Buy Talopram (phthalapromine) Cas 7182-51-6

Talopram (Lu 3-010),^[1] also known as phthalapromine, is a selective norepinephrine reuptake inhibitor (NRI) which was researched for the management of depression in the 1960s and 1970s but was never commercialized. Along with talsupram, talopram is structurally related to the selective serotonin reuptake inhibitor (SSRI) citalopram,^[2] as well as to melitracen:^[3]

In 1971, the company hired Klaus Bøgesø as a medicinal chemist. Over the years Bøgesø turned out to have a Midas touch at the game of drug hunting, creating more molecules that made it to the market than almost any other medicinal chemist in the field. The challenge facing him in 1971 following his recruitment was to produce a selective norepinephrine reuptake inhibitor. Like other companies at the time, Lundbeck had little interest in an SSRI. Bøgesø began from an accident in the laboratory. Trying to create a derivative of their norepinephrine reuptake inhibiting antidepressant melitracen, Lundbeck chemists accidentally produced a new chemical — a phenylphthalene. Against all the odds, just like melitracen, this was also a selective norepinephrine reuptake inhibitor. Two potential antidepressants came out of this — talopram and tasulopram, which were pressed into clinical trials. Both however turned out to be energizing, and in a number of cases there were suicide attempts. The fact that there were suicide attempts appeared to confirm another proposal of Paul Kielholz, that activating antidepressants might lead to suicide. Lundbeck’s experience suggested that norepinephrine reuptake inhibitors were likely to lead to just this problem. Lundbeck retreated, scared. If norepinephrine reuptake inhibitors were likely to trigger suicide, the greatest hazard of an antidepressant, then Kielholz’s view suggested that an SSRI would be less likely to lead to suicide. Bøgesø’s job was to see whether the new series of drugs could be converted into a series of SSRIs. Following a lead from Carlsson on how to do this, he converted talopram into citalopram, the most selective serotonin reuptake inhibitor to come to the market.

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Buy Talopram (phthalapromine) Cas 7182-51-6

Synthesis

An unexpected/fortuitous rearrangement product in the synthesis of litracen is what led to talopram.^[3]^[4]

7182-51-6

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Basic information
1. Product Name: Talopram
2. Synonyms: phthalapromine
3. CAS NO:7182-51-6
4. Molecular Formula: C20H25NO
5. Molecular Weight: 295.423
6. EINECS: N/A
7. Product Categories: N/A
8. Mol File: 7182-51-6.mol
Chemical Properties
1. Melting Point: N/A
2. Boiling Point: 403.1°C at 760 mmHg
3. Flash Point: 175.3°C
4. Appearance: /
5. Density: 1.018g/cm³
6. Vapor Pressure: 1.04E-06mmHg at 25°C
7. Refractive Index: 1.542
8. Storage Temp.: N/A
9. Solubility: N/A
10. CAS DataBase Reference: Talopram(CAS DataBase Reference)
11. NIST Chemistry Reference: Talopram(7182-51-6)
12. EPA Substance Registry System: Talopram(7182-51-6)
Safety Data
1. Hazard Codes: N/A
2. Statements: N/A
3. Safety Statements: N/A
4. WGK Germany:
5. RTECS:
6. HazardClass: N/A
7. PackingGroup: N/A
8. Hazardous Substances Data: 7182-51-6(Hazardous Substances Data)

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7182-51-6 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 7182-51-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,1,8 and 2 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 7182-51:
(6*7)+(5*1)+(4*8)+(3*2)+(2*5)+(1*1)=96
96 % 10 = 6
So 7182-51-6 is a valid CAS Registry Number.

InChI:InChI=1/C20H25NO/c1-19(2)17-12-7-8-13-18(17)20(22-19,14-9-15-21-3)16-10-5-4-6-11-16/h4-8,10-13,21H,9,14-15H2,1-3H3

7182-51-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) – Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name	3-(3,3-Dimethyl-1-phenyl-1,3-dihydro-2-benzofuran-1-yl)-N-methyl- 1-propanamine

1.2 Other means of identification

Product number	–
Other names	3,3-dimethyl-1-(2-trimethylsilyl-1,3-dithian-2-yl)-butan-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses	For industry use only.
Uses advised against	no data available

1.4 Supplier’s details

1.5 Emergency phone number

Emergency phone number	–
Service hours	Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

Talopram

Norepinephrine transporterDopamine transporterSelectivity profiling

Talopram (CAS 7182-51-6) is a selective norepinephrine reuptake inhibitor (NRI) that addresses the critical need for experimental specificity in NET research, particularly where DAT crosstalk confounds results. Its unique binding profile and extreme selectivity make it an irreplaceable tool compound.

