10-[3-(dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile

• ChemBase ID: 126770
• Molecular Formular: C19H21N3S
• Molecular Mass: 323.45514
• Monoisotopic Mass: 323.14561869
• SMILES: N#Cc1cc2N(c3c(Sc2cc1)cccc3)CC(C)CN(C)C
• Canonical SMILES: N#Cc1ccc2c(c1)N(CC(CN(C)C)C)c1c(S2)cccc1
• InChI: InChI=1S/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3
• InChIKey: SLFGIOIONGJGRT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-[3-(dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile
• IUPAC Traditional name: cyamemazine
• Synonyms: Cyamemazine; 10-[3-(Dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile; 2-Cyano-10-(3-dimethylamino-2-methylpropyl)phenothiazine; Ciamatil; Cianatil; Cyamemazin; Cyamemazine; Cyamepromazine; Cyamepromezine; F. I. 6229; Kyamepromazine; R.P. 7204; TH 2602; Tercian

Database IDs

• CAS Number: 3546-03-0
• PubChem SID: 162221098
• PubChem CID: 62865
• ATC CODE: N05AA06
• Chemspider ID: 56597
• IUPHAR ligand ID: 84
• KEGG ID: D07307
• Unique Ingredient Identifier: A2JGV5CNU4
• Wikipedia Title: Cyamemazine

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.90487546
• LogD (pH = 7.4): 2.2550392
• Log P: 4.2663755
• Molar Refractivity: 99.0895 cm^3
• Polarizability: 37.804035 Å^3
• Polar Surface Area: 30.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Greenish Yellow Solid
• Melting Point: 90-95°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Admin Routes: Oral, IM, IV
• Bioavailability: 10-70%
• Excretion: Urine
• Half Life: 10 hours
• Metabolism: Hepatic
• Legal Status: Rx-Only

DETAILS

Toronto Research Chemicals - C951500

Cyamemazine is an anxiolytic antipsychotic, which reduces ethanol withdrawal symptoms.

REFERENCES

• Robinson, et al.: J. Pharm. Pharmacol., 18, 19 (1966)
• Miller, L., et al.: J. Pharmacol. Exp. Ther., 246, 170 (1966)
• Podhorna, J., et al.: Curr. Pharm. Des., 8, 23 (1966)
• Hameg, A., et al.: Biochem. Pharmacol., 65, 435 (1966)