多巴胺 | 51-61-6

• 物质功能分类: 原料药 - 循环系统用药 - 抗休克血管活性药
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 多巴胺
• 中文别名: 2-(3,4-二羟基苯基)乙胺
• 英文名称: 3,4-dihydroxyphenylethylamine
• 英文别名: dopamine；4-(2-aminoethyl)-1,2-benzenediol；[3H]-dopamine；4-(2-amino-ethyl)-benzene-1,2-diol；4-(2-aminoethyl)benzene-1,2-diol
• CAS: 51-61-6
• 化学式: C₈H₁₁NO₂
• mdl: MFCD00130258
• 分子量: 153.181
• InChiKey: VYFYYTLLBUKUHU-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220 ºC
• 沸点：
  276.1°C (rough estimate)
• 密度：
  1.1577 (rough estimate)
• 溶解度：
  可溶于酸性水溶液（轻微）、DMSO（轻微、加热）、甲醇（轻微）
• 物理描述：
  Solid
• 颜色/状态：
  Stout prisms
• 蒸汽压力：
  1.6X10-5 mm Hg at 25 °C (est)
• 稳定性/保质期：

  多巴胺自由基呈棱状结晶，对氧气极为敏感，遇到氧气会迅速自动氧化变色。

• 分解：
  When heated to decomposition it emits toxic fumes of /nitrous oxides/.
• Caco2细胞的药物渗透性：
  -5.03
• 解离常数：
  pKa = 8.93 (conjugate acid)
• 碰撞截面：
  129.51 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

ADMET

代谢

多巴胺的生物转化迅速进行，产生主要排泄产物，3-4-二羟基-苯乙酸（DOPAC）和3-甲氧基-4-羟基-苯乙酸（香草酸，HVA）。

Biotransformation of dopamine proceeds rapidly to yield the principal excretion products, 3-4-dihydroxy-phenylacetic acid (DOPAC) and 3-methoxy-4-hydroxy-phenylacetic acid (homovanillic acid, HVA).

来源:DrugBank

代谢

多巴胺在肝脏中广泛代谢。肝脏代谢会产生无活性的代谢物（剂量的75%）和去甲肾上腺素（活性，剂量的25%）在肾上腺素能神经末梢。主要的消除途径似乎是儿茶酚-O-甲基转移酶进行O-甲基化，形成3-甲氧基酪胺，然后通过磺酸结合（通过酚磺酸转移酶）或通过脱氨（通过单胺氧化酶（MAO））到高香草酸。大约80%的药物在24小时内以高香草酸、高香草酸代谢物和去甲肾上腺素代谢物的形式通过尿液排出。

Dopamine is extensively metabolized in the liver. ... Hepatic metabolism results in inactive metabolites (75% of the dose) and norepinephrine (active, 25% of the dose) in the adrenergic nerve terminals. The principal means of elimination appear to be O-methylation by catechol-O-methyltransferase to form 3-methoxytyramine, followed either by sulfoconjugation (by phenosulfotransferase) or by deamination (by monoamine oxidase (MAO)) to homovanillic acid. Approximately 80% of the drug is excreted in the urine as homovanillic acid, homovanillic acid metabolites, and norepinephrine metabolites within 24 hours.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在人中产生N-乙酰-3,4-二羟基苯乙醇胺，在大鼠中产生；Hauson A, Studnitz W Von；《临床化学学报》11: 384 (1965)；Goldstein M, Musacchio Jm；《生物化学与生物物理学报》58: 607 (1962)。在大鼠中产生3,4-二羟基-N-甲基苯乙醇胺；Laduron P；《自然新生物学》238: 212 (1972)。/来自表格/

Yields N-acetyl-3,4-dihydroxyphenethylamine in man, in rat; Hauson A, Studnitz W Von; Clinica Chim Acta 11: 384 (1965); Goldstein M, Musacchio Jm; Biochim Biophys Acta 58: 607 (1962). Yields 3,4-dihydroxy-n-methylphenethylamine in rat; Laduron P; Nature New Biology 238: 212 (1972). /From table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中产生3,4-二羟基苯乙醇胺-O-β-D-葡萄糖苷酸；Young Ja, Edwards Kdg；J Pharmac Exp Ther 145: 102 (1964)。在人和大鼠中产生3,4-二羟基苯乙醛；Nagatsu T等人；Enzymologia 39: 15 (1970)；Goldstein M等人；Biochim Biophys Acta 33: 572 (1959)。/来自表格/

