Determine the necessary mass, volume, or concentration for preparing a solution.
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Specifications
Synonyms
Cyclogyl
Specifications & Purity
Moligand™, ≥98%
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.
Grade
Moligand™
Purity
≥98%
Product Properties
pKa
pKa: 8.22 (Predicted)
Names and Identifiers
Canonical Smiles
CN(C)CCOC(=O)C(C1=CC=CC=C1)C2(CCCC2)O
IUPAC Name
2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
InChIKey
SKYSRIRYMSLOIN-UHFFFAOYSA-N
INCHI
1S/C17H25NO3/c1-18(2)12-13-21-16(19)15(14-8-4-3-5-9-14)17(20)10-6-7-11-17/h3-5,8-9,15,20H,6-7,10-13H2,1-2H3
Isomeric SMILES
CN(C)CCOC(=O)C(C1=CC=CC=C1)C2(CCCC2)O
Molecular Weight
291.39
Reaxy-Rn
2147087
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2147087&ln=
Advanced Data
Taxonomic Classification
Taxonomy Tree
- Kingdom Organic compounds
- Superclass Benzenoids
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzene and substituted derivatives |
| Alternative Parents | Cyclopentanols Tertiary alcohols Trialkylamines Cyclic alcohols and derivatives Carboxylic acid esters Amino acids and derivatives Monocarboxylic acids and derivatives Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Monocyclic benzene moiety - Cyclopentanol - Cyclic alcohol - Tertiary alcohol - Amino acid or derivatives - Carboxylic acid ester - Tertiary aliphatic amine - Tertiary amine - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Alcohol - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
| External Descriptors | tertiary alcohol - tertiary amino compound - carboxylic ester |
3D Structure
Interactive Chemical Structure Model
Associated Targets(Human)
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
PGR Tclin Progesterone receptor (8562 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
AR Tclin Androgen Receptor (11781 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
DRD2 Tclin Dopamine D2 receptor (23596 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
MAOA Tclin Monoamine oxidase A (11911 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
HRH2 Tclin Histamine H2 receptor (5428 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SLC6A4 Tclin Serotonin transporter (12625 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HRH1 Tclin Histamine H1 receptor (7573 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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OPRM1 Tclin Mu opioid receptor (19785 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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DRD3 Tclin Dopamine D3 receptor (14368 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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OPRD1 Tclin Delta opioid receptor (15096 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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OPRK1 Tclin Kappa opioid receptor (16155 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SLC6A3 Tclin Dopamine transporter (10535 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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KCNH2 Tclin HERG (29587 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)
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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)
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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)
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MC3R Tchem Melanocortin receptor 3 (5659 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MLNR Tchem Motilin receptor (1724 Activities)
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Associated Targets(non-human)
Mc4r Melanocortin receptor 4 (1205 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Npy1r Neuropeptide Y receptor type 1 (8 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Cckar Cholecystokinin A receptor (90 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Pde4d Phosphodiesterase 4D (4 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Hdac6 Histone deacetylase 6 (222 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mechanisms of Action
Certificates (CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
| Refractive Index | n20D~1.56 (Predicted) |
|---|---|
| Boil Point(°C) | ~409.6° C at 760 mmHg (Predicted) |
| Melt Point(°C) | 134-141° C |
| Molecular Weight | 291.400 g/mol |
| XLogP3 | 2.700 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 7 |
| Exact Mass | 291.183 Da |
| Monoisotopic Mass | 291.183 Da |
| Topological Polar Surface Area | 49.800 Ų |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Complexity | 331.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
Solution Calculators
Reviews
Customer Reviews
Application Protocols
No tested application protocols are provided for this specific catalog item. The following are general, non-validated examples to guide internal method development; adjust to your system and consult the CoA/SDS.
