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Meclozine
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Name

Meclozine

 EINECS 209-323-3
CAS No. 569-65-3 Density 1.159 g/cm3
PSA 6.48000 LogP 6.23340
Solubility N/A Melting Point 153-157oC
Formula C25H27ClN2 Boiling Point 495.3 °C at 760 mmHg
Molecular Weight 390.956 Flash Point 253.3 °C
Transport Information N/A Appearance N/A
Safety Risk Codes  Xn:;
Molecular Structure Molecular Structure of 569-65-3 (Meclozine) Hazard Symbols R22;R36/37/38:;
Synonyms

Piperazine,1-(p-chloro-a-phenylbenzyl)-4-(m-methylbenzyl)-(6CI,8CI);1-(p-Chlorobenzhydryl)-4-(m-methylbenzyl)diethylenediamine;Ancolan;Bonine;Histametizyne;Meclizine;NSC 169189;Navicalm;Neo-Istafene;Parachloramine;Postafene;Ravelon;Sabari;Suprimal;U.C.B. 5062;Vomisseis;

Article Data 9

Meclozine Synthetic route

5321-48-2

1-(3-methylbenzyl)piperazine

104-88-1

4-chlorobenzaldehyde

569-65-3

meclizine

Conditions
ConditionsYield
With hydrogenchloride; potassium cyanide; toluene anschl. Erh. der nach Abtrennung der wss. Phase erhaltenen Loesung mit Phenylmagnesiumbromid in Toluol;
With calcium sulfate; mercury dichloride; butan-1-ol anschl. mit methanol. Natriummethylat, Erw. des Rktprod. mit Phenylmagnesiumbromid in Aether;
(+-)-1-<4-chloro-benzhydryl>-piperazine

(+-)-1-<4-chloro-benzhydryl>-piperazine

3-methyl-benzyl halide

3-methyl-benzyl halide

569-65-3

meclizine

TentaGel-NEtC(O)CH2C2F4OC2F4SO3-{4-(1-[(α-4-chlorophenyl)benzyl]piperazin-4-yl)methyl-2-methylphenyl} resin

TentaGel-NEtC(O)CH2C2F4OC2F4SO3-{4-(1-[(α-4-chlorophenyl)benzyl]piperazin-4-yl)methyl-2-methylphenyl} resin

569-65-3

meclizine

Conditions
ConditionsYield
With formic acid; 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In N,N-dimethyl-formamide at 85℃; for 2h;
303-26-4

N-(4-chlorobenzhydryl)piperazine

620-23-5

m-tolyl aldehyde

569-65-3

meclizine

Conditions
ConditionsYield
With formic acid; C18H24Cl2IrN3 In water at 20℃; for 12h; Schlenk technique; Green chemistry;1.56 g
569-65-3

meclizine

831-81-2

4-chlorophenyl(phenyl)methane

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate; phenylsilane at 120℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;97%
10273-89-9

2-(2-methylphenyl)pyridine

569-65-3

meclizine

C37H37N3

Conditions
ConditionsYield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 24h; Inert atmosphere;90%
13675-18-8

tetrahydroxydiboron

569-65-3

meclizine

126-30-7

2,2-Dimethyl-1,3-propanediol

1-((4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)(phenyl)methyl)-4-(3-methylbenzyl)piperazine

Conditions
ConditionsYield
Stage #1: tetrahydroxydiboron; meclizine With XPhos-Pd-G; potassium acetate; XPhos at 80℃; for 12h; Schlenk technique; Inert atmosphere;
Stage #2: 2,2-Dimethyl-1,3-propanediol In dichloromethane at 20℃; for 12h; Schlenk technique; Inert atmosphere;		85%
76-09-5

2,3-dimethyl-2,3-butane diol

13675-18-8

tetrahydroxydiboron

569-65-3

meclizine

1-(3-methylbenzyl)-4-(phenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl)piperazine

Conditions
ConditionsYield
Stage #1: tetrahydroxydiboron; meclizine With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate; XPhos In ethanol at 80℃; for 4h; Inert atmosphere; Schlenk technique;
Stage #2: 2,3-dimethyl-2,3-butane diol In dichloromethane at 20℃; for 8h; Inert atmosphere; Schlenk technique;		75%
569-65-3

meclizine

(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)(m-tolyl)methanone

Conditions
ConditionsYield
With DBN; oxygen; rose bengal In N,N-dimethyl-formamide at 20℃; for 48h; Irradiation;61%

Grushin’s reagent

569-65-3

meclizine

1-((4-chlorophenyl)(phenyl)methyl)-4-(3-(2,2,2-trifluoroethyl)benzyl)piperazine

Conditions
ConditionsYield
With ammonium peroxydisulfate; chlorotriisopropylsilane; trifluoroacetic acid In water; acetone at 20℃; for 18h; Inert atmosphere; Sealed tube; Irradiation; Green chemistry;26%

Meclozine Chemical Properties

Chemical Name: Meclozine
IUPAC NAME: 1-[(4-Chlorophenyl)-phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine
CAS No.: 569-65-3
EINECS: 209-323-3
RTECS Class: Drug ;  Reproductive Effector ;  Human Data
Molecular Formula: C25H27ClN2
Molecular Weight: 390.95 g/mol
Density: 1.159 g/cm3 
Flash Point: 253.3 °C
Boiling Point: 495.3 °C at 760 mmHg
Following is the structure of Histamethizine (569-65-3):


The chemical synonymous of Histamethizine (569-65-3) are 1-[(4-Chlorophenyl)-phenyl-methyl]-4-[(3-methylphenyl)methyl]piperazine ; Meclizine ; Meclozine ; 1-(P-chloro-alpha-phenylbenzyl)-4-(m-methylbenzyl)piperazine ; 1-(P-chlorobenzhydryl)-4-(m-methylbenzyl)diethylenediamine ; 1-(P-chlorobenzhydryl)-4-(m-methylbenzyl)piperazine ; 1-[(4-Chlorophenyl)(phenyl)methyl]-4-(3-methylbenzyl)piperazine ; Ancolan

Meclozine Uses

Histamethizine (569-65-3) is used as a surface active agent and as a penetrating agent in printing and dyeing industry.

Meclozine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 625mg/kg (625mg/kg)   Compilation of LD50 Values of New Drugs.
mouse LD50 oral 1650mg/kg (1650mg/kg)   Compilation of LD50 Values of New Drugs.
rat LD50 oral 1750mg/kg (1750mg/kg)   Proceedings of the European Society for the Study of Drug Toxicity. Vol. 9, Pg. 134, 1968.

Meclozine Consensus Reports

Reported in EPA TSCA Inventory.

Meclozine Safety Profile

A poison by intravenous route. Moderate toxicity by ingestion and intramuscular routes. Human reproductive effects by an unspecified route: reduced viability of newborn. Experimental teratogenic and reproductive effects. An antihistamine. When heated to decomposition it emits very toxic fumes of Cl− and NOx.
Attention:
1. Storage: Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
2. Handling: All chemicals should be considered hazardous. Avoid direct physical contact. Use appropriate, approved safety equipment. Untrained individuals should not handle this chemical or its container. Handling should occur in a chemical fume hood.

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