dimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine

• ChemBase编号: 1115
• 分子式: C18H22N2S
• 平均质量: 298.44568
• 单一同位素质量: 298.15036971
• SMILES: S1c2c(N(CC(CN(C)C)C)c3c1cccc3)cccc2
• Canonical SMILES: CN(CC(CN1c2ccccc2Sc2c1cccc2)C)C
• InChI: InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3
• InChIKey: ZZHLYYDVIOPZBE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: dimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine
• IUPAC传统名: spansule; trimeprazine
• 商标名: Alimezine; Dosegran; Doxergan; Dysedon; Imakol; Levoprome; Panectyl; Repeltin; Repetin; Temaril; Teralen; Theralene; Vallergan
• 别名: (+-)-Alimemazine; (+-)-Trimeprazine; Alimemazine; Alimemazine S,S-dioxide; Bayer 1219; Oxomemazin; Oxomemazina [INN-Spanish]; Oxomemazine; Methylpromazine; Oxomemazine [DCF:INN]; Oxomemazinum [INN-Latin]; Oxymemazine; Trimeperazine; Trimeprazine 5,5-dioxide; Trimeprazine hemi-(+)tartrate; Trimeprazine Tartrat; Trimeprazine Tartrate; Trimeprazine; N,N,β-Trimethyl-10H-phenothiazine-10-propanamine Tartrate; 10-(2-Methyl-3-dimethylaminopropyl)phenothiazine Tartrate; 10-[3-(Dimethylamino)-2-methylpropyl]phenothiazine Tartrate; (+/-)-Alimemazine Tartrate; Panectyl; Repeltin; Temaril; Temaril 16; Theralene; Vallergan; Vanectyl; NSC 17475; Trimeprazine Hemitartrate Salt

登记号

• CAS号: 84-96-8; 4330-99-8
• PubChem SID: 160964578; 46508449
• PubChem CID: 5574

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.0487792
• LogD (pH = 7.4): 2.398943
• Log P: 4.4102793
• 摩尔折射率: 93.3679 cm^3
• 极化性: 36.0012 Å^3
• 极化表面积: 6.48 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.82
• LOG S: -4.55
• 溶解度: 8.35e-03 g/l

分子性质

理化性质

• 溶解度: 0.942 mg/L; Methanol; Water
• 外观: White to Off-White Solid
• 熔点: 153-155°C
• 疏水性(logP): 4.6

安全信息

• 保存条件: Refrigerator

详细说明

DrugBank - DB01246

• Drug Groups: approved
• Description: A phenothiazine derivative that is used as an antipruritic. [PubChem]
• Indication: Used to prevent and relieve allergic conditions which cause pruritus (itching) and urticaria (some allergic skin reactions).
• Pharmacology: Trimeprazine (also known as Alimemazine) is a tricyclic antihistamine, similar in structure to the phenothiazine antipsychotics, but differing in the ring-substitution and chain characteristics. Trimeprazine is in the same class of drugs as chlorpromazine (Thorazine) and trifluoperazine (Stelazine); however, unlike the other drugs in this class, trimeprazine is not used clinically as an anti-psychotic. It acts as an anti-histamine, a sedative, and an anti-emetic (anti-nausea). Trimeprazine is used principally as an anti-emetic, to prevent motion sickness or as an anti-histamine in combination with other medications in cough and cold preparations. Tricyclic antihistamines are also structurally-related to the tricyclic antidepressants, explaining the antihistaminergic adverse effects of these two drug classes and also the poor tolerability profile of tricyclic H₁-antihistamines.
• Toxicity: Symptoms of overdose clumsiness or unsteadiness, seizures, severe drowsiness, flushing or redness of face, hallucinations, muscle spasms (especially of neck and back), restlessness, shortness of breath, shuffling walk, tic-like (jerky) movements of head and face, trembling and shaking of hands, and insomnia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Well absorbed in the digestive tract.

Toronto Research Chemicals - T795700

Antipruritic. Antibacterial, antimicrobial agent.

参考文献

• Robinson, et al.: J. Pharm. Pharmacol., 18, 19 (1966)
• Abdel-Moety, E., et al.: Eur. J. Pharm. Sci., 5, 1 (1966)
• Basavaiah, K., et al.: Chem. Pharm. Bull., 47, 1351 (1966)