(±)-Promethazine
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(±)-Promethazine
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CAS No:
60-87-7
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Formula:
C17H20N2S
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Chemical Name:
(±)-Promethazine
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Synonyms:
10H-Phenothiazine-10-ethanamine,N,N,α-trimethyl-;Phenothiazine,10-[2-(dimethylamino)propyl]-;N,N,α-Trimethyl-10H-phenothiazine-10-ethanamine;Dimapp;(2-Dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine;10-[2-(Dimethylamino)propyl]phenothiazine;Proazamine;Procit;Promethazine;Vallergine;RP 3277;Prothazin;Diphergan;Protazine;(±)-Promethazine;Prometazin;NSC 30321;73745-50-3
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CAS No:
Description
ChEBI: A tertiary amine that is a substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropan-2-amine moiety.
Characteristics
31.8
4.4
Crystals. Melting point 60°C. Used as an antihistamine.
1.131
60 °C
190-192 °C @ Press: 3 Torr
1.6000 (estimate)
H2O: 383.9ug/L(22.5 ºC)
Store in tight, light-resistant container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.
1.03X10-5 mm Hg at 25 deg C (est)
LD50 oral in rabbit: 580mg/kg
9.1None
Safety Information
Turns blue on prolonged exposure to air and moisture.
P264, P270, P273, P280, P301+P312, P305+P351+P338, P310, P330, P337+P313, P391, P501
H302
(±)-Promethazine Use and Manufacturing
Phenothiol and alkali were added to toluene and heated to reflux for 1h. Cool slightly, add the toluene solution of 2-chloro-1-dimethylaminopropane, reflux with water for 10-12h. Cool to below 50°C, filter the reaction solution, wash the filter residue with a small amount of acetone and water, combine and wash the filtrate, stand still, separate the toluene layer, recover the toluene by vacuum distillation, and collect the 220-260°C (1.33-2.66kPa) fraction, Get promethazine (base). The promethazine base is added to acetone, and dried hydrogen chloride gas is passed into it at about 50° C. for salt formation reaction to generate promethazine hydrochloride.
Antihistamines. It is suitable for allergic diseases (such as asthma, urticaria, allergic rhinitis, bronchial asthma, etc.) and vomiting during pregnancy. It can also be combined with chlorpromazine and the like to form a Keming mixture for artificial hibernation.
Computed Properties
Molecular Weight:284.4
XLogP3:4.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:284.13471982
Monoisotopic Mass:284.13471982
Topological Polar Surface Area:31.8
Heavy Atom Count:20
Complexity:298
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Antihistamines and sedatives
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