Harmol | 40580-83-4

• 物质功能分类: 分析化学 - 标准品
• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: Harmol
• 英文别名: 1-methyl-2,9-dihydropyrido[3,4-b]indol-7-one
• CAS: 40580-83-4；487-03-6
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.22
• InChiKey: LBBJNGFCXDOYMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  231°C
• 沸点：
  460.4±40.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶，加热）、甲醇（微溶）
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

6-羟基哈马林已知的人类代谢物包括硫酸哈莫尔和葡萄糖醛酸哈莫尔