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132539-06-1

Basic Information
CAS No.: 132539-06-1
Name: 10H-Thieno[2,3-b][1,5]benzodiazepine, 2-methyl-4-(4-methyl-1-piperazinyl)-
Article Data: 57
Cas Database
Molecular Structure:
Molecular Structure of 132539-06-1 (10H-Thieno[2,3-b][1,5]benzodiazepine, 2-methyl-4-(4-methyl-1-piperazinyl)-)
Formula: C17H20N4S
Molecular Weight: 312.439
Synonyms: 2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno(2,3-b)(1,5)benzodiazepine;Olansek;10H-Thieno(2,3-b)(1,5)benzodiazepine, 2-methyl-4-(4-methyl-1-piperazinyl)-;Symbyax;Zyprexa (TN);Olanzapine [USAN:INN];2-methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[b]thieno[2,3-e][1,4]diazepine;Olanzapine;
EINECS: 200-835-2
Density: 1.32 g/cm3
Melting Point: 195 °C
Boiling Point: 476.035 °C at 760 mmHg
Flash Point: 241.697 °C
Solubility: N/A
Appearance: yellowish crystalline powder
Hazard Symbols: Xi,Xn,F
Risk Codes: 36/38-36-20/21/22-11
Safety: 26-36/37-16
Transport Information: N/A
PSA: 59.11000
LogP: 2.88860
Synthetic route

2-methyl-4-(4-methylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine acetic acid monosolvate

Conditions
ConditionsYield
at 65 - 70℃; for 18h; Vacuo;100%
161696-76-0

N-desmethyl olanzapine

74-88-4

methyl iodide

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0℃; for 2h; Product distribution / selectivity;99%
With sodium hydride In tetrahydrofuran at -10℃; for 3h; Product distribution / selectivity;98%
With sodium hydroxide In tetrahydrofuran at -15℃; for 4h; Product distribution / selectivity;98%
With triethylamine In tetrahydrofuran at -10℃; for 4h; Product distribution / selectivity;82%
109-01-3

1-methyl-piperazine

4-amino-2-methyl-10H-thiene [2,3-b][1,5]-benzodiazepine hydrochloride

Conditions
ConditionsYield
In ethanol; dimethyl sulfoxide at 100 - 130℃; Solvent; Temperature;92.5%
In dimethyl sulfoxide at 100 - 120℃; for 8h;84.2%
109-01-3

1-methyl-piperazine

612503-08-9

2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-amine

Conditions
ConditionsYield
In propan-1-ol at 110℃; Product distribution / selectivity; Heating / reflux;89%
In iso-butanol at 118℃; Product distribution / selectivity; Heating / reflux;84%
In isopropyl alcohol at 100 - 102℃; Product distribution / selectivity; Heating / reflux;80%
109-01-3

1-methyl-piperazine

4-amino-2-methyl-10H-thieno[2,3-b][1,5]benzodiazepine hydrochloride

Conditions
ConditionsYield
at 125 - 145℃; for 5 - 12h; Product distribution / selectivity; Neat (no solvent);84%
at 120℃; for 5h;83.8%
In dimethyl sulfoxide at 112 - 115℃; for 16h;82%

olanzapinium oxalate

Conditions
ConditionsYield
With sodium hydroxide In water pH=9;72.6%
With sodium hydroxide In water pH=8 - 10;
With sodium hydroxide In water pH=9 - 10; Product distribution / selectivity;

2,4-bis(4-methyl-1-piperazinyl)-3-propylidene-3H-[1,5]benzodiazepine

Conditions
ConditionsYield
With quinoline p-toluenesulfonate; sulfur In benzonitrile at 140℃; for 13.5h;69.5%
With pyridinium p-toluenesulfonate; sulfur In benzonitrile at 140℃; for 13.5h;66.6%
With sulfur; 1-methyl-imidazolium p-toluenesulfonic acid In benzonitrile at 140℃; for 10h;54.2%
With toluene-4-sulfonic acid; sulfur In benzonitrile at 140℃; for 9h;51.7%
With sulfur; triethylamine In propan-1-ol; dimethyl sulfoxide at 100℃; for 120h;12%
77-78-1

dimethyl sulfate

161696-76-0

N-desmethyl olanzapine

Conditions
ConditionsYield
With potassium carbonate In methanol at 25℃; for 2h; Product distribution / selectivity;60%
With potassium carbonate In acetone at -10℃; for 4h; Product distribution / selectivity;46%
Stage #1: dimethyl sulfate; N-desmethyl olanzapine With sodium hydroxide In methanol at 0 - 5℃;
Stage #2: With water In methanol Product distribution / selectivity;
Stage #1: dimethyl sulfate; N-desmethyl olanzapine With sodium hydroxide In methanol; dichloromethane at 0 - 5℃;
Stage #2: With water In methanol; dichloromethane Product distribution / selectivity;
Stage #1: dimethyl sulfate; N-desmethyl olanzapine With sodium hydroxide; potassium carbonate In tetrahydrofuran; water at 10 - 30℃; for 7.5 - 8.5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 50℃;
109-01-3

