Name: Dilthiazem hydrochloride
SKU: 33286-22-5

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Basic Information

Molecular Structure:
CAS No.:	33286-22-5
Name:	Dilthiazem hydrochloride
Article Data:	11

Formula:	C₂₂H₂₆N₂O₄S^.HCl
Molecular Weight:	450.986
Synonyms:	1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,monohydrochloride, (2S,3S)- (9CI);1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,monohydrochloride, (2S-cis)-;(+)-Diltiazem hydrochloride;(2S,3S)-(+)-cis-Diltiazem hydrochloride;(S,S)-Diltiazem hydrochloride;Adizem;Altiazem;Anginyl;Blocalcin 60;Britiazim;CRD401;Calcicard;Cardizem SR;Dilacor XR;Diladel;Dilcardia;Dilgard;Dilzene;d-cis-3-Acetoxy-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-onehydrochloride;d-cis-Diltiazem hydrochloride;
EINECS:	251-443-3
Density:	1.26g/cm3
Melting Point:	212-214 ºC
Boiling Point:	594.4 ºC at 760 mmHg
Flash Point:	313.3 ºC
Solubility:	Soluble in water
Appearance:	Fine needles
Hazard Symbols:	Xn,Xi
Risk Codes:	22-40-36/37/38
Safety:	36-45-36/37-26
Transport Information:	UN 3249
PSA:	84.38000
LogP:	4.23550

Synthetic route

: 42399-40-6
O-desacetyldiltiazem

: 108-24-7
acetic anhydride

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
Stage #1: O-desacetyldiltiazem; acetic anhydride With dmap; triethylamine In dichloromethane for 3h; Heating / reflux; Stage #2: With hydrogenchloride In methanol pH=2;	92%
With hydrogenchloride In ethanol; butanone at 90℃; for 1h;	80%
With dmap In dichloromethane for 3h; Heating; Yield given;

: 75472-91-2
(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

: 108-24-7
acetic anhydride

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
Stage #1: (2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride; acetic anhydride With dmap; triethylamine In dichloromethane Stage #2: With hydrogenchloride In methanol pH=2;	92%
With pyridine; dmap

: 108-22-5
Isopropenyl acetate

: 75472-91-2
(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
With methanesulfonic acid In chloroform for 0.75h; Heating;	88.8%

: 2419-67-2, 24470-83-5, 41564-61-8
(E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 70 percent / urea hydrogen peroxide, DBU, immobilised poly-L-leucine / tetrahydrofuran / 28 h 2: 84 percent / MCPBA, KF / CH2Cl2 / 24 h 3: 90 percent / toluene / 17 h / Heating 4: 94 percent / xylene / 216 h / Heating 5: K2CO3 / ethyl acetate 6: pyridine, DMAP View Scheme

: 42399-49-5
(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / ethyl acetate 2: pyridine, DMAP View Scheme
Multi-step reaction with 2 steps 1: 67 percent / NaH / dimethylformamide; paraffin; diethyl ether / 3 h / 70 °C 2: 80 percent / 2.) HCl / butan-2-one; ethanol / 1 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating 2: DMAP / CH2Cl2 / 3 h / Heating View Scheme

: 123-11-5
4-methoxy-benzaldehyde

(+-)-2-cyano-3-m-tolyl-propionic acid hydrazide: (+-)-2-cyano-3-m-tolyl-propionic acid hydrazide

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 87 percent / NaOMe / methanol / 40 h / Heating 2: 70 percent / urea hydrogen peroxide, DBU, immobilised poly-L-leucine / tetrahydrofuran / 28 h 3: 84 percent / MCPBA, KF / CH2Cl2 / 24 h 4: 90 percent / toluene / 17 h / Heating 5: 94 percent / xylene / 216 h / Heating 6: K2CO3 / ethyl acetate 7: pyridine, DMAP View Scheme

: 201804-22-0
tert-butyl (2R,3S)-3-(4-methoxyphenyl)glycidate

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / toluene / 17 h / Heating 2: 94 percent / xylene / 216 h / Heating 3: K2CO3 / ethyl acetate 4: pyridine, DMAP View Scheme

: 201804-23-1
(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid tert-butyl ester

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / xylene / 216 h / Heating 2: K2CO3 / ethyl acetate 3: pyridine, DMAP View Scheme

: 201804-19-5
1-((2R,3S)-4-methoxyphenyloxiranyl)-2,2-dimethylpropan-1-one

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 84 percent / MCPBA, KF / CH2Cl2 / 24 h 2: 90 percent / toluene / 17 h / Heating 3: 94 percent / xylene / 216 h / Heating 4: K2CO3 / ethyl acetate 5: pyridine, DMAP View Scheme

: 42399-48-4
(2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid

: 33286-22-5
diltiazem hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / PTSA / xylene / 16 h / Heating 2: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating 3: DMAP / CH2Cl2 / 3 h / Heating View Scheme

Raw Materials

108-22-5

123-11-5

108-24-7

Downstream Products

42399-40-6

42399-41-7

Total:174 Page 1 of 5 1 2 3 4 5 Next>>

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Specification

The Diltiazem HCl, with the CAS registry number 33286-22-5, is also known as (+)-cis-3-(Acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)one monohydrochloride. It belongs to the product categories of Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals; Calcium Channel; Ion Channels; Aromatics; Chiral Reagents; Sulfur & Selenium Compounds. Its EINECS registry number is 251-443-3. This chemical's molecular formula is C₂₂H₂₇ClN₂O₄S and molecular weight is 450.98. What's more, both its IUPAC name and systematic name are the same which is called [(2S,3S)-5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate hydrochloride. It is used as a calcium channel blocher with vasodilating activity and an antianginal, antihypertensive.