Exclusive Selectivity: Offers the highest documented hDAT/hNET selectivity ratio (17,531) among clinically-relevant NET inhibitors, ensuring clean pharmacology.
Distinct Binding Site: Unaffected by S1 pocket mutations, making it ideal for studying allosteric modulation and validating mutagenesis models.
Stereochemical Probe: The 685-fold affinity difference between R- and S-enantiomers provides a powerful reference for chiral pharmacology studies.

Molecular FormulaC20H25NO

Molecular Weight295.4 g/mol

CAS No.7182-51-6

Talopram is a novel and potent PET ligand

Biological Activity I Assay Protocols (From Reference)

Additional Infomation	Taropram is a selective norepinephrine reuptake inhibitor (SNRI) with a structure similar to citalopram and melitracen. It was investigated in the 1960s and 1970s but was never marketed.

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

Physicochemical Properties

Molecular Formula	C20H25NO
Molecular Weight	295.4186
Exact Mass	295.194
CAS #	7182-51-6
Related CAS #	7013-41-4 (hydrochloride)
PubChem CID	23573
Appearance	Typically exists as solid at room temperature
Density	1.018g/cm3
Boiling Point	403.1ºC at 760 mmHg
Flash Point	175.3ºC
Index of Refraction	1.542
LogP	4.586
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Heavy Atom Count	22
Complexity	361
Defined Atom Stereocenter Count	0
SMILES	CC1(C2=CC=CC=C2C(O1)(CCCNC)C3=CC=CC=C3)C
InChi Key	LJBBMCNHIUJBDU-UHFFFAOYSA-N
InChi Code	InChI=1S/C20H25NO/c1-19(2)17-12-7-8-13-18(17)20(22-19,14-9-15-21-3)16-10-5-4-6-11-16/h4-8,10-13,21H,9,14-15H2,1-3H3
Chemical Name	3-(3,3-dimethyl-1-phenyl-2-benzofuran-1-yl)-N-methylpropan-1-amine
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	3.3850 mL	16.9251 mL	33.8501 mL
	5 mM	0.6770 mL	3.3850 mL	6.7700 mL
	10 mM	0.3385 mL	1.6925 mL	3.3850 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycl

Talopram

For research use only. Not for therapeutic Use.

CAT Number: I036977
CAS Number: 7182-51-6
Molecular Formula: C20H25NO
Molecular Weight: 295.43
Purity: 98%

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Related Small Molecules: Poloxime BMS-820132 Monomethyl auristatin E

Talopram(CAT: I036977) is a potent and selective inhibitor of the presynaptic norepinephrine transporter (NET), making it a valuable tool for research on mood disorders, particularly depression and anxiety. By modulating norepinephrine reuptake, Talopram enhances neurotransmitter availability, offering insights into the mechanisms of antidepressant activity and catecholaminergic signaling. Its high specificity for NET over other monoamine transporters ensures precise experimental outcomes. Widely utilized in neuropharmacological studies, Talopram supports the investigation of therapeutic strategies targeting norepinephrine modulation in mood and stress-related disorders.

CAS Number	7182-51-6
Synonyms	Talopram; Phthalapromine; Talopramum; Talopran
Molecular Formula	C20H25NO
Purity	98%
Solubility	Soluble in DMSO
Appearance	Solid powder
Storage	Dry, dark and at 0 – 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name	N,3,3-Trimethyl-1-phenyl-1-phthalanpropylamin
InChI	InChI=1S/C20H25NO/c1-19(2)17-12-7-8-13-18(17)20(22-19,14-9-15-21-3)16-10-5-4-6-11-16/h4-8,10-13,21H,9,14-15H2,1-3H3
InChIKey	LJBBMCNHIUJBDU-UHFFFAOYSA-N
SMILES	CC1(C)OC(CCCNC)(C2=CC=CC=C2)C3=CC=CC=C13
Chemistry Calculators	Dilution Calculator In vivo Formulation Calculator Molarity Calculator Molecular Weight Calculator Reconstitution Calculator

Talopram

Catalog No.

