Buy Desipramine (Norpramin) Cas 50-47-5

Desipramine, sold under the brand name Norpramin among others, is a tricyclic antidepressant (TCA) used in the treatment of depression.^[7] It acts as a relatively selective norepinephrine reuptake inhibitor, though it does also have other activities such as weak serotonin reuptake inhibitory, α₁-blocking, antihistamine, and anticholinergic effects. The drug has not been considered a first-line treatment for depression since the introduction of selective serotonin reuptake inhibitor (SSRI) antidepressants, which have fewer side effects and are safer in overdose.

Desipramine is primarily used for the treatment of depression.^[7] It may also be useful to treat symptoms of attention-deficit hyperactivity disorder (ADHD).^[8] Evidence of benefit is only in the short term, and with concerns of side effects its overall usefulness is not clear.^[9] Desipramine at very low doses is also used to help reduce the pain associated with functional dyspepsia.^[10] It has also been tried, albeit with little evidence of effectiveness, in the treatment of cocaine dependence.^[11] Evidence for usefulness in neuropathic pain is also poor.^[12]

Desipramine tends to be less sedating than other TCAs and tends to produce fewer anticholinergic effects such as dry mouth, constipation, urinary retention, blurred vision, and cognitive or memory impairments.^[13]

Desipramine is particularly toxic in cases of overdose, compared to other antidepressants.^[14] Any overdose or suspected overdose of desipramine is considered to be a medical emergency and can result in death without prompt medical intervention.

Desipramine is a very potent and relatively selective norepinephrine reuptake inhibitor (NRI), which is thought to enhance noradrenergic neurotransmission.^[33][34] Based on one study, it has the highest affinity for the norepinephrine transporter (NET) of any other TCA,^[16] and is said to be the most noradrenergic^[35] and the most selective for the NET of the TCAs.^[33] The observed effectiveness of desipramine in the treatment of ADHD was the basis for the development of the selective NRI atomoxetine and its use in ADHD.^[33]

Desipramine has the weakest antihistamine and anticholinergic effects of the TCAs.^[36][35][37] It tends to be slightly activating/stimulating rather than sedating, unlike most others TCAs.^[35] Whereas other TCAs are useful for treating insomnia, desipramine can cause insomnia as a side effect due to its activating properties.^[35] The drug is also not associated with weight gain, in contrast to many other TCAs.^[35] Secondary amine TCAs like desipramine and nortriptyline have a lower risk of orthostatic hypotension than other TCAs,^[38][39] although desipramine can still cause moderate orthostatic hypotension.^[40]

Desipramine is the major metabolite of imipramine and lofepramine.

AS 50-47-5 Desipramine | Products & Prices & Suppliers

• • Desipramine, with the chemical formula C18H22N2, has the CAS number 50-47-5. It is a tricyclic antidepressant belonging to the class of dibenzazepines. Desipramine appears as a white crystalline powder with a slight amine odor. Its basic structure consists of three benzene rings fused together with a central nitrogen atom. This compound is slightly soluble in water. Desipramine may cause irritation to the skin and eyes. It is important to handle this chemical with care to avoid any potential harm. Safety precautions should be taken when working with desipramine to prevent exposure to high temperatures or flames. The primary hazard is the potential for adverse effects on human health. Proper measures should be taken to ensure its safe handling and disposal to protect both individuals and the environment.

    Applicable Fields

    Depression Treatment: Desipramine is primarily used as an antidepressant medication. Its purpose in this field involves its ability to regulate the levels of certain neurotransmitters in the brain, such as norepinephrine. The mechanism of action in depression treatment involves blocking the reuptake of these neurotransmitters, thereby increasing their availability and improving mood.

    Pain Management: Desipramine has also been used in the management of chronic pain conditions. Its mechanism of action in pain management is not fully understood, but it is believed to involve the modulation of certain pain pathways in the central nervous system. Desipramine may help reduce the perception of pain and improve overall pain control.

    Storage

    Conditions: Store in a cool and dry place.

