proparacaine - Moligand™ , CAS No.499-67-2

CAS: 499-67-2 Cat. No.: P612944 Formula: C16H27ClN2O3 Molecular Weight: 330.86 PubChem CID: 4935

GRADE & PURITY Moligand™

Synonyms

Ophthaine | S01HA04 | HMS3604H05 | SCHEMBL23334 | AB00444123_07 | Proximetacaina (INN-Spanish) | FT-0658833 | Prestwick1_000959 | Prossimetacaina [DCIT] | DTXSID30198146 | KCLANYCVBBTKTO-UHFFFAOYSA-N | Proxymetacainum | EN300-22731623 | J-017667 | C07383

Storage

Room temperature

Specifications

Synonyms

Ophthaine | S01HA04 | HMS3604H05 | SCHEMBL23334 | AB00444123_07 | Proximetacaina (INN-Spanish) | FT-0658833 | Prestwick1_000959 | Prossimetacaina [DCIT] | DTXSID30198146 | KCLANYCVBBTKTO-UHFFFAOYSA-N | Proxymetacainum | EN300-22731623 | J-017667 | C07383

Specifications & Purity

Moligand™

Storage

Room temperature

Grade

Moligand™

Names and Identifiers

• Canonical Smiles: CCCOC1=C(C=C(C=C1)C(=O)OCCN(CC)CC)N
• IUPAC Name: 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
• InChIKey: KCLANYCVBBTKTO-UHFFFAOYSA-N
• INCHI: 1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3
• Isomeric SMILES: CCCOC1=C(C=C(C=C1)C(=O)OCCN(CC)CC)N
• PubChem CID: 4935
• Molecular Weight: 330.86

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acid esters
• Alternative Parents: Aminobenzoic acids and derivatives Aminophenyl ethers Phenoxy compounds Benzoyl derivatives Aniline and substituted anilines Alkyl aryl ethers Trialkylamines Carboxylic acid esters Amino acids and derivatives Monocarboxylic acids and derivatives Primary amines Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aminobenzoic acid or derivatives - Benzoate ester - Aminophenyl ether - Phenoxy compound - Benzoyl - Aniline or substituted anilines - Phenol ether - Alkyl aryl ether - Amino acid or derivatives - Tertiary aliphatic amine - Tertiary amine - Carboxylic acid ester - Carboxylic acid derivative - Ether - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Amine - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
• External Descriptors: benzoate ester

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

Associated Targets(Human)

SIGMAR1 Tclin Sigma non-opioid intracellular receptor 1 (2 Activities)

Discover Target: SIGMAR1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

Discover Target: PDE5A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HMGCR Tclin HMG-CoA reductase (2475 Activities)

Discover Target: HMGCR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

INSR Tclin Insulin receptor (5558 Activities)

Discover Target: INSR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

Discover Target: ADRB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

Discover Target: ACE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

Discover Target: DRD2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

Discover Target: GABRA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

Discover Target: CNR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD4 Tchem Dopamine D4 receptor (7907 Activities)

Discover Target: DRD4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH2 Tclin Histamine H2 receptor (5428 Activities)

Discover Target: HRH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

Discover Target: ADRA1D

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

Discover Target: HTR1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

Discover Target: HTR2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

Discover Target: HTR2C

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

Discover Target: AVPR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

Discover Target: AGTR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CALCR Tclin Calcitonin receptor (2215 Activities)

Discover Target: CALCR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

Discover Target: SLC6A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH1 Tclin Histamine H1 receptor (7573 Activities)

Discover Target: HRH1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

Discover Target: ADRA1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

Discover Target: OPRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

Discover Target: DRD3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

Discover Target: PPARG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

Discover Target: AVPR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRD1 Tclin Delta opioid receptor (15096 Activities)

Discover Target: OPRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRK1 Tclin Kappa opioid receptor (16155 Activities)

Discover Target: OPRK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

Discover Target: HTR3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

Discover Target: GRIN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

Discover Target: HTR4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

Discover Target: Agtr2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mc4r Melanocortin receptor 4 (1205 Activities)

Discover Target: Mc4r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ltc4s Leukotriene C4 synthase (1 Activities)

Discover Target: Ltc4s

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Sigmar1 Sigma opioid receptor (160 Activities)

Discover Target: Sigmar1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

Discover Target: Npy1r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cckar Cholecystokinin A receptor (90 Activities)

Discover Target: Cckar

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pde4d Phosphodiesterase 4D (4 Activities)

Discover Target: Pde4d

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nos2 Nitric oxide synthase, inducible (3573 Activities)

Discover Target: Nos2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp9 Matrix metalloproteinase 9 (38 Activities)

Discover Target: Mmp9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

lef Anthrax lethal factor (7585 Activities)

Discover Target: lef

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Scn2a Sodium channel alpha subunits; brain (Types I, II, III) (344 Activities)

Discover Target: Scn2a

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Glra2 Glycine receptor (1745 Activities)

Discover Target: Glra2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SARS-CoV-2 (38078 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 294.390 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 294.194 Da
• Monoisotopic Mass: 294.194 Da
• Topological Polar Surface Area: 64.800 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 295.000
• 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 vendor-validated protocols (WB, IHC, IF, FC, etc.) apply to this small-molecule library compound.