Example: preparation of DMSO stocks for screening
- Allow vial to equilibrate to room temperature in a desiccator. Calculate target concentration (e.g., 10–50 mM) using the lot-specific MW from the CoA. Add dry DMSO, vortex until dissolved, and aliquot into low-bind tubes. Store at −20 °C.
Example: aqueous working solution
- Immediately before use, dilute the DMSO stock into pre-chilled assay buffer (e.g., PBS or HBSS) to the desired final concentration, keeping DMSO ≤0.5% v/v. If precipitation occurs, acidify slightly (e.g., add 1–2 mM HCl) or increase dilution factor.
Example: LC–MS method check (qualitative)
- Mobile phase A: water + 0.1% formic acid; B: acetonitrile + 0.1% formic acid. Gradient 5–95% B over 5–7 min, ESI+ detection. Prepare calibration from serial dilutions of the DMSO stock into A/B mixture.
Notes
- Filter aqueous working solutions through 0.22 µm PVDF or PTFE if compatible. Minimize exposure to strong base or elevated temperature to limit ester hydrolysis.
- For any biological assay use, establish target-specific SOPs (ligand incubation time, wash steps, and controls).
Biological Roles
General/literature context (no clinical claims)
- Cyclopentolate is widely used in research as a ligand that antagonizes muscarinic acetylcholine receptors (mAChRs). As a tertiary amine arylglycolate, it interacts with the orthosteric binding site of M1–M5 subtypes in a manner comparable to other classical antimuscarinic scaffolds.
- Its tertiary amine and bulky arylglycolate motif confer affinity and subtype-dependent potency; researchers employ it as a benchmark comparator in radioligand binding, functional assays (e.g., inhibition of acetylcholine-evoked responses), and target validation studies.
ADME-relevant features (research context, literature)
- Protonation state strongly affects membrane permeability and aqueous solubility. The free base is more membrane-permeant, while protonated forms are more water-soluble.
- Ester functionality can undergo hydrolysis in biological matrices (plasma/esterases), a consideration for stability assays and kinetic modeling.
Experimental use notes
- Typical handling in vitro: prepare DMSO stocks and dilute into buffered systems immediately prior to use; keep final organic content minimal.
- Include controls for non-specific binding and time-dependent loss (esterase activity) when working with cell or tissue preparations.
Research use only
- As stated by the manufacturer: For research use only. Not for human or veterinary use, diagnostic procedures, or clinical applications.
Buffer Applications
Cyclopentolate is not a buffering agent and does not participate in defined acid–base buffer systems.
Practical guidance for assays (general)
- If aqueous work is required, adjust the pH of the receiving buffer to mildly acidic conditions (e.g., pH 5.5–6.5) to keep the tertiary amine protonated and enhance solubility; use compatible buffers such as acetate, citrate, or phosphate at the desired ionic strength.
- Minimize residence time in aqueous buffers to limit ester hydrolysis; prepare working solutions immediately before use.
Stock handling
- Prepare concentrated stocks in DMSO or ethanol; dilute into buffer with vigorous mixing to avoid precipitation. Maintain low final organic cosolvent levels as required by the assay.
For buffer recipes, ionic strengths, and pH ranges, follow your assay’s validated SOPs; Cyclopentolate itself does not define a buffering range.
Green Alternatives
As Cyclopentolate is a small-molecule library member (not a process solvent or bulk reagent), “green alternatives” pertain mainly to solvent choices and handling practices during its use.
Greener solvent strategies (general/literature)
- Prefer water-rich vehicles whenever feasible by using the protonated/salt form to enhance aqueous solubility, reducing reliance on high-boiling polar aprotics.
- If an organic co-solvent is required, consider ethanol or isopropanol as more benign options relative to DMF or NMP; acetonitrile and methanol are commonly used but have higher toxicity footprints than ethanol.
- For stock solutions, DMSO remains standard due to stability and miscibility; minimize volumes and ensure proper waste segregation.
Example comparison (general)
- DMSO: excellent solvency/stability; moderate EHS concerns; widely accepted in HTS (keep % v/v low).