S544494

CAS No.

7182-51-6

M.F

C20H25NO

M. Wt

295.4 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

Substituting talopram with generic NRIs compromises assay selectivity and synthetic yields. Talopram (CAS 7182-51-6) overcomes these limitations as a selective NET inhibitor. • Selective NET inhibition avoids SERT off-target binding common with citalopram. • Secondary amine enables single-step [11C] N-alkylation, eliminating low-yield demethylation in radiotracer synthesis. • 685-fold R/S affinity difference enables stereospecific discrimination of true target engagement from non-specific binding. Procure as a racemic reference standard for SAR studies, fluorescent probe development, and PET tracer production.

CAS Number

7182-51-6

Product Name

Talopram

IUPAC Name

3-(3,3-dimethyl-1-phenyl-2-benzofuran-1-yl)-N-methylpropan-1-amine

Molecular Formula

C20H25NO

Molecular Weight

295.4 g/mol

InChI

InChI=1S/C20H25NO/c1-19(2)17-12-7-8-13-18(17)20(22-19,14-9-15-21-3)16-10-5-4-6-11-16/h4-8,10-13,21H,9,14-15H2,1-3H3

InChI Key

LJBBMCNHIUJBDU-UHFFFAOYSA-N

SMILES

CC1(C2=CC=CC=C2C(O1)(CCCNC)C3=CC=CC=C3)C

solubility

Soluble in DMSO

Synonyms

(11C)talopram, 1,3-dihydro-N,3,3-trimethyl-1-phenylbenzo(c)furan-1-propanamine, talopram

Canonical SMILES

CC1(C2=CC=CC=C2C(O1)(CCCNC)C3=CC=CC=C3)C

The exact mass of the compound Talopram is 295.1936 and the complexity rating of the compound is unknown. The solubility of this chemical has been described as Soluble in DMSO. The compound has been submitted to the National Cancer Institute (NCI) for testing and evaluation and the Cancer Chemotherapy National Service Center (NSC) number is 104350. Its Medical Subject Headings (MeSH) category is Chemicals and Drugs Category – Organic Chemicals – Amines – Propylamines – Supplementary Records. The storage condition is described as Dry, dark and at 0 – 4 C for short term (days to weeks) or -20 C for long term (months to years)..

Purity

≥98%

Package Size

5 mg, 10 mg, 25 mg

Talopram Procurement Overview

Talopram is a secondary amine phthalane derivative and a highly selective norepinephrine reuptake inhibitor (NRI) [1]. Structurally characterized by a gem-dimethyl substituted dihydro-isobenzofuran core and the absence of aromatic cyano or fluoro substitutions, it serves as a critical pharmacological benchmark [2]. In industrial and academic procurement, talopram is primarily sourced as a reference standard for monoamine transporter assays, a structural scaffold for synthesizing fluorescent probes, and a precursor for positron emission tomography (PET) radiotracers. Its well-defined physicochemical properties and high target specificity make it an essential tool for isolating norepinephrine transporter (NET) mechanisms from serotonin transporter (SERT) activity [2].

Research Fit

Selective NET inhibitor for norepinephrine transporter pharmacology studies

Hydrochloride salt form suited for in vitro and ex vivo applications

Characterized binding and functional inhibition for reference use

References

Generic Substitution Failures with Talopram

Substituting talopram with generic NRIs like desipramine or closely related phthalanes like citalopram critically compromises assay integrity and synthetic yields. While citalopram shares the same basic phthalane scaffold, its tertiary amine structure and aromatic substitutions functionally invert its selectivity, making it a highly potent SERT inhibitor rather than a NET inhibitor [1]. Conversely, utilizing tricyclic antidepressants (TCAs) like desipramine introduces different steric bulk and broader off-target receptor binding profiles. Furthermore, talopram’s specific secondary amine configuration is a prerequisite for direct N-alkylation in radiotracer synthesis; substituting it with a tertiary amine analog necessitates complex, low-yield demethylation steps before radiolabeling can occur [2].

Substitution Risk

Structural analogs may target different transporter binding sites; talopram binds outside the S1 pocket, unlike citalopram.

Enantiomer preference differs: R-talopram is the active form for NET, whereas S-citalopram is active for SERT.

Selectivity profiles diverge: talopram is NET-selective; citalopram is SERT-selective, limiting direct functional substitution.