50-47-5 desipramine
Chemical Name	desipramine
Synonyms	3-(10,11-dihydrodibenz(b,f)azepin-5-yl)methylpropylamine
Molecular Formula	C18H22N2
Molecular Weight	266.38
InChl	InChI=1/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3
CAS Registry Number	50-47-5
EINECS	200-040-0
Molecular Structure
MSDS	Material Safety Data Sheet

Desipramine Application Scenarios

Selective NET Assays

Due to its 12-fold higher affinity for NET over imipramine and its >20-fold selectivity over SERT, desipramine serves as a benchmark standard for in vitro competitive binding assays and functional reuptake models where precise blockade of the norepinephrine transporter is required without serotonergic interference [1].

Neuropathic Pain and Behavioral Models

Desipramine provides a highly controlled TCA baseline for animal models of chronic pain and depression where researchers must isolate noradrenergic mechanisms. Its significantly lower affinity for H1 and muscarinic receptors prevents the profound sedative and anticholinergic effects seen with amitriptyline, ensuring that behavioral readouts are not confounded by off-target toxicity [2].

Pharmacokinetic and Receptor-Occupancy Benchmarking

Because desipramine is a stable secondary amine that does not metabolize into another highly active compound, it is highly suited for in vivo pharmacokinetic tracking and PET imaging validation, avoiding the dual-agent complexity inherent to imipramine administration [3].

Lysosomal FIASMA Research

Utilized as a cationic amphiphilic drug (CAD) standard in cell culture assays, desipramine’s specific pKa (10.65) allows it to be efficiently trapped in acidic lysosomes, making it a reliable tool compound for inducing and studying the functional inhibition of acid sphingomyelinase and subsequent phospholipidosis [4].

References

• [1] Galli, A., et al. ‘Kinetics and inhibitor insensitivity of [3H]norepinephrine (NE) transport…’ ResearchGate, 1995.
• [2] Tran, V. T., et al. ‘Histamine H1 receptors identified in mammalian brain membranes with [3H]mepyramine.’ PNAS, 1978.
• [3] Gillman, P. K. ‘Tricyclic antidepressant pharmacology and therapeutic drug interactions updated.’ British Journal of Pharmacology, 2007.
• [4] Fujikawa, M., et al. ‘A Strategy for in Silico Prediction of the Membrane Permeability of Drugs.’ Kobe University, 2014.

Desipramine is a dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group. It has a role as an adrenergic uptake inhibitor, a serotonin uptake inhibitor, a cholinergic antagonist, an alpha-adrenergic antagonist, a H1-receptor antagonist, an EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an antidepressant and a drug allergen. It is a dibenzoazepine and a secondary amino compound.
Desipramine hydrochloride is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, desipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, desipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as desipramine and nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline and doxepine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Desipramine exerts less anticholinergic and sedative side effects compared to tertiary amine TCAs, such as amitriptyline and clomipramine. Desipramine may be used to treat depression, neuropathic pain (unlabeled use), agitation and insomnia (unlabeled use) and attention-deficit hyperactivity disorder (unlabeled use).
Desipramine is a Tricyclic Antidepressant.
Desipramine is an oral tricyclic antidepressant that widely used in the therapy of depression. Desipramine can cause mild and transient serum enzyme elevations and is rare cause of clinically apparent acute cholestatic liver injury.
Desipramine is an active metabolite of imipramine, a tertiary amine and a synthetic tricyclic derivative of the antidepressant. Desipramine enhances monoamine neurotransmission in certain areas of the brain by inhibiting the re-uptake of noradrenaline and serotonin at the noradrenergic and serotoninergic nerve endings, respectively. It also induces sedation through histamine 1 receptor blockage and hypotension through beta-adrenergic blockage.
DESIPRAMINE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1964 and is indicated for major depressive disorder and depressive disorder and has 13 investigational indications. This drug has a black box warning from the FDA.
Desipramine hydrochloride is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, desipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, desipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as desipramine and nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline and doxepine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H₁ receptors, α₁-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Desipramine exerts less anticholinergic and sedative side effects compared to tertiary amine TCAs, such as amitriptyline and clomipramine. Desipramine may be used to treat depression, neuropathic pain (unlabeled use), agitation and insomnia (unlabeled use) and attention-deficit hyperactivity disorder (unlabeled use).
A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.
See also: Imipramine (related); Clomipramine (related); Trimipramine (related) … View More …