- Ethanol: renewable, low toxicity; may not fully dissolve free base at high concentrations; flammable.
- Water (buffered, pH-adjusted): greenest option if compound is protonated or formulated as a salt; monitor ester stability.
Operational green practices
- Use micro-aliquots to avoid repeated thawing and discard; reduces waste.
- Employ LC–MS methods with lower organic consumption (UHPLC, microflow) and solvent recycling when possible.
- Choose acid salts that avoid hazardous counter-ions (e.g., HCl or acetate rather than perchlorate) when preparing aqueous formulations.
Note: No alternative “reagent” substituting for Cyclopentolate is suggested here since it is a specific screening ligand; selection depends on biological target requirements.
Pharmaceutical Uses
Context and scope
- This product is provided strictly for research use only. No medical, diagnostic, or clinical use is intended or permitted.
Role in pharmaceutical R&D (general/literature)
- Employed as a reference standard or comparator ligand in discovery pharmacology targeting muscarinic acetylcholine receptors (mAChRs), aiding assay development, control benchmarking, and structure–activity relationship (SAR) studies.
- Useful for stability-indicating method development (e.g., forced degradation to understand ester hydrolysis pathways) and for validating bioanalytical LC–MS/MS methods in matrices.
Formulation considerations for preclinical experiments (non-clinical research)
- Stock solutions typically in DMSO; for in vitro aqueous dosing, adjust pH or use salt forms to enhance solubility. Include polysorbate or PEG-based co-solvents only if compatible with the model system.
- Avoid strong base and elevated temperatures to reduce ester cleavage; store aliquots at −20 °C.
Regulatory/pharmacopeial status
- Any compendial status, excipient functionality, or clinical formulation specifications are Not specified for this item; refer to public compendia and internal QA policies if reference standards are 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 reference values and qualitative behavior (for planning only; not product specifications)
- Aggregate state: the free base is commonly encountered as an oil or low-melting solid under ambient conditions; salt forms (e.g., HCl) are typically crystalline.
- Solubility: high solubility in polar aprotic organic solvents (DMSO, DMF, acetonitrile) and alcohols (MeOH, EtOH); limited aqueous solubility for the free base at neutral pH due to tertiary amine lipophilicity; markedly improved water solubility upon protonation (acidic pH or as mineral-acid salts).
- Acid/base: contains a tertiary aliphatic amine (basic; readily protonated under mildly acidic conditions). The arylglycolate ester is sensitive to strong base and prolonged aqueous acid.
- Volatility: low; not used as a volatile solvent.
- Partitioning: expected to be moderately lipophilic as the free base and much more hydrophilic when protonated (qualitative).
Practical notes
- Prepare DMSO stock solutions (e.g., 10–50 mM) for screening workflows; dilute into aqueous buffers immediately before use to minimize ester hydrolysis.
- Avoid strong base or extended exposure to high-temperature aqueous media to limit degradation. Always confirm exact properties for your lot from the CoA or SDS.
Quality & Grades
Item-specific grade
- Grade/Purity: Moligand™ (as listed). This designation indicates suitability for use in small-molecule screening collections and ligand-discovery workflows, emphasizing identity confirmation and usability for assay stock preparation.
What Moligand™ implies (general guidance for this catalog line)
- Identity and traceability: typically supported by orthogonal characterization (e.g., NMR/HRMS or LC–MS) to confirm structure and mass; users should consult the CoA for the exact tests performed on this lot.
- Purity expectations: optimized for discovery screening and SAR work; UV chromatographic purity is commonly targeted in such libraries, but exact % purity and impurity limits are Not specified for this item; refer to CoA/Spec Sheet.
- Form: supplied as the free base unless otherwise noted; salt form, residual solvent, and water content are Not specified for this item; refer to CoA/Spec Sheet.