References

Talopram Quantitative Evidence & Comparators

Transporter Selectivity: NET vs. SERT

Talopram demonstrates profound selectivity for the norepinephrine transporter (NET) over the serotonin transporter (SERT), effectively mirroring and inverting the profile of its structural analog, citalopram. In competitive radioligand binding assays using recombinantly expressed human transporters, talopram exhibited a Ki of 9 nM for NET and 719 nM for SERT. In direct contrast, citalopram showed a Ki of 1,414 nM for NET and 4 nM for SERT [1].

Evidence Dimension	Binding Affinity (Ki)
Target Compound Data	Ki = 9 nM (NET); 719 nM (SERT)
Comparator Or Baseline	Citalopram (Ki = 1,414 nM for NET; 4 nM for SERT)
Quantified Difference	Talopram is ~80-fold selective for NET over SERT, whereas citalopram is ~350-fold selective for SERT over NET.
Conditions	Displacement of [125I]β-CIT in recombinantly expressed human NET and SERT.

Procurement of talopram ensures strict isolation of NET-driven mechanisms in high-throughput screening and functional assays without confounding SERT inhibition.

hDAT/hNET Selectivity

Head-to-head

17,531

vs Nisoxetine 412

Reported highest NET selectivity among tested NRIs; supports NET-specific studies

[3H]dopamine uptake in hNET/hDAT COS-7 cells

Enantiomer-Specific Transporter Activity

The inhibitory potency of talopram is highly stereospecific, residing almost exclusively in its R-enantiomer, which contrasts sharply with citalopram, whose activity is driven by the S-enantiomer. Pharmacological evaluation reveals that R-talopram possesses a Ki of 3 nM for NET, whereas S-talopram exhibits a dramatically lower affinity with a Ki of 1,986 nM [1].

Evidence Dimension	Enantiomeric Binding Affinity (Ki for NET)
Target Compound Data	R-talopram Ki = 3 nM
Comparator Or Baseline	S-talopram Ki = 1,986 nM
Quantified Difference	685-fold higher affinity for the R-enantiomer over the S-enantiomer at NET.
Conditions	Enantiomer-specific competitive radioligand binding at human NET.

This massive enantiomeric divergence makes resolved R-talopram an indispensable chiral probe for mapping the central substrate binding sites of monoamine transporters.

R- vs S-Talopram NET Ki

Head-to-head

R: 3 nM / S: 1,986 nM

Enantiomeric affinity difference necessitates chiral purity verification for accurate dosing

Competitive radioligand binding at human NET

Fluorescent Probe Scaffold Viability

Talopram serves as a highly viable parent scaffold for the development of bulky fluorescent probes without losing target specificity. When conjugated to a rhodamine fluorophore, the resulting talopram-based probe maintained high binding affinity for NET (Ki = 43 nM) while demonstrating quantitative selectivity against the dopamine transporter (DAT; Ki = 1540 nM) and SERT (Ki = 785 nM)[1].

Evidence Dimension	Retained Affinity of Labeled Derivatives (Ki)
Target Compound Data	Talopram-rhodamine probe Ki = 43 nM (NET)
Comparator Or Baseline	Off-target binding (DAT Ki = 1540 nM; SERT Ki = 785 nM)
Quantified Difference	>18-fold selectivity for NET over SERT and >35-fold over DAT despite the addition of a bulky fluorophore.
Conditions	Competitive radioligand binding and live-cell confocal microscopy in transporter-expressing cells.

Validates the procurement of the talopram scaffold for custom synthesis of fluorescent ligands used in live-cell imaging of NET distribution.

Non-S1 Binding Site

Head-to-head

S1-insensitive

Distinct binding site enables allosteric mechanism studies without S1 interference

Citalopram altered up to 515-fold by S1 mutations

PET Radiotracer Precursor Efficiency

The secondary amine structure of talopram makes its nor-derivative (N-desmethyltalopram) an ideal precursor for direct radiolabeling. Synthesis of [11C]talopram via direct methylation with [11C]methyl triflate achieves high radiochemical yields and high specific radioactivity (58-75 GBq/μmol). In contrast, utilizing tertiary amine analogs requires complex, multi-step demethylation procedures prior to radiolabeling [1].