General research handling (for planning only):

• Prepare concentrated stock solutions in anhydrous DMSO (e.g., 10–50 mM). Vortex and, if needed, sonicate briefly to dissolve.
• For biological assays, dilute stock into pre-warmed buffer/media to the desired concentration, keeping final DMSO typically ≤0.5–1% v/v. Filter (0.22 µm) if particulate persists.
• Include appropriate vehicle controls and confirm pH to ensure amine protonation if solubility/activity is pH-dependent.

For any application-specific protocol, consult primary literature relevant to your assay system.

Biological Roles

• Context (literature; no clinical/therapeutic claims):

  • Proparacaine is widely used in research as an ester-type local-anesthetic scaffold. Its primary biophysical action is reversible inhibition of voltage-gated sodium channels (Nav), stabilizing the inactivated state and reducing action potential propagation in excitable membranes.

• Target class and SAR (literature, general):

  • Shares the classic aromatic ring–ester–tertiary amine pharmacophore with procaine/tetracaine; lipophilicity and amine basicity influence membrane partitioning and channel affinity.
  • Protonated amine forms access the channel from the intracellular side; neutral form contributes to membrane permeation. Therefore, activity in cellular assays is pH-dependent.

• ADME-relevant features for in vitro studies (general):

  • Ester bond is susceptible to esterase-mediated hydrolysis; useful as a positive control in metabolic stability assays (plasma/carboxylesterases).
  • Tertiary amine promotes lysosomal trapping in cells at low pH; consider this for intracellular distribution studies.

• Off-target considerations (research literature):

  • At higher concentrations, ester-type anesthetics may interact with other ion channels and receptors (e.g., K+ channels, NMDA receptor modulation), which can be relevant in polypharmacology screens; design controls accordingly.

• Form considerations:

  • Free base vs hydrochloride: The hydrochloride exhibits improved aqueous solubility and more predictable protonation in physiological buffers, often preferred for biological assays.

Buffer Applications

This product is not a buffering reagent and is not typically used to prepare defined pH buffer systems.

• Practical guidance:
  • When used in biological assays, select a buffer (e.g., PBS, HEPES, Tris) with pH below the tertiary amine pKa to ensure adequate protonation and solubility of the compound or use a soluble salt form (e.g., HCl).
  • Maintain low organic cosolvent content (commonly ≤0.5–1% v/v DMSO) to minimize assay interference.

For buffer recipes and pH ranges, refer to dedicated buffering agents rather than this compound.

Green Alternatives

Because proparacaine is a specific small-molecule scaffold rather than a commodity reagent or solvent, “green alternative” considerations center on solvent choice, handling, and minimizing waste rather than replacing the compound itself.

• Solvent and process considerations (general, literature):

  • Prefer greener dipolar aprotics (e.g., propylene carbonate, Cyrene) or bio-based esters when compatible with your assay/synthesis, as alternatives to DMF/NMP.
  • Use ethanol or isopropanol in place of halogenated solvents for routine cleaning or where solubility permits.
  • For salt formation and crystallization, ethyl acetate and isopropyl acetate can substitute for dichloromethane/diethyl ether in many cases.

• Waste minimization:

  • Prepare concentrated DMSO stocks and aliquot to reduce freeze–thaw cycles and disposal of partially used solutions.
  • Apply micro-scale reaction/assay formats to reduce solvent and sample consumption.

• Tradeoffs:

  • Greener solvents may alter solubility or assay performance; confirm compatibility and target engagement empirically. Avoid conditions that promote ester hydrolysis (strong base, high temperature in alcohols) when swapping media.

Note: No greener “substitute molecule” is suggested since the compound’s identity drives the biology; focus on greener media and workflows.

Pharmaceutical Uses

This catalog item is provided strictly for research use only. It is not an excipient and is not supplied under pharmacopeial monograph compliance.

