Buy Daledalin (UK-3557-15) Cas 22136-27-2

Daledalin (UK-3557-15) is an antidepressant which was synthesized and trialed for depression in the early 1970s, but was never marketed.^[1]^[2]^[3] It is a selective norepinephrine reuptake inhibitor, with no significant effects on the reuptake of serotonin and dopamine, and no antihistamine or anticholinergic properties.^[2]^[4]

Synthesis

Daledalin can be prepared by the reduction of amedalin with diborane.^[2]

Daledalin

Norepinephrine Transporter (NET)Selectivity ProfilingAntidepressant Pharmacology

Sourcing a pure, selective NRI reference standard with verified NET specificity is challenging – many analogs exhibit off-target SERT/DAT activity that confounds neuropharmacology assays.

Daledalin (UK-3557-15) is a strictly selective norepinephrine reuptake inhibitor that solves this:

• Confirmed selective NET blockade; no measurable affinity at serotonin or dopamine transporters.

• Indoline scaffold distinct from aryloxypropanamine/tetralin NRIs – enables unique SAR exploration.

• Clinically precedented in depression trials; validated for use in [³H]-NE uptake assays and rodent behavioral models.

For researchers requiring reliable, target-specific NRI reference material with global shipping support.

Daledalin

Catalog No.

S584804

CAS No.

22136-27-2

M.F

C19H24N2

M. Wt

280.4 g/mol

Availability

In Stock

* This item is exclusively intended for research purposes and is not designed for human therapeutic applications or veterinary use.

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General Information

Researchers requiring pure adrenergic pathway mapping often face anticholinergic and sedative artifacts from tricyclic antidepressants. Daledalin (CAS 22136-27-2) provides a highly selective norepinephrine reuptake inhibitor with negligible affinity for serotonin and dopamine transporters. Key advantages: – Clean pharmacological baseline for in vivo models. – Fully reduced indoline core ready for synthetic derivatization. – Reference standard for NET binding calibration. Available with consistent quality and global shipping.

CAS Number

22136-27-2

Product Name

Daledalin

IUPAC Name

N-methyl-3-(3-methyl-1-phenyl-2H-indol-3-yl)propan-1-amine

Molecular Formula

C19H24N2

Molecular Weight

280.4 g/mol

InChI

InChI=1S/C19H24N2/c1-19(13-8-14-20-2)15-21(16-9-4-3-5-10-16)18-12-7-6-11-17(18)19/h3-7,9-12,20H,8,13-15H2,1-2H3

InChI Key

YFAIJBZEDDOCAN-UHFFFAOYSA-N

Synonyms

daledalin, UK 3557

Canonical SMILES

CC1(CN(C2=CC=CC=C21)C3=CC=CC=C3)CCCNC

Daledin (UK-3557-15) is a selective norepinephrine reuptake inhibitor. It has no effects on the reuptake of serotonin or dopamine, and no antihistamine or anticholinergic properties. It was in trials for depression in the 1970s but never marketed.
structure

Purity

≥98%

Package Size

10 mg, 25 mg, 50 mg

Daledalin Overview

Daledalin (CAS 22136-27-2) is a highly selective norepinephrine reuptake inhibitor (NRI) featuring a fully reduced 1-phenylindoline core. Originally synthesized as a targeted alternative to classical tricyclic compounds, it is distinguished by its potent inhibition of the norepinephrine transporter (NET) without significant cross-reactivity at serotonin or dopamine transporters. For procurement professionals and chemical biologists, Daledalin serves as an essential reference standard for monoaminergic neurotransmission assays and a highly processable synthetic precursor for novel indoline derivatives, offering a cleaner pharmacological baseline than broad-spectrum monoamine modulators [1].

Research Fit

WorkflowNET-selective tool compound for noradrenergic signaling studies

SelectionIndoline scaffold distinct from aryloxypropanamine or tetralin NRIs

Use ContextSupports NET pathway research without SERT/DAT interference

References

[1] Koe BK (1976). Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain. Journal of Pharmacology and Experimental Therapeutics. 199 (3): 649–661.

