Amylmetacresol
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Amylmetacresol
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CAS No:
1300-94-3
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Formula:
C12H18O
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Chemical Name:
Amylmetacresol
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Synonyms:
Phenol,5-methyl-2-pentyl-;m-Cresol,6-pentyl-;5-Methyl-2-pentylphenol;6-n-Amyl-m-cresol;Amylmetacresol;53043-14-4
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CAS No:
Description
Clear or almost clear liquid, or solid crystalline mass, colourless or slightly yellow when freshly prepared. The substance changes colour during storage by darkening and/or discolouration to dark yellow, brownish-yellow or pink.ChEBI: A phenol having the structure of m-cresol substituted at the 6-position with an amyl group.
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 derives from a m-cresol.|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.
Characteristics
20.2
4.4
0.9414 (estimate)
24 °C
119-122 °C @ Press: 10 Torr
125.3ºC
1.5120 to 1.5160
not soluble
0.00348mmHg at 25°C
Safety Information
III
8
UN 3145 8/PG III
22
GP3100000
Xn
P301 + P312 + P330
H302
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P273, P280, P281, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P321, P330, P363, P391, P405, and P501|Aggregated GHS information provided by 46 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Oral LD50: 1500 mg/kg (rat) [MSDS] Adverse effects include hypersensitivity reactions, tongue soreness. Occasionally, hypersensitivity reactions may occur, manifested by digestive problems such as nausea or dyspepsia. This is extremely rare. In the case of overdose, management should be symptomatic. In cases of severe overdosage, gastric lavage may be warranted to empty the stomach contents. Saline laxatives and activated charcoal may be administered orally.
Drug Information
Sore throat, minor mouth and throat infections,,.
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.
Rapidly absorbed and eliminated.
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.
amylmetacresol
Amylmetacresol Use and Manufacturing
AMC Stage 1: Amyl m-cresol; VMC stage 2 (45.5g) and palladium on carbon catalyst (Johnson Matthey type 394 5% w/w, 5% water wet) (4.6g) were charged to a jacketed hydrogenator vessel, followed by citric acid (0.5g). Iso-propanol (220ml) was charged to the vessel and the jacket temperature was set to 12.5C. The vessel was pressurised to 0.7bar with hydrogen and stirred at this pressure until judged complete by GC analysis. Once reaction completion had been achieved (after around 16 hr) the reaction mixture was filtered to remove the catalyst. The catalyst was then washed with IP A (10 ml) and the washings added to the reaction mixture. The reaction mixture was concentrated by distillation or rotary evaporation. Crude yield 56.5g.
Antiseptic.
Computed Properties
Molecular Weight:178.27
XLogP3:4.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:178.135765193
Monoisotopic Mass:178.135765193
Topological Polar Surface Area:20.2
Heavy Atom Count:13
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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