1-{10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethan-1-one; but-2-enedioic acid

• ChemBase ID: 154679
• Molecular Formular: C23H26N2O5S
• Molecular Mass: 442.52794
• Monoisotopic Mass: 442.15624294
• SMILES: CC(=O)c1ccc2c(c1)N(c1ccccc1S2)CCCN(C)C.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.CN(CCCN1c2ccccc2Sc2c1cc(cc2)C(=O)C)C
• InChI: InChI=1S/C19H22N2OS.C4H4O4/c1-14(22)15-9-10-19-17(13-15)21(12-6-11-20(2)3)16-7-4-5-8-18(16)23-19;5-3(6)1-2-4(7)8/h4-5,7-10,13H,6,11-12H2,1-3H3;1-2H,(H,5,6)(H,7,8)
• InChIKey: FQRHOOHLUYHMGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethan-1-one; but-2-enedioic acid
• IUPAC Traditional name: Ace; butenedioic acid
• Synonyms: 2-Acetyl-10-(3-dimethylaminopropyl)phenothiazine maleate salt; Acepromazine maleate salt; Acetopromazine maleate salt; Acepromazine maleate

Database IDs

• CAS Number: 3598-37-6
• EC Number: 222-748-9
• MDL Number: MFCD00082473
• PubChem SID: 162248817
• PubChem CID: 5476753

CALCULATED PROPERTIES

• Acid pKa: 16.055948
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.6094632
• LogD (pH = 7.4): 2.3599155
• Log P: 3.488603
• Molar Refractivity: 99.3543 cm^3
• Polarizability: 37.856915 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: yellow powder

Safety Information

• Storage Condition: protect from light
• RTECS: OB2450000
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H22N2OS · C4H4O4

DETAILS

Sigma Aldrich - A7111

Application
Acepromazine is a phenothiazine and an analogue of the antipsychotic drug chlorpromazine (Cat. No. C8138). Acepromazine is thought to block dopamine receptors in the brain, and inhibit ABCG2 transport protein whose overexpression in tumors is associated with drug resistance.
Biochem/physiol Actions
Acepromazine is a phenothiazine antipsychotic comonly used as a veterinary drug (horses, dogs and cats). The compound is an analogue antipsychotic drug chlorpromazine (#C8138). The drug is thought to block receptors of dopamine in the brain. Recently it was discover that the compound inhibits ABCG2 transported protein, which overexpression in tumors is associated with drug resistance.