Generic Substitution Risks for Daledalin

Substituting Daledalin with generic tricyclic antidepressants (TCAs) like amitriptyline or imipramine introduces severe confounding variables in both chemical and biological workflows. While TCAs provide baseline monoamine inhibition, they possess high off-target affinities for histaminergic and cholinergic receptors, which generate unwanted parasympatholytic and sedative artifacts in complex tissue models [1]. Furthermore, substituting Daledalin with its immediate structural precursor, amedalin, requires an additional, hazardous diborane reduction step to convert the indolinone into the active indoline pharmacophore [1]. Procuring the exact Daledalin compound ensures immediate synthetic processability and guarantees a clean, selective adrenergic profile free from serotonergic or anticholinergic noise.

Substitution Risk

DaledalinNET-selective with no reported SERT or DAT activity

AtomoxetineMeasurable SERT/DAT affinity may confound NET-specific pathway interpretation

DaledalinReported absence of antihistaminic and anticholinergic activity

TCAs (e.g., amitriptyline)Receptor-class activity may alter behavioral endpoints and sedation confounds

DaledalinIndoline core; calculated LogP ~4.2; distinct physicochemical profile

Reboxetine / TametralineScaffold-dependent permeability and metabolic stability may not transfer directly

References

[1] Cañas-Rodriguez A, Leeming PR (1972). N-Phenyl-2-indolinones and N-phenylindolines. A new class of antidepressant agents. Journal of Medicinal Chemistry. 15 (7): 762–770.

Daledalin Comparative Evidence

Selective NET Inhibition

In rat brain synaptosomal preparations, Daledalin demonstrates potent and highly selective inhibition of norepinephrine uptake while exhibiting negligible affinity for the serotonin transporter (SERT) and dopamine transporter (DAT). This contrasts sharply with classical tricyclic comparators like imipramine or amitriptyline, which display mixed NET/SERT inhibition and confound target-specific readouts [1].

Evidence Dimension	Monoamine reuptake selectivity (NET vs. SERT/DAT)
Target Compound Data	Selective NET inhibition with no significant SERT/DAT blockade
Comparator Or Baseline	Imipramine / Amitriptyline (mixed NET/SERT inhibition)
Quantified Difference	Complete absence of significant SERT/DAT cross-reactivity for Daledalin
Conditions	Rat brain synaptosomal uptake assays

Ensures high-fidelity data in neuropharmacological assays by isolating norepinephrine-driven pathways without serotonergic or dopaminergic confounding variables.

NET selectivity

Cross-study

Negligible SERT/DAT activity vs. atomoxetine’s 26-fold NET/SERT and 44-fold NET/DAT selectivity

Supports NET-specific pathway studies without serotonergic or dopaminergic confounds

Cross-study comparison; verify under assay conditions

Minimal Anticholinergic & Antihistaminic Activity

Pharmacological profiling of Daledalin reveals appreciably lower to non-existent antihistaminic and anticholinergic activities compared to standard tricyclic comparators. While baseline TCAs frequently induce parasympatholytic and sedative artifacts in complex tissue or in vivo models, Daledalin maintains a clean receptor binding profile, ensuring that observed physiological responses are strictly driven by adrenergic potentiation [1].

Evidence Dimension	Antihistaminic and anticholinergic receptor affinity
Target Compound Data	Negligible off-target receptor binding
Comparator Or Baseline	Standard tricyclic antidepressants (high anticholinergic/antihistaminic activity)
Quantified Difference	Appreciably lower off-target receptor interference
Conditions	In vivo and in vitro receptor binding models

Prevents confounding sedative or parasympatholytic artifacts during complex behavioral or tissue-slice assays, streamlining data interpretation.

Receptor profile

Class-level

No measurable antihistaminic or anticholinergic activity reported; >100-fold lower affinity than amitriptyline at H1/M1 receptors inferred

Supports noradrenergic pathway interpretation without receptor-class confounds

Class-level inference; receptor panel verification advised

Fully Reduced Indoline Core Advantage

Daledalin is the fully reduced indoline analog of the indolinone precursor amedalin. Procuring Daledalin directly bypasses the necessary and hazardous diborane reduction step required to convert amedalin into the active indoline pharmacophore, ensuring immediate readiness for downstream structural modifications or biological testing[1].

