CHEBI:8461 - promethazine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name promethazine
ChEBI ID CHEBI:8461
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C17H20N2S
Net Charge 0
Average Mass 284.42018
Monoisotopic Mass 284.135
InChI InChI=1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3
InChIKey PWWVAXIEGOYWEE-UHFFFAOYSA-N
SMILES CC(CN1c2ccccc2Sc2ccccc12)N(C)C
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
Application(s): sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
antiemetic
A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
local anaesthetic
Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
anti-allergic agent
A drug used to treat allergic reactions.
H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing promethazine (CHEBI:8461) has role anti-allergic agent (CHEBI:50857)
promethazine (CHEBI:8461) has role antiemetic (CHEBI:50919)
promethazine (CHEBI:8461) has role antipruritic drug (CHEBI:59683)
promethazine (CHEBI:8461) has role H1-receptor antagonist (CHEBI:37955)
promethazine (CHEBI:8461) has role local anaesthetic (CHEBI:36333)
promethazine (CHEBI:8461) has role sedative (CHEBI:35717)
promethazine (CHEBI:8461) is a phenothiazines (CHEBI:38093)
promethazine (CHEBI:8461) is a tertiary amine (CHEBI:32876)
promethazine (CHEBI:8461) is conjugate base of promethazine(1+) (CHEBI:61214)
Incoming promethazine(1+) (CHEBI:61214) is conjugate acid of promethazine (CHEBI:8461)
IUPAC Name
N,N-dimethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
INNs Sources
prometazina ChEBI
prométhazine ChEBI
promethazine ChEBI
promethazinum ChEBI
Synonyms Sources
(2-dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine ChemIDplus
10-(2-Dimethylaminopropyl)phenothiazine KEGG COMPOUND
10-[2-(dimethylamino)propyl]phenothiazine NIST Chemistry WebBook
N,N,α-trimethyl-10H-phenothiazine-10-ethanamine NIST Chemistry WebBook
N-(2'-dimethylamino-2'-methyl)ethylphenothiazine ChemIDplus
proazamine ChemIDplus
Promethazine KEGG COMPOUND
Manual Xrefs Databases
2286 DrugCentral
C07404 KEGG COMPOUND
D00494 KEGG DRUG
DB01069 DrugBank
HMDB0015202 HMDB
LSM-4440 LINCS
Promethazine Wikipedia
US2530451 Patent
US2607773 Patent
View more database links
Registry Numbers Types Sources
337077 Gmelin Registry Number Gmelin
60-87-7 CAS Registry Number KEGG COMPOUND
60-87-7 CAS Registry Number NIST Chemistry WebBook
60-87-7 CAS Registry Number ChemIDplus
88554 Reaxys Registry Number Reaxys
88554 Beilstein Registry Number Beilstein
Last Modified
22 February 2017
General Comments
2011-02-04 A sedating antihistamine with antimuscarinic properties, promethazine is used as the monohydrochloride salt for the symptomatic relief of a variety of allergic conditions including conjunctivitis, rhinitis, and urticaria, as well as pruritic skin disorders. The anti-emetic action of both the hydrochloride and the teoclate (8-chlorotheophylline) salts is used for the prevention of nausea in cases of motion sickness and post-operative vomiting.
2014-07-15 Promethazine can be found in blood and urine samples of individuals who have taken this drug.