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3546-03-0

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3546-03-0 Usage

Chemical Properties

Greenish Yellow Solid

Originator

Terckian,Theraplix,France,1972

Uses

Cyamemazine is an anxiolytic antipsychotic, which reduces ethanol withdrawal symptoms.

Manufacturing Process

The following is taken from US Patent 3,057,851. Milorganite was extracted with water to obtain an aqueous extract containing vitamin B12 active substances. This aqueous extract was purified by treatment with an ion exchange resin according to the following method. An aqueous extract of milorganite, 100 ml containing 300 μg of vitamin B12 active substances and 4.5 grams of total solids, was combined with 0.5 gram of sodium nitrite and 0.4 gram of potassium cyanide. The resulting solution was adjusted to pH 4.0 with hydrochloric acid and heated to boiling. The boiled solution was filtered through a Super-Cel filter surface, and the filter was then washed with water. The filtrate was obtained in a total volume of 130 ml including the washings.Amerlite XE-97, an ion exchange resin of the carboxyl type (Rohm and Haas), was classified to an average wet particle size of 100 to 150 mesh. The classified resin was utilized in the hydrogen form, and was not buffered during the ion exchange fractionation. The classified resin, in the amount of 35 ml, was packed into a glass column having a diameter of 25 mm and a height of 250 mm. The cyanide-treated aqueous extract of milorganite was infused gravitationally into the ion exchange bed at a rate of 3 ml per minute.The effluent was discarded and the resin bed was then washed with the following solutions in the specified sequence: (1) 120 ml of an aqueous 0.1 N hydrochloric acid solution; (2) 75 ml of an aqueous 85% acetone solution; and (3) 70 ml of an aqueous 0.1 N hydrochloric acid solution. After washing, the resin bed was eluted with an aqueous 60% dioxane solution containing 0.1 N of hydrochloric acid. In this elution, 8 ml of colored eluate was collected. This portion of the eluate was found to contain 295 μg of cyanocobalamin and 9 mg of total solids.

Therapeutic Function

Tranquilizer

Check Digit Verification of cas no

The CAS Registry Mumber 3546-03-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,4 and 6 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3546-03:
(6*3)+(5*5)+(4*4)+(3*6)+(2*0)+(1*3)=80
80 % 10 = 0
So 3546-03-0 is a valid CAS Registry Number.
InChI:InChI=1/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3

3546-03-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Sigma

  • (SML0321)  Cyamemazine  ≥98% (HPLC)

  • 3546-03-0

  • SML0321-10MG

  • 1,213.29CNY

  • Detail
  • Sigma

  • (SML0321)  Cyamemazine  ≥98% (HPLC)

  • 3546-03-0

  • SML0321-50MG

  • 4,898.79CNY

  • Detail

3546-03-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyamemazine

1.2 Other means of identification

Product number -
Other names 10H-Phenothiazine-2-carbonitrile, 10-[3-(dimethylamino)-2-methylpropyl]-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3546-03-0 SDS

3546-03-0Synthetic route

cyamemazine N-oxide
1366180-94-0

cyamemazine N-oxide

A

N-Demethylcyamemazine
108014-19-3

N-Demethylcyamemazine

B

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate In methanol at 0℃; for 2h; Polonovski reaction;A 70%
B n/a
10H-phenothiazine-2-carbonitrile
38642-74-9

10H-phenothiazine-2-carbonitrile

3-(dimethylamino)-2-methylpropylchloride
23349-86-2

3-(dimethylamino)-2-methylpropylchloride

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
(i) NaNH2, toluene, (ii) /BRN= 506000/; Multistep reaction;
(+-)-4-<2-bromo-phenylsulfanyl>-3-<γ-dimethylamino-isobutylamino>-benzonitrile

(+-)-4-<2-bromo-phenylsulfanyl>-3-<γ-dimethylamino-isobutylamino>-benzonitrile

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
With copper; potassium carbonate; N,N-dimethyl-formamide at 155℃;
10H-phenothiazine-2-carbonitrile
38642-74-9

10H-phenothiazine-2-carbonitrile

(+-)-<γ-chloro-isobutyl>-dimethyl-amine

(+-)-<γ-chloro-isobutyl>-dimethyl-amine

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
With sodium amide; xylene
2-chlorophenothiazine
92-39-7

2-chlorophenothiazine

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: quinoline
2: sodium amide; xylene
View Scheme
10H-phenothiazine-2-carboxylic acid
25234-50-8