• Formulation-relevant notes (literature/general; not a use claim):
  • The free base can be converted to pharmaceutically relevant salts (e.g., hydrochloride) to enhance aqueous solubility and enable aqueous dosing in pre-formulation studies.
  • The ester functionality is hydrolytically labile; formulation pH and excipient selection should minimize acid/base-catalyzed cleavage. Inclusion of buffers at mildly acidic pH and control of ionic strength can improve stability in solution during short-term studies.
  • For solid-state work, polymorphism/solvate formation may be explored, but batch-specific solid-state data are Not specified for this item; refer to CoA/Spec Sheet if needed.

No therapeutic claims are made or implied; for any regulated use, source GMP-grade material via appropriate channels.

Physical Properties

• Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general values (for contextual planning; not lot-specific specifications):

  • Molecular formula: C16H26N2O3 (free base)
  • Molecular weight: ~293.39 g/mol (free base)
  • Ionization/basicity: tertiary amine pKa (conjugate acid) typically ~8.5–9.2 for diethylaminoethyl esters (literature, class value). The aromatic aniline is far less basic (pKaH << 5).
  • LogP: ester-type local anesthetic scaffolds typically exhibit logP in the ~2–3.5 range (literature, scaffold class; exact measured value should be confirmed from primary sources).
  • Solubility (qualitative, literature):
    • Free base: readily soluble in polar aprotic organics (DMSO, DMF, acetone), alcohols; sparingly soluble in water due to tertiary amine being unprotonated at neutral pH.
    • Protonated salts (e.g., HCl): high aqueous solubility; reduced solubility in nonpolar media.
  • Physical state/appearance: Typically a solid for the free base; exact appearance Not specified for this item; refer to CoA/Spec Sheet.

Notes:

• Always verify exact solubility and refractive index, BP/MP, and density against the Certificate of Analysis for the supplied lot. Where precise numeric values are critical (e.g., formulation concentration limits), rely on experimentally determined data for this batch.

Quality and Grades

• Grade provided: Moligand™ (per Product Data)

  • Moligand™ is Aladdin’s research-grade small-molecule screening quality suitable for chemical biology, ligand discovery, and assay development. It emphasizes structural fidelity and suitability for library use (e.g., DMSO stock preparation, screening plate compatibility).

• Purity and analytical specifications:

  • Exact purity, water content, residual solvents, metal content, and chromatographic purity: Not specified for this item; refer to CoA/Spec Sheet.

• Implications of grade for use:

  • Intended for research use only (as stated). Suitable for SAR exploration, reference control experiments, or as a scaffold in medicinal chemistry campaigns.
  • UV background/LC-MS behavior: Aromatic ester with tertiary amine typically shows strong UV absorbance in the 200–280 nm region and ionizes well in positive-mode ESI; confirm background/UV cutoff on the CoA before HPLC/UPLC method development.

• Stabilizers/additives:

  • None specified for this item; refer to CoA/Spec Sheet. As a tertiary amine/ester, stability is typically good under dry, neutral conditions; avoid prolonged exposure to moisture or base which may elevate hydrolysis risk.

• Documentation provided on request:

  • CoA (batch-specific analytical results), NMR/LC-MS traces where available, and Safety Data Sheet.

Reaction and Applications

• Research applications (manufacturer category: small molecule/compound library):

  • Employed as a reference scaffold in ion-channel research, particularly for studies on voltage-gated sodium channels (literature), and as a comparator in esterase/metabolic stability assays.

• Chemical behavior and transformations (literature, general):

  • Ester hydrolysis: Subject to acid- or base-catalyzed hydrolysis to yield 3-amino-4-propoxybenzoic acid and 2-(diethylamino)ethanol. Base-catalyzed pathways are typically faster; care is advised in alkaline media.
  • Salt formation: The tertiary amine readily forms crystalline salts (e.g., HCl), enhancing aqueous solubility and enabling alternative crystallization/handling.
  • N-acylation/alkylation: The aniline (ring –NH2) is less nucleophilic; selective acylation under activated conditions is feasible for probe derivatization. The tertiary amine can be quaternized (e.g., methyl iodide) to generate permanently charged analogs for SAR or transport studies.
  • Oxidative dealkylation: Tertiary amines may undergo N-dealkylation with appropriate oxidants or via metabolic systems (literature model reactions).

• Assay and analytical notes:

  • Strong UV chromophore facilitates HPLC/UPLC detection at 220–260 nm; MS detection in ESI(+). Monitor for ester cleavage products in stability-indicating methods.
  • For binding/functional assays, prepare fresh aqueous working dilutions from DMSO stocks; verify final pH to ensure the amine is appropriately protonated if target studies require.

