Basic information
- CAS
150-59-4- Standard SMILES
CCN(CCCc1ccccc1)CCCc1ccccc1- InChIKey
ZPFXAOWNKLFJDN-UHFFFAOYSA-N- Molecular formula
- C20H27N
- Average molar mass
- 281.4 g/mol
- Monoisotopic mass
- 281.21434987
Overview
Alverine is a tertiary amine having one ethyl and two 3-phenylprop-1-yl groups attached to the nitrogen. An antispasmodic that acts directly on intestinal and uterine smooth muscle, it is used (particularly as the citrate salt) in the treatment of irritable bowel syndrome. It has a role as an antispasmodic drug. It is a conjugate base of an alverine(1+).
Names & identifiers
- Preferred name
- Alverine
- IUPAC
- N-ethyl-3-phenyl-N-(3-phenylpropyl)propan-1-amine
- English name
- Alverine
- Molecular formula
- C20H27N
- Molecular weight
- 281.44
Names & synonyms
ALVERINE150-59-4PhenopropaminePhenpropamineProfenilDipropylinDipropylineSestronDi(phenylpropyl)ethylamineN-Ethyl-3,3'-diphenyldipropylamineAlverinaSestron base
Show more names
sestronbaseSeston baseAlverine base
Bis(gamma-phenylpropyl)ethylamineethylbis(3-phenylpropyl)amineAlverinumN,N-Bis(3-phenylpropyl)ethylamineN-Ethyl-N-(3-phenylpropyl)benzenepropanamineDipropylamine, N-ethyl-3,3'-diphenyl-N-Ethyl-3-phenyl-N-(3-phenylpropyl)-1-propanamine46TIR1560O
Database identifiers
- CAS
150-59-4、5560-59-8- PubChem CID
- 3678
- DTXSID
DTXSID0048557- ChEMBL
CHEMBL253371- ChEBI
CHEBI:518413- UNII
- 46TIR1560O
- EC Number
- 205-763-5
- Nikkaji
- J5.855F
Properties
Computed structural properties
- XLogP
- 5.3
- Topological polar surface area
- 3.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 9
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 214
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Color/FormLIQUID
Solubility
SIRUP; SOL IN WATER /HYDROCHLORIDE/
FREELY SOL IN WATER; CRYSTALS /CITRATE/
SLIGHTLY SOL IN CHLOROFORM; SOL IN DIL ACIDS; SPARINGLY SOL IN ALC; VERY SLIGHTLY SOL IN ETHER; SWEET ODOR & SLIGHTLY BITTER TASTE /CITRATE/
9.60e-04 g/L
Human DrugsPharmaceuticals
Boiling Point165-168 °C @ 0.3 MM HG
Melting Point< 25 °C
Physical DescriptionSolid
Collision Cross Section167.12 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Other Experimental Properties10% AQ SOLN IS NEUTRAL TO LITMUS /CITRATE/
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
This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.
Warning
H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: Alverine (EC: 205-763-5)
Other Safety InformationIMAP assessments - Benzenepropanamine, N-ethyl-N-(3-phenylpropyl)-: Human health tier I assessment
Safety data
- Toxicity
- women,TDLo,oral,126mg/kg/5W-I (126mg/kg),BEHAVIORAL: ANOREXIA (HUMANLIVER: LIVER FUNCTION TESTS IMPAIREDLIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE",Journal of Hepathology. Vol. 27, Pg. 399, 1997.
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H317-H319
- REACH Registrations
- Active
- Precautionary statements
- P305+P351+P338-P280
- Hazardous Substances Data
- 150-59-4(Hazardous Substances Data)
Chemistry & industry
Pharmacology
ATC Code
A03AX08
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Pharmacodynamics
Alverine is a smooth muscle relaxant. Smooth muscle is a type of muscle that is not under voluntary control; it is the muscle present in places such as the gut and uterus. Alverine acts directly on the muscle in the gut, causing it to relax. This prevents the muscle spasms which occur in the gut in conditions such as irritable bowel syndrome and diverticular disease. Diverticular disease is a condition in which small pouches form in the gut lining. These pouches can trap particles of food and become inflamed and painful. In irritable bowel syndrome the normal activity of the gut muscle is lost. The muscle spasms result in symptoms such as heartburn, abdominal pain and bloating, constipation or diarrhoea. By relaxing the gut muscle, alverine citrate relieves the symptoms of this condition. Alverine also relaxes the smooth muscle in the womb (uterus). It is therefore also used to treat painful menstruation, which is caused by muscle spasms in the uterus (dysmenorrhea).
Biological Half-LifeThe plasma half-life averages 0.8 hours for alverine and 5.7 hours for the active primary metabolite.
Metabolism/MetabolitesRapidly converted to its primary active metabolite, which is then further converted to two secondary metabolites.
MeSH Pharmacological ClassificationAgents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS.
Absorption, Distribution and ExcretionHigh renal clearance of all metabolites indicating that they are eliminated by active renal secretion.
Cellular LocationsMembrane
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…