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14028-44-5

Basic Information
CAS No.: 14028-44-5
Name: Amoxapine
Molecular Structure:
Molecular Structure of 14028-44-5 (Amoxapine)
Formula: C17H16ClN3O
Molecular Weight: 313.787
Synonyms: 2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine;
EINECS: 237-867-1
Density: 1.37 g/cm3
Melting Point: 175-176 °C
Boiling Point: 469.9 °C at 760 mmHg
Flash Point: 238 °C
Appearance: Crystalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
PSA: 36.86000
LogP: 3.13150
Synthetic route
110-85-0

piperazine

3455-14-9

2,11-dichloro-dibenzo[b,f][1,4]oxazepine

14028-44-5

amoxapine

Conditions
ConditionsYield
In xylene for 5h; Heating;
1977-10-2

loxapine

14028-44-5

amoxapine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. HCl / 16 h / Heating
2: POCl3, PhNMe2 / 5 h / Heating
3: xylene / 5 h / Heating
View Scheme
3158-91-6

2-chlorodibenzo[b,f][1,4]oxazepin-11(10H)-one

14028-44-5

amoxapine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POCl3, PhNMe2 / 5 h / Heating
2: xylene / 5 h / Heating
View Scheme
148550-51-0

ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate

14028-44-5

amoxapine

1024010-80-7

ethyl 2-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)pyrimidine-5-carboxylate

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 20℃; for 1h;100%
In 1,2-dimethoxyethane at 20℃; for 1h;100%
677-25-8

ethylenesulfonyl fluoride

14028-44-5

amoxapine

2-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)ethanesulfonyl fluoride

Conditions
ConditionsYield
In dichloromethane at 20℃;100%

(4-ethynylphenyl)sulfurimidoyl difluoride

14028-44-5

amoxapine

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)-N-(4-ethynylphenyl)piperazine-1-sulfonimidoyl fluoride

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃; for 2h;99%
14028-44-5

amoxapine

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-sulfonyl fluoride

Conditions
ConditionsYield
With dmap; potassium fluoride; N-ethyl-N,N-diisopropylamine; N,N`-sulfuryldiimidazole; trifluoroacetic acid In dichloromethane at 20℃; for 16h;99%
With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 1h;95%
With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 1h;95%
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.166667h;93%
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; potassium carbonate In dimethyl sulfoxide at 20℃; for 1h;89%
811-68-7

silver(I) trifluoromethanethiolate

14028-44-5

amoxapine

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-carbothioyl fluoride

Conditions
ConditionsYield
With potassium bromide In acetonitrile at 20℃; for 1h; Inert atmosphere;98%
With potassium bromide In acetonitrile at 25℃; for 1h;89%
3582-05-6

trifluoromethyl trifluoromethanesulfonate

14028-44-5

amoxapine

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-carbonyl fluoride

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.0833333h; Sealed tube;97%
67-56-1

methanol

14028-44-5

amoxapine

1977-10-2

loxapine

Conditions
ConditionsYield
With aluminum (III) chloride; water In acetonitrile at 20℃; Irradiation;95%
With [(Cp*IrCl)2(4,4′,6,6′-tetrahydroxy-2,2′-bipyrimidine)][Cl]2; potassium hydroxide In water at 130℃; for 12h; Schlenk technique;73%
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Consensus Reports

AMOXAPINE is reported in EPA TSCA Inventory.

Specification

The Amoxapine, with the CAS registry number 14028-44-5 and EINECS registry number 237-867-1, has the systematic name of 2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine. It is a kind of crystalline solid, and belongs to the following product categories: Intermediates & Fine Chemicals; Pharmaceuticals; Adrenoceptor. It is a strong norepinephrine reuptake inhibitor and weak serotonin reuptake inhibitor. It also possesses antiadrenergic, anticholinergic, antidopaminergic, antihistamine, and antiserotonergic actions. The molecular formula of this chemical is C17H16ClN3O.

The physical properties of Amoxapine are as following: (1)ACD/LogP: 2.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.06; (4)ACD/LogD (pH 7.4): 1.76; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 9.32; (7)ACD/KOC (pH 5.5): 2.32; (8)ACD/KOC (pH 7.4): 117.52; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 28.07 Å2; (13)Index of Refraction: 1.685; (14)Molar Refractivity: 86.74 cm3; (15)Molar Volume: 228.2 cm3; (16)Polarizability: 34.39×10-24cm3; (17)Surface Tension: 52.1 dyne/cm; (18)Density: 1.37 g/cm3; (19)Flash Point: 238 °C; (20)Enthalpy of Vaporization: 73.23 kJ/mol; (21)Boiling Point: 469.9 °C at 760 mmHg; (22)Vapour Pressure: 5.32E-09 mmHg at 25°C.

