Α-二甲氨基-3',4'-二羟基苯乙酮盐酸盐 | 16899-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: Α-二甲氨基-3',4'-二羟基苯乙酮盐酸盐
• 中文别名: Alpha-二甲氨基-3,4-二羟基苯乙酮盐酸盐
• 英文名称: α-(dimethylamino)-3',4'-dihydroxyacetophenone hydrochloride
• 英文别名: 1-(3,4-dihydroxy-phenyl)-2-dimethylamino-ethanone; hydrochloride；1-(3,4-Dihydroxy-phenyl)-2-dimethylamino-aethanon; Hydrochlorid；1-(3,4-Dihydroxyphenyl)-2-(dimethylamino)ethan-1-one hydrochloride；1-(3,4-dihydroxyphenyl)-2-(dimethylamino)ethanone;hydrochloride
• CAS: 16899-83-5
• 化学式: C₁₀H₁₃NO₃*ClH
• mdl: MFCD00044781
• 分子量: 231.679
• InChiKey: LVRPQCAWIVYJTP-UHFFFAOYSA-N

物化性质

• 熔点：
  236-237 °C
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2922509090

SDS

Name:	alpha-Dimethylamino-3 4 -dihydroxyaceto- phenone hydrochloride Material Safety Data Sheet
Synonym:
CAS:	16899-83-5

Section 1 - Chemical Product MSDS Name:alpha-Dimethylamino-3 4 -dihydroxyaceto- phenone hydrochloride Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16899-83-5	alpha-Dimethylamino-3',4'-dihydroxyace	100	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Antidote: None reported.

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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 water spray, dry chemical, carbon dioxide, or appropriate foam.

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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. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 16899-83-5: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: light gray
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H13NO3
Molecular Weight: 195.22

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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:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16899-83-5: AM7700250 LD50/LC50:
Not available.
Carcinogenicity:
alpha-Dimethylamino-3',4'-dihydroxyaceto- phenone, hydrochloride - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 16899-83-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16899-83-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16899-83-5 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

反应信息

• 作为反应物：
  描述：

  Α-二甲氨基-3',4'-二羟基苯乙酮盐酸盐 在 乙醇 、 L-酒石酸 、 铂 作用下， 生成 (S)-1-(3,4-dihydroxy-phenyl)-2-dimethylamino-ethanol
  参考文献：
  名称：

  La Manna; Campiglio, Farmaco, Edizione Scientifica, 1959, vol. 14, p. 317,320

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二羟基-2'-氯苯乙酮 、 二甲胺 生成 Α-二甲氨基-3',4'-二羟基苯乙酮盐酸盐
  参考文献：
  名称：

  Inhibition and inactivation of presynaptic cholinergic markers using redox-reactive choline analogs

  摘要：

  Inhibition and inactivation of two presynaptic cholinergic ''markers'', choline acetyltransferase and high affinity choline transporter, has been investigated using inhibitors designed with a redox-reactive catechol tethered to a quaternary ammonium group. Two quaternary ammonium alkyl-substituted catechols, 3[(trimethylammonio)methyl]catechol (TMC, 1) and NN-dimethylepinephrine (catecholine, 2) were shown to bind weakly and noncompetitively to bovine choline acetyltransferase yet inactivated the enzyme in a time course consistent with the involvement of early intermediates in the spontaneous oxidation of these catechols. Both agents also inhibited high-affinity choline uptake. The time course of TMC and catecholine spontaneous oxidation-dependent inactivation of high affinity choline uptake sites was slower than, if it occurred at all, the spontaneous degradation of measurable choline transport in synaptosomes. When compared with inhibition of uptake of other neurotransmitters, it was shown that catecholine demonstrated more selectivity than TMC toward inhibition of choline transport. K(m) (muM) and V(max) (pmol/min per mg of protein) were measured for high affinity transport of choline, dopamine, and serotonin and were observed to be K(m) = 2.04 +/- 0.31, V(max) = 22 +/- 1; K(m) = 1.4, V(max) = 53; and K(m) = 0.15, V(max) = 23, respectively, in good agreement with published literature values. K(i)'s (mM) for catecholine and TMC, calculated from experimentally determined IC50's, were for catecholine 0.13 +/- 0.06, 0.53 +/- 0.09, and 0.39 +/- 0.10, and for TMC 0.06 +/- 0.03, 0.09 +/- 0.03, and 0.09 +/- 0.08, for choline, dopamine, and serotonin transport, respectively. In vivo studies using catecholine suggest that this compound impairs learning ability associated with long-term memory. Thus, catecholine represents a lead compound in a potential series of redox-reactive choline analogs, which may become useful irreversible antagonists of the critical cholinergic macromolecular targets underlying cholinergic hypofunction in disorders such as Alzheimer's disease.

