58-28-6

Basic information

• Product Name: DESIPRAMINE HYDROCHLORIDE
• Synonyms: 10,11-dihydro-5-(3-(methylamino)propyl)-5h-dibenz(b,f)azepinehydrochloride;demethylimipraminehydrochloride;desmethylimipraminehydrochloride;dmihydrochloride;ex4355;f)azepine,10,11-dihydro-5-(3-(methylamino)propyl)-5h-dibenz(hydrochlorid;f)azepine,10,11-dihydro-5-(3-(methylamino)propyl)-5h-dibenz(monohydrochlor;g35020
• CAS NO: 58-28-6
• Molecular Formula: C₁₈H₂₂N₂*ClH
• Molecular Weight: 302.84
• EINECS: 200-373-1
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Biogenic Amine Transport Inhibitors;Biogenic Amine Transport InhibitorsObesity Research;Neurotransmission;Neurotransmission (Obesity);Neurotransmitters;Adrenoceptor;NORPRAMIN
• Mol File: 58-28-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 214-2160C
• Boiling Point: 407.4 °C at 760 mmHg
• Flash Point: 11 °C
• Appearance: white to off-white/powder
• Vapor Pressure: 7.56E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL
• CAS DataBase Reference: DESIPRAMINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DESIPRAMINE HYDROCHLORIDE(58-28-6)
• EPA Substance Registry System: DESIPRAMINE HYDROCHLORIDE(58-28-6)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 22-36/37/38-42/43-48/23/24/25-23/24/25-11-39/23/24/25
• Safety Statements: 7-16-36/37-45-26-24-22
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• RTECS: HO0525000
• Hazardous Substances Data: 58-28-6(Hazardous Substances Data)

Usage

Chemical Properties

White To Off-White Solid

Uses

Different sources of media describe the Uses of 58-28-6 differently. You can refer to the following data:
1. Desipramine hydrochloride has been used: to prevent norepinephrine neuron degeneration and to maximize uptake into DA neurons to protect unselective damage to the?noradrenergic system as a norepinephrine re-uptake inhibitor to treat rats for lesioning
2. Tricyclic antidepresant that is a more potent inhibitor of the norepinephrine transporter than the serotonin transporter.
3. Tricyclic antidepressant that is a more potent inhibitor of the norepinephrine transporter than the serotonin transporter.

Definition

ChEBI: The hydrochloride salt of desipramine.

Therapeutic Function

Psychostimulant

General Description

The structure and salient properties of desipramine hydrochloride,10,11-dihydro-N-methyl-5H-dibenz[b,f]azepine-5-propanamine monohydrochloride, 5-(3-methylaminopropyl)-10,11-dihydro-5H-dibenz[b,f]azepine hydrochloride(Norpramin, Pertofrane), are discussed under the heading,Imipramine. Among tricyclics, desipramine would be consideredwhen few anticholinergic effects or a low level of sedationare important. It is a SNERI.

Biological Activity

Tricyclic antidepressant that is a selective inhibitor of noradrenalin transporters (K i values are 4, 61 and 78720 nM for NET, SERT and DAT transporters respectively).

Biochem/physiol Actions

Desipramine is used to treat depression. It is also used to manage enuresis in children. Desipramine helps to eliminate the pain triggered by diabetic neuropathy.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Human systemic effects by ingestion: decreased urine volume, sodium level changes, chlorine level changes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO, and HCI.