Overview

Desipramine is a tricyclic antidepressant primarily used to treat depression and certain anxiety disorders. It is a secondary amine derivative of imipramine, exhibiting a similar pharmacological profile but with distinct chemical properties and mechanisms of action. Desipramine is classified as a selective norepinephrine reuptake inhibitor, which enhances the availability of norepinephrine in the synaptic cleft, thereby alleviating depressive symptoms.

Source

Desipramine was first synthesized in the 1950s as part of research into tricyclic antidepressants. It is derived from the dibenzazepine structure, which forms the backbone of many antidepressants in this class.

Classification

• Chemical Class: Tricyclic antidepressant
• Chemical Formula: C1818​H2222​N
• Molecular Weight: 262.38 g/mol

Synthesis Analysis

Methods

Desipramine can be synthesized through several methods, primarily involving the alkylation of 10,11-dihydro-5H-dibenz[b,f]azepine. One common approach is the reaction with 1-bromo-3-chloropropane in the presence of sodium amide, which facilitates the formation of desipramine via nucleophilic substitution.

Another method includes the synthesis of deuterium-labeled desipramine for pharmacokinetic studies, which involves deuteration at specific positions to trace metabolic pathways in biological systems  .

Technical Details

The synthesis typically requires controlled conditions to ensure high yield and purity. For instance, reactions are often conducted under inert atmospheres to minimize oxidation and degradation of sensitive intermediates.

Molecular Structure Analysis

Data

• Melting Point: Approximately 150-152 °C
• Solubility: Soluble in organic solvents like ethanol and methanol but poorly soluble in water.

Chemical Reactions Analysis

Reactions

Desipramine undergoes various chemical reactions typical for amines and aromatic compounds. Notable reactions include:

• N-Alkylation: Can react with alkyl halides to form quaternary ammonium salts.
• Hydroxylation: Desipramine can be metabolized in vivo to form 2-hydroxydesipramine, which is an active metabolite contributing to its pharmacological effects .

Technical Details

The stability of desipramine under different pH conditions has been studied, revealing that it remains stable in acidic environments but may degrade under prolonged exposure to alkaline conditions.

Mechanism of Action

Desipramine primarily acts by inhibiting the reuptake of norepinephrine at presynaptic neuronal membranes. This action increases the levels of norepinephrine available for neurotransmission, which is crucial for mood regulation. Additionally, desipramine has some affinity for serotonin receptors, although its primary mechanism remains norepinephrine reuptake inhibition.

Process and Data

Research indicates that desipramine’s effects on norepinephrine levels contribute to its efficacy in treating depressive disorders. Studies utilizing positron emission tomography have shown increased norepinephrine transporter occupancy correlating with clinical improvement .

Physical and Chemical Properties Analysis

Physical Properties

• Appearance: White to off-white crystalline powder.
• Odor: Odorless.
• Density: Approximately 1.04 g/cm³.

Chemical Properties

• pKa: Approximately 9.5 (indicating it behaves as a weak base).
• Stability: Stable under normal conditions but sensitive to light and moisture.

Relevant analyses have shown that desipramine’s solubility profile affects its bioavailability and therapeutic efficacy, necessitating careful formulation in pharmaceutical applications  .

Applications

Desipramine is primarily used in clinical settings for:

• Treatment of Depression: Effective for major depressive disorder.
• Anxiety Disorders: Sometimes prescribed off-label for anxiety management.
• Pain Management: Utilized in neuropathic pain syndromes due to its analgesic properties.

Moreover, desipramine has been studied for its potential roles in treating other conditions such as attention-deficit hyperactivity disorder and post-traumatic stress disorder due to its influence on neurotransmitter systems  .