Evidence Dimension	Synthetic reduction state and processability
Target Compound Data	Fully reduced 1-phenylindoline core (Daledalin)
Comparator Or Baseline	Amedalin (1-phenyl-2-indolinone core)
Quantified Difference	Elimination of one hazardous diborane reduction step
Conditions	Laboratory-scale synthesis of indoline derivatives

Procuring the fully reduced indoline core accelerates synthetic workflows and eliminates the need for handling hazardous borane reagents.

Scaffold properties

Reported

Indoline core; MW 280.4; calculated LogP ~4.2 vs. reboxetine LogP ~2.5 and tametraline LogP ~3.8

Distinct chemotype supports NET SAR studies independent of morpholine or tetralin series

Calculated properties; confirm experimentally

Trial context

Phase II double-blind trial (n=28) vs. amitriptyline; reported antidepressant endpoint response with tolerability signal

Reported model-response context; may support research model interpretation

Historical trial data; RUO; not for clinical guidance

Daledalin Application Scenarios

NET Assay Reference Standard

Because of its high NET selectivity and lack of SERT/DAT activity, Daledalin is the ideal reference compound for calibrating synaptosomal uptake assays and mapping isolated adrenergic pathways [1].

Indoline Scaffold for Drug Discovery

Daledalin’s fully reduced 1-phenylindoline core serves as a highly processable starting material or benchmark for synthesizing next-generation selective monoamine modulators, bypassing the need for initial indolinone reduction [2].

In Vivo Behavioral Pharmacology

Due to its lack of anticholinergic and antihistaminic side effects, Daledalin is perfectly suited for in vivo models assessing pure adrenergic potentiation without the sedative confounding typical of tricyclic agents [2].

Application Fit

NET pathway inhibition assay studies

NET selectivity profile review

SERT and DAT activity exclusion

Noradrenergic behavioral model studies

Receptor-class specificity context

Sedation and motor confound control

Indoline scaffold SAR studies

Indoline core chemotype comparison

NET pharmacophore property mapping

Daledalin is an orally effective indoline antidepressant that targets norepinephrine and serotonin transporters in the brain. Daledalin alleviates depressive symptoms by enhancing central monoamine neurotransmission. Daledalin shows promise in research on depression, including endogenous depression and neurotic depression.

Biological Activity I Assay Protocols (From Reference)

References	[1]. Daledalin tosylate: a controlled trial in depressive illness. Curr Med Res Opin. 1974;2(6):305-12.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C19H24N2
Molecular Weight	280.41
CAS #	22136-27-2
Appearance	Typically exists as solids at room temperature
SMILES	CNCCCC1(C)CN(C2=CC=CC=C2)C3=C1C=CC=C3
Synonyms	UK 3557
HS Tariff Code	2934.99.9001
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)	May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)	Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2:* DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5:* 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.)

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)

Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

View More

Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

Oral Formulations

Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

View More

Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.5662 mL	17.8310 mL	35.6621 mL
	5 mM	0.7132 mL	3.5662 mL	7.1324 mL
	10 mM	0.3566 mL	1.7831 mL	3.5662 mL

References

Specification

XLogP3

4.3

Hydrogen Bond Acceptor Count

Hydrogen Bond Donor Count

Exact Mass

280.193948774 Da

Monoisotopic Mass

280.193948774 Da

Heavy Atom Count

Others

UNII

IT56261A5A

Other CAS

22136-27-2

Wikipedia

Daledalin

molecular formulaC19H24N2

molecular weight280.4 g/mol

CAS No.22136-27-2

Cat. No.B1208716

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Technical parameters

basic information

Product name	Daledalin
CAS	22136-27-2
alias	daledalin, UK 3557
molecular formula	C19H24N2
molecular weight	280.4 g/mol

Structural identifier

SMILES	CC1(CN(C2=CC=CC=C21)C3=CC=CC=C3)CCCNC
InChI	InChI=1S/C19H24N2/c1-19(13-8-14-20-2)15-21(16-9-4-3-5-10-16)18-12-7-6-11-17(18)19/h3-7,9-12,20H,8,13-15H2,1-2H3
InChIKey	YFAIJBZEDDOCAN-UHFFFAOYSA-N

Sales and supply

Standard packaging size	25 mg / 50 mg / 100 mg / Custom Large Capacity
Supply status	In Stock
Custom Synthesis	Available upon request

Structure and identifiers

Daledalin (UK-3557-15) Compound Profile

2,3-Dihydro-N,3-dimethyl-1-phenyl-1H-indole-3-propanamine (CAS 22136-27-2), also known as Daledalin or UK-3557-15, is an indoline derivative developed as a selective norepinephrine reuptake inhibitor (NRI) . It was synthesized and clinically trialed as an antidepressant in the early 1970s but never commercialized [ 1 ]. The compound exhibits no significant activity at serotonin or dopamine transporters and lacks antihistaminergic or anticholinergic properties [ 2 ].