InChI:InChI=1/C18H22N2.ClH/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;1H

Synthetic route

desipramine hydrochloride (58-28-6) + 3,4-diethoxy-3-cyclobuten-1,2-dione (5231-87-8) → 4-<<3'-(10'',11''-Dihydro-5H-dibenzazepin-5''-yl)propyl>(methyl)amino>-3-ethoxy-3-cyclobutene-1,2-dione (131589-04-3)

Conditions	Yield
With triethylamine In ethanol for 5h; Ambient temperature;	100%

(S)-ibuprofen (51146-56-6) + desipramine hydrochloride (58-28-6) → (S)-N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-2-(4-isobutylphenyl)-N-methylpropanamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	97%

butanoic acid anhydride (106-31-0) + desipramine hydrochloride (58-28-6) → N-butyryldesipramine

Conditions	Yield
With pyridine In toluene for 1h; Heating;	95%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + desipramine hydrochloride (58-28-6) → N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-4,4-bis(4-hydroxyphenyl)-N-methylpentanamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	82%

desipramine hydrochloride (58-28-6) + 6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid (88574-06-5) → (9H-fluoren-9-yl)methyl (6-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)amino)-6-oxohexyl)carbamate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	80%

desipramine hydrochloride (58-28-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N-Formyldesipramine + N-[3-(2-formyl-10,11-dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-N-methyl-formamide

Conditions	Yield
With trichlorophosphate at 95℃; Formylation; Vilsmeier reaction;	A 22% B 72%

sodium tetraphenyl borate (143-66-8) + desipramine hydrochloride (58-28-6) → C18H22N2*C24H20B(1-)*H(1+)

Conditions	Yield
In ethanol at 78℃;	68%

carbon dioxide (124-38-9) + desipramine hydrochloride (58-28-6) → (3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)carbamic fluoride

Conditions	Yield
With dmap; diethylamino-sulfur trifluoride In acetonitrile at 25℃; under 760.051 Torr; for 2h; Schlenk technique;	64%

2,2'-oxybis-acetic acid (110-99-6) + desipramine hydrochloride (58-28-6) → 2,2’-oxybis(N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-N-methylacetamide) (1423770-96-0)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere;	62%

carbon dioxide (1111-72-4) + desipramine hydrochloride (58-28-6) → (3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)carbamic fluoride-[13C]

Conditions	Yield
With dmap; diethylamino-sulfur trifluoride In acetonitrile at 25℃; under 760.051 Torr; for 2h; Schlenk technique;	62%

tetraglycolic acid (13887-98-4) + desipramine hydrochloride (58-28-6) → 2,2’-((oxybis(ethane-1,2-diyl))bis(oxy))bis(N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-N-methylacetamide) (1423770-98-2)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere;	54%

3,6-dioxasuberic acid (23243-68-7) + desipramine hydrochloride (58-28-6) → C42H50N4O4 (1423770-97-1)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere;	50%

desipramine hydrochloride (58-28-6) + benzaldehyde (100-52-7) → N-Benzyldesipramine (3978-87-8)

Conditions	Yield
With potassium hydroxide; sodium cyanoborohydride In methanol reductive amination; N-benzylation;	48%

desipramine hydrochloride (58-28-6) + Boc-Dap(Fmoc)-OH (131570-56-4, 122235-70-5) → C41H46N4O5

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	46%

desipramine hydrochloride (58-28-6) → N-nitrosodesipramine

Conditions	Yield
Yield given. Multistep reaction;

desipramine hydrochloride (58-28-6) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → [3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-trimethylsilanyl-amine

Conditions	Yield
With ammonium sulfate at 110℃;

desipramine hydrochloride (58-28-6) → Desipramine sulphamate

Conditions	Yield
With rat brain cytosolic fraction; magnesium(II); PAPS In phosphate buffer for 0.166667h; pH=7.0; Enzyme kinetics; N-sulphation;

desipramine hydrochloride (58-28-6) → 2-Hydroxydesipramine (1977-15-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 48 percent / KOH; NaBH3CN / methanol 2: 68 percent / POCl3 / 4 h / 100 °C 3: m-CPBA; TFA / CH2Cl2 / 2 h / 5 - 20 °C 4: conc. HCl / methanol / 2 h 5: 99 percent / H2 / 10 percent Pd/C / ethanol / 5 h / 760 Torr View Scheme

