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Home > Encyclopedia > (±)-Promethazine

(±)-Promethazine

pharmaceutical raw materials
(±)-Promethazine structure

(±)-Promethazine 

structure
  • CAS No:

    60-87-7

  • Formula:

    C17H20N2S

  • Chemical Name:

    (±)-Promethazine

  • 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

  • Categories:

    Active Pharmaceutical Ingredients  >  Antiallergic Drugs

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.

(±)-Promethazine Basic Attributes

284.42

284.42

200-489-2

2934300000

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

Methods of 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.

Uses

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

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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