Pharmacological Profile of Desipramine

Neurotransmitter Reuptake Inhibition Dynamics

Noradrenergic vs. Serotonergic Selectivity Gradients

Desipramine is characterized by its potent and relatively selective inhibition of the norepinephrine transporter (NET). Binding studies reveal a Ki value of 0.63–3.5 nM for human NET, compared to 17.6–163 nM for the serotonin transporter (SERT), indicating a 25- to 400-fold higher affinity for NET [1] [3] [7]. This selectivity arises from desipramine’s structural interaction with the extracellular cavity of NET, where it stabilizes the transporter’s closed conformation via a salt bridge with residue D401 and hydrophobic interactions with F320, preventing norepinephrine reuptake [5].

However, the active metabolite desmethyldesipramine exhibits altered selectivity. In rat models, it shows a 12-fold higher affinity for SERT (Ki = 12.8 nM) than NET (Ki = 153 nM), suggesting that chronic desipramine administration may indirectly enhance serotonergic neurotransmission [2] [4]. This shift underscores the dynamic interplay between parent compounds and metabolites in vivo.

Comparative Affinity Analysis Across Tricyclic Analogues

Among tricyclic antidepressants (TCAs), desipramine demonstrates the highest NET selectivity. Key affinity comparisons include:

Table 1: Reuptake Inhibition Profiles of Selected Tricyclic Antidepressants

Compound	NET Ki (nM)	SERT Ki (nM)	NET:SERT Selectivity Ratio
Desipramine	0.63–3.5	17.6–163	25- to 400-fold
Nortriptyline	4.4–18	18–200	4- to 10-fold
Amitriptyline	20–100	2.8–35	0.3- to 5-fold
Clomipramine	38–85	0.14–0.6	0.01- to 0.05-fold

Desipramine

Desipramine structure

CAS No.

50-47-5

Chemical Name:

Desipramine

Synonyms

DMI 50475;Pentofran;Sertofran;Desipramin;Pertrofane;esipramine;Desipramine;Desimpramine;Desimipramine;Norimipramine

CBNumber:

CB3257775

Molecular Formula:

C18H22N2

Molecular Weight:

266.38

MDL Number:

MFCD00242884

MOL File:

50-47-5.mol

MSDS File:

SDS

TDS File:

TDS

Last updated:2026-09-12 18:51:58

Product description	Number	Pack Size	Price
(3-{2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine >95%	AA00DEIS	100mg	$238
(3-{2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine >95%	AA00DEIS	250mg	$298
(3-{2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine >95%	AA00DEIS	500mg	$383
(3-{2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine >95%	AA00DEIS	1g	$529
3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine 95.00%	Y225274	100MG	$210

Request For Quotation

Desipramine Properties

Melting point	212°C
Boiling point	bp0.02 172-174°
Density	0.9934 (rough estimate)
refractive index	1.5200 (estimate)
pka	pKa 10.21(-)(H2O t=20) (Uncertain)
form	powder
color	white
FDA UNII	TG537D343B
ATC code	N06AA01
EPA Substance Registry System	Desipramine (50-47-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS08,GHS07
Signal word	Danger
Hazard statements	H370-H336-H302
Precautionary statements	P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P403+P233-P405-P501-P260-P264-P270-P307+P311-P321-P405-P501
Hazard Codes	Xn
Risk Statements	20/21/22
Safety Statements	36
WGK Germany	3
Hazardous Substances Data	50-47-5(Hazardous Substances Data)
REACH Registrations	Active

Desipramine price

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
aablocks	AA00DEIS	(3-{2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine >95%	50-47-5	100mg	$238	2026-05-28	Buy
aablocks	AA00DEIS	(3-{2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine >95%	50-47-5	250mg	$298	2026-05-28	Buy
aablocks	AA00DEIS	(3-{2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine >95%	50-47-5	500mg	$383	2026-05-28	Buy
aablocks	AA00DEIS	(3-{2-azatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine >95%	50-47-5	1g	$529	2026-05-28	Buy
ACHEMBLOCK	Y225274	3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine 95.00%	50-47-5	100MG	$210	2026-05-27	Buy

Desipramine Chemical Properties, Uses, Production

Originator

Pertofran,Geigy,UK,1963

Uses

Desipramine is used for depression of various etiology and in particular for endogenous depression.