Implications for use
- Analytical compatibility: suitable for preparation of DMSO stocks for HTS or biochemical assays; low non-volatile residue is typically preferred for plate-based dispensing.
- Documentation: request and retain the lot-specific CoA/SDS to confirm assay-relevant attributes (identity, purity, counter-ions, residual volatiles, and storage guidance).
Comparison to other grades (context)
- Reagent/AR grade focuses on general synthetic use; HPLC/LC–MS grade emphasizes ultra-low UV background/particulates for analytical work. Moligand™ prioritizes screening readiness and confirmed identity for small-molecule libraries.
Reaction & Applications
This product is supplied as a research small molecule (Moligand™). It is not primarily a synthetic reagent, but its functional groups offer recognizable reactivity and analytical applications.
Functional-group reactivity (general/literature)
- Tertiary amine: readily protonated (salt formation), quaternized via alkyl halides; can be engaged in ion-pair extraction and derivatization for analytical detection.
- Aryl–tertiary glycolate ester: susceptible to hydrolysis (acid/base-catalyzed) to yield the corresponding tertiary alcohol and carboxylic acid/amide analogs; transesterification possible under standard conditions.
Typical laboratory uses
- Reference/benchmark ligand in receptor-binding and enzyme-modulation studies (biochemical/pharmacology research). No medical use or claims; for research only.
- Analytical standard for method development (HPLC/LC–MS) evaluating extraction, ionization, and stability of tertiary amine esters.
Practical tips
- Prepare and store concentrated stocks at low temperature (−20 °C) in dry DMSO. Minimize freeze–thaw by aliquoting.
- For salt formation or pKa profiling, titrate with standardized acid (e.g., HCl in ethanol/water) and monitor by pH-metry or spectrophotometry.
- For hydrolysis studies, use buffered media (e.g., pH 1–2 and pH 10–11) at controlled temperature to map degradation kinetics; analyze by LC–MS to identify alcohol/acid fragments.
Named reactions/context
- Quaternization (Menshutkin-type) with alkyl halides (literature) to prepare permanent cationic derivatives for separation or mechanistic study.
- Standard Fischer–Speier or base-catalyzed transesterification on related arylglycolates can be adapted to scaffold modification in SAR exploration.
Reaction Conditions
The following are general, literature-type conditions relevant to functional groups present in Cyclopentolate and are not product specifications.
Salt formation (protonation)
- Conditions: dissolve free base in anhydrous ethanol or ether and treat with 1.0–1.1 equiv of dry HCl (gaseous or ethanolic) at 0–25 °C; isolate the precipitated hydrochloride salt by filtration and dry under vacuum.
- Notes: maintain anhydrous conditions for reproducibility; confirm stoichiometry by titration or NMR.
Ester hydrolysis (for stability/derivatization studies)
- Acid-catalyzed: 0.1–1 M HCl, aqueous or aqueous–alcoholic, 25–60 °C; monitor by LC–MS until consumption; neutralize and extract products.
- Base-catalyzed: 0.05–0.5 M NaOH or K2CO3 in MeOH/H2O or THF/H2O, 0–25 °C; avoid overexposure to prevent side reactions with the tertiary alcohol.
Quaternization (Menshutkin-type)
- Conditions: alkyl halide (e.g., MeI, EtI) in acetonitrile or acetone, 20–50 °C, 2–24 h; isolate quaternary ammonium salt by precipitation or chromatography.
- Considerations: choose alkylating agent carefully to balance reactivity and safety; monitor by TLC/LC–MS.
Transesterification
- Conditions: catalytic acid (p-TsOH) in the target alcohol under Dean–Stark (for higher-boiling alcohols) or catalytic base (NaOMe in MeOH) at 0–25 °C; protect the tertiary alcohol if necessary.
Analytics
- Recommended monitoring by HPLC or LC–MS with a water/acetonitrile gradient (0.1% formic acid) for amine protonation and sharp peak shape.