Yields 3,4-dihydroxyphenethylamine-o-beta-d-glucuronide in rat; Young Ja, Edwards Kdg; J Pharmac Exp Ther 145: 102 (1964). Yields 3,4-dihydroxyphenylacetaldehyde in man and rat; Nagatsu T et al; Enzymologia 39: 15 (1970); Goldstein M et al; Biochim Biophys Acta 33: 572 (1959). /From table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中产生4-羟基苯乙醇胺-3-yl硫酸盐；Jenner Wn, Rose Fa；《生物化学杂志》135: 109 (1973)。在人体中产生3-甲氧基酪胺；Goodall MCC, Alton A；《生物化学药理学》17: 905 (1968)。在人体中产生d-去甲肾上腺素；Sjoerdsma AJ等；《临床研究杂志》38: 31 (1959)。/来自表格/

Yields 4-hydroxyphenethyamin-3-yl sulfate in rat; Jenner Wn, Rose Fa; Biochem J 135: 109 (1973). Yields 3-methoxytyramine in man; Goodall MCC, Alton A; Biochem Pharmac 17: 905 (1968). Yields d-noradrenaline in man; Sjoerdsma AJ et al; J Clin Invest 38: 31 (1959). /From table/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

多巴胺是去甲肾上腺素能神经中的去甲肾上腺素的前体，也是中枢神经系统某些区域的神经递质。多巴胺对心肌产生正性的变时和变力作用，导致心率增加和心肌收缩力增强。这是通过直接对β-肾上腺素受体产生激动剂作用，以及间接通过引起交感神经末梢储存位点释放去甲肾上腺素来实现的。在大脑中，多巴胺作为五种多巴胺受体亚型（D1、D2、D3、D4、D5）的激动剂。

Dopamine is a precursor to norepinephrine in noradrenergic nerves and is also a neurotransmitter in certain areas of the central nervous system. Dopamine produces positive chronotropic and inotropic effects on the myocardium, resulting in increased heart rate and cardiac contractility. This is accomplished directly by exerting an agonist action on beta-adrenoceptors and indirectly by causing release of norepinephrine from storage sites in sympathetic nerve endings. In the brain, dopamine actas as an agonist to the five dopamine receptor subtypes (D!, D2, D3, D4, D5).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 药物性肝损伤

多巴胺

Compound:dopamine

来源:Drug Induced Liver Injury Rank (DILIrank) Dataset

毒理性

• 药物性肝损伤

DILI 注解：无 DILI 关注

DILI Annotation:No-DILI-Concern

来源:Drug Induced Liver Injury Rank (DILIrank) Dataset

毒理性

• 药物性肝损伤

标签部分：没有匹配项

Label Section:No match

来源:Drug Induced Liver Injury Rank (DILIrank) Dataset

毒理性

• 药物性肝损伤

参考文献：M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. 用于研究药物诱导肝损伤的FDA批准药物标签，药物发现今日，16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007 M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank：按在人类中发展药物诱导肝损伤风险排名的最大参考药物清单。药物发现今日2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

References:M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007 M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

来源:Drug Induced Liver Injury Rank (DILIrank) Dataset

吸收、分配和排泄

• 吸收

多巴胺在小肠中被迅速吸收。

Dopamine is rapidly absorbed from the small intestine.

来源:DrugBank

吸收、分配和排泄

• 消除途径

据报道，大约80%的药物在24小时内以HVA及其硫酸盐和葡萄糖醛酸苷形式以及3,4-二羟基苯乙酸的形式主要随尿液排出，极少量以原型药物形式排出。

It has been reported that about 80% of the drug is excreted in the urine within 24 hours, primarily as HVA and its sulfate and glucuronide conjugates and as 3,4-dihydroxyphenylacetic acid. A very small portion is excreted unchanged.

来源:DrugBank

吸收、分配和排泄

多巴胺经常用于治疗重症新生儿的休克和心衰，但其药代动力学尚未通过特定的分析方法进行评估。在11名接受多巴胺输注的重症婴儿中测量了多巴胺的稳态动脉血浆浓度，这些婴儿因为疑似或确诊的败血症和低血压性休克而接受5-20 ug/kg-1.min-1的多巴胺输注。多巴胺的稳态浓度范围为0.013-0.3 ug/mL。总体清除率平均为115 mL/kg-1.min-1。表观分布容积和消除半衰期平均分别为1.8 l.kg-1和6.9分钟。多巴胺的药代动力学与胎龄、出生后年龄或出生体重之间没有观察到相关性。在重症婴儿中，多巴胺的药代动力学存在显著个体间差异，血浆浓度不能从输注率准确预测。清除率的显著变化部分解释了在重症新生儿中需要大量多巴胺剂量来引发临床反应的原因。

