3D Mol Similar

Loperamide hydrochloride

Iupac Name：4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide;hydrochloride

CAS No.: 34552-83-5

Molecular Weight：513.503

Modify Date.: 2022-11-22 16:06

Introduction: Labeled Loperamide, which is used as an antidiarrheal View more+

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1. Names and Identifiers

1.1 Name: Loperamide hydrochloride
1.2 Synonyms: 1-piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-a,a-diphenyl-, hydrochloride (1:1) 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-, hydrochloride (1:1) 4-(4-(p-chlorophenyl)-4-hydroxy-1-piperidyl)-n,n-dimethyl-2,2-diphenylbutyra 4-(p-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-1-piperidine 4-[4-(4-chlorophényl)-4-hydroxypipéridin-1-yl]-N,N-diméthyl-2,2-diphénylbutanamide chlorhydrate 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-N,N-dimethyl-2,2-diphenylbutanamide hydrochloride 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-N,N-dimethyl-2,2-diphenylbutanamide hydrochloride (1:1) 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide hydrochloride 4-[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide hydrochloride (1:1) 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide,hydrochloride 4-[4-(4-Chlorphenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamidhydrochlorid arret blox BREK butyramidehcl dissenten EINECS 252-082-4 fortasec imodium imosec Lopemid Lopemin Loperamide (hydrochloride) LOPERAMIDE HCL Loperyl MFCD00058581 Suprasec Tebloc

1.3 CAS No.: 34552-83-5

1.4 CID: 71420

1.5 EINECS(EC#): 252-082-4

1.6 Molecular Formula: C29H34Cl2N2O2 (isomer)

1.7 Inchi: InChI=1S/C29H33ClN2O2.ClH/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23;/h3-16,34H,17-22H2,1-2H3;1H

1.8 InChkey: PGYPOBZJRVSMDS-UHFFFAOYSA-N

1.9 Canonical Smiles: CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4.Cl

1.10 Isomers Smiles: CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4.Cl

2. Properties

2.1 Density: ==

2.1 Melting point: 223-225°C

2.1 Boiling point: 647.2 °C at 760 mmHg

2.1 Refractive index: 1.6100 (estimate)

2.1 Flash Point: 345.2 °C

2.1 Precise Quality: 512.20000

2.1 PSA: 43.78000

2.1 logP: 5.82790

2.1 Appearance: Crystals, practically insoluble in water

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: White Solid

2.4 Color/Form: Powder

2.5 pKa: 8.66(at 25℃)

2.6 Water Solubility: >77 [ug/mL]

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A hydrochloride obtained by combining loperamide with one equivalent of hydrochloric acid. Used for treatment of diarrhoea resulting from gastroenteritis or inflammatory bowel disease.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 73 companies from 5 notifications to the ECHA C&L Inventory.

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P270, P301+P310, P321, P330, P405, and P501

3.3 Methods of Manufacturing: Preparation of 4-[4-(4-diphenyl)-4-hvdroxypiperidino1-N, N- dimethyl-2, 2-diphenylbutyramide hydrochloride (loperamide)0.111 g (5.2-10-4 mol, 1 eq) of 4, 4-chlorophenyl-4-hydroxypiperidine, 0.062 g (5.8-10-4 mol, 1.11 eq) of sodium carbonate, 0.0009 g (0.24percent by weight) of potassium iodide were weighed and dissolved in 0.5 ml_ of glycerol formal. The resulting mixture was stirred for 15 minutes. Afterwards 0.2089 g (6.03-10-4 mol, 1.15 eq) of N, N-dimethyl-(3, 3-diphenyltetrahydro-2- furyliden)ammonium bromide were added and heated at 6O

3.4 Usage: Labeled Loperamide, which is used as an antidiarrheal

4. Safety and Handling

4.1 Symbol: GHS06

4.1 Hazard Codes: T

4.1 Signal Word: Danger

4.1 Risk Statements: R25

4.1 Safety Statements: S45

4.1 Packing Group: III

4.1 Hazard Class: 6.1(b)

4.1 Hazard Declaration: H301

4.1 RIDADR: UN 2811

4.1 Caution Statement: P301 + P310

4.1 WGK Germany: 3

4.1 RTECS: TM4960000

4.1 Toxicity: LD50 in mice (mg/kg): 75 s.c.; 28 i.p.; 105 orally; in rats (mg/kg): 185 orally (Niemegeers)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

Predict 1H proton NMR

7. Synthesis Route

34552-83-5Total: 2 Synthesis Route

39512-49-7 126 Suppliers

37743-18-3 28 Suppliers

34552-83-5 230 Suppliers

Literatures:
INSTITUT UNIVERSITARI DE CIENCIA I TECNOLOGIA Patent: WO2008/80601 A2, 2008 ; Location in patent: Page/Page column 10 ;
Yield: ~67%

39512-49-7 126 Suppliers

37743-18-3 28 Suppliers

108-10-1 216 Suppliers

34552-83-5 230 Suppliers

Literatures:
US5798093 A1, ;
Yield: null

8. Precursor and Product

precursor:

108-10-1

37743-18-3

39512-49-7

9. Other Information

9.0 Usage: At nanomolar concentrations, binds to mu-opioid receptors. L-type calcium channel blocker

9.1 Merck: 14,5571

9.2 Chemical Properties: White Solid

9.3 Originator: Imodium,Janssen,UK,1975

9.4 Uses: Labeled Loperamide, which is used as an antidiarrheal

9.5 Uses: Ca channel blocker

9.6 Uses: Loperamide hydrochloride is a Ca2+ channel protein inhibitor and MOR activator.

9.7 Indications: Loperamide hydrochloride (Imodium) structurally resembles both haloperidol and meperidine. In equal doses, loperamide protects against diarrhea longer than does diphenoxylate. It reduces the daily fecal volume and decreases intestinal fluid and electrolyte loss. Loperamide produces rapid and sustained inhibition of the peristaltic reflex through depression of longitudinal and circular muscle activity.The drug also possesses antisecretory activity, presumably through an effect on intestinal opioid receptors.

