Amylmetacresol
Basic information
- CAS
1300-94-3- Standard SMILES
CCCCCc1ccc(C)cc1O- InChIKey
CKGWFZQGEQJZIL-UHFFFAOYSA-N- Molecular formula
- C12H18O
- Average molar mass
- 178.27 g/mol
- Monoisotopic mass
- 178.13576519
Overview
Amylmetacresol is a phenol having the structure of m-cresol substituted at the 6-position with an amyl group. It has a role as an antiseptic drug. It is functionally related to a m-cresol.
Names & identifiers
- Preferred name
- Amylmetacresol
- IUPAC
- 5-methyl-2-pentylphenol
- English name
- Amylmetacresol
- Molecular formula
- C12H18O
- Molecular weight
- 178.27
Names & synonyms
Amylmetacresol5-Methyl-2-pentylphenol1300-94-36-Pentyl-m-cresol6-Amyl-m-cresol6-n-Amyl-m-cresolamylmetacresolumPhenol, 5-methyl-2-pentyl-6-n-Pentyl-m-cresolAmilmetacresolAmyl metacresolDTXSID8046791
Show more names
AmyleineAMYL-M-CRESOLamylmetacresoPENTYL-M-CRESOL6-pentyl-m-cresoAMYL META CRESOLAMYL(6-)-M-CRESOL
05W904P57FDTXCID6026791CHEBI:48213amilmetacresoloThroatiesRefChem:112402215-094-05-methyl-2-n-pentylphenol
Database identifiers
- CAS
1300-94-3- PubChem CID
- 14759
- DTXSID
DTXSID8046791- ChEMBL
CHEMBL1512677- ChEBI
CHEBI:48213- UNII
- 05W904P57F
- EC Number
- 215-094-0
- Nikkaji
- J118.441E
Properties
Computed structural properties
- XLogP
- 4.4
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 4
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 133
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubilitynot soluble
Physicochemical properties
- Melting point
- 24 °C · 24°C
- Boiling point
- 139 °C/15mmHg · 139°C/15mmHg(lit.)
- Density
- 0.9414 · 0.9414 (estimate)
- refractive index
- 1.512 to · 1.5120 to 1.5160
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Practically insoluble in water, very soluble in acetone and in ethanol (96 per cent).
- pka
- 10.55 · 10.55±0.35(Predicted)
- form
- Liquid
- color
- Yellow to Dark Orange
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C12H18O/c1-3-4-5-6-11-8-7-10(2)9-12(11)13/h7-9,13H,3-6H2,1-2H3
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
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P264, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P318, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- WGK 3
- rtecs
- GP3100000
- ridadr
- UN 3145 8/PG III
- hs_code
- 2907199090
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- hazard_class
- 8
- Storage Class
- 10 - Combustible liquids
- packing_group
- III
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
Pharmacodynamics
The mixture of amylmetacresol throat lozenge medications markedly reduces the infectivity of certain infectious viruses in the throat and in cough droplets, thus reducing opportunities for person-to-person transmission. In addition, it relieves symptoms of sore throat/irritation of the throat,. Amylmetacresol is thought to inhibit the inflammatory and pain mediators that are involved in the inflammation of the mouth and throat mucous membranes, as well as the sore throat.
Mechanism of Action
The mechanism of virucidal action is not fully elucidated, however it is suggested that denaturation of external protein spikes, a pH-induced rearrangement of the tertiary structure of attachment proteins, or a selective effect on viral lipid membranes/protein–lipid interaction is responsible for this action. Amylmetacresol is an antibacterial and antiviral agent, and blocks voltage-gated Na channels in a local anesthetic-like manner.
Absorption, Distribution and ExcretionRapidly absorbed and eliminated.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >50
Applications
UsesAntiseptic. Amylmetacresol is an antiseptic available in Canada over-the-counter in a number of lozenges for the treatment of sore throat and minor mouth infections,. Amylmetacresol is often combined with dichlorobenzyl alcohol and menthol in the commonly used sore throat lozenges, known as Strepsils. The acute sore throat (pharyngitis) is one of the most common conditions for which children are seen in the primary care setting. Pharyngitis is normally caused by viruses and proves benign and self-limiting. Clinically proven, over-the-counter throat lozenges offer rapid and effective relief of acute sore throat symptoms, and are increasingly important in the management of this condition.
Related reactions
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Compound notes
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