Selective NET ProbeReported high selectivity for norepinephrine transporter; no significant SERT or DAT activity.

Minimal Receptor ConfoundsNo antihistamine or anticholinergic properties reported, reducing sedation/cognitive interference.

Distinct Chemical ScaffoldIndoline core differentiates from aryloxypropanamine and tetralin NRI chemotypes.

Why Daledalin Generic Substitution Fails

Substituting 2,3-dihydro-N,3-dimethyl-1-phenyl-1H-indole-3-propanamine with another norepinephrine reuptake inhibitor (NRI) or antidepressant is not straightforward due to its unique pharmacological fingerprint. Unlike non-selective NRIs or those with dual mechanisms, this compound demonstrates strict selectivity for the norepinephrine transporter (NET) without measurable affinity for serotonin or dopamine transporters [ 1 ]. Additionally, its indoline scaffold confers distinct physicochemical properties compared to aryloxypropanamine or tetralin-based NRIs [ 2 ]. These differences can significantly impact experimental outcomes in neuropharmacology research, making direct interchange with analogs such as reboxetine, atomoxetine, or amedalin inappropriate without careful validation.

Non-Selective NRIsCompounds with dual SERT/DAT activity may introduce serotonergic or dopaminergic confounds, altering NET-specific study outcomes.

Alternative ChemotypesAryloxypropanamine or tetralin scaffolds may exhibit different permeability, metabolism, or off-target binding profiles.

Analog AmedalinStructurally related NRI showed divergent clinical endpoint outcomes, emphasizing that minor structural changes can shift in vivo response.

Daledalin Differentiation from Comparator Compounds

Selective NET Inhibition with Minimal Off-Target Activity

2,3-Dihydro-N,3-dimethyl-1-phenyl-1H-indole-3-propanamine selectively inhibits the norepinephrine transporter (NET) with no significant effect on serotonin (SERT) or dopamine (DAT) transporters [1]. In contrast, the structurally related NRI atomoxetine exhibits an IC50 of 3.4 nM for NET but also shows measurable activity at SERT (IC50 = 90 nM) and DAT (IC50 = 150 nM) [2]. Daledalin’s cleaner selectivity profile reduces the potential for confounding serotonergic or dopaminergic effects in experimental models.

NET Selectivity vs Atomoxetine

Cross-study comparable

No measurable SERT/DAT inhibition
vs. Atomoxetine: SERT IC50=90 nM, DAT IC50=150 nM (26–44× selectivity)

Supports norepinephrine-specific pathway studies without serotonergic/dopaminergic confounds.

Target compound NET IC50 not publicly available; cross-study comparison.

Norepinephrine Transporter (NET)Selectivity ProfilingAntidepressant Pharmacology

Absence of Antihistaminic and Anticholinergic Properties

2,3-Dihydro-N,3-dimethyl-1-phenyl-1H-indole-3-propanamine has been characterized as lacking antihistaminic and anticholinergic activity [1]. This contrasts sharply with tricyclic antidepressants (TCAs) like amitriptyline, which displays high affinity for histamine H1 receptors (Ki = 1.1 nM) and muscarinic acetylcholine receptors (Ki = 18 nM), contributing to sedation and cognitive impairment [2]. Daledalin’s cleaner receptor profile is advantageous for experiments requiring isolated NET modulation without confounding sedation or cognitive disruption.

No Antihistamine/Anticholinergic

Class-level inference

No H1 or M1 receptor activity reported
vs. Amitriptyline: H1 Ki=1.1 nM, M1 Ki=18 nM

May reduce sedation/cognitive confounds in behavioral research models.

Receptor panel data inferred; direct binding assays recommended to verify.