Evidence Dimension	Specific Radioactivity and Synthesis Route
Target Compound Data	Direct N-alkylation yielding 58-75 GBq/μmol.
Comparator Or Baseline	Tertiary amine analogs (require prior demethylation).
Quantified Difference	Single-step radiolabeling vs. multi-step synthesis.
Conditions	Radiosynthesis of [11C]talopram for in vivo PET imaging evaluation.

Basic Identity

Product Name	Talopram
CAS	7182-51-6
Synonyms	(11C)talopram, 1,3-dihydro-N,3,3-trimethyl-1-phenylbenzo(c)furan-1-propanamine, talopram
Molecular Formula	C20H25NO
Molecular Weight	295.4 g/mol

Structural Identifiers

SMILES	CC1(C2=CC=CC=C2C(O1)(CCCNC)C3=CC=CC=C3)C
InChI	InChI=1S/C20H25NO/c1-19(2)17-12-7-8-13-18(17)20(22-19,14-9-15-21-3)16-10-5-4-6-11-16/h4-8,10-13,21H,9,14-15H2,1-3H3
InChIKey	LJBBMCNHIUJBDU-UHFFFAOYSA-N

Commercial & Availability

Standard Pack Sizes	10 mg / 50 mg / Bulk Custom
Availability	In Stock
Custom Synthesis	Available on request

Handling Information

Appearance	Solid powder
Solubility	Soluble in DMSO
Storage	Dry, dark and at 0 – 4 C for short term (days to weeks) or -20 C for long term (months to years).

Structure & Identifiers

Talopram: Selective NET Inhibitor Overview

Talopram (Lu 3-010, phthalapromine) is a selective norepinephrine reuptake inhibitor (NRI) originally developed by Lundbeck in the 1960s–1970s for depression research [1]. Structurally belonging to the phenylphthalane class, talopram is closely related to the SSRI citalopram and the tricyclic antidepressant melitracen, yet possesses a fundamentally distinct pharmacological profile [2]. Although never commercialized therapeutically, talopram remains a valuable research tool for studying norepinephrine transporter (NET) pharmacology, with characterized binding affinity (Ki = 4.5 nM for rat NET) and functional inhibition (IC50 = 2.9 nM for human NET) [3]. The compound is available as the hydrochloride salt (CAS 7013-41-4) from research chemical suppliers for in vitro and ex vivo applications.

Selective norepinephrine transporter (NET) inhibitor tool compound

Structurally distinct from SSRIs and tricyclic antidepressants

Characterized binding and functional profile for NET pharmacology research

Suitable for in vitro and ex vivo NET studies

Why Talopram Cannot Be Substituted

Despite high structural homology, talopram and its close analogs exhibit critical differences in molecular target engagement that preclude functional substitution. Talopram is a selective NET inhibitor with a fundamentally distinct binding site from citalopram, which selectively inhibits SERT [1]. Mutagenesis studies demonstrate that talopram activity is largely unaffected by mutations in the central substrate binding site (S1) of NET or SERT, whereas citalopram’s potency can be altered up to 515-fold by specific S1 mutations [1]. Furthermore, talopram exhibits a binding mode distinct from other NET inhibitors including reboxetine, which demonstrates a noncompetitive inhibition profile [1]. The stereochemical determinants of potency also differ markedly: talopram’s R-enantiomer shows 685-fold higher NET affinity than the S-enantiomer (3 nM vs. 1,986 nM), while citalopram’s activity resides in the S-enantiomer for SERT [1]. These fundamental differences in binding site recognition, stereochemical preference, and selectivity profile mean that talopram cannot be reliably replaced by citalopram, melitracen, talsupram, or even other NET inhibitors without compromising experimental specificity.

SSRI binding site mismatch

Citalopram and other SSRIs target SERT, not NET; talopram binds a non-S1 site in NET, preventing direct interchange.

Stereochemical context reversal

R-enantiomer is 685-fold more affine for NET than S-enantiomer; racemic material may shift effective concentration and experimental specificity.

NET inhibitor profile divergence

Reboxetine shows noncompetitive inhibition and talsupram has different DAT selectivity; NET inhibitor class members may not replicate talopram binding mode.

Talopram Quantitative Evidence Guide

hDAT/hNET Selectivity Profiling

Talopram exhibits an hDAT/hNET selectivity ratio of 17,531, which is 42.5-fold higher than nisoxetine (412), 2.5-fold higher than reboxetine (6,952), and 109.6-fold higher than atomoxetine (160), as determined by [3H]dopamine uptake inhibition in COS-7 cells expressing human transporters [1]. This ratio, calculated as Ki(hDAT)/Ki(hNET), reflects the compound’s preferential inhibition of NET over DAT, with higher values indicating greater NET selectivity [1].

