characteristics. If using in receptor assays, confirm absence of interfering amines or residual catalysts.

Contact Aladdin Scientific for batch-specific CoA and extended analytical data on request.

Reaction and Applications

This product is generally used as a small-molecule probe/ligand in receptor biology and signaling research rather than as a synthetic reagent. Nonetheless, the scaffold’s basic heterocycles inform its handling and potential derivatization.

Research applications (literature, non-clinical):

• Tool compound for studying imidazoline receptor pharmacology and alpha-adrenergic signaling cross-talk in cell and tissue models.
• Chemical biology studies exploring structure–activity relationships (SAR) of imidazoline-class ligands via substitution around the heterocyclic core.

Analytical applications:

• Reference standard in LC–MS/MS method development for bioanalytical quantification (e.g., spike-and-recover experiments, calibration curves). Ensure traceable purity and salt form confirmation for accurate mass and response factors.

Derivatization/synthesis context (general):

• If free amine functionality is present, it can be acylated, sulfonylated, or carbamoylated to tune basicity and permeability.
• Heterocycle N-oxidation or ring-opening can be explored under controlled conditions to probe metabolic liabilities (mechanistic studies).

Practical tips:

• Prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into assay buffers last to minimize precipitation.
• Avoid prolonged exposure to strong base or strong oxidants that could degrade nitrogen-rich heterocycles.
• For LC–MS bioanalytical methods, include an internal standard and evaluate matrix effects due to the compound’s basicity and potential ion suppression.

Reaction Conditions

Because rilmenidine is typically used as a research ligand/standard rather than a reagent, there are no canonical “reaction conditions” for its use. For chemists pursuing analog synthesis or derivatization, general conditions applicable to basic, nitrogen-rich heterocycles are summarized (literature, general):

• N-Acylation: acyl chloride or anhydride, base (DIPEA, Na2CO3), CH2Cl2/MeCN, 0–25°C, 1–12 h; monitor to avoid over-acylation if multiple nitrogens are present.
• Sulfonylation: sulfonyl chloride, base (pyridine/TEA), 0–25°C, 1–6 h.
• Carbamate formation: chloroformates or CDI with alcohols, DMF/THF, 0–25°C.
• Salt formation: treat free base with anhydrous HCl or organic acids (e.g., fumaric, citric) in Et2O/THF/alcohol to precipitate crystalline salts; characterize by XRPD and DSC.
• Analytical LC–MS method development (for quantitation): water (0.1% formic acid)–acetonitrile gradient, C18 column, ESI+ detection; typical retention 2–6 min depending on gradient and pH; include matrix effect evaluation and recovery assessment.

Expected yields/times are highly substrate- and position-dependent; the above are starting points only. Optimize to the specific substitution pattern of rilmenidine and desired analogs. Always confirm identity/purity by NMR and HRMS.

Safety and Handling

Hazard information in the Product Data is not specified; consult the SDS for authoritative guidance. The notes below are general best practices for small, basic heterocyclic amines/imidazoline derivatives used in research.

• GHS classification, signal word, pictograms, H/P statements: Not specified for this item; refer to SDS.
• Likely hazards (general for basic amines/heterocycles): may cause irritation to eyes, skin, and respiratory tract upon contact or inhalation; harmful if swallowed. Avoid dust formation and aerosols.
• PPE: lab coat, nitrile gloves, and safety glasses as minimum. Use a certified chemical fume hood when weighing or preparing solutions.
• Handling: avoid contact with oxidizers and strong acids/bases unless intentionally reacting. Prevent electrostatic discharge when handling powders. For hygroscopic or deliquescent salts, minimize air exposure.
• First aid (general):
  • Inhalation: move to fresh air; seek medical advice if symptoms persist.
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation develops.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Spills: cover solid with inert absorbent (vermiculite), collect into suitable waste. For solutions, absorb with spill pads and decontaminate surfaces with appropriate solvent and detergent.
• Fire safety: use CO2, dry chemical, or foam. Combustion may produce nitrogen oxides and CO/CO2 (general for N-containing organics).
• Waste: collect as halogen-free organic waste unless neutralized/aqueous; follow institutional and local regulations.

Always defer to the product SDS for definitive hazard and response information.

Solvent Selection

Rilmenidine is a small, basic heterocycle-rich compound. Without item-specific solubility data, select solvents based on general behavior of imidazoline-class ligands. Always verify with a small test dissolution and your lot’s CoA.