• Practical tips:

  • Exclude moisture and base during storage and sample prep to minimize hydrolysis.
  • For long runs, add stabilizing acid (trace HOAc) to mobile phases to maintain protonation and sharper peaks in RP-HPLC.

Reaction Conditions

General literature guidance for transformations involving this scaffold (not specifications for this item):

• Ester hydrolysis:

  • Base-catalyzed: NaOH or K2CO3 (0.5–2.0 M aqueous or alcoholic), 20–50°C, minutes to hours; monitor by HPLC/TLC. Quench carefully and acidify to isolate the acid.
  • Acid-catalyzed: HCl or H2SO4 (0.1–1.0 M, aqueous or MeOH), reflux if needed; slower and may cause transesterification in alcohols.

• Salt formation (hydrochloride):

  • Dissolve free base in dry EtOAc or ether (0.05–0.2 M). Bubble dry HCl in ether or add 2–3 eq of 2 M HCl in ether at 0–25°C. Stir 0.5–2 h; collect crystalline salt, wash with cold ether, dry under vacuum.

• Quaternization of tertiary amine:

  • MeI or MeOTf (1.1–2.0 eq) in MeCN or acetone, 0–25°C, 1–12 h; isolate the quaternary ammonium salt by precipitation with ether.

• N-acylation of aniline:

  • Activated acyl donors (acyl chlorides/anhydrides) with base (Et3N, pyridine) in DCM 0–25°C; protect the tertiary amine if selectivity is required (e.g., Boc2O to protect as ammonium salt is insufficient due to tertiary amine).

• Analytical monitoring:

  • RP-HPLC with acidic modifier (0.1% formic acid) improves peak shape via amine protonation; ESI(+) MS readily detects [M+H]+.

These conditions are representative from literature for analogous ester/tertiary amine scaffolds; optimize for your substrate and scale.

Safety and Handling

• Item-specific GHS classification, signal word, H-statements, and pictograms: Not specified for this item; refer to the SDS for authoritative safety information.

• General hazards (literature/analog-based; for planning only):

  • Organic tertiary amine/aryl-ester may cause irritation to skin, eyes, and respiratory tract. Avoid inhalation of dust and contact with eyes/skin.
  • Combustible organic solid; keep away from ignition sources and oxidizers.

• Recommended PPE and controls (good laboratory practice):

  • Wear lab coat, appropriate chemically resistant gloves (e.g., nitrile), and safety glasses or face shield when handling powders/solutions.
  • Handle in a fume hood to minimize exposure to dust or vapors from solvents used for dissolution.

• Incompatibilities (general):

  • Strong oxidizing agents; strong acids/bases can promote decomposition (acid/base-catalyzed ester hydrolysis). For salt formation, use controlled acidification with compatible mineral acids; avoid excess strong base in aqueous media if ester integrity is required.

• First-aid overview (summary; refer to SDS/site procedures):

  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation occurs.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Waste and spill response:

  • Absorb small spills with inert material; dispose per institutional hazardous waste protocols. Avoid release to the environment.

Always defer to the Aladdin SDS for this catalog item before use.

Solvent Selection

Proparacaine (free base) behaves as a moderately lipophilic, basic aromatic ester.

• Polarity/miscibility (literature, general):

  • Highly soluble: DMSO, DMF, acetonitrile, acetone, ethanol, methanol, dichloromethane, ethyl acetate.
  • Limited solubility: Water at neutral/basic pH (free base). Aqueous solubility increases markedly upon protonation (e.g., HCl salt) or in buffered media below the pKa of the tertiary amine.
  • Partitioning: Expected to favor organic phase in biphasic systems unless protonated.

• Practical selection by application:

  • Screening stocks: Prepare 10–50 mM in anhydrous DMSO; dilute into assay buffers ensuring final DMSO ≤0.5–1% v/v if biological assays are planned.
  • Synthetic manipulations: Use aprotic solvents (DCM, EtOAc, MeCN) to preserve the ester; avoid prolonged exposure to aqueous base or hot alcohols under strongly acidic/basic conditions.
  • Salt formation/ion-exchange: For generating hydrochloride, dissolve base in anhydrous ether/EtOAc and introduce dry HCl in ether; isolate crystalline salt with improved aqueous handling.

• Comparison notes (literature, general):

  • DMSO vs DMF: DMSO offers superior solvating power and biological compatibility for stock solutions; DMF is more challenging to remove and has regulatory concerns.
  • MeOH/EtOH: Convenient for NMR and preparative work; monitor for potential transesterification under strongly acidic/basic conditions at elevated temperature.

Always confirm solubility and compatibility with your specific assay/route.

Storage and Reconstitution

• Item-specific storage (from Product Data): Room temperature.

• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Stability and handling (general guidance for the free base):

  • Store tightly capped, in a desiccator or with desiccant, protected from light and moisture to limit ester hydrolysis.
  • Avoid prolonged exposure to strong acids/bases. Under dry, neutral conditions, aromatic esters with tertiary amines are typically stable for extended periods.

• Reconstitution/preparation of solutions (general, not lot-specific):

  • For screening stocks, dissolve in anhydrous DMSO to 10–50 mM. If needed, warm gently (≤40°C) and/or sonicate briefly. Alternatively, prepare a soluble salt (e.g., HCl) for aqueous work.
  • Filter sterilize solutions intended for cell-based assays (0.22 µm PTFE/nylon). Prepare fresh working dilutions immediately before use.
  • Aliquot DMSO stocks to avoid repeated freeze–thaw; store aliquots at −20°C to −80°C for long-term solution stability. Note: These are general practices for solutions and do not override the item’s solid storage condition.

• Expiry/retention:

  • Refer to the product label/CoA for retest or expiration dating. Inspect periodically for discoloration or degradation by HPLC.

For any deviations or critical applications, consult the CoA and SDS for this specific lot.

Structure and Identity

Brief description: Proparacaine is an aromatic ester bearing a tertiary diethylaminoethyl side chain and a propoxy- and amino-substituted benzoate core; it is an ester-type local-anesthetic scaffold used widely as a small-molecule reference compound in research.

• Item-specific (from Product Data):

  • SKU: P612944
  • Product name: proparacaine
  • CAS: 499-67-2
  • CID: 4935
  • InChIKey: 176473 (as provided; see literature identifiers below)
  • Grade: Moligand™
  • Storage condition: Room temperature

• Literature identifiers (for reference; not a specification of this lot):

  • Synonyms: 3-amino-4-propoxybenzoic acid 2-(diethylamino)ethyl ester; proparacaine free base
  • Molecular formula (literature): C16H26N2O3
  • Molecular weight (literature): ~293.39 g/mol
  • SMILES (literature): CCCOC1=CC(=C(C=C1)N)C(=O)OCCN(CC)CC
  • InChIKey (literature): commonly reported as a 27-character hash corresponding to the above structure (consult NIST/PubChem for definitive string)

• Structural features (general description):

  • Aromatic ring (benzene) bearing a meta-amino (–NH2) and para-propoxy (–O–CH2–CH2–CH3) substituent relative to the benzoate carbonyl.
  • Benzoate ester linking to a 2-(diethylamino)ethyl moiety; the amine is a tertiary amine (basic, readily forms salts).
  • Functional groups: aromatic amine, aryl ether, aryl ester, tertiary aliphatic amine.
  • 2D structure in words: A substituted benzoate where the ring carries –NH2 and –O–Pr groups, the carboxyl is esterified with –O–CH2–CH2–N(Et)2.

Synthetic Utility

Although proparacaine is most often a research probe rather than a starting reagent, its functional groups enable several useful synthetic manipulations and derivative preparations (literature/general):

• Transformations on the ester:

  • Hydrolysis to the corresponding acid and alcohol under acidic or basic conditions.
  • Transesterification under acidic catalysis with alternative alcohols to tune lipophilicity.
  • Formation of activated esters (e.g., p-nitrophenyl, NHS) from the acid after hydrolysis for subsequent coupling.

• Amine derivatization:

  • Tertiary amine quaternization (e.g., MeI, MeOTf) to yield permanently charged analogs for permeability/uptake studies.
  • Formation of acid–base salts with mineral or organic acids for crystallization and solubility modulation.

• Aromatic amine (aniline) chemistry:

  • Electrophilic acylation/sulfonylation under activated conditions to prepare labeled or bulkier derivatives.
  • Diazonium chemistry is generally disfavored due to ring substitution pattern and potential deactivation; proceed only with careful control if attempted.

• Labeling/probe development:

  • Introduction of reporter groups (fluorophores, affinity tags) via linker installation after initial hydrolysis/re-esterification or via amide formation on the aniline nitrogen to create tool compounds.

• Retrosynthetic note:

  • The scaffold arises from esterification of 3-amino-4-propoxybenzoic acid with 2-(diethylamino)ethanol; both fragments are accessible, enabling isotopic or structurally modified analogs through convergent coupling.

Target Specificity

Not an antibody or biologic; no immunochemical target specificity, clone, isotype, or species reactivity applies.

• For small-molecule target engagement (literature context): proparacaine is commonly studied as a blocker of voltage-gated sodium channels (Nav), but this is pharmacological activity rather than “specificity” in the immunoreagent sense.