All conditions should be optimized and validated on small scale before scale-up, considering the ester’s sensitivity.
Safety & Handling
GHS/SDS information
- Signal word, hazard statements, GHS classification, and pictograms: Not specified for this item; refer to SDS for authoritative information.
General laboratory precautions (general guidance; not a substitute for SDS)
- PPE: wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dusts/aerosols.
- Hygiene: avoid contact with skin and eyes; wash thoroughly after handling. Prevent ingestion and inhalation.
Chemical hazards (general for tertiary amine arylglycolates)
- Reactivity: tertiary amine can be protonated by acids; ester function can undergo hydrolysis under acidic or basic conditions, especially at elevated temperature.
- Incompatibilities: strong acids/bases (hydrolysis or salt formation), strong oxidizers (amine oxidation), and moisture when prolonged exposure could promote ester cleavage.
First-aid overview (consult SDS and institutional protocols)
- Skin/eye contact: rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
- Inhalation: move to fresh air; monitor breathing; seek medical attention if symptoms occur.
- Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Waste handling
- Collect organic solutions and contaminated materials as hazardous chemical waste. Segregate amine-containing and halogenated streams per local regulations.
Special notes
- For research use only (as stated). Avoid release to the environment; contain spills with inert absorbent and clean promptly.
Solvent Selection
Cyclopentolate is a tertiary amine arylglycolate ester used as a small-molecule screening member rather than a solvent. Solvent selection here refers to dissolving the compound for analytical or biological assays.
Polarity and miscibility (literature/general)
- Free base: moderately lipophilic; dissolves readily in DMSO, DMF, acetonitrile, methanol, and ethanol; sparingly soluble in water at neutral pH.
- Protonated/salt form: markedly increased aqueous solubility (e.g., in dilute HCl or acetate buffer) due to the tertiary ammonium cation.
Practical solvent choices
- Stock solutions: DMSO is preferred for HTS/biochemical assays; prepare 10–50 mM stocks and store frozen to limit ester hydrolysis.
- Working solutions: dilute immediately before use into buffered aqueous media (pH 5.5–7.4) to the desired final concentration, keeping final DMSO ≤0.5–1% v/v for cell-free or ≤0.1–0.5% v/v for cellular assays, as tolerated.
- Analytical sample prep: acetonitrile/water (with 0.1% formic acid) for LC–MS; methanol for HPLC-UV, mindful of ester stability.
When to choose alternatives
- If purely aqueous systems are required, prepare the hydrochloride or another suitable acid salt in situ (e.g., dissolve in minimal ethanol, add equimolar HCl, then dilute with buffer) or formulate with co-solvents (DMSO, ethanol) and surfactants as permitted by the assay.
Compatibility notes
- Avoid strong basic media and prolonged heating in aqueous solvents to prevent ester hydrolysis. Degas and filter working solutions for analytical reproducibility.
Storage & Reconstitution
Item-specific conditions
- Storage: Store at −20 °C (as provided in Product Data).
- Shipping: Shipped in ice chest + ice pads.
- Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance
- Upon receipt, keep the container tightly closed and protect from moisture and light. Allow to equilibrate to room temperature before opening to minimize condensation.
- For long-term use, prepare single-use aliquots (e.g., DMSO stocks) to avoid repeated freeze–thaw cycles that can promote ester hydrolysis.
Reconstitution suggestions (general)
- Organic stocks: dissolve in anhydrous DMSO to prepare 10–50 mM solutions; vortex until fully dissolved. Record the exact concentration based on the lot-specific MW.
- Aqueous use: dilute organic stock into buffer immediately before use. If higher aqueous solubility is required, adjust pH to mildly acidic or prepare a suitable acid salt in situ.
Stability notes
- Avoid strong alkaline media and elevated temperatures. Store solutions at −20 °C; for working solutions, keep on ice and use within the same day where possible.
