lofepramide (CED0059636)

Record Information

Version

1.0

Creation Date

2016-06-03 11:14:01 UTC

Update Date

2026-08-22 06:21:52 UTC

Accession Number

CHEM043749

Identification

Common Name

lofepramide

Class

Small Molecule

Description

Lofepramide is an organic compound with the chemical formula $\text{C}_{26}\text{H}_{27}\text{ClN}_2\text{O}$ and an average molecular weight of 418.97 g/mol. Lofepramide belongs to the dibenzazepines, a subclass of benzazepines within the organic compounds. It is further categorized under the superclass of organoheterocyclic compounds. The substance is found in or released from 12 recorded sources. These include various categories of electrical and electronic equipment, specifically amplifiers, antennas, auxiliary devices, colour television systems, and electric hearing aids, among six other types of equipment. Additionally, lofepramide is associated with household cleaning and consumer products, specifically non electric simulated smoking devices.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(4-Chlorophenyl)-2-{[3-(10,11-dihydro-5H-dibenzo[b,F]azepin-5-yl)propyl]methylamino}ethanone	ChEBI
4'-Chlor-2-((3-(10,11-dihydro-5H-dibenz(b,F)azepin-5-yl)propyl)methylamino)acetophenon	ChEBI
4'-Chloro-2-((3-(10,11-dihydro-5H-dibenz(b,F)azepin5-yl)propyl)methylamino)acetophenone	ChEBI
Lopramine	ChEBI
Feprapax	MeSH
Ashbourne brand OF lofepramine hydrochloride	MeSH
leo 640	MeSH
Lomont	MeSH
Gamanil	MeSH
Hydrochloride, lofepramine	MeSH
Merck brand OF lofepramine hydrochloride	MeSH
Rosemont brand OF lofepramine hydrochloride	MeSH
Deftan	MeSH
Lofepramine hydrochloride	MeSH
Gamonil	MeSH

Chemical Formula

C₂₆H₂₇ClN₂O

Average Molecular Mass

418.970 g/mol

Monoisotopic Mass

418.181 g/mol

CAS Registry Number

23047-25-8

IUPAC Name

2-[(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amino]-1-(4-chlorophenyl)ethan-1-one

Traditional Name

2-[(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amino]-1-(4-chlorophenyl)ethanone

SMILES

CN(CCCN1C2=CC=CC=C2CCC2=CC=CC=C12)CC(=O)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C26H27ClN2O/c1-28(19-26(30)22-13-15-23(27)16-14-22)17-6-18-29-24-9-4-2-7-20(24)11-12-21-8-3-5-10-25(21)29/h2-5,7-10,13-16H,6,11-12,17-19H2,1H3

InChI Key

SAPNXPWPAUFAJU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Dibenzazepines

Direct Parent

Dibenzazepines

Alternative Parents

Substituents

Dibenzazepine
Alkyl-phenylketone
Alkyldiarylamine
Phenylketone
Benzoyl
Tertiary aliphatic/aromatic amine
Aryl ketone
Aryl alkyl ketone
Azepine
Chlorobenzene
Halobenzene
Aryl halide
Aryl chloride
Benzenoid
Monocyclic benzene moiety
Alpha-aminoketone
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Organic oxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:47782 )
monochlorobenzenes (CHEBI:47782 )
aromatic ketone (CHEBI:47782 )
dibenzoazepine (CHEBI:47782 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00084 g/L	ALOGPS
logP	5.79	ALOGPS
logP	6.11	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	17.02	ChemAxon
pKa (Strongest Basic)	6.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	125.31 m³·mol⁻¹	ChemAxon
Polarizability	46.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-052r-3930000000-7f3233101e9bc3c16ac2	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0190000000-939eaff7e4c449d10e95	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0030900000-f2c1472e308c1b5aef4b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00tr-1390200000-e0f7a25f6e2c3cf8cf45	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0017-7950000000-f7cfdbd1d08c3c9e7b07	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0100900000-0c66d04816128a1bd142	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-015c-0911400000-f3a351150cd2f078f73a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kf-1900000000-239b62d416a315bf9bef	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0010900000-417d70665e251f5a9161	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00yr-3790300000-35b025799d6e47a8cf30	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-2950000000-3b5dd2fb9a45903de9ec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0000900000-b75a2d50ee5a83773f68	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00l6-1970700000-92d67c757a3b7ac10b0e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9310100000-31a976888a2df4b86577	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1599.0	Log mg/kg	[900:2800]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
507	Auxiliary Devices	Electrical & Electronic Equipment	Not Available
509	Colour Television Systems	Electrical & Electronic Equipment	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
535	Superconducting Magnets And Superconducting Coils	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
579	Manufacture Of Iron Or Steel	Industrial manufacturing & chemical processing	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
581	Paper Making Machines	Industrial manufacturing & chemical processing	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
654	Sleeve Links	Textiles, leather & furnishings	Not Available
655	Slide Fasteners	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	10.1982
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	14.5578
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	23.8219
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	82.3645
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	58.4648
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	30.7504
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	13.5458
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	26.2352
Click to view 3D structure	Norepinephrine transporter	Q9WTR4	Rattus norvegicus	Predicted (SEA)	9.57545
Click to view 3D structure	Histamine H1 receptor	P31390	Rattus norvegicus	Predicted (SEA)	3.19182
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	52.5482
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	87.1133
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	48.033
Click to view 3D structure	Histamine H2 receptor	P47747	Cavia porcellus	Predicted (SEA)	4.35956
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	37.3676
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	14.0907
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	196.647
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	62.5908
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	25.1453
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	31.4511
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	12.0666
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	18.606
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	17.9053
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	88.7481
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	107.588