ContaminantDB: Promethazine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (13)XML

Record Information

Version

1.0

Creation Date

2014-08-30 21:04:24 UTC

Update Date

2026-03-31 19:07:59 UTC

Accession Number

CHEM003520

Identification

Common Name

Promethazine

Class

Small Molecule

Description

A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals. [PubChem]

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anti-Allergic Agent
Antipruritic
Drug
Ether
Histamine H1 Antagonist
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2-Dimethylamino-2-methyl)ethyl-N-dibenzoparathiazine	ChEBI
10-(2-Dimethylaminopropyl)phenothiazine	ChEBI
10-[2-(Dimethylamino)propyl]phenothiazine	ChEBI
N,N,alpha-Trimethyl-10H-phenothiazine-10-ethanamine	ChEBI
N-(2'-Dimethylamino-2'-methyl)ethylphenothiazine	ChEBI
Proazamine	ChEBI
Prometazina	ChEBI
Promethazinum	ChEBI
N,N,a-Trimethyl-10H-phenothiazine-10-ethanamine	Generator
N,N,Α-trimethyl-10H-phenothiazine-10-ethanamine	Generator
Isopromethazine	HMDB
Lilly 1516	HMDB
Proazaimine	HMDB
Promazinamide	HMDB
Prometazine	HMDB
Promethazin	HMDB
Promethiazine	HMDB
Promezathine	HMDB
Prothazin	HMDB
Prothazine	HMDB
Diprazin	HMDB
Rumergan	HMDB
Phenargan	HMDB
Phensedyl	HMDB
Promet	HMDB
Promethazine hydrochloride	HMDB
Remsed	HMDB
Prometazin	HMDB
Pyrethia	HMDB
Atosil	HMDB
Diphergan	HMDB
Hydrochloride, promethazine	HMDB
Phenergan	HMDB
Pipolfen	HMDB
Pipolphen	HMDB

Chemical Formula

C₁₇H₂₀N₂S

Average Molecular Mass

284.419 g/mol

Monoisotopic Mass

284.135 g/mol

CAS Registry Number

60-87-7

IUPAC Name

dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine

Traditional Name

promethazine

SMILES

CC(CN1C2=CC=CC=C2SC2=CC=CC=C12)N(C)C

InChI Identifier

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

InChI Key

PWWVAXIEGOYWEE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Aryl thioether
Tertiary aliphatic/aromatic amine
Para-thiazine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Thioether
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:8461 )
tertiary amine (CHEBI:8461 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

H1-receptor antagonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	60 °C
Boiling Point	190-192 °C at 3.00E+00 mm Hg
Solubility	15.6 mg/L (at 24 °C)

Predicted Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	4.52	ALOGPS
logP	4.29	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	9.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.5 m³·mol⁻¹	ChemAxon
Polarizability	32.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-0090000000-f1fe9756bed13819bbb4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9000000000-abbdf5514dccef4821b2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9100000000-9bef9a6b83d662fc7e2c	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0079-8290000000-fe5d6b4e9f62b7270798	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-0090000000-f1fe9756bed13819bbb4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9000000000-abbdf5514dccef4821b2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9100000000-9bef9a6b83d662fc7e2c	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0079-8290000000-fe5d6b4e9f62b7270798	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0229-9150000000-19753aa755aa19143e9b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000j-0690000000-0b4dfbac9712d2e36046	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-9220000000-9d761be1437f10dcc94b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-9120000000-53ae2d83de014d922ec7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0920000000-c051699dc72e950f2e98	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0002-0910000000-e92aacd8ca86df8a0e18	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0910000000-0ce89af1c9b2c4633eda	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0950000000-70d959c63d9e713a865a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-842e411dfa4c9fad1f7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2090000000-76a910470a52a47a6757	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-8090000000-d597b4b7604e8276f449	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-9110000000-cbed4a551fc77cf0e5b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-e24a248a31f0e31f1ec5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-009t-0940000000-afb556a81c40edffb9a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-3910000000-3daef27d94a5cac7d4a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9070000000-e74135a63711b2ca001f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9020000000-25ad7e0e10410cbe88c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000j-9610000000-32a1e6113f4291e6a186	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-a26692bb509bb9fc8701	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000t-0590000000-3a84419d780b185fa21a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ot-0940000000-7c01990eb3e291008595	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9210000000-7167670dff3395a6ade2	Spectrum

Toxicity Profile

Route of Exposure

On average, 88% of a promethazine dose is absorbed after oral administration; however, the absolute bioavailability is only 25% because of first-pass clearance.

Mechanism of Toxicity

Like other H1-antagonists, promethazine competes with free histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. The relief of nausea appears to be related to central anticholinergic actions and may implicate activity on the medullary chemoreceptor trigger zone.

Metabolism

Hepatic Route of Elimination: Promethazine hydrochloride is metabolized in the liver, with the sulfoxides of promethazine and N-desmethylpromethazine being the predominant metabolites appearing in the urine. Half Life: 16-19 hours

Toxicity Values

IV, Mouse: LD₅₀=55mg/kg

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of allergic disorders, and nausea/vomiting.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include mild depression of the central nervous system and cardiovascular system to profound hypotension, respiratory depression, unconsciousness, and sudden death. Other reported reactions include hyperreflexia, hypertonia, ataxia, athetosis, and extensor-plantar reflexes (Babinski reflex).

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01069

HMDB ID

HMDB0015202

FooDB ID

Not Available

Phenol Explorer ID