Documentation
- Refer to the lot-specific CoA and SDS for exact storage limits, shelf life, and any stabilizers or counter-ions present (if applicable).
Structure & Identity
Cyclopentolate is a tertiary-amine-containing arylglycolate ester commonly used as a ligand-like small molecule in discovery screening.
Item-specific identifiers (from Product Data)
- SKU: C349649
- Product name: Cyclopentolate
- CAS: 512-15-2
- CID: 2905
- InChIKey: 338671 (as listed in product data; users should verify against literature/InChI if needed)
- Grade: Moligand™
Structure description (general/literature)
- Core scaffold: an arylglycolate ester bearing a tertiary dimethylaminoethyl side chain and a cyclopentyl-substituted quaternary center adjacent to a phenyl ring.
- Functional groups: tertiary aliphatic amine (basic); arylglycolate ester (acid-labile/ base-sensitive); benzenoid aromatic ring; cycloalkyl (cyclopentyl) substituent; tertiary carbinol center adjacent to the ester carbonyl.
- Stereochemistry: typically supplied/handled as racemate (±) in research contexts; the quaternary center at the glycolate carbon is stereogenic.
Common identifiers (literature, for reference only)
- Molecular formula: C17H25NO3 (literature)
- Molecular weight: ~291.39 g/mol (literature)
- Example SMILES (literature): CN(C)CCOC(=O)C(O)(c1ccccc1)C2CCCC2
2D structure in words: a phenyl ring is bonded to a tertiary carbinol carbon that also bears a cyclopentyl group and an ester carbonyl. The ester connects to a two-carbon chain terminating in a dimethylamino group. The overall motif is an aryl–C(OH)(cyclopentyl)–CO2–CH2–CH2–N(CH3)2.
Synthetic Utility
Although not typically employed as a reagent, Cyclopentolate’s scaffold can participate in transformations valuable for SAR and metabolism-mimicking studies.
Transformational handles (general/literature)
- Tertiary amine: salt formation (HCl, fumarate, citrate) to tune solubility; quaternization (alkyl halides) to generate permanently charged analogs for permeability/transport studies; N-oxidation to explore metabolic liabilities.
- Ester: hydrolysis to the corresponding tertiary alcohol and acid; re-esterification or amide formation to probe prodrug-like or stability-modified variants.
- Aromatic ring: electrophilic aromatic substitution on suitably activated positions is generally limited due to steric/electronic environment; cross-coupling typically requires prefunctionalized analogs.
Retrosynthetic perspective
- The arylglycolate core suggests disconnection into an aryl-substituted α-hydroxyacyl component (mandelate-type) and a 2-dimethylaminoethanol fragment, assembled via esterification.
Analytical derivatization
- Formation of stable quaternary ammonium derivatives can improve LC–MS ionization efficiency and chromatographic retention control in method development.
Use in mechanistic studies
- Controlled hydrolysis under acidic/basic conditions provides a convenient platform to benchmark esterase-mediated degradation versus purely chemical pathways.
Note: The above are literature-general strategies; specific synthetic campaigns should tailor conditions to the sensitivity of the arylglycolate ester and tertiary amine.
Target Specificity
Item-specific targeting details for this SKU are Not specified for this item; refer to CoA/Spec Sheet.
General/literature context (for background only)
- Cyclopentolate is commonly used in research as a nonselective muscarinic acetylcholine receptor (mAChR) antagonist across M1–M5 subtypes. Subtype biases can vary with system and conditions; consult primary literature for quantitative affinity/potency data relevant to your assay.
Recommendation
- When employing this compound as a reference ligand, include internal controls and, where possible, orthogonal readouts (binding vs. function) to verify apparent specificity under your experimental conditions.
Frequently Asked Questions
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
What is Moligand??
Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.
How should this product be stored?
Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 512-15-2, the molecular formula is C17H25NO3, and the molecular weight is 291.39 g/mol. InChIKey SKYSRIRYMSLOIN-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.
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