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58-28-6

Basic Information
CAS No.: 58-28-6
Name: DESIPRAMINE HYDROCHLORIDE
Molecular Structure:
Molecular Structure of 58-28-6 (DESIPRAMINE HYDROCHLORIDE)
Formula: C18H23ClN2
Molecular Weight: 302.847
Synonyms: 5H-Dibenz[b,f]azepine,10,11-dihydro-5-[3-(methylamino)propyl]-, monohydrochloride (8CI);5H-Dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-N-methyl-, monohydrochloride(9CI);10,11-Dihydro-5-[3-(methylamino)propyl]-5H-dibenz[b,f]azepinemonohydrochloride;5-[3-(Methylamino)propyl]-5H-dibenz[b,f]azepinehydrochloride;DMI hydrochloride;Demethylimipramine hydrochloride;Desimipramine-hydrochloride;Desipramine hydrochloride;Desipraminemonohydrochloride;Desmethylimipramine chloride;Desmethylimipraminemonohydrochloride;Desmethylimipramine-hydrochloride;GMI;JB8181;N-(g-Methylaminopropyl)iminodibenzylhydrochloride;Norpramin;Nortrimil;Pertofran;Pertofrane;
EINECS: 200-373-1
Melting Point: 214-216°C
Boiling Point: 407.4 °C at 760 mmHg
Flash Point: 160.5 °C
Solubility: H2O: 50 mg/mL
Appearance: white to off-white powder
Hazard Symbols: HarmfulXn FlammableF ToxicT
Risk Codes: R22; R36/37/38; R42/43; R48/23/24/25; R11
Safety: S7; S16; S36/37S45; S26; S24; S22
Transport Information: UN 1230 3/PG 2
PSA: 15.27000
LogP: 4.79070
Synthetic route
58-28-6

desipramine hydrochloride

5231-87-8

3,4-diethoxy-3-cyclobuten-1,2-dione

131589-04-3

4-<<3'-(10'',11''-Dihydro-5H-dibenzazepin-5''-yl)propyl>(methyl)amino>-3-ethoxy-3-cyclobutene-1,2-dione

Conditions
ConditionsYield
With triethylamine In ethanol for 5h; Ambient temperature;100%
51146-56-6

(S)-ibuprofen

58-28-6

desipramine hydrochloride

(S)-N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-2-(4-isobutylphenyl)-N-methylpropanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;97%
106-31-0

butanoic acid anhydride

58-28-6

desipramine hydrochloride

N-butyryldesipramine

Conditions
ConditionsYield
With pyridine In toluene for 1h; Heating;95%
126-00-1

4,4-bis(4-hydroxyphenyl)valeric acid

58-28-6

desipramine hydrochloride

N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-4,4-bis(4-hydroxyphenyl)-N-methylpentanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;82%
58-28-6

desipramine hydrochloride

88574-06-5

6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid

(9H-fluoren-9-yl)methyl (6-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)amino)-6-oxohexyl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;80%
58-28-6

desipramine hydrochloride

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

N-Formyldesipramine

B

N-[3-(2-formyl-10,11-dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-N-methyl-formamide

Conditions
ConditionsYield
With trichlorophosphate at 95℃; Formylation; Vilsmeier reaction;A 22%
B 72%
143-66-8

sodium tetraphenyl borate

58-28-6

desipramine hydrochloride

C18H22N2*C24H20B(1-)*H(1+)

Conditions
ConditionsYield
In ethanol at 78℃;68%
124-38-9

carbon dioxide

58-28-6

desipramine hydrochloride

(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)carbamic fluoride

Conditions
ConditionsYield
With dmap; diethylamino-sulfur trifluoride In acetonitrile at 25℃; under 760.051 Torr; for 2h; Schlenk technique;64%
110-99-6

2,2'-oxybis-acetic acid

58-28-6

desipramine hydrochloride

1423770-96-0

2,2’-oxybis(N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-N-methylacetamide)

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere;62%
1111-72-4

carbon dioxide

58-28-6

desipramine hydrochloride

(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)carbamic fluoride-[13C]

Conditions
ConditionsYield
With dmap; diethylamino-sulfur trifluoride In acetonitrile at 25℃; under 760.051 Torr; for 2h; Schlenk technique;62%
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  • 5-[3-(Methylamino)propyl]-5H-dibenz[b,f]azepine hydrochloride cas  58-28-6

