[3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine hydrochloride

• ChemBase ID: 53503
• Molecular Formular: C17H20Cl2N2S
• Molecular Mass: 355.3251
• Monoisotopic Mass: 354.07242501
• SMILES: N1(c2c(Sc3c1cccc3)ccc(c2)Cl)CCCN(C)C.Cl
• Canonical SMILES: CN(CCCN1c2ccccc2Sc2c1cc(Cl)cc2)C.Cl
• InChI: InChI=1S/C17H19ClN2S.ClH/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20;/h3-4,6-9,12H,5,10-11H2,1-2H3;1H
• InChIKey: FBSMERQALIEGJT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine hydrochloride
• IUPAC Traditional name: chlorpromazine hydrochloride
• Synonyms: Sonazine; Chloractil; Klorpromex; Promacid; Chlorpromazine hydrochloride; [3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-dimethylamine hydrochloride; 2-Chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine Hydrochloride; 2-Chloro-10-[3-(dimethylamino)propyl]phenothiazine Hydrochloride; Klorproman; Marazine; Norcozine; Torazina; Tranzene; CPZ; Chlorpromazine hydrochloride; 3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine hydrochloride; 2-Chloro-10-[3-dimethylamino-propyl] phenothiazine; 2-Chloro-10-(3-dimethylaminopropyl)phenothiazine hydrochloride; Largactil; 2-氯-10-(3-二甲氨基丙基)吩噻嗪 盐酸盐; 氯普马嗪; 氯丙嗪 盐酸盐

Database IDs

• CAS Number: 69-09-0
• EC Number: 200-701-3
• MDL Number: MFCD00012654
• Beilstein Number: 3779989
• PubChem SID: 24892290; 24869837; 162058266; 24277891
• PubChem CID: 6240

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.2476761
• LogD (pH = 7.4): 2.739641
• Log P: 4.5350003
• Molar Refractivity: 93.7563 cm^3
• Polarizability: 35.9708 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 196-198°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: SO1750000
• European Hazard Symbols: Toxic (T); Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; III
• Australian Hazchem: 2X
• Risk Statements: 25-26; R:25
• Safety Statements: 28-36/37-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H330
• GHS Precautionary statements: P260-P284-P301 + P310-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1

Pharmacology Properties

• Gene Information: human ... DRD2(1813), HRH1(3269)

Product Information

• Purity: ≥95.0% (AT); ≥98% (TLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: HCl; hydrochloride
• Suitability: meets USP testing specifications
• Ignition Residue: ≤0.1%
• Empirical Formula (Hill Notation): C17H19ClN2S · HCl

DETAILS

MP Biomedicals - 02190326

Hydrochloride
Reported to be useful as a substitute for benzidine, o-dianisidine and o-tolidine in the determination of microquantities of hemoglobin and peroxidase.

Selleck Chemicals - S2456

Research Area: Neurological Disease
Biological Activity:
Chlorpromazine (Sonazine) is a dopamine and potassium channel inhibitor with IC50 of 6.1 and 16 µM for nward-rectifying K+ currents and time-independent outward currents.In inhibits prolactin release inhibitory factor, thus stimulating the release of prolactin.  The turnover of dopamine in the brain is also increased. [1] Chlorpromazine blocks a variety of K+ channels in heart muscle cells. Inasmuch as the potency of inhibition is less than the previously reported use-dependent block of Na+ channels, the cardiovascular adverse effects of chlorpromazine are probably caused mainly by the latter effect. [2]

Sigma Aldrich - C8138

Application
在血红蛋白和过氧化物酶的微量测定中替代联苯胺、邻联茴香胺和邻联甲苯胺。
Biochem/physiol Actions
吩噻嗪类抗精神病药;D2 多巴胺受体拮抗剂，H1 组胺受体拮抗剂;抑制钙调蛋白依赖性环核苷酸磷酸二酯酶和一氧化氮合成酶的活化。
氯丙嗪表现出对白血病细胞的细胞毒性和抗增殖活性，但是不会影响正常淋巴细胞的活力。

Sigma Aldrich - 31679

Application
Substitute for benzidine, o-dianisidine, and o-tolidine in the determination of microquantities of hemoglobin and peroxidase.
Biochem/physiol Actions
Chlorpromazine demonstrates cytotoxic and antiproliferative activity against leukemic cells, but does not affect the viability of normal lymphocytes.
Phenothiazine antipsychotic; D2 dopamine receptor antagonist, H1 histamine receptor antagonist; inhibits calmodulin-dependent stimulation of cyclic nucleotide phosphodiesterase and nitric oxide synthase.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 26060

Application
Substitute for benzidine, o-dianisidine, and o-tolidine in the determination of microquantities of hemoglobin and peroxidase.
Biochem/physiol Actions
Chlorpromazine demonstrates cytotoxic and antiproliferative activity against leukemic cells, but does not affect the viability of normal lymphocytes.
Phenothiazine antipsychotic; D2 dopamine receptor antagonist, H1 histamine receptor antagonist; inhibits calmodulin-dependent stimulation of cyclic nucleotide phosphodiesterase and nitric oxide synthase.
Other Notes
Uncouples and inhibits oxidative phoshorylation at 10-3-10-4 M1,2; Interaction of phenothiazine antipsychotics with calmodulin3

Sigma Aldrich - 46125

Application
Substitute for benzidine, o-dianisidine, and o-tolidine in the determination of microquantities of hemoglobin and peroxidase.
Biochem/physiol Actions
Chlorpromazine demonstrates cytotoxic and antiproliferative activity against leukemic cells, but does not affect the viability of normal lymphocytes.
Phenothiazine antipsychotic; D2 dopamine receptor antagonist, H1 histamine receptor antagonist; inhibits calmodulin-dependent stimulation of cyclic nucleotide phosphodiesterase and nitric oxide synthase.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - C0982

Application
在血红蛋白和过氧化物酶的微量测定中替代联苯胺、邻联茴香胺和邻联甲苯胺。
Biochem/physiol Actions
吩噻嗪类抗精神病药;D2 多巴胺受体拮抗剂，H1 组胺受体拮抗剂;抑制钙调蛋白依赖性环核苷酸磷酸二酯酶和一氧化氮合成酶的活化。
氯丙嗪表现出对白血病细胞的细胞毒性和抗增殖活性，但是不会影响正常淋巴细胞的活力。

Toronto Research Chemicals - C424750

Used as an antiemetic; antipsychotic.

REFERENCES

• Lee, K.T. and Ling, H., Microchim. Acta. , 995 (1969).
• http://en.wikipedia.org/wiki/Chlorpromazine
• Anden, N.-E., et al.: Eur. J. Pharmacol., 11, 303 (1970)
• Curzon, G., et al.: Trends Pharmacol. Sci., 11, 61 (1990)