基本情報
- 標準SMILES
CN(C)CCC=C1c2ccccc2CCc2ccccc21.Cl- InChIKey
KFYRPLNVJVHZGT-UHFFFAOYSA-N- 分子式
- C20H24ClN
- 平均分子量
- 313.9 g/mol
- 単同位体質量
- 313.1597275
名称と識別子
- 優先名称
- Amitriptyline Hydrochloride
- IUPAC
- N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine;hydrochloride
- 現地名
- アミトリプチリン 塩酸塩
- 英語名
- Amitriptyline hydrochloride
- 分子式
- C20H24ClN
- 分子量
- 313.86
名称と別名
名称をさらに表示
データベース識別子
- CAS
549-18-8- PubChem CID
- 11065
- DTXSID
DTXSID9033187- ChEMBL
CHEMBL1200964- ChEBI
CHEBI:2667- UNII
- 26LUD4JO9K
- EC Number
- 208-964-6
物性
構造計算による物性
- 極性表面積
- 3.2 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 1
- 回転可能結合数
- 3
- 重原子数
- 22
- 形式電荷
- 0
- 複雑度
- 331
実験および物理化学的性質
物理化学的性質
- 融点
- 196 · 196-197°C
- 闪点
- 11 °C · 11 °C
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 2 O: · H2O: 可溶
- 外見
- 粉
- 酸解離定数(Pka)
- 9.4 · 9.4(at 25℃)
- 色
- ホワイトからオフホワイト
- PH
- 4.5 · 4.5~6.0 (10g/l, 25℃)
- 水溶解度
- ほとんど透明
- Merck
- 14 · 14,487
- Henry's Law Constant
- 1.4 · 1.4×102 mol/(m3Pa) at 25℃, HSDB (2015)
- BCS Class
- 1 · 1
- InChI
- InChI=1S/C20H23N.ClH/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;1H
- InChIKey
- KFYRPLNVJVHZGT-UHFFFAOYSA-N
- SMILES
- CN(CC/C=C1/C2=C(C=CC=C2)CCC2=C/1C=CC=C2)C.[H]Cl
- CAS データベース
- 549 · 549-18-8(CAS DataBase Reference)
- EPAの化学物質情報
- Amitriptyline hydrochloride (549-18-8)
化学的性質
化学的特性White to Off-White Solid
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 0.7% (1 of 136) of reports.
Danger
H301 (71.3%): Toxic if swallowed [Danger Acute toxicity, oral];H302 (27.9%): Harmful if swallowed [Warning Acute toxicity, oral];H318 (27.2%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H319 (35.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H361 (25.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];H361d (13.2%): Suspected of damaging the unborn child [Warning Reproductive toxicity];H362 (26.5%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation];H370 (40.4%): Causes damage to organs [Danger Specific target organ toxicity, single exposure];H400 (72.1%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (72.8%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P203, P260, P263, P264, P264+P265, P270, P273, P280, P301+P316, P301+P317, P305+P351+P338, P305+P354+P338, P308+P316, P317, P318, P321, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 136 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 136 reports by companies.;There are 20 notifications provided by 135 of 136 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
危険有害性情報
Regulatory Information
Status: Active Update: 04-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24044
Amitriptyline hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety Information
IMAP assessments - 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride: Human health tier I assessment;IMAP assessments - 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride: Environment tier I assessment
毒性情報
Treatment
Consider gastric lavage only if within one hour of a potentially fatal overdose. Give 50 grams of charcoal if within one hour of ingestion. Prolonged resuscitation may be successful in case of cardiac arrest. Give sodium bicarbonate in case of arrhythmias. (A311)
Health Effects
Some rare side effects include tinnitus, hypotension, mania, psychosis, heart block, arrhythmias, lip and mouth ulcers, extrapyramidal symptoms, depression, and hepatic toxicity.Amitriptyline exhibits strong anticholinergic activity, cardiovascular effects including orthostatic hypotension, changes in heart rhythm and conduction, and a lowering of the seizure threshold (A308, L1032).
Toxicity Summary
Amitriptyline is metabolized to nortriptyline which inhibits the reuptake of norepinephrine and serotonin almost equally. Amitriptyline inhibits the membrane pump mechanism responsible for uptake of norepinephrine and serotonin in adrenergic and serotonergic neurons. Pharmacologically this action may potentiate or prolong neuronal activity since reuptake of these biogenic amines is important physiologically in terminating transmitting activity. This interference with the reuptake of norepinephrine and/or serotonin is believed by some to underlie the antidepressant activity of amitriptyline.
Signs and Symptoms
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.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Amitriptyline hydrochloride
vLess-DILI-concern
5
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
法規制情報
Regulatory Information
Status: Active Update: 04-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24044
Amitriptyline hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- HO9450000
- ridadr
- UN 2811 6.1/PG 3
- 毒性
- LD50 in mice, rats (mg/kg): 350, 380 orally; 65, 75 i.p. (Tobe)
- hs_code
- 29214990
- risk_code
- 23/24/25-36/37/38-42/43-63-39/23/24/25-11-50/53-36-22
- hazard_code
- T,F,N,Xn
- safety_code
- 22-26-36/37/39-45-36/37-16-61-60-7
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard Classifications
- Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Repr. 2
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
化学と産業
薬理情報
Metabolism/Metabolites
Amitriptyline is rapidly and well absorbed following oral administration. Exclusively hepatic, with first pass effect. Amitriptyline is demethylated in the liver to its primary active metabolite, nortriptyline. Route of 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. Half Life: 10 to 50 hours, with an average of 15 hours
FDA Pharmacological Classification
AMITRIPTYLINE HCL
Tricyclic Antidepressant [EPC]
AMITRIPTYLINE HYDROCHLORIDE
Tricyclic Antidepressant [EPC]
MeSH Pharmacological Classification
Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system.
A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS.
Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
用途と製造
応用分野
用途薬理研究用。
説明Amitriptyline (hydrochloride) (CRM) (Item No. 19031) is a certified reference material categorized as a tricyclic antidepressant. This product is intended for analytical forensic applications. This product is also available as a general research tool .
使用Amitriptyline hydrochloride is a tricyclic antidepressant drug. Amitriptyline hydrochloride inhibits the norepinephrine and serotonin transporters but has a high affinity for α1-adrenergic, serotonin and muscarinic acetylcholine receptors.
一般的な説明Amitriptyline, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine hydrochloride,5-(3-dimethylaminopropylidene)-10,11-dihydro-5Hdibenzo[a,d]cycloheptene hydrochloride (Elavil), is one ofthe most anticholinergic and sedative of the TCAs. Becauseit lacks the ring-electron–enriching nitrogen atom ofimipramine, metabolic inactivation mainly proceeds not at theanalogous 2-position but at the benzylic 10-position (i.e.,toluene-like metabolism predominates). Because of the 5-exocyclic double bond, E- and Z-hydroxy isomers are producedby oxidation metabolism. Conjugation produces excretablemetabolites. As is typical of the dimethyl compounds,N-demethylation occurs, and nortriptyline is produced, whichhas a less anticholinergic, less sedative, and more stimulantaction than amitriptyline. Nortriptyline is a SNERI; thecomposite action of drug and metabolite is nonselective.
上流・下流製品情報
上流原料
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