Preparation and uses of Amoxapine: o-(p-chlorophenoxy) benzene Ethyl carbamate react with N-ethyl piperazine-based to give 4-[[o-(p-chlorophenoxy)phenyl]carbamoyl]-1-piperazine carboxylate. Then heat it with phosphorus pentoxide and phosphorus oxychloride to reflux. And you can get the aim product with this cyclization reaction. What's more, Amoxapine is used in the treatment of depression, anxiety disorders, panic disorder, and bipolar disorder.

You should be cautious while dealing with this chemical. It is harmful if swallowed. Therefore, you had better take the wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc2ccc1Oc4c(/N=C(\c1c2)N3CCNCC3)cccc4
(2)InChI: InChI=1/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2
(3)InChIKey: QWGDMFLQWFTERH-UHFFFAOYAA

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD unreported > 20mg/kg (20mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: IRRITABILITY
Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
child LDLo oral 25mg/kg (25mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Southern Medical Journal. Vol. 76, Pg. 543, 1983.
child TDLo oral 10mg/kg (10mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP JAMA, Journal of the American Medical Association. Vol. 250, Pg. 1069, 1983.
dog LD unreported > 20mg/kg (20mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: IRRITABILITY
Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
dog LDLo intraperitoneal 20mg/kg (20mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
man TDLo oral 4285ug/kg/2D- (4.285mg/kg) BEHAVIORAL: EXCITEMENT American Journal of Psychiatry. Vol. 140, Pg. 115, 1983.
man TDLo oral 4286ug/kg (4.286mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: REGIDITY
Southern Medical Journal. Vol. 77, Pg. 94, 1984.
man TDLo oral 14mg/kg (14mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" JAMA, Journal of the American Medical Association. Vol. 248, Pg. 3141, 1982.
man TDLo oral 27mg/kg (27mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Pharmacotherapy Vol. 15, Pg. 528, 1995.
man TDLo oral 70mg/kg/3W-I (70mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Clinical Psychiatry. Vol. 45, Pg. 358, 1984.
man TDLo unreported 5714ug/kg/2D- (5.714mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Southern Medical Journal. Vol. 76, Pg. 1077, 1983.
monkey LD unreported > 20mg/kg (20mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
mouse LD50 intraperitoneal 112mg/kg (112mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: REGIDITY
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 233, Pg. 107, 1978.
mouse LD50 oral 104mg/kg (104mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979.
mouse LD50 subcutaneous 385mg/kg (385mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1852, 1971.
rat LD50 intraperitoneal 201mg/kg (201mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: REGIDITY

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 233, Pg. 107, 1978.
rat LD50 oral 313mg/kg (313mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1852, 1971.
rat LD50 subcutaneous > 4500mg/kg (4500mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1852, 1971.
women LDLo oral 40mg/kg (40mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: CHANGE IN RATE

CARDIAC: OTHER CHANGES
Annals of Emergency Medicine. Vol. 17, Pg. 274, 1988.
women LDLo oral 40mg/kg (40mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
JAMA, Journal of the American Medical Association. Vol. 250, Pg. 1069, 1983.
women LDLo oral 75953ug/kg (75.953mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: OTHER CHANGES

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Forensic Science International. Vol. 26, Pg. 33, 1984.
women TDLo oral 5mg/kg (5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD JAMA, Journal of the American Medical Association. Vol. 250, Pg. 1069, 1983.
women TDLo oral 15mg/kg/5D-I (15mg/kg) ENDOCRINE: HYPERGLYCEMIA Journal of Clinical Psychiatry. Vol. 44, Pg. 347, 1983.
women TDLo oral 17mg/kg (17mg/kg) BEHAVIORAL: COMA

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 101, 1983.
women TDLo oral 30mg/kg (30mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
JAMA, Journal of the American Medical Association. Vol. 248, Pg. 1092, 1982.
women TDLo oral 50mg/kg (50mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA
Ugeskrift for Laeger. Doctor's Weekly. Vol. 146, Pg. 3285, 1984.