Promethazine
Title: Promethazine
CAS Registry Number: 60-87-7
CAS Name: N,N,a-Trimethyl-10H-phenothiazine-10-ethanamine
Additional Names: 10-(2-dimethylaminopropyl)phenothiazine; 10-(2-dimethylamino-2-methylethyl)phenothiazine; N-(2¢-dimethylamino-2¢-methyl)ethylphenothiazine; proazamine
Manufacturers' Codes: RP-3277
Trademarks: Fargan (Pfizer)
Molecular Formula: C17H20N2S
Molecular Weight: 284.42
Percent Composition: C 71.79%, H 7.09%, N 9.85%, S 11.27%
Literature References: Prepn from 10-phenothiazinepropyl chloride and dimethylamine in presence of Cu: Charpentier, Compt. Rend. 225, 306 (1947); US 2530451 (1950 to Rhône-Poulenc); from Grignard complexes of dimethylaminopropyl halide and phenothiazine: Berg, Ashley, US 2607773 (1952 to Rhône-Poulenc). Structure and isomerism: Edge, Wragg, J. Pharm. Pharmacol. 5, 279 (1953). Metabolic studies: Huang et al., J. Pharm. Sci. 59, 772 (1970). Toxicity: Rajsner, Collect. Czech. Chem. Commun. 34, 1019 (1969). Comprehensive description: C. M. Shearer, S. M. Miller, Anal. Profiles Drug Subs. 5, 429-465 (1976).
Properties: Crystals, mp 60°. bp3 190-192°.
Melting point: mp 60°
Boiling point: bp3 190-192°
 
Derivative Type: Hydrochloride
CAS Registry Number: 58-33-3
Manufacturers' Codes: RP-3389
Trademarks: Atosil (Bayer); Farganesse (Pfizer); Fenazil (Sella); Hiberna (Mitsubishi); Lergigan (Recip); Phenergan (Sanofi-Aventis); Prothazin (Rodleben)
Molecular Formula: C17H20N2S.HCl
Molecular Weight: 320.88
Percent Composition: C 63.63%, H 6.60%, N 8.73%, S 9.99%, Cl 11.05%
Properties: Crystals from ethylene dichloride, mp 230-232° (some dec). Turns blue on prolonged exposure to air and moisture. uv max (water): 249, 297 nm (e 28770, 3400). pH of 10% aq soln 5.3. Freely sol in water. Sol in alcohol, chloroform. Practically insol in acetone, ether, ethyl acetate. LD50 i.v. in mice: 55.0 mg/kg (Rajsner).
Melting point: mp 230-232° (some dec)
Absorption maximum: uv max (water): 249, 297 nm (e 28770, 3400)
Toxicity data: LD50 i.v. in mice: 55.0 mg/kg (Rajsner)
 
Derivative Type: Compd with 8-chlorotheophylline
CAS Registry Number: 17693-51-5
Additional Names: Promethazine teoclate
Trademarks: Avomine (Sanofi-Aventis)
Molecular Formula: C17H20N2S.C7H7ClN4O2
Molecular Weight: 499.03
Percent Composition: C 57.76%, H 5.45%, N 16.84%, S 6.43%, Cl 7.10%, O 6.41%
 
Therap-Cat: Antihistaminic.
Therap-Cat-Vet: Antihistaminic, antiemetic, CNS depressant.
Keywords: Antihistaminic; Tricyclics; Phenothiazines.

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