Amisulpride (CED0004404)

Record Information

Version

1.0

Creation Date

2016-05-22 04:41:09 UTC

Update Date

2026-08-19 21:55:49 UTC

Accession Number

CHEM017838

Identification

Common Name

Amisulpride

Class

Small Molecule

Description

Amisulpride is an organic compound with the formula C17H27N3O4S and an average molecular weight of 369.48 g/mol. Amisulpride belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. The substance is identified as being found in or released from five recorded sources. These include healthcare, pharmaceuticals, and veterinary products where it is used as an antipsychotic, as well as electrical and electronic equipment, specifically radio transmission systems and electrically stimulated smoking devices. Additionally, it is found in household cleaning and consumer products, including tobacco smoke filters and non-electric simulated smoking devices. The recorded route of exposure for this compound is intravenous. In terms of its biological activity, amisulpride interacts with seven recorded protein targets. It acts as an agonist or antagonist of the D(2) dopamine receptor (DRD2), the D(3) dopamine receptor (DRD3), 5-hydroxytryptamine receptor 7 (HTR7), and 5-hydroxytryptamine receptor 2A (HTR2A), in addition to three other proteins.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide	ChEBI
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-O-anisamide	ChEBI
Aminosultopride	ChEBI
Amisulprida	ChEBI
Amisulpridum	ChEBI
Deniban	Kegg
Solian	Kegg
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulphonyl)-2-methoxybenzamide	Generator
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulphonyl)-O-anisamide	Generator
Barnetil	HMDB
Sultopride hydrochloride	HMDB
N-(Ethyl-1-pyrrolidinyl- 2-methyl)methoxy-2-ethylsulfonyl-5-benzamide	HMDB
Sultopride	HMDB

Chemical Formula

C₁₇H₂₇N₃O₄S

Average Molecular Mass

369.479 g/mol

Monoisotopic Mass

369.172 g/mol

CAS Registry Number

71675-85-9

IUPAC Name

4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide

Traditional Name

amisulpride

SMILES

CCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC

InChI Identifier

InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21)

InChI Key

NTJOBXMMWNYJFB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzamides

Alternative Parents

Substituents

Aminobenzamide
Methoxyaniline
Benzamide
Aminophenyl ether
Benzenesulfonyl group
Phenol ether
Aniline or substituted anilines
Methoxybenzene
Benzoyl
Phenoxy compound
Anisole
Alkyl aryl ether
N-alkylpyrrolidine
Pyrrolidine
Sulfone
Sulfonyl
Carboxamide group
Tertiary aliphatic amine
Secondary carboxylic acid amide
Amino acid or derivatives
Tertiary amine
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfone (CHEBI:64045 )
benzamides (CHEBI:64045 )
pyrrolidines (CHEBI:64045 )
aromatic amine (CHEBI:64045 )
aromatic amide (CHEBI:64045 )