DAT/NET selectivity

Head-to-head

hDAT/hNET Ki ratio 17,531
(nisoxetine 412, reboxetine 6,952, atomoxetine 160)

Supports DAT-sparing NET pharmacology context

COS-7 cell uptake assay; 42.5‑109.6× higher than comparators

Norepinephrine transporterDopamine transporterSelectivity profilingUptake inhibition

R- vs S-Talopram NET Binding Affinity

The R-enantiomer of talopram displays a Ki of 3 nM for NET, which is 685-fold higher affinity than the S-enantiomer (Ki = 1,986 nM) [1]. This pronounced stereochemical preference is opposite to that observed for the structurally related SSRI citalopram, where the S-enantiomer exhibits 35-fold higher SERT affinity than the R-enantiomer [1].

Enantiomer NET affinity

Head-to-head

R‑talopram Ki 3 nM
S‑talopram Ki 1,986 nM
685‑fold difference

Stereochemical context may shift target engagement

Chiral purity critical for effective concentration interpretation

Enantiomer selectivityStereochemistryNET bindingChiral pharmacology

Non-S1 Binding Site in NET

Mutagenesis studies demonstrate that talopram activity is largely unaffected by any mutations in the central S1 substrate binding site of SERT and NET (<4-fold changes in Ki across 30 single-point S1 mutants), nor by mutations in the S2 outer vestibule site [1]. In contrast, citalopram’s potency can be altered up to 515-fold by specific S1 mutations (N7 mutant: F72Y-A77G-M424L-A426G-T453C), indicating that citalopram and talopram bind to distinct sites on these transporters [1].

Non‑S1 binding site

Method context

Talopram unaffected by S1/S2 mutants; citalopram altered ≤515‑fold

Supports allosteric / non-classical binding mechanism studies

COS-7 cell mutagenesis; competitive binding assay

Binding site mappingMutagenesisTransporter pharmacologyAllosteric modulation

NET/SERT Selectivity in Rat Brain Tissue

In native rat brain tissue, talopram displays a Ki of 4.5 nM for NET (prefrontal cortex) versus a Ki of 795 nM for SERT (brainstem), yielding a SERT/NET selectivity ratio of approximately 177-fold [1]. The compound shows even greater discrimination against DAT, with Ki >10,000 nM in rat striatal tissue, representing a DAT/NET selectivity ratio exceeding 2,200-fold [1]. While direct comparator data for other NRIs in identical tissue preparations is not available from this source, the absolute values establish a clear selectivity benchmark [1].

Native tissue selectivity

Cross-study comparable

NET Ki 4.5 nM, SERT Ki 795 nM, DAT Ki >10,000 nM (rat brain)

Ex vivo NET selectivity benchmark

SERT/NET ratio 177; DAT/NET >2,200

Selectivity indexRadioligand bindingNative tissueOff-target profiling

Functional NET Inhibition in Human Cells

Talopram hydrochloride exhibits potent functional inhibition of the human norepinephrine transporter with an IC50 of 2.9 nM . At 100 nM, talopram inhibits 63% of human NET activity . As a class-level reference point, the closely related NRI talsupram (Lu 5-003) shows an IC50 of 0.79 nM for NET, approximately 3.7-fold more potent than talopram, though talsupram has substantially different DAT selectivity characteristics .

Functional NET inhibition

Data to verify

IC₅₀ 2.9 nM; 63% inhibition at 100 nM (human NET)

Supports functional NET inhibition assay context

Supplier-reported IC₅₀; class-level inference

Functional assayUptake inhibitionHuman NETIC50

Norepinephrine Uptake vs Desipramine

The bicyclic phthalane compound Lu 3-010 (talopram) is approximately equipotent with the tricyclic antidepressant desipramine in inhibiting the amine pump in adrenergic neurons, despite containing a ring system entirely distinct from the tricyclic scaffold [1]. Molecular modeling reveals that talopram’s phenyl rings coincide closely with the phenyl rings of desipramine when superimposed, but talopram possesses additional methyl groups on its bicyclic ring system that engage supplementary ancillary binding sites not utilized by tricyclic compounds [1]. In vitro studies confirm that Lu 3-010, desipramine, and imipramine were considerably more powerful in inhibiting noradrenaline uptake than dopamine uptake [2].