  DOI：

  10.1021/jm00065a012

文献信息

• �ber Alkylamino- und Aralkylaminothioschwefels�uren
  作者：H. Bretschneider

  DOI：10.1007/bf00903040

  日期：——
• Saito et al., Tanabe seiyaku kenkyu nenpo = Annual report of Gohei Tanabe Co., 1957, vol. 2, # 1, p. 7
  作者：Saito et al.

  DOI：——

  日期：——
• Remisow, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2530,2536
  作者：Remisow

  DOI：——

  日期：——
• La Manna; Campiglio, Farmaco, Edizione Scientifica, 1959, vol. 14, p. 317,320
  作者：La Manna、Campiglio

  DOI：——

  日期：——
• Inhibition and inactivation of presynaptic cholinergic markers using redox-reactive choline analogs
  作者：Phenil J. Patel、William S. Messer、Richard A. Hudson

  DOI：10.1021/jm00065a012

  日期：1993.6

  Inhibition and inactivation of two presynaptic cholinergic ''markers'', choline acetyltransferase and high affinity choline transporter, has been investigated using inhibitors designed with a redox-reactive catechol tethered to a quaternary ammonium group. Two quaternary ammonium alkyl-substituted catechols, 3[(trimethylammonio)methyl]catechol (TMC, 1) and NN-dimethylepinephrine (catecholine, 2) were shown to bind weakly and noncompetitively to bovine choline acetyltransferase yet inactivated the enzyme in a time course consistent with the involvement of early intermediates in the spontaneous oxidation of these catechols. Both agents also inhibited high-affinity choline uptake. The time course of TMC and catecholine spontaneous oxidation-dependent inactivation of high affinity choline uptake sites was slower than, if it occurred at all, the spontaneous degradation of measurable choline transport in synaptosomes. When compared with inhibition of uptake of other neurotransmitters, it was shown that catecholine demonstrated more selectivity than TMC toward inhibition of choline transport. K(m) (muM) and V(max) (pmol/min per mg of protein) were measured for high affinity transport of choline, dopamine, and serotonin and were observed to be K(m) = 2.04 +/- 0.31, V(max) = 22 +/- 1; K(m) = 1.4, V(max) = 53; and K(m) = 0.15, V(max) = 23, respectively, in good agreement with published literature values. K(i)'s (mM) for catecholine and TMC, calculated from experimentally determined IC50's, were for catecholine 0.13 +/- 0.06, 0.53 +/- 0.09, and 0.39 +/- 0.10, and for TMC 0.06 +/- 0.03, 0.09 +/- 0.03, and 0.09 +/- 0.08, for choline, dopamine, and serotonin transport, respectively. In vivo studies using catecholine suggest that this compound impairs learning ability associated with long-term memory. Thus, catecholine represents a lead compound in a potential series of redox-reactive choline analogs, which may become useful irreversible antagonists of the critical cholinergic macromolecular targets underlying cholinergic hypofunction in disorders such as Alzheimer's disease.