1-methyl-piperazine

138564-59-7

2-(2-nitroanilino)-5-methylthiophene-3-carbonitrile

Conditions
ConditionsYield
With hydrogen In mesytilene at 160℃; for 48h; chemoselective reaction;54%

N-{5-methyl-3-[(4-methylpiperazin-1-yl)carbonyl]thien-2-yl}-N-(2-nitrophenyl)amine

Conditions
ConditionsYield
With tributylphosphine at 220℃; for 48h;41%
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Specification

The Olanzapine, with the CAS registry number 132539-06-1,is also known as 2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine; Lanzac; Zyprexa. It belongs to the product categories of Active Pharmaceutical Ingredients;APIs;Olanzapine;Intermediates & Fine Chemicals. This chemical's molecular formula is C17H20N4S and molecular weight is 312.43. What's more,Its systematic name is 10H-Thieno(2,3-b)(1,5)benzodiazepine, 2-methyl-4-(4-methyl-1-piperazinyl)-.It is a yellow crystalline powder which is a benzothiazepine.

Physical properties about Olanzapine are:
(1)ACD/LogP:  3.076; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  0.42; (4)ACD/LogD (pH 7.4):  2.35; (5)ACD/BCF (pH 5.5):  1.00; (6)ACD/BCF (pH 7.4):  23.98; (7)ACD/KOC (pH 5.5):  2.50; (8)ACD/KOC (pH 7.4):  210.04; (9)#H bond acceptors:  4; (10)#H bond donors:  1; (11)#Freely Rotating Bonds:  1; (12)Index of Refraction:  1.709; (13)Molar Refractivity:  92.156 cm3; (14)Molar Volume:  235.993 cm3; (15)Surface Tension:  52.015998840332 dyne/cm; (16)Density:  1.324 g/cm3; (17)Flash Point:  241.697 °C; (18)Enthalpy of Vaporization:  73.967 kJ/mol; (19)Boiling Point:  476.035 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:N=1c4c(N\C(=C/2\C=C(/SC=1\2)C)N3CCN(C)CC3)cccc4;
(2)Std. InChI:InChI=1S/C17H20N4S/c1-12-11-13-16(21-9-7-20(2)8-10-21)18-14-5-3-4-6-15(14)19-17(13)22-12/h3-6,11,18H,7-10H2,1-2H3;
(3)Std. InChIKey:WXPNDRBBWZMPQG-UHFFFAOYSA-N.

The toxicity data of Olanzapine are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 16560ug/kg/12 (16.56mg/kg)   Journal of Clinical Psychiatry. Vol. 60, Pg. 767, 1999.
human TDLo oral 16560ug/kg/12 (16.56mg/kg) BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)" Journal of Clinical Psychiatry. Vol. 60, Pg. 767, 1999.
human TDLo oral 43mg/kg/30W-I (43mg/kg)   Journal of Clinical Pyschopharmacology. Vol. 19, Pg. 273, 1999.
man LDLo oral 7067ug/kg (7.067mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"
Journal of Forensic Sciences. Vol. 41, Pg. 1252, 1998.
man TDLo oral 2570ug/kg/12D (2.57mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC Journal of Clinical Pyschopharmacology. Vol. 19, Pg. 192, 1999.
women LDLo oral 30mg/kg/22W-I (30mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Annals of Pharmacotherpy. Vol. 33, Pg. 787, 1999.
women TDLo oral 400ug/kg (.4mg/kg)   American Journal of Psychiatry. Vol. 156, Pg. 1835, 1999.
women TDLo oral 400ug/kg (.4mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: REGIDITY
American Journal of Psychiatry. Vol. 156, Pg. 1835, 1999.
women TDLo oral 12mg/kg (12mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Annals of Emergency Medicine. Vol. 32, Pg. 275, 1998.
women TDLo oral 12mg/kg/60D-I (12mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Annals of Internal Medicine. Vol. 131, Pg. 72, 1999.