Side-Effect ProfileReceptor BindingBehavioral Pharmacology

Unique Indoline Scaffold and Physicochemical Properties

The compound features an N-phenylindoline core (C19H24N2, MW 280.4 g/mol) with a 3-methyl-3-(methylaminopropyl) substitution pattern . This scaffold differs fundamentally from aryloxypropanamine-based NRIs like reboxetine (C19H23NO3, MW 313.4 g/mol) and tetralin-based tametraline (C17H19N, MW 237.3 g/mol) [1]. The indoline ring system confers distinct lipophilicity (calculated LogP ~4.2) and hydrogen bonding capacity that may influence brain penetration and pharmacokinetics, as noted in the original medicinal chemistry studies of this class [2].

Indoline Scaffold Properties

Reported

MW 280.4, LogP ~4.2
vs. Reboxetine (MW 313.4, LogP ~2.5); Tametraline (MW 237.3, LogP ~3.8)

Distinct lipophilicity and hydrogen-bonding may influence brain penetration and PK.

Calculated properties; experimental ADME data needed.

Medicinal ChemistryStructure-Activity RelationshipDrug Design

Clinical Antidepressant Efficacy vs. Amedalin

In a double-blind controlled trial comparing daledalin tosylate (UK-3557) with amitriptyline in 28 patients with depressive illness, daledalin demonstrated antidepressant efficacy with a suggestion of fewer autonomic side effects [1]. In contrast, its close analog amedalin (UK-3540-1), also a selective NRI, advanced to clinical trials but showed less favorable efficacy in preliminary studies and was never pursued [2]. While both compounds share an indoline core, daledalin’s 3-methyl-3-(methylaminopropyl) substitution distinguishes it from amedalin’s 3,3-dimethylaminoethyl pattern, potentially explaining differences in clinical outcomes.

Trial Endpoint vs Amedalin

Head-to-head

Phase II trial completed (n=28) vs amitriptyline
Amedalin: development halted after early-phase trials

Reported endpoint context supports NET probe selection for in vivo models.

Trial-derived evidence; model-specific endpoint interpretation required.

Clinical PharmacologyAntidepressant ActivityTranslational Research

Optimal Research Applications for Daledalin

Positive Control for Selective NET Inhibition Assays

Use as a reference standard in norepinephrine uptake assays (e.g., synaptosomal [³H]-NE uptake) to confirm assay sensitivity and define maximal NET blockade. Its clean selectivity profile minimizes interference from SERT/DAT activity, ensuring that observed effects are attributable to NET modulation [1]. This is particularly valuable when screening novel NRI candidates or evaluating NET function in disease models.

In Vivo Behavioral Studies of Noradrenergic Systems

Employ in rodent models of depression (eg, forced swim test, tail suspension test) or anxiety to probe noradrenergic contributions without the confounding sedation or anticholinergic effects seen with TCAs like amitriptyline [ 2 ]. The compound’s clinical precedent in depression trials supports its translational relevance [ 3 ].

SAR Studies of Indoline-Based NRIs

Serve as a starting scaffold for medicinal chemistry optimization. The 3-methyl-3-(methylaminopropyl) indoline core offers a distinct template for exploring NET pharmacophore requirements compared to aryloxypropanamine or tetralin series [ 4 ]. Modifications to the N-phenyl or amine substituents can analog yields with selectivity or PK properties.

.NET Uptake Assay Reference

Clean NET selectivity context

Confirm absence of SERT/DAT interference in assay

In Vivo Noradrenergic Pathway Studies

Lack of antihistamine/anticholinergic confounds

Verify no sedation or cognitive impairment in behavioral models

Indoline SAR Template

Unique indoline scaffold

Evaluate physicochemical divergence from aryloxypropanamine/tetralin series

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Daledalin (CAS 22136-27-2) | Selective NRI | BenchChem

2,3-Dihydro-N,3-dimethyl-1-phenyl-1H-indole-3-propanamine (CAS 22136-27-2), also known as Daledalin or UK-3557-15, is an …
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Daledalin (UK 3557) is an orally active indoline antidepressant targeting …
CAS No.: 22136-27-2

Molecular Weight: 280.41

Formula: C 19 H 24 N 2

SMILES: CNCCCC1 (C)CN (C2=CC=CC=C2)C3=C1C=CC=C3
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