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	0.29 g/L	ALOGPS
logP	1.5	ALOGPS
logP	0.25	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.03	ChemAxon
pKa (Strongest Basic)	7.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	101.73 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	99.84 m³·mol⁻¹	ChemAxon
Polarizability	39.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-002g-9054000000-b1dc7fa1718d7f3a0b9c	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0609000000-2b372299b7870a4920eb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0009000000-99c1cc37ab9cf4683323	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0409000000-4e053b8ec1d55ced8499	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004l-0974000000-de9354d79437a4df60bc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01q9-0900000000-f91d53fb9c883bae9ca3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-324b93e2df83509f8048	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0009000000-99ab45809f8e56fbb616	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014l-0109000000-93205a0e84bbb061506a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-057i-0960000000-23d53c22f66a40ded55b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0509000000-de0803e7c69539424a4e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0019000000-7dec57b5001ab24504cc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0019000000-c532dacf370f0075220b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0092000000-6deb7fed54b4631e9813	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-0980000000-c78d2a361bbc674b41ce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-0960000000-6a4706ff5588c4035137	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0190000000-e410c0158058e8740df0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0009000000-2237ffbc12b8e6459da5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0029000000-2143af7abc829fd8cacd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0290000000-bb210e691e1906ae74a7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0590000000-5f6a35609afc11e248ef	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0920000000-b89e4616edb7a54d2976	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-1900000000-15fd75a1097964a2b372	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0009000000-34c03de48e9e080e3c47	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0029000000-35268399499c0c04d5f5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0290000000-ad61214eeef71e97665b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0590000000-8322cbf2d5910eb0bd03	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0920000000-cbc60b473b3fb0de43ab	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-1900000000-c32487a90cfd10db9961	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0190000000-458205e2fa61496c6a54	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dl-2689000000-c4a31e81f70bf838ae8f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dl-0269000000-e2c8021fa5c019a7a29e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-0960000000-6b124e0dd8afe6c4684e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0092000000-d7e96187c0bebf25d210	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0509000000-de0803e7c69539424a4e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-057i-0960000000-23d53c22f66a40ded55b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0009000000-99ab45809f8e56fbb616	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0920000000-61ca1439f295c7354f51	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0009000000-7088f31a005af16fc3c2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014l-0109000000-93205a0e84bbb061506a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-324b93e2df83509f8048	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01q9-0900000000-f91d53fb9c883bae9ca3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0409000000-4e053b8ec1d55ced8499	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0190000000-5eada0301a24761b7e67	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004l-0974000000-de9354d79437a4df60bc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0009000000-99c1cc37ab9cf4683323	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0609000000-48da09a702144684652b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0009000000-e8f1f5c15bf17a274e81	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0290000000-809b495d9536129ce8cf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0490000000-943031cff28e6c016f8f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0029000000-aa43cd8bca68cf011be4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0190000000-443938808bab72c3fbfd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0590000000-4c5f41d91ccb36e79121	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0290000000-16998cbb88a2228d0f2c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0920000000-34be129522e87f3b8c42	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-0980000000-509ea3d2d33cdb09b1a5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-016r-0469000000-560a9272032d12f85242	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-0960000000-5d6f35cd391cc354ab2d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0029000000-207cc899837fcd7f4f88	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01vo-0796000000-f3eca7c101c4628750e6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0019000000-64242ffe3291699b1617	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0019000000-7dec57b5001ab24504cc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0092000000-b371281f609586744405	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0005-0980000000-172cdbc38c28312a01fb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0h90-0519000000-5ab63698962ae89e61c4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-2931000000-0389f02977c474a38ddb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0inc-9410000000-85d4a156f97187c4fdbe	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0009000000-5027ef7cd64034ec73ed	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-1239000000-9ed19ba6319c5152a548	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00r6-8961000000-6b1c70a700a07ca0e565	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-aa6e77896a93253faa5d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-1319000000-40e5d00e15abf07a79ba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-6940000000-c1c8472eff864e02ed19	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0009000000-bb14fc66f1a788217f07	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-3159000000-82f21ec0cc988f081119	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-3294000000-21a72ca6ac13fbe07763	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
2520.0	Log mg/kg	[1400:4500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
374	Antipsychotics	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
596	Acaricides	Agriculture & land management	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
606	Plant Growth Regulators	Agriculture & land management	Not Available
609	Aftershave	Personal care & cosmetics	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
630	Toys	Recreation & sports surfaces	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
651	Purses Money Bags Wallets	Textiles, leather & furnishings	Not Available

Pathways

3 pathways

Amisulpride Serotonin Antagonist Action Pathway

Amisulpride Drug Metabolism Action Pathway

Amisulpride Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	8.09632
Click to view 3D structure	D(2) dopamine receptor	Q9GJU1	Canis lupus familiaris	Predicted (SEA)	0.233548
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	9.18621
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	9.26406
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	15.1027
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	25.6124
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	27.7143
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	34.4872
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	77.8492
Click to view 3D structure	5-hydroxytryptamine receptor 4	Q62758	Rattus norvegicus	Predicted (SEA)	5.2159
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	29.427
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	60.7224
Click to view 3D structure	D(1A) dopamine receptor	P18901	Rattus norvegicus	Predicted (SEA)	35.11
Click to view 3D structure	5-hydroxytryptamine receptor 4	O70528	Cavia porcellus	Predicted (SEA)	7.78492
Click to view 3D structure	5-hydroxytryptamine receptor 4	Q13639	Humans	Predicted (SEA)	9.6533
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	50.2906
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	107.665
Click to view 3D structure	5-hydroxytryptamine receptor 3A	P46098	Humans	Predicted (SEA)	24.9118
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	54.6502
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	45.931
Click to view 3D structure	Carbonic anhydrase 6	P23280	Humans	Predicted (SEA)	22.6541
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	81.8195
Click to view 3D structure	Carbonic anhydrase 5B, mitochondrial	Q9Y2D0	Humans	Predicted (SEA)	30.1276
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	71.6213
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	33.3195

Concentrations

Status	Value	Unit	Sample Location	Reference
Detected and Semi Quantified	4900	ng/L	Bioggio,Lugano
Detected and Semi Quantified	32	ng/L	Bussigny-prés-Lausanne	24417318
Detected and Semi Quantified	120	ng/L	Hallau,Klettgau	24417318
Detected and Semi Quantified	75	ng/L	Thal,Altenrhein	24417318
Detected and Semi Quantified	140	ng/L	Uetendorf,Thun	24417318
Detected and Semi Quantified	230	ng/L	Vernier,Aïre	24417318
Detected and Semi Quantified	300	ng/L	Winterthur	24417318
Detected and Semi Quantified	180	ng/L	Werdhölzli,Zürich	24417318
Detected and Semi Quantified	240	ng/L	Schönau,Zug	24417318
Detected and Semi Quantified	34	ng/L	Affoltern,Zwillikon	24417318