Physical properties about Diltiazem HCl are: (1)ACD/LogP: 3.63; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.76; (4)ACD/LogD (pH 7.4): 2.26; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 14.49; (7)ACD/KOC (pH 5.5): 3.03; (8)ACD/KOC (pH 7.4): 96.24; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 84.38 Å²; (13)Flash Point: 313.3 °C; (14)Enthalpy of Vaporization: 88.6 kJ/mol; (15)Boiling Point: 594.4 °C at 760 mmHg; (16)Vapour Pressure: 4.27E-14 mmHg at 25 °C.

Preparation of Diltiazem HCl: this chemical can be prepared by 2-Acetoxy-propene with (2S,3S)-5-(2-Dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride. This reaction needs reagent methanesulfonic acid, solvent CHCl₃ and other condition of heating for 45 min. The yield is 88.8 %.

Diltiazem HCl can be prepared by 2-Acetoxy-propene with (2S,3S)-5-(2-Dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. If swallowed, it's harmful to health. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: Cl.O=C2N(c3c(S[C@@H](c1ccc(OC)cc1)[C@H]2OC(=O)C)cccc3)CCN(C)C
(2) InChI: InChI=1S/C22H26N2O4S.ClH/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3;/h5-12,20-21H,13-14H2,1-4H3;1H/t20-,21+;/m1./s1
(3) InChIKey: HDRXZJPWHTXQRI-BHDTVMLSSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	intravenous	40mg/kg (40mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: NAUSEA OR VOMITING	Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 4843, 1987.
man	LDLo	oral	21mg/kg (21mg/kg)	CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION CARDIAC: PULSE RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Postgraduate Medical Journal. Vol. 69, Pg. 474, 1993.
man	TDLo	oral	3429ug/kg/2D- (3.429mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Lancet. Vol. 341, Pg. 967, 1993.
man	TDLo	oral	15420ug/kg/7D (15.42mg/kg)	VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Archives of Internal Medicine. Vol. 151, Pg. 1869, 1991.
man	TDLo	oral	36mg/kg/13D-I (36mg/kg)	LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"	Gastroenterology. Vol. 88, Pg. 1260, 1985.
mouse	LD50	intraperitoneal	177mg/kg (177mg/kg)		Journal of Medicinal Chemistry. Vol. 29, Pg. 820, 1986.
mouse	LD50	intravenous	58mg/kg (58mg/kg)	BEHAVIORAL: ANTIPSYCHOTIC	Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
mouse	LD50	oral	508mg/kg (508mg/kg)		Journal of Medicinal Chemistry. Vol. 33, Pg. 2192, 1990.
mouse	LD50	subcutaneous	260mg/kg (260mg/kg)	BEHAVIORAL: ANTIPSYCHOTIC	Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
rat	LD50	intravenous	38mg/kg (38mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TETANY	Japan Medical Gazette. Vol. 11(1), Pg. 12, 1974.
rat	LD50	oral	560mg/kg (560mg/kg)	BEHAVIORAL: ANTIPSYCHOTIC	Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
rat	LD50	subcutaneous	520mg/kg (520mg/kg)	BEHAVIORAL: ANTIPSYCHOTIC	Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
women	LDLo	oral	120mg/kg (120mg/kg)	CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION	Human & Experimental Toxicology. Vol. 13, Pg. 161, 1994.
women	TDLo	oral	7200ug/kg/2D- (7.2mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: TOXIC PSYCHOSIS	Journal of the Royal Society of Medicine. Vol. 81, Pg. 296, 1988.
women	TDLo	oral	7200ug/kg (7.2mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: TOXIC PSYCHOSIS	Journal of the Royal Society of Medicine. Vol. 81, Pg. 296, 1988.
women	TDLo	oral	8400ug/kg (8.4mg/kg)	CARDIAC: PULSE RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Annals of Emergency Medicine. Vol. 22, Pg. 196, 1993.
women	TDLo	oral	18mg/kg (18mg/kg)	CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION CARDIAC: PULSE RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 45, 1991.
women	TDLo	oral	18mg/kg (18mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION SKIN AND APPENDAGES (SKIN): SWEATING: OTHER	Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 45, 1991.
women	TDLo	oral	19mg/kg (19mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Postgraduate Medical Journal. Vol. 64, Pg. 467, 1988.

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Specification