Basic information
- CAS
174508-13-5- Standard SMILES
CC(CN(C)C)CN1c2ccccc2S(=O)(=O)c2ccccc21- InChIKey
QTQPVLDZQVPLGV-UHFFFAOYSA-N- Molecular formula
- C18H22N2O2S
- Average molar mass
- 330.4 g/mol
- Monoisotopic mass
- 330.14019912
Overview
Oxomemazine is a member of phenothiazines.
Names & identifiers
- Preferred name
- Oxomemazine
- IUPAC
- 3-(5,5-dioxophenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
- English name
- OXOMEMAZINE
- Molecular formula
- C18H22N2O2S
- Molecular weight
- 330.44
Names & synonyms
Oxomemazine3689-50-7DysedonDoxerganImakolOxomemazinumOxomemazinaTrimeprazine 5,5-dioxideOplexExe-topRP 6847RP-6847
Show more names
6847 RP6487 RPDosegran6847 R.P.OxomemazinOXOEMAZINE
305MB38V1C6487-RP6847-RPDTXSID5023405PHENOTHIAZINE, 10-(3-(DIMETHYLAMINO)-2-METHYLPROPYL)-, 5,5-DIOXIDEPhenothiazine, 10-[3-(dimethylamino)-2-methylpropyl]-, 5,5-dioxide(+-)-OxomemazineRefChem:857801
Database identifiers
- CAS
174508-13-5、174508-14-6、3689-50-7- PubChem CID
- 19396
- DTXSID
DTXSID5023405- ChEMBL
CHEMBL2104734- ChEBI
CHEBI:135408- UNII
- 305MB38V1C、5GP9538P4S、Q824SGH3RN
- EC Number
- 222-996-8
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 49 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 470
Physicochemical properties
- Melting point
- 115 ° · 115°
- Boiling point
- 492.4 · 492.4±34.0 °C(Predicted)
- Density
- 1.1453 · 1.1453 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 33 mg/mL · ≥ 33mg/mL in DMSO
- form
- Solid
- pka
- 9.31 · 9.31±0.28(Predicted)
- color
- White to off-white
- InChI
- InChI=1S/C18H22N2O2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)23(21,22)18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3
- InChIKey
- QTQPVLDZQVPLGV-UHFFFAOYSA-N
- SMILES
- N1(CC(C)CN(C)C)C2C=CC=CC=2S(=O)(=O)C2C=CC=CC1=2
- FDA UNII
- 305 MB38V1C · 305MB38V1C
- ATC code
- 6 AD08 · R06AD08
- Symbol(GHS)
- 6 · GHS06
- Signal word
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (83.3%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P262, P264, P270, P271, P272, P273, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P316, P320, P321, P330, P333+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 6 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (83.3%)
Safety data
- Toxicity
- LD50 oral in mouse: 140mg/kg
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H330-H311-H301
- Precautionary statements
- P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501-P280-P302+P352-P312-P322-P361-P363-P405-P501
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
Mechanism of ActionOxomemazine is an antagonist at histamine H1 receptors. It exhibits antimuscarinic properties.
Metabolite PathwaysOxomemazine H1-Antihistamine Action
Applications
HistoryThe development of oxomemazine is the result of a systematic exploration of phenothiazine compounds in the mid-20th century. Following the significant sedative effects of the first-generation antihistamine promethazine, scientists focused on optimizing its pharmacological properties through structural modification. In the late 1950s and early 1960s, researchers synthesized oxomemazine by chemically modifying the side chains of promethazine. This new compound retained potent antihistamine activity while enhancing its antitussive and sedative effects. Based on these properties, oxomemazine was marketed as an antitussive in the 1960s, often under the brand name Toplexil®, and was particularly suitable for treating allergic dry cough accompanied by sleep disturbances.
Uses(±)-Oxomemazine, is a phenothiazine-type antihistamines, that has also shown antibacterial activity against Mycobacterium tuberculosis.
Upstream & downstream products
Upstream raw materials
Suppliers40 total
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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