• Polarity class: moderately polar, basic organic (general, literature for imidazoline derivatives).
• Stock solutions for screening assays (general practice):
  • DMSO: frequently the solvent of choice up to 10–50 mM stocks; compatible with most in vitro assay systems at ≤0.5% v/v final.
  • Methanol/ethanol: viable alternatives for UV/LC prep and some biological assays; confirm tolerance with assay system.
  • Water or aqueous buffers: solubility depends strongly on form; protonated salts (e.g., HCl) are generally more soluble than free bases.
• Partitioning considerations: protonation state (pH) governs aqueous solubility and LC retention; adjust pH below the pKa to enhance water solubility.
• Chromatography solvents (analytical): water–acetonitrile or water–methanol with volatile acids/bases (0.1% formic acid or 10–20 mM ammonium formate) often give robust peak shape for basic analytes (general guidance).
• When to choose alternatives:
  • If water solubility is essential and the free base is supplied, prepare a dilute acid salt in situ (e.g., HCl, citrate) after confirming compatibility.
  • If UV interference near low wavelengths is a concern, prefer acetonitrile over methanol for LC–UV methods due to a lower UV cutoff (general).

Note: Confirm the supplied form (free base vs. salt) and adjust solvent strategy accordingly.

Storage and Reconstitution

Item-specific conditions from Product Data:

• Storage: Store at −20°C.
• Shipping: Shipped in ice chest with ice pads.

Additional guidance (general best practices for small-molecule heterocycles; not item-specific specifications):

• Container: keep tightly closed in original amber vial to protect from light and ambient moisture. If hygroscopic (salt forms may be), handle quickly under low-humidity conditions and re-cap promptly.
• Stability: minimize freeze–thaw by aliquoting solid or concentrated solutions. For DMSO stocks, store at −20°C in sealed, inerted vials; for aqueous stocks, refrigerate (2–8°C) short term; freeze for longer-term storage and avoid repeated freeze–thaw cycles.
• Reconstitution:
  • For analytical/biological assays, prepare a 10–50 mM stock in anhydrous DMSO. Mix thoroughly (vortex/sonication). If needed, warm gently to room temperature to aid dissolution.
  • For aqueous working solutions, dilute DMSO stock into buffer as the final step to avoid precipitation; keep final DMSO ≤0.5% v/v where assay-sensitive.
  • If supplied as free base and water solubility is insufficient, form an aqueous salt in situ with a stoichiometric mild acid (e.g., HCl) after verifying compatibility.
• Documentation: record preparation date, solvent, concentration, and lot number on vial and in ELN for traceability.

Always refer to the lot-specific CoA/SDS for definitive guidance on storage stability and reconstitution.

Structure and Identity

Brief overview: Rilmenidine is a small-molecule imidazoline-class research reagent often used as a pharmacological tool in receptor biology studies (literature). Item-specific identifiers below reflect the catalog entry.

• SKU: R769888
• Product name: Rilmenidine
• CAS: 54187-04-1
• PubChem CID: 68712 (literature identifier)
• InChIKey (from Product Data): 51277
• 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):

• Contains a cationic, nitrogen-rich heterocycle of the imidazoline/imidazolidine family, characteristic of I1-imidazoline receptor ligands.
• Typically bears an additional heterocycle or amino substituent that tunes basicity and receptor engagement; the structure is compact and polar enough to enable solubility in polar organics and, in salt form, in water.
• No stereogenic centers are commonly reported for rilmenidine; the 2D structure features a five-membered di-aza ring (imidazoline-like) linked to an additional heteroatom-containing moiety.

2D description in words (literature): a five-membered, partially saturated, di-aza ring (imidazoline-like) bearing an exocyclic amino/heterocyclic substituent; overall a small, basic heterocycle-dense scaffold.

Synthetic Utility

Rilmenidine is primarily a finished small molecule used as a research ligand rather than a building block. Nonetheless, its functional groups suggest possible transformations in a medicinal chemistry context (general, literature-informed):

• Basic heterocycle(s): the imidazoline/imidazolidine moiety can be selectively protected (e.g., as an N-acyl or carbamate derivative) to modulate basicity and permeability for prodrug or SAR exploration.
• N-functionalization: acylation/sulfonylation/carbamoylation on an exocyclic amine (if present) enables analog generation to probe receptor selectivity.
• Heterocycle editing: ring opening of imidazoline under acidic or nucleophilic conditions or conversion to amidines/guanidines provides access to analog series to map activity cliffs (requires careful control to avoid over-degradation).
• Isotopic labeling: 2H/13C/15N labeling can be introduced synthetically on the heterocycle or side chain to create internal standards for LC–MS quantitation.

Caveats:

• Nitrogen-rich heterocycles can show sticky chromatography and peak tailing; use basic modifiers (e.g., 0.1–0.5% Et3N or ammonium buffers) in flash/prep HPLC.
• Avoid strong oxidants and high-temperature basic conditions that may degrade imidazoline cores.

These are general strategies; specific reaction schemes depend on the exact substitution pattern and supplied form (free base vs. salt).

Target Specificity

No antibody or biologic target information is associated with this catalog entry. This product is a small-molecule chemical, not an antibody or protein reagent.

• Target specificity data (clone, isotype, species reactivity, antigen, epitope): Not applicable.

For small-molecule biological studies, consult primary literature for receptor binding profiles, off-target panels, and functional selectivity of rilmenidine under your assay conditions.