File:Promethazine.svg · Wikimedia Commons · See Wikimedia Commons
(±)-promethazine
Sign in to saveAlso known as proazamine, (2-dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine, 10-[2-(dimethylamino)propyl]phenothiazine, N,N,alpha-trimethyl-10H-phenothiazine-10-ethanamine, N,N,α-trimethyl-10H-phenothiazine-10-ethanamine, 10-(2-dimethylaminopropyl)phenothiazine, N-(2′-dimethylamino-2′-methyl)ethylphenothiazine
OverviewAI-generated
(±)-promethazine is a chemical compound with the formula C₁₇H₂₀N₂S. Its IUPAC name is N,N-dimethyl-1-phenothiazin-10-ylpropan-2-amine. The substance has a mass of 284.13472 and a weight of 284.4. It carries a defined daily dose of 25.
Chemical properties include an xlogp value of 4.8 and a topological polar surface area of 31.8. The molecule contains zero hydrogen bond donors and three hydrogen bond acceptors, with a charge of 0. Its canonical SMILES notation is CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C. The compound is associated with the MCN code 2934.30.30.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C17H20N2S
- Molecular weight
- 284.4 g/mol
- IUPAC name
- N,N-dimethyl-1-phenothiazin-10-ylpropan-2-amine
- SMILES
- CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C
- InChIKey
- PWWVAXIEGOYWEE-UHFFFAOYSA-N
- XLogP
- 4.8
- Polar surface area
- 31.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
4,281 papers- Sedation.Pediatric annals · 2005
- Promethazine: A Review of Therapeutic Uses and Toxicity.The Journal of emergency medicine · 2025
- [Haloperidol and promethazine in psychotic aggression].Ugeskrift for laeger · 2017
- Promethazine-induced dystonic reaction.Pediatric emergency care · 1987
- Promethazine use among chronic pain patients.Drug and alcohol dependence · 2015
via PubMed
Wikidata facts
- Subclass of
- medication
- Has part
- carbon
- Mass
- 284.13472
Show 10 more facts
- medical condition treated
- pain
- chemical formula
- C₁₇H₂₀N₂S
- canonical SMILES
- CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C
- World Health Organisation international non-proprietary name
- promethazine
- Commons category
- Promethazine
- MCN code
- 2934.30.30
- physically interacts with
- Histamine receptor H1
- significant drug interaction
- sodium oxybate
- defined daily dose
- 25
- native label
- Promethazine
via Wikidata · CC0
~12 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Side effects
- Overdose
- Pharmacology
- Chemistry
- History
- Society and culture
- Recreational use
- Product liability lawsuit
- References
Promethazine, sold under the brand name Phenergan among others, is a first-generation antihistamine, sedative, and antiemetic used to treat allergies, nausea, and vomiting. It may also help with some symptoms associated with the common cold and may also be used for sedating people who are agitated or anxious, an effect that has led to some recreational use (especially with codeine). Promethazine is taken by mouth (oral), as a rectal suppository, or by injection into a muscle (IM).
Common side effects of promethazine include confusion and sleepiness; consumption of alcohol or other sedatives can make these symptoms worse. It is unclear if use of promethazine during pregnancy or breastfeeding is safe. Use of promethazine is not recommended in those less than two years old, due to potentially negative effects on breathing. Use of promethazine by injection into a vein is not recommended, due to potential skin damage. Promethazine is in the phenothiazine family of medications. It is also a strong anticholinergic and at high or toxic doses can act as a deliriant.
Excerpted from Wikipedia’s “(±)-promethazine” article, available under the CC BY-SA 4.0 licence.