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Chemistry

Molecular Structure of 10,11-Dihydro-5-(3-(methylamino)prop-yl)-5h-dibenz(b,f)azepine hydro-chloride (CAS NO.58-28-6):

IUPAC Name: 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N-methylpropan-1-amine hydrochloride
Empirical Formula: C18H23ClN2
Molecular Weight: 302.8416
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 6.48 Å2
Flash Point: 160.5 °C
Enthalpy of Vaporization: 65.93 kJ/mol
Boiling Point: 407.4 °C at 760 mmHg
Vapour Pressure: 7.56E-07 mmHg at 25°C
Melting point: 214-216°C
Storage temp: 2-8°C
Solubility: H2O: 50 mg/mL
Form: powder
Color: white to off-white
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
Smiles
N1(c2c(CCc3c1cccc3)cccc2)CCCNC.Cl
EINECS: 200-373-1
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals; Biogenic Amine Transport Inhibitors; Biogenic Amine Transport InhibitorsObesity Research; Neurotransmission; Neurotransmission (Obesity); Neurotransmitters;Adrenoceptor

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 25mg/kg (25mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
guinea pig LDLo intravenous 55mg/kg (55mg/kg) CARDIAC: OTHER CHANGES Therapie. Vol. 20, Pg. 67, 1965.
man TDLo oral 490ug/kg (0.49mg/kg) BEHAVIORAL: SLEEP Journal of Clinical Psychiatry. Vol. 47, Pg. 210, 1986.
man TDLo oral 5mg/kg/5D-I (5mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS
American Journal of Psychiatry. Vol. 142, Pg. 386, 1985.
mouse LD50 intraperitoneal 88mg/kg (88mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
mouse LD50 intravenous 37mg/kg (37mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: REGIDITY
International Journal of Neuropharmacology. Vol. 4, Pg. 111, 1965.
mouse LD50 oral 315mg/kg (315mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
rat LD50 intraperitoneal 55mg/kg (55mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
rat LD50 intravenous 19mg/kg (19mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
rat LD50 oral 871mg/kg (871mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 1411, 1983.
women TDLo oral 14mg/kg/1W-I (14mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED Journal of Clinical Psychiatry. Vol. 44, Pg. 153, 1983.
women TDLo oral 36mg/kg/6D-I (36mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION
Journal of Clinical Psychiatry. Vol. 53, Pg. 160, 1992.
women TDLo oral 45mg/kg (45mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Annals of Pharmacotherpy. Vol. 27, Pg. 572, 1993.
women TDLo oral 70mg/kg/4W-I (70mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS
American Journal of Psychiatry. Vol. 142, Pg. 386, 1985.

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 NOx and HCl.
Hazard Codes: HarmfulXn,ToxicT,FlammableF
Risk Statements: 22-36/37/38-42/43-48/23/24/25-23/24/25-11
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R42/43:May cause sensitization by inhalation and skin contact. 
R48:Danger of serious damage to health by prolonged exposure. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R11:Highly flammable.
Safety Statements: 7-16-36/37-45-26-24-22
S7:Keep container tightly closed. 
S16:Keep away from sources of ignition. 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S24:Avoid contact with skin. 
S22:Do not breathe dust.
RIDADR: UN 1230 3/PG 2
WGK Germany: 3
RTECS: HO0525000

Specification

  10,11-Dihydro-5-(3-(methylamino)prop-yl)-5h-dibenz(b,f)azepine hydro-chloride , with CAS number of 58-28-6, can be called 10,11-dihydro-5-(3-(methylamino)propyl)-5h-dibenz(b,f)azepinehydrochloride ; demethylimipraminehydrochloride ; desmethylimipraminehydrochloride ; dmihydrochloride ; f)azepine,10,11-dihydro-5-(3-(methylamino)propyl)-5h-dibenz(hydrochlorid ; f)azepine,10,11-dihydro-5-(3-(methylamino)propyl)-5h-dibenz(monohydrochlor . It is a white to off-white powder, 10,11-Dihydro-5-(3-(methylamino)prop-yl)-5h-dibenz(b,f)azepine hydro-chloride (CAS NO.58-28-6) can be used as a more potent inhibitor of the norepinephrine transporter than the serotonin transporter.