Uses

Antidepressant.

Definition

ChEBI: A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.

Manufacturing Process

Oxidative coupling of o-nitrotoluene gives 4,4′-dinitrodibenzyl which is reduced with hydrogen to the diamine. The diamine is pyrolyzed to give dihydrobenzazepine. This is reacted with N-(3-chloropropyl)-Nmethylbenzamine to give N-benzyldesipramine. This is debenzylated by reductive cleavage and then reacted with HCl.

brand name

Norpramin (Sanofi Aventis); Pertofrane (Sanofi Aventis).

Therapeutic Function

Psychostimulant

Mechanism of action

Its antidepressant effect results from increases in the level of NE in CNS synapses, and long-term administration causes a downregulation of α1-adrenoceptors and desensitization of presynaptic α2-receptors, equilibrating the noradrenergic system and, thus, correcting the dysregulated output of depressed patients. The SSRIs do not produce this effect. Desipramine also downregulates the NET, but not the 5-SERT . Substantial loss of NE transporter–binding sites takes 15 days to occur and is accompanied by a marked reduction of NET function in vivo. Desipramine has weak effects on 5-HT reuptake.

Synthesis

Desipramine, 10,11-dihydro-5-[3-(methylamino)propyl]-5H-dibenz[b,f] azepine (7.1.13), differs from imipramine in that it contains only one methyl group on the nitrogen atom of the propylamine side chain. The suggested methods of desipramine synthesis are very simple, and the difference lies only in the manner in which the secondary methylamine group is introduced into the structure of the drug.
The first way of synthesis is by the alkylation of 10,11-dihydro-5H-dibenz[b,f]azepine using 1-bromo-3-chloropropane in the presence of sodium amide into a chloro derivative (7.1.12) and the subsequent reaction of this with methylamine, giving desipramine (7.1.13) [18–20].

Finally, a second way of synthesis is from imipramine (7.1.1), which undergoes demethylation by successive reaction with ethyl chloroformate, giving 5-[3-(N-carbethoxy-N-methyl)aminopropyl]-10,11-dihydro-5H-dibenz[b,f]azepine (7.1.15), the alkaline hydrolysis of which leads to desipramine (7.1.13) [23,24].

Metabolism

Desipramine is a dihydrodibenzazepine secondary amine TCA that also is the active metabolite of imipramine. Desipramine appears to have a bioavailability comparable to the other secondary TCAs. Desipramine is distributed into milk in concentrations similar to those present at steady state in maternal plasma. This drug is metabolized primarily by CYP2D6 to its 2-hydroxy metabolite and by CYP1A2 and CYP2C19 to its N-demethylated (primary amine) metabolite . Desipramine exhibits a greater potency and selectivity for the NET than the other secondary TCAs do.

Desipramine Preparation Products And Raw materials

Desipramine’s superior NET affinity stems from its secondary amine structure, which reduces steric hindrance at the transporter’s active site compared to tertiary amines (e.g., imipramine). Molecular analyses confirm that its three-ring system and methylaminopropyl side chain optimize binding to NET’s hydrophobic pocket [5] [7].

Receptor Modulation Pathways

• Product Name: Desipramine
• Molecular Weight: 266.38068
• Molecular Formula: C₁₈H₂₂N₂
• Synonyms: [14C]-Desipramine; [3H]-Desipramine; 10,11-Dihydro-5-(3-methylaminopropyl)-5H-dibenz(b,f)azepine; 10,11-dihydro-5-[3-(methylamino)propyl]-5H-dibenz(b,f)azepin; 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methyl-1-propanamine; 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine;

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   • Boiling point: bp0.02 172-174°
   • Melting point: 212°C

   • Density: 0.9934 (rough estimate)
   • refractive index: 1.5200 (estimate)

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   • Boiling point: bp0.02 172-174°
   • Melting point: 212°C

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   • refractive index: 1.5200 (estimate)
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