9.8 Definition: ChEBI: A hydrochloride obtained by combining loperamide with one equivalent of hydrochloric acid. Used for treatment of diarrhoea resulting from gastroenteritis or inflammatory bowel disease.

9.9 Manufacturing Process: 23.6 parts of 2-oxo-3,3-diphenyl-tetrahydrofuranare melted at 100°C in an oil-bath and gaseous hydrogen bromide is introduced into it during 3 hours. The reaction mixture is cooled and triturated in benzene. The product is filtered off, washed with petroleum ether and dried in an exsiccator, yielding 4-bromo-2,2-diphenylbutyric acid; MP 127.5%.
To a stirred suspension of 16 parts of 4-bromo-2,2-diphenylbutyric acid in 150 parts of chloroform are added dropwise 16 parts of thionyl chloride and the whole is stirred and refluxed for 2 hours. The reaction mixture is evaporated,yielding 4-bromo-2,2-diphenyl-butyrylchloride as a residue.
60 parts of 4-bromo-2,2-diphenylbutyrylchloride are dissolved in 400 parts of toluene and gaseous dimethylamine is introduced slowly into the solution while cooling (temperature is kept at about 0°C). The introduction is ceased when dimethylamine escapes from the cooler, and stirring is continued for 2 hours at ordinary temperature. The precipitated product is filtered off and dissolved in a minimum quantity of water. The product is extracted with chloroform. The extract is dried and evaporated. The residue solidifies on triturating in 4-methyl-2-pentanone. The solid is filtered off and dried, yielding dimethyl -(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide; MP 169° to 171.5°C.
A mixture of 6.33 parts of 4-(p-chlorophenyl)-4-piperidinol, 8 parts of sodium carbonate, 0.2 part of potassium iodide and 240 parts of 4-methyl-2- pentanone is distilled azeotropically. Then there are added 12.12 parts of dimethyl-(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide (from the preceding step) and the whole is stirred and refluxed for about 15 hours. The reaction mixture is filtered hot and the filtrate is evaporated.
The oily residue is dissolved in 2-propanol and to this solution is added an excess of 2-propanol previously saturated with gaseous hydrogen chloride. The whole is evaporated and the oily residue is warmed in diluted hydrochloric acid solution. Upon the addition of toluene, the salt is precipitated. It is filtered off, boiled in acetone, and filtered off again after cooling, yielding 4- (p-chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenylpiperidine-1-butyramide hydrochloride; MP 222.1°C.

9.10 Brand name: Imodium (Janssen); Imodium (McNeil).

9.11 Therapeutic Function: Antidiarrheal

9.12 General Description: Loperamide is an antidiarrheal agent used in controlling acute nonspecific diarrhea and chronic diarrhea associated with inflammatory bowel diseases.

9.13 Storage Conditions: Preparation of 4-[4-(4-diphenyl)-4-hvdroxypiperidino1-N, N- dimethyl-2, 2-diphenylbutyramide hydrochloride (loperamide)0.111 g (5.2-10-4 mol, 1 eq) of 4, 4-chlorophenyl-4-hydroxypiperidine, 0.062 g (5.8-10-4 mol, 1.11 eq) of sodium carbonate, 0.0009 g (0.24percent by weight) of potassium iodide were weighed and dissolved in 0.5 ml_ of glycerol formal. The resulting mixture was stirred for 15 minutes. Afterwards 0.2089 g (6.03-10-4 mol, 1.15 eq) of N, N-dimethyl-(3, 3-diphenyltetrahydro-2- furyliden)ammonium bromide were added and heated at 6O

9.14 Collision Cross Section: 219.4 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

9.15 Mesh: Miscellaneous agents found useful in the symptomatic treatment of diarrhea. They have no effect on the agent(s) that cause diarrhea, but merely alleviate the condition. (See all compounds classified as Antidiarrheals.)

9.16 Mesh Entry Terms: Hydrochloride, Loperamide

9.17 Use Classification: Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

10. Computational chemical data

Molecular Weight: 513.503g/mol
Molecular Formula: C₂₉H₃₄Cl₂N₂O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 512.1997337
Monoisotopic Mass: 512.1997337
Complexity: 623
Rotatable Bond Count: 7
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 43.8
Heavy Atom Count: 35
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADcfB7MAAGAAAAAAAAAAAAAAAAAAAAAAA8YMEAAAAAAAABUAAAHgIACAAADkbBmCQyAIMAAgCIAiFSEAACAAAgBQAIiAEICogIJjKBlxGEcAAmwgGImAecyOCPhAAAAAAAAAAIAAAAAAAAAAAAAAAAAA==

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