Basic information
- CAS
140-65-8- Standard SMILES
CCCCOc1ccc(OCCCN2CCOCC2)cc1- InChIKey
DQKXQSGTHWVTAD-UHFFFAOYSA-N- Molecular formula
- C17H27NO3
- Average molar mass
- 293.4 g/mol
- Monoisotopic mass
- 293.19909372
Overview
Pramocaine is a member of the class of morpholines that is morpholine substituted at the nitrogen atom by a 3-(4-butoxyphenoxy)propyl group. It has a role as a local anaesthetic. It is an aromatic ether and a member of morpholines.
Names & identifiers
- Preferred name
- Pramoxine
- IUPAC
- 4-[3-(4-butoxyphenoxy)propyl]morpholine
- English name
- pramocaine
- Molecular formula
- C17H27NO3
- Molecular weight
- 293.4
Names & synonyms
Pramocainepramoxine140-65-8Proxazocain4-[3-(4-Butoxyphenoxy)propyl]morpholinepramocainumPramocaina4-(3-(p-Butoxyphenoxy)propyl)morpholinep-Butoxyphenyl gamma-morpholinopropyl ethergamma-Morpholinopropyl 4-n-butoxyphenyl ether4-(3-(4-butoxyphenoxy)propyl)morpholineCHEBI:8357
Show more names
PramoxinTronoteneTronothane4-[3-(4-Butoxyphenoxy)propyl]morphorine4-(3-(4-BUTOXYPHENOXY)PROPYL)-MORPHOLINEMorpholine, 4-[3-(4-butoxyphenoxy)propyl]-
068X84E056DTXSID8040692RefChem:55901DTXCID6020692C05AD07D04AB07205-425-7Tronopthane
Database identifiers
- CAS
140-65-8- PubChem CID
- 4886
- DTXSID
DTXSID8040692- ChEMBL
CHEMBL1198- ChEBI
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 30.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 248
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP3.56
Human DrugsPharmaceuticals
Collision Cross Section177.42 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Boiling point
- 6 · bp6 196°; bp2.8 183-184°
- Density
- 1.0112 · 1.0112 (rough estimate)
- refractive index
- 1.542 · 1.5420 (estimate)
- pka
- 7.18 · 7.18±0.10(Predicted)
- Water Solubility
- 3.574 mg/L · 3.574mg/L(22.5 ºC)
- CAS DataBase Reference
- 140 · 140-65-8
- FDA UNII
- 68 X84E056 · 068X84E056
- ATC code
- 5 AD07,D04AB07 · C05AD07,D04AB07
- Symbol(GHS)
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 ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- Toxicity
- LD50 in mice (mg/kg): 300 i.p., 900 s.c. (Monash, Gibbs)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
D - Dermatologicals
QC - Cardiovascular system
QD - Dermatologicals
PharmacodynamicsPramocaine temporarily relieves pain, pruritis, burning and discomfort associated with minor lip and skin irritations and hemorrhoid's by inhibiting voltage gated sodium channels on neurons.
Mechanism of Action
Pramocaine reversibly binds and inhibits voltage gated sodium channels on neurons decreasing sodium permeability into the cell. This stabilizes the membrane and prevents ionic fluctuations needed for depolarization stopping any action potential propagation.
MeSH Pharmacological Classification
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.
Absorption, Distribution and ExcretionThere is minimal absorption after topical administration and it is not given orally.
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesAnesthetic (topical).
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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