Asenapine (CED0006229)

Record Information

Version

1.0

Creation Date

2016-05-22 06:57:34 UTC

Update Date

2026-05-14 18:18:41 UTC

Accession Number

CHEM020258

Identification

Common Name

Asenapine

Class

Small Molecule

Description

Asenapine is an organic compound with the chemical formula C17H16ClNO and an average molecular weight of 285.77 g/mol. Asenapine belongs to the dibenzoxepines, a subclass of benzoxepines within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from three recorded sources, which include antipsychotics within healthcare, pharmaceuticals, and veterinary products, as well as other smoking requisites and non-electric simulated smoking devices within household cleaning and consumer products. Recorded routes of exposure for this substance include transdermal and sublingual administration. In terms of biological activity, asenapine has 20 recorded protein targets. It acts as an antagonist of 5-hydroxytryptamine receptor 1A (HTR1A), 5-hydroxytryptamine receptor 1B (HTR1B), 5-hydroxytryptamine receptor 2A (HTR2A), and 5-hydroxytryptamine receptor 2B (HTR2B), in addition to 16 other proteins.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Saphris	MeSH
5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3-6,7)oxepino(4,5-c)pyrrole	MeSH
Asenapine maleate	MeSH

Chemical Formula

C₁₇H₁₆ClNO

Average Molecular Mass

285.770 g/mol

Monoisotopic Mass

285.092 g/mol

CAS Registry Number

65576-45-6

IUPAC Name

(2R,6R)-17-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.0²,⁶.0⁷,¹²]octadeca-1(14),7,9,11,15,17-hexaene

Traditional Name

asenapine

SMILES

[H][C@@]12CN(C)C[C@@]1([H])C1=C(OC3=CC=CC=C23)C=CC(Cl)=C1

InChI Identifier

InChI=1S/C17H16ClNO/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19/h2-8,14-15H,9-10H2,1H3/t14-,15-/m0/s1

InChI Key

VSWBSWWIRNCQIJ-GJZGRUSLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Dibenzoxepines

Direct Parent

Dibenzoxepines

Alternative Parents

Substituents

Dibenzoxepine
Diaryl ether
Aralkylamine
Aryl chloride
Aryl halide
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Ether
Organopnictogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole (CHEBI:71256 )

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	0.031 g/L	ALOGPS
logP	4.35	ALOGPS
logP	3.72	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	7.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.65 m³·mol⁻¹	ChemAxon
Polarizability	30.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-d95ab67e5b635f43eeb9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-042a006ceeb6b059dc0d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f9f-3940000000-e21059b160e0a93a0d6e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0090000000-7e24e647d36b4471609d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0090000000-cd7fa4741766f3c4dbc9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pbc-1790000000-339cbcf33d6b8be569a8	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
287.0	Log mg/kg	[160:510]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
374	Antipsychotics	Healthcare, pharmaceuticals & veterinary products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
651	Purses Money Bags Wallets	Textiles, leather & furnishings	Not Available

Pathways

4 pathways

Asenapine Dopamine Antagonist Action Pathway

Asenapine Serotonin antagonist Action Pathway

Asenapine Drug Metabolism

Asenapine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Histamine H1 receptor	P31390	Rattus norvegicus	Predicted (SEA)	49.5121
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	210.582
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	162.549
Click to view 3D structure	5-hydroxytryptamine receptor 7	P32305	Rattus norvegicus	Predicted (SEA)	133.667
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	37.9904
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	14.9471
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	34.4094
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	42.1164
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	18.5281
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	32.2296
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	18.9952
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	36.2777
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	39.1582
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	60.7224
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	128.607
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P08909	Rat	Predicted (SEA)	48.2665
Click to view 3D structure	Histamine H4 receptor	Q9H3N8	Humans	Predicted (SEA)	30.0498
Click to view 3D structure	D(3) dopamine receptor	P19020	Rattus norvegicus	Predicted (SEA)	86.8019
Click to view 3D structure	D(1A) dopamine receptor	P18901	Rattus norvegicus	Predicted (SEA)	88.826
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	88.5924
Click to view 3D structure	Alpha-1A adrenergic receptor	P18130	Bos taurus	Predicted (SEA)	42.8949
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	221.87
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	178.586
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	350.555
Click to view 3D structure	Norepinephrine transporter	Q9WTR4	Rattus norvegicus	Predicted (SEA)	78.5499