desipramine hydrochloride
3,4-diethoxy-3-cyclobuten-1,2-dione
4-<<3'-(10'',11''-Dihydro-5H-dibenzazepin-5''-yl)propyl>(methyl)amino>-3-ethoxy-3-cyclobutene-1,2-dione
Conditions | Yield |
---|---|
With triethylamine In ethanol for 5h; Ambient temperature; | 100% |
(S)-ibuprofen
desipramine hydrochloride
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% |
Conditions | Yield |
---|---|
With pyridine In toluene for 1h; Heating; | 95% |
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
6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid
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
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
With trichlorophosphate at 95℃; Formylation; Vilsmeier reaction; | A 22% B 72% |
Conditions | Yield |
---|---|
In ethanol at 78℃; | 68% |
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
desipramine hydrochloride
2,2’-oxybis(N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-N-methylacetamide)
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere; | 62% |
Conditions | Yield |
---|---|
With dmap; diethylamino-sulfur trifluoride In acetonitrile at 25℃; under 760.051 Torr; for 2h; Schlenk technique; | 62% |
tetraglycolic acid
desipramine hydrochloride
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)
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere; | 54% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere; | 50% |
Conditions | Yield |
---|---|
With potassium hydroxide; sodium cyanoborohydride In methanol reductive amination; N-benzylation; | 48% |
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
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With ammonium sulfate at 110℃; |
desipramine hydrochloride
Conditions | Yield |
---|---|
With rat brain cytosolic fraction; magnesium(II); PAPS In phosphate buffer for 0.166667h; pH=7.0; Enzyme kinetics; N-sulphation; |
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
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
N-Benzyl-2-formyldesipramine
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
N-Benzyl-2-hydroxydesipramine
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 |
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
diethyl chlorophosphate
[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-phosphoramidic acid diethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h; |
octyl chloroformate
desipramine hydrochloride
[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-carbamic acid octyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h; |
desipramine hydrochloride
methyl chloroformate
N'-(4-carbomethoxy)desimipramine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6h; |
desipramine hydrochloride
propoxycarbonyl chloride
[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-carbamic acid propyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6h; |
desipramine hydrochloride
isobutyl chloroformate
[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-carbamic acid isobutyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6h; |
desipramine
Ethyl 3-bromopropionate
desipramine hydrochloride
3-{[3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propyl]-methyl-amino}-propionic Acid Ethyl Ester
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
chloroformic acid ethyl ester
Ethyl 2-bromo-3-pyridinecarboxylate
sodium hydrogencarbonate
desipramine hydrochloride
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 |
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%) |
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
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. |
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: Xn,T,F
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
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.
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