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Dyclonine Hydrochloride

HCID 68304
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
536-43-6
Standard SMILES
CCCCOc1ccc(C(=O)CCN2CCCCC2)cc1.Cl
InChIKey
KNZADIMHVBBPOA-UHFFFAOYSA-N
Molecular formula
C18H28ClNO2
Average molar mass
325.9 g/mol
Monoisotopic mass
325.1808568

Overview

Dyclonine Hydrochloride is the hydrochloride salt of Dyclonine, an unclassified compound with local anesthetic effect. Dyclonine reversibly binds to activated sodium channels on the neuronal membrane, thereby decreasing the neuronal membrane's permeability to sodium ions, leading to an increased threshold for excitation. This reversibly stabilizes the membrane and inhibits depolarization, leading to the failure of a propagated action potential and subsequent conduction blockade. This results in a transient and reversible loss of sensation in a localized area of the body.

Names & identifiers

Preferred name
Dyclonine Hydrochloride
IUPAC
1-(4-butoxyphenyl)-3-piperidin-1-ylpropan-1-one;hydrochloride
English name
Dyclonine hydrochloride
Molecular formula
C18H28ClNO2
Molecular weight
325.87

Names & synonyms

Dyclonine hydrochloride536-43-6Dyclonine HCLDyclone4'-Butoxy-3-piperidinopropiophenone hydrochlorideDTXSID6045323NSC-23018ZEC193879QDyclonine hydrochloride (USP)Dyclonine hydrochloride [USP]DTXCID4025323NSC23018
Show more names
c5422tanaclone1-(4-butoxyphenyl)-3-(1-piperidinyl)-1-propanone1-(4-Butoxyphenyl)-3-(piperidin-1-yl)propan-1-one hydrochlorides154p-267dicloniaDYCLONLNEdyclothane
4-n-Butoxy-beta-(1-piperidyl)propiophenone hydrochlorideCHEBI:4725DycloproRefChem:55083Sucrets Sore Throat Wild Cherry1-Propanone,1-(4-butoxyphenyl)-3-(1-piperidinyl)-,hydrochloride208-633-61-(3-(4-butoxyphenyl)-3-oxopropyl)piperidinium chloride

Database identifiers

CAS
536-43-6
PubChem CID
68304
DTXSID
DTXSID6045323

Properties

Computed structural properties

Topological polar surface area
29.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
8
Heavy atoms
22
Formal charge
0
Complexity
292

Experimental & physicochemical properties

Solubility>48.9 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs · 3 items

Breast Feeding; Lactation; Anesthetics, Local

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Collision Cross Section179.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
175 · 175-176°C
storage temp.
2 · Inert atmosphere,2-8°C
solubility
Soluble in DMSO (20 mg/ml); Water (25 mg/ml)
form
solid
color
White
Water Solubility
Partly soluble in water. Soluble in chloroform, ethanol, acetone and methanol.
Merck
14 · 14,3473
Stability
2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 2 months.

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 · 4 items

Danger

H301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (97.5%)

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
3
rtecs
UG8750000
ridadr
3249
hs_code
2933399090
risk_code
22-37/38-41
Signal word
Danger
Symbol(GHS)
GHS05,GHS06
hazard_code
Xn
safety_code
26-36
hazard_class
6.1(b)
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.

Applications · 7 items

DescriptionDyclonine hydrochloride is the hydrochloride salt of Dyclonine. Dyclonine belongs to a kind of oral anaesthetic. It is contained in the “Sucrets” as well as some kinds of Cepacol sore throat spray as an active ingredient. Dyclonine takes effect through reversibly binding to the activated sodium channels located on the neuronal membrane. This decreases the permeability of sodium across the neuronal membrane, further increasing the threshold for excitation. Overall, Dyclonine stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and further suppressing the subsequent conduction. This causes a transient and reversible anaesthetic effect in a local area of the body.

UsesDyclonine hydrochloride is used for the temporary relief of the following occasional mouth and throat symptoms: pain, minor irritation, sore mouth and sore throat. It is a sodium channel blocker and a HSP90 chaperone protein inhibitor. It shows local anesthetic effects in vivo and is orally active.

DescriptionDyclonine (536-43-6) is a topical anesthetic which has been used for oral and throat analgesia.1 Enhances neuronal mitochondrial function, potentiating respiration and providing protection against insults associated with neurodegenerative disorders.2 Inhibits aldehyde dehydrogenase ALDH3A1 resulting in accumulation of 4-hydroxynonenal, which renders head and neck squamous cell carcinoma cells sensitive to the cystine-glutamate antiporter inhibitor, sulfasalazine.3 Rescues frataxin deficiency in animal models as well as in buccal cells of patients with Friedreich’s Ataxia.4 Enhances the cytotoxic effect of proteasome inhibitors MG-1325 and bortezomib6 in cancer cells.

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Related reactions

1 records
New reaction record
HRID 1660099 reaction equation
HRID 1660099As reactantuspto-grants-1981_12

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
ChEMBL
CHEMBL1200478
UNII
ZEC193879Q
EC Number
208-633-6
Major Application
pharmaceutical (small molecule)
InChI
InChI=1S/C18H27NO2.ClH/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19;/h7-10H,2-6,11-15H2,1H3;1H
InChIKey
KNZADIMHVBBPOA-UHFFFAOYSA-N
SMILES
C1(C(=O)CCN2CCCCC2)C=CC(OCCCC)=CC=1.Cl
CAS DataBase Reference
536 · 536-43-6(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
193879 Q · ZEC193879Q
NCI Drug Dictionary
dyclonine hydrochloride
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
5 · GHS05,GHS06
Signal word
Danger
Hazard statements
301 · H301-H315-H318-H335
Precautionary statements
261 · P261-P264-P280-P301+P310-P302+P352-P305+P351+P338
target organs
Respiratory system
Hazard Codes
Xn
Risk Statements
22 · 22-37/38-41
Safety Statements
26 · 26-36
RIDADR
3249 · 3249
WGK Germany
3 · 3
RTECS
8750000 · UG8750000
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
2933399090 · 2933399090
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 OralEye · Acute Tox. 3 OralEye Dam. 1Skin Irrit. 2STOT SE 3
packing_group
III
target organs
Respiratory system
Hazard statements
H301-H315-H318-H335
Hazard Classifications
Acute Tox. 3 OralEye Dam. 1Skin Irrit. 2STOT SE 3
Precautionary statements
P261-P264-P280-P301+P310-P302+P352-P305+P351+P338

UsesProvides anesthesia of mucous membranes. Apply 5 to 10 minutes before a procedure; apply b.i.d. to t.i.d. for pain relief. Onset of action is within 2 to 10 minutes. Anesthesia lasts 30 to 60 minutes.

Usesanesthetic (topical)

UsesUsed as a local anesthetic

UsesDyclonine hydrochloride is used for the temporary relief of the following occasional mouth and throat symptoms: pain, minor irritation, sore mouth and sore throat. It is a sodium channel blocker and a HSP90 chaperone protein inhibitor. It shows local anesthetic effects in vivo and is orally active.

Upstream & downstream products

Upstream raw materials

Sodium bromideHydrochloric acidParaformaldehydePiperidine hydrochloride

Additional notes

DefinitionChEBI: The hydrochloride salt of dyclonine.