desipramine hydrochloride (58-28-6) → formic acid 5-[3-(benzyl-methyl-amino)-propyl]-10,11-dihydro-5H-dibenzo[b,f]azepin-2-yl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 48 percent / KOH; NaBH3CN / methanol 2: 68 percent / POCl3 / 4 h / 100 °C 3: m-CPBA; TFA / CH2Cl2 / 2 h / 5 - 20 °C View Scheme

desipramine hydrochloride (58-28-6) → N-Benzyl-2-formyldesipramine (134150-70-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / KOH; NaBH3CN / methanol 2: 68 percent / POCl3 / 4 h / 100 °C View Scheme

desipramine hydrochloride (58-28-6) → N-Benzyl-2-hydroxydesipramine (134150-71-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 48 percent / KOH; NaBH3CN / methanol 2: 68 percent / POCl3 / 4 h / 100 °C 3: m-CPBA; TFA / CH2Cl2 / 2 h / 5 - 20 °C 4: conc. HCl / methanol / 2 h View Scheme

desipramine hydrochloride (58-28-6) → impramine (50-49-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: (NH4)2SO4 / 110 °C 2: 2.) LiAlH4 / 1.) THF, -45 deg C - 60 deg C, 2.) 60 deg C, 10 min View Scheme

desipramine hydrochloride (58-28-6) + diethyl chlorophosphate (814-49-3) → [3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-phosphoramidic acid diethyl ester (876124-38-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;

octyl chloroformate (7452-59-7) + desipramine hydrochloride (58-28-6) → [3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-carbamic acid octyl ester (876124-42-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;

desipramine hydrochloride (58-28-6) + methyl chloroformate (79-22-1) → N'-(4-carbomethoxy)desimipramine (876124-39-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6h;

desipramine hydrochloride (58-28-6) + propoxycarbonyl chloride (109-61-5) → [3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-carbamic acid propyl ester (876124-40-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6h;

desipramine hydrochloride (58-28-6) + isobutyl chloroformate (543-27-1) → [3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-carbamic acid isobutyl ester (876124-41-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6h;

desipramine (50-47-5) + Ethyl 3-bromopropionate (539-74-2) + desipramine hydrochloride (58-28-6) → 3-{[3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propyl]-methyl-amino}-propionic Acid Ethyl Ester (408502-89-6)

Conditions	Yield
With sodium iodide; potassium carbonate In methanol; ethyl acetate; N,N-dimethyl-formamide; acetone	3.45 g (9.41 mmol, 89%)

2-bromo-pyridine (109-04-6) + chloroformic acid ethyl ester (541-41-3) + Ethyl 2-bromo-3-pyridinecarboxylate (53087-78-8) + sodium hydrogencarbonate (144-55-8) + desipramine hydrochloride (58-28-6) → 2-(N-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-N-methylamino)nicotinic acid ethyl ester

Conditions	Yield
With n-butyllithium; potassium iodide; diisopropylamine; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane; n-heptane; water; ethyl acetate; acetonitrile
With n-butyllithium; potassium iodide; diisopropylamine; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane; n-heptane; water; ethyl acetate; acetonitrile

tetrachloromethane (56-23-5) + ethyl 2-methylbenzoate (87-24-1) + desipramine hydrochloride (58-28-6) → 2-((N-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-N-methyl amino)methyl)-benzoic acid ethyl ester

Conditions	Yield
With N-Bromosuccinimide; lithium bromide; potassium carbonate; dibenzoyl peroxide In n-heptane; water; ethyl acetate; acetonitrile	1.09 g (49%)
With N-Bromosuccinimide; lithium bromide; potassium carbonate; dibenzoyl peroxide In n-heptane; water; ethyl acetate; acetonitrile	1.09 g (49%)

Downstream Products

• 494-19-9 9,10-dihydrodibenzazepine 
• 50-47-5 desipramine 
• 50-49-7 impramine 
• 134150-71-3 N-Benzyl-2-hydroxydesipramine 
• 134150-70-2 N-Benzyl-2-formyldesipramine 
• 1977-15-7 2-Hydroxydesipramine 
• 3978-87-8 N-Benzyldesipramine