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50-48-6 分子结构
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dimethyl(3-{tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine

ChemBase编号:206
分子式:C20H23N
平均质量:277.40332
单一同位素质量:277.18304974
SMILES和InChIs

SMILES:
N(CC/C=C/1\c2c(CCc3c1cccc3)cccc2)(C)C
Canonical SMILES:
CN(CC/C=C/1\c2ccccc2CCc2c1cccc2)C
InChI:
InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
InChIKey:
KRMDCWKBEZIMAB-UHFFFAOYSA-N

引用这个纪录

CBID:206 http://www.chembase.cn/molecule-206.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
dimethyl(3-{tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine
dimethyl({3-[(2Z)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine
dimethyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine
IUPAC传统名
amitriptyline
dimethyl({3-[(2Z)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine
dimethyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine
商标名
Tryptomer, Triplent(Talent India)
Adepress
Adepril
Amitid
Amitril
Damilan
Damilen
dAmitriptyline
Elanil
Elavil
Endep
Flavyl
Hexathane
Horizon
Lantron
Laroxil
Laroxyl
Lentizol
Proheptadiene
Redomex
Saroten
Sarotex
Seroten
Sylvemid
Triptanol
Triptilin
Triptisol
Tryptanol
Tryptizol
别名
Amitriptyline Hydrochloride
Amitriptyline HCL
Amitriprolidine
Amitriptylin
Amitryptiline
Amitryptyline
Amytriptiline
Amitriptyline
3-(10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethyl-1-propanamine
CAS号
50-48-6
MDL号
MFCD00412072
PubChem SID
46508798
160963669
PubChem CID
2160
CHEBI ID
2666
ATC码
N06AA09
CHEMBL
629
Chemspider ID
2075
DrugBank ID
DB00321
IUPHAR配体索引
200
KEGG ID
D07448
美国药典/FDA物质标识码
1806D8D52K
维基百科标题
Amitriptyline
Medline Plus
a682388

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格
Matrix Scientific
059673 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) 1.3778014  LogD (pH = 7.4) 2.477238 
Log P 4.809535  摩尔折射率 101.5072 cm3
极化性 35.254482 Å3 极化表面积 3.24 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P 5.1  LOG S -4.79 
溶解度 4.50e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 生物活性(PubChem)
溶解度
9.7 mg/mL expand 查看数据来源
疏水性(logP)
4.9 expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
TSCA收录
false expand 查看数据来源
给药途径
Oral expand 查看数据来源
生物利用度
30–60% due to first pass metabolism expand 查看数据来源
排泄
Renal expand 查看数据来源
半衰期
10–50 hours, with an average of 15 hours expand 查看数据来源
代谢
Hepatic
CYP2C19, CYP1A2, CYP2D6
expand 查看数据来源
蛋白结合率
> 90% expand 查看数据来源
法定药品分级
Rx-only expand 查看数据来源
妊娠期药物分类
D (US) expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB00321 external link
Item Information
Drug Groups approved
Description Amitriptyline hydrochloride is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, amitriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, amitriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Amitriptyline may be used to treat depression, chronic pain (unlabeled use), irritable bowel syndrome (unlabeled use), diabetic neuropathy (unlabeled use), post-traumatic stress disorder (unlabeled use), and for migraine prophylaxis (unlabeled use).
Indication For the treatment of depression, chronic pain, irritable bowel syndrome, sleep disorders, diabetic neuropathy, agitation and insomnia, and migraine prophylaxis.
Pharmacology Amitriptyline, a tertiary amine tricyclic antidepressant, is structurally related to both the skeletal muscle relaxant cyclobenzaprine and the thioxanthene antipsychotics such as thiothixene. It is extremely sedating, and thus improvement of sleep patterns can be the first benefit of treatment. Amitriptyline exhibits strong anticholinergic activity, cardiovascular effects including orthostatic hypotension, changes in heart rhythm and conduction, and a lowering of the seizure threshold. As with other antidepressants, several weeks of therapy may be required in order to realize the full clinical benefit of amitriptyline. Although not a labelled indication, amitriptyline is widely used in the management of chronic nonmalignant pain (e.g., post-herpetic neuralgia, fibromyalgia).
Toxicity LD50=350 mg/kg (in mice). Symptoms of overdose include abnormally low blood pressure, confusion, convulsions, dilated pupils and other eye problems, disturbed concentration, drowsiness, hallucinations, impaired heart function, rapid or irregular heartbeat, reduced body temperature, stupor, and unresponsiveness or coma.
Side effects include: sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression.
Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.
Affected Organisms
Humans and other mammals
Biotransformation Exclusively hepatic, with first pass effect. Amitriptyline is demethylated in the liver to its primary active metabolite, nortriptyline.
Absorption Rapidly and well absorbed following oral administration (bioavailability is 30-60% due to first pass metabolism). Peak plasma concentrations occur 2-12 hours following oral or intramuscular administration.
Half Life 10 to 50 hours, with an average of 15 hours
Protein Binding Very highly protein bound (90% or more) in plasma and tissues
Elimination Virtually the entire dose is excreted as glucuronide or sulfate conjugate of metabolites, with little unchanged drug appearing in the urine. 25-50% of a single orally administered dose is excreted in urine as inactive metabolites within 24 hours. Small amounts are excreted in feces via biliary elimination.
References
Otaka M, Jin M, Odashima M, Matsuhashi T, Wada I, Horikawa Y, Komatsu K, Ohba R, Oyake J, Hatakeyama N, Watanabe S: New strategy of therapy for functional dyspepsia using famotidine, mosapride and amitriptyline. Aliment Pharmacol Ther. 2005 Jun;21 Suppl 2:42-6. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Otaka M, Jin M, Odashima M, Matsuhashi T, Wada I, Horikawa Y, Komatsu K, Ohba R, Oyake J, Hatakeyama N, Watanabe S: New strategy of therapy for functional dyspepsia using famotidine, mosapride and amitriptyline. Aliment Pharmacol Ther. 2005 Jun;21 Suppl 2:42-6. Pubmed
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专利

专利

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