Uptake vs desipramine

Head-to-head

Approximately equipotent to desipramine in adrenergic neuron amine pump

Non‑tricyclic scaffold with comparable NET inhibition context

Distinct ancillary binding sites not used by tricyclics

Structure-activity relationshipTricyclic comparatorUptake inhibitionMolecular modeling

Talopram Research Applications

NET Studies with Minimal DAT Interference

For researchers investigating NET-mediated signaling pathways where dopamine transporter (DAT) crosstalk would confound interpretation, talopram offers the highest documented hDAT/hNET selectivity ratio (17,531) among clinically-relevant NET inhibitors [1]. This is 42.5-fold higher than nisoxetine and 109.6-fold higher than atomoxetine, making talopram the preferred tool compound for experiments requiring clean NET pharmacology without DAT engagement [1].

Enantiomer-Specific NET Binding and Chiral Pharmacology

The 685-fold difference in NET affinity between R-talopram (3 nM) and S-talopram (1,986 nM) positions talopram as a valuable probe for investigating stereochemical determinants of transporter recognition [1]. Researchers studying enantiomer-specific pharmacology or developing chiral NET inhibitors can utilize talopram as a reference standard where stereochemistry profoundly impacts target engagement, contrasting with compounds where enantiomeric differences are less pronounced [1].

Allosteric and Non-S1 Binding Studies

Mutagenesis data demonstrate that talopram binds to a site distinct from the central S1 substrate binding pocket, with activity unaffected by any S1 or S2 mutations tested (<4-fold Ki changes) [1]. This property makes talopram uniquely suitable for experiments designed to characterize alternative inhibitor binding sites, allosteric modulation mechanisms, or for use as a control compound when validating S1 site-directed mutations [1].

Non-Tricyclic NET Inhibitor SAR Studies

Talopram achieves desipramine-equivalent NET inhibitory potency despite its bicyclic phthalane scaffold, which engages ancillary binding sites not utilized by tricyclic compounds [1]. This feature makes talopram a critical reference compound for SAR programs aimed at developing next-generation NET inhibitors that diverge from the classical tricyclic pharmacophore, enabling researchers to deconvolute the contributions of distinct binding site interactions to overall transporter inhibition [1].

NET pharmacology without DAT crosstalk

Reported DAT/NET selectivity ratio

DAT-free NET endpoint validation

Enantiomer-specific NET binding studies

Chiral purity / enantiomeric ratio

Stereochemical binding context review

Non‑S1 binding site mapping

S1-independent binding profile

Allosteric modulation mechanism review

NET inhibitor SAR independent of tricyclic scaffold

Bicyclic phthalane scaffold binding

Scaffold-specific binding site deconvolution

Technical Documentation Hub

Structured technical reading across foundational, methodological, troubleshooting, and validation/comparative pathways. Use the hub when you need more detail before procurement.

36 linked technical documents

Explore Hub

FoundationalNovember 2025

Talopram’s Interaction with the Norepinephrine Transporter: A Technical Guide

FoundationalNovember 2025

An In-depth Technical Guide to the Pharmacological Profile and Receptor Binding Affinity of Talopram

FoundationalNovember 2025

An In-depth Technical Guide to the Synthesis and Chemical Properties of Talopram

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Talopram

Talopram

Talopram

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Transporter Selectivity: NET vs. SERT

Enantiomer-Specific Transporter Activity

Fluorescent Probe Scaffold Viability

PET Radiotracer Precursor Efficiency

Structure & Identifiers

Talopram: Selective NET Inhibitor Overview

Why Talopram Cannot Be Substituted

Talopram Quantitative Evidence Guide

hDAT/hNET Selectivity Profiling

R- vs S-Talopram NET Binding Affinity

Non-S1 Binding Site in NET

NET/SERT Selectivity in Rat Brain Tissue

Functional NET Inhibition in Human Cells

Norepinephrine Uptake vs Desipramine

Talopram Research Applications

NET Studies with Minimal DAT Interference

Enantiomer-Specific NET Binding and Chiral Pharmacology

Allosteric and Non-S1 Binding Studies

Non-Tricyclic NET Inhibitor SAR Studies