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60-87-7

Basic Information
CAS No.: 60-87-7
Name: PROMETHAZINE
Article Data: 29
Molecular Structure:
Molecular Structure of 60-87-7 (PROMETHAZINE)
Formula: C17H20 N2 S
Molecular Weight: 284.425
Synonyms: Phenothiazine,10-[2-(dimethylamino)propyl]- (8CI);(2-Dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine; (?à)-Promethazine;10-[2-(Dimethylamino)propyl]phenothiazine; Dimapp; Diphergan; NSC 30321;Proazamine; Procit; Prometazin; Promethazine; Protazine; Prothazin; RP 3277;Vallergine
Density: 1.131
Melting Point: 60
Boiling Point: 190-192oC at 3 mm Hg
Solubility: 383.9ug/L(22.5 oC)
Safety: Poison by ingestion, intravenous, intramuscular, intraperitoneal, and subcutaneous routes. Human systemic effects by ingestion: pupillary dilation, wakefulness, hallucinations, and distorted perceptions. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. A severe eye irritant. When heated to decomposition it emits very toxic fumes of NOx and SOx.
PSA: 31.78000
LogP: 4.30440
Synthetic route
58-33-3

phenergan

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water Reagent/catalyst;96%
With sodium hydroxide In diethyl ether Purification / work up;90%
124-40-3

dimethyl amine

15375-56-1

1-(10H-phenothiazin-10-yl)acetone

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In N,N-dimethyl acetamide at 50℃;75%
92-84-2

10H-phenothiazine

17256-39-2

2-(dimethyl-amino)-1-methylethylchloride hydrochloride

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 at 80℃; for 1h;71%
92-84-2

10H-phenothiazine

108-14-5

2-chloro-1-dimethylaminopropane

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
racemat;
racemat;
92-84-2

10H-phenothiazine

108-14-5

2-chloro-1-dimethylaminopropane

A

303-14-0

isopromethazine

B

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
racemat;
92-84-2

10H-phenothiazine

53309-35-6

(2-chloro-1-methyl-ethyl)-dimethyl-amine

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
(i) NaNH2, toluene, (ii) /BRN= 505990/; Multistep reaction;
72332-06-0

2-<2-(dimethylamino)propyl> phenothiazine-10-carboxylate

A

92-84-2

10H-phenothiazine

B

303-14-0

isopromethazine

C

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
at 180 - 220℃; for 2.5h;A 840 mg
B 148 mg
C 454 mg
at 180 - 220℃; for 2.5h; Mechanism;A 840 mg
B 148 mg
C 454 mg
38878-40-9

promethazine cation

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
With hydrogen sulfite In water Rate constant; Irradiation; variation of pH;

C17H20N2S(1+)*ClO4(1-)

A

7640-51-9

Promethazine 5-sulfoxide

B

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
With water Product distribution; Mechanism; pH 7; var. phenothiazine cation radicals, var. buffers;
(+-)-N2-<2-(2-bromo-phenylsulfanyl)-phenyl>-1,N1,N1-trimethyl-ethanediyldiamine

(+-)-N2-<2-(2-bromo-phenylsulfanyl)-phenyl>-1,N1,N1-trimethyl-ethanediyldiamine

60-87-7

10-[2-(dimethylamino)propyl]phenothiazine

Conditions
ConditionsYield
With copper; potassium carbonate; N,N-dimethyl-formamide racemat;
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Chemistry

Chemical Name: Promethazine
IUPAC NAME: N,N-Dimethyl-1-phenothiazin-10-ylpropan-2-amine
CAS No.: 60-87-7
EINECS: 200-489-2
Molecular Formula: C17H20N2S
Molecular Weight: 284.42 g/mol
Density: 1.131 g/cm3
Flash Point: 198 °C
Boiling Point: 403.7 °C at 760 mmHg
Following is the structure of 10-(2-(Dimethylamino)propyl)pheno-thiazine (CAS No.60-87-7):


The chemical synonymous of 10-(2-(Dimethylamino)propyl)pheno-thiazine (CAS No.60-87-7) are (2-Dimethylamino-2-Methyl)Ethyl-N-Dibenzoparathiazine ; (Dimethylamino-2-Propyl-10-Phenothiazine Hydrochloride ; 10-(2-(Dimethylamino)-2-Methylethyl)Phenothiazine ; 10-[2-(Dimethylamino)Propyl]Phenothiazine ; 10h-Phenothiazine-10-Ethanamine, N,N,Alpha-Trimethyl-

Toxicity Data With Reference

1.    

eye-rbt 100 mg SEV

    FCTOD7    Food and Chemical Toxicology. 20 (1982),573.
2.    

eye-rbt 100 mg/4S rns MLD

    FCTOD7    Food and Chemical Toxicology. 20 (1982),573.
3.    

dni-hmn:fbr 80 nmol/L

    DNSYAG    Diseases of the Nervous System. 29 (1968),829.
4.    

otr-ham:emb 10 mg/L

    ENMUDM    Environmental Mutagenesis. 8 (Suppl 6)(1986),4.
5.    

msc-ham:lng 10 mg/L

    SHIGAZ    Shigaku. Ondotology. 70 (1983),943.
6.    

skn-cld TDLo:13 mg/kg:EYE,PSY

    CMAJAX    Canadian Medical Association Journal. 130 (1984),1460.
7.    

ipr-rat LDLo:140 mg/kg

    TXAPA9    Toxicology and Applied Pharmacology. 1 (1959),156.
8.    

scu-rat LD50:700 mg/kg

    CRSBAW    Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. 144 (1950),887.
9.    

ivn-rat LD50:45 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 120 (1959),450.
10.    

ims-rat LD50:169 mg/kg

    TXAPA9    Toxicology and Applied Pharmacology. 18 (1971),185.
11. &

Safety Profile

Poison by ingestion, intravenous, intramuscular, intraperitoneal, and subcutaneous routes. Human systemic effects by ingestion: pupillary dilation, wakefulness, hallucinations, and distorted perceptions. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. A severe eye irritant. When heated to decomposition it emits very toxic fumes of NOx and SOx.