Dopamine is frequently used in critically ill newborn infants for treatment of shock and cardiac failure, but its pharmacokinetics has not been evaluated using a specific analytical method. Steady-state arterial plasma concentrations of dopamine were measured in 11 seriously ill infants receiving dopamine infusion, 5-20 ug/kg-1.min-1, for presumed or proven sepsis and hypotensive shock. Steady-state concentrations of dopamine ranged from 0.013-0.3 ug/mL. Total body clearance averaged 115 mL/kg-1.min-1. The apparent volume of distribution and elimination half life averaged 1.8 l.kg-1 and 6.9 min, respectively. No relationship was observed between dopamine pharmacokinetics and gestational age, postnatal age or birthweight. Substantial interindividual variation was seen in dopamine pharmacokinetics in seriously ill infants, and plasma concentrations could not be predicted accurately from its infusion rate. Marked variation in clearance explains in part, the wide dose requirements of dopamine needed to elicit clinical response in critically ill newborn infants.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

不到10%的剂量在尿液中以未改变的形式被排出。

Less than 10% of a dose is recovered unchanged in the urine.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

儿童（年龄3个月至13岁）在心脏手术或休克恢复期间，使用高效液相色谱法测量了血浆多巴胺浓度。分布和消除的半衰期分别为1.8 +/- 1.1和26 +/- 14（标准差）分钟。表观分布容积为2952 +/- 2332 mL/kg。清除率为454 +/- 900 mL/kg.min。只有在同时接受多巴酚丁胺的患者中，多巴胺的清除率与剂量呈线性关系（r2 = .76, p小于.05）。肝脏和肾脏功能障碍并未影响多巴胺的药代动力学。多巴胺和多巴酚丁胺之间可能存在一种影响这两种药物处置的关系。即使在血流动力学稳定的儿童中，多巴胺的药代动力学也是可变的。肝脏或肾脏功能不会对多巴胺的药代动力学产生不利影响。

Plasma dopamine concentrations /of children (age 3 months to 13 yrs) recovering from cardiac surgery or shock/ were measured at the steady state or at termination of infusion using high-performance liquid chromatography. The half-lives of distribution and elimination were 1.8 +/- 1.1 and 26 +/- 14 (SD) mins, respectively. The apparent volume of distribution was 2952 +/- 2332 mL/kg. The clearance rate was 454 +/- 900 mL/kg.min. Dopamine clearance was linearly related to dose only in patients who were also receiving dobutamine (r2 = .76, p less than .05). Hepatic and renal dysfunction did not affect the pharmacokinetics of dopamine. A relationship between dopamine and dobutamine that affects the disposition of these two drugs may exist. The pharmacokinetics of dopamine are variable even in hemodynamically stable children. Hepatic or renal function does not adversely affect the pharmacokinetics of dopamine.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  库房应保持低温、通风和干燥。

SDS

Name:	3-Hydroxytyramine hydrobromide 99% Material Safety Data Sheet
Synonym:
CAS:	51-61-6

Section 1 - Chemical Product MSDS Name:3-Hydroxytyramine hydrobromide 99% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
51-61-6	3-hydroxytyramine hydrobromide, 99%	99	200-110-0

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 51-61-6: Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: grey
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: @ 760.00mm Hg
Freezing/Melting Point: 218.00 - 220.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H11NO2.HBr
Molecular Weight: 234.10

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 51-61-6: UX1088000 LD50/LC50:
Not available.
Carcinogenicity:
3-hydroxytyramine hydrobromide, 99% - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 51-61-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 51-61-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 51-61-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

多巴胺是一种化学物质，用于帮助细胞传递脉冲信号，是神经传导物质的一种。它主要负责大脑的情欲、感觉以及兴奋和开心信息的传递。

来源

多巴胺是一种有机化合物，在脑部和身体中扮演多种重要角色，属于儿茶酚胺和苯乙胺家族的一员。它的名称来源于其化学结构：多巴胺由左旋多巴分子通过去除羧基合成而来。在大脑中，它作为神经递质通过神经元释放化学物质来传递信号至其他神经细胞。

作用

多巴胺是哺乳动物大脑中的主要儿茶酚胺类神经递质，控制着运动、认知、情感、正性强化、摄食及内分泌调节等多种功能。

受体作用

多巴胺通过其相应的膜受体发挥作用。这些受体属于G蛋白偶联受体家族，共有五个类型：D1至D5。根据它们的生物化学和药理学性质，可分为D1类（包括D1和D5）和D2类（包括D2、D3及D4）。两类受体的C端含有磷酸化和棕榈酰化位点，参与激动剂依赖性的去敏感化过程及第四胞内环的形成。多巴胺的配体化合物很容易将D1受体与D2受体家族区分开来，但大多数化合物不能区分相同家族的不同亚型。

类别 毒性分级

• 急性毒性：大鼠腹腔 LD50: 163 毫克/公斤；小鼠腹腔 LD50: 950 毫克/公斤
• 中毒状态

可燃性危险特性

多巴胺是可燃物质，燃烧时会产生有毒的氮氧化物气体。

储运特性

• 应储存在低温、通风和干燥的地方。
• 运输时需遵循相应的安全规定。

灭火剂

推荐使用水、二氧化碳、干粉或砂土进行灭火。