10H-phenothiazine-2-carboxylic acid

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) PCl5, benzene, (ii) NH3
2: POCl3 / Heating
3: (i) NaNH2, toluene, (ii) /BRN= 506000/
View Scheme
phenothiazine-2-carboxamide
1778-82-1

phenothiazine-2-carboxamide

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POCl3 / Heating
2: (i) NaNH2, toluene, (ii) /BRN= 506000/
View Scheme
Cyamemazine tartrate

Cyamemazine tartrate

A

N-Demethylcyamemazine
108014-19-3

N-Demethylcyamemazine

B

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid; sodium hydroxide / dichloromethane / 4 h / 0 - 20 °C
2: ferrous(II) sulfate heptahydrate / methanol / 2 h / 0 °C
View Scheme
10-(3-(1,3-dioxoisoindolin-2-yl)-2-methylpropyl)-10H-phenothiazine-2-carbonitrile
1590417-42-7

10-(3-(1,3-dioxoisoindolin-2-yl)-2-methylpropyl)-10H-phenothiazine-2-carbonitrile

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrazine hydrate / ethanol / 4 h / 70 °C / Inert atmosphere
2.1: tetrahydrofuran / 2 h / 70 °C
2.2: 2 h / 0 °C / Reflux
View Scheme
Desmethyl cyamemazine

Desmethyl cyamemazine

dimethyl sulfate
77-78-1

dimethyl sulfate

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
Stage #1: Desmethyl cyamemazine; dimethyl sulfate In tetrahydrofuran at 70℃; for 2h;
Stage #2: dimethyl sulfate With sodium hydroxide In tetrahydrofuran; water at 0℃; for 2h; Reflux;
Cyamemazine tartrate

Cyamemazine tartrate

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
In [(2)H6]acetone; water; ethyl acetate
In di-isopropyl ether; water
3-(dimethylamino)-2-methylpropylchloride
23349-86-2

3-(dimethylamino)-2-methylpropylchloride

cyamemazine
3546-03-0

cyamemazine

Conditions
ConditionsYield
With sodium hydroxide In toluene
cyamemazine
3546-03-0

cyamemazine

C19H21N3O2S

C19H21N3O2S

Conditions
ConditionsYield
With air In phosphate buffer for 0.0666667h; pH=7; Quantum yield;
With air In phosphate buffer for 0.0666667h; pH=7; UV-irradiation;
2-butenedioic acid
6915-18-0

2-butenedioic acid

cyamemazine
3546-03-0

cyamemazine

10-(3-(dimethylamino)-2-methylpropyl)-10H-phenothiazine-2-carbonitrile maleate

10-(3-(dimethylamino)-2-methylpropyl)-10H-phenothiazine-2-carbonitrile maleate

Conditions
ConditionsYield
In ethanol for 0.5h;250 mg
cyamemazine
3546-03-0

cyamemazine

A

(R)-cyamemazine

(R)-cyamemazine

B

(S)-cyamemazine

(S)-cyamemazine

Conditions
ConditionsYield
With Chiralpak AGP column for 0.5h; Resolution of racemate; enantioselective reaction;

3546-03-0Downstream Products

3546-03-0Relevant articles and documents

N-demethylation of cyamemazine via non-classical Polonovski reaction and its conjugation to bovine serum albumin

Singh, Gurmit,Koerner, Terry B.,Godefroy, Samuel Benrejeb,Armand, Claude

, p. 2160 - 2162 (2012)

A modified Polonovski reaction has been employed to obtain the N-demethylated metabolite of the neuroleptic drug cyamemazine. The synthesis involves N-oxide formation, isolation of the corresponding N-oxide, and a FeSO4·7H2O mediated Polonovski reaction to afford the desired monodesmethyl cyamemazine. In a subsequent step the hapten N-demethylcyamemazine-hemiglutarate was synthesized and its conjugated to bovine serum albumin (BSA).

Synthesis of deuterium-labeled cyamemazine and monodesmethyl cyamemazine

Bolla, R. Sekhar,Kasi Viswanath

, p. 82 - 85 (2014/03/21)

A novel approach is presented for the synthesis of cyamemazine maleate and N-desmethyl cyamemazine maleate using a 10-(amino-2-methylpropyl)phenothiazine derivative. This method was successfully applied to the synthesis of [ 2H6]cyamemazine maleate and N-desmethyl-[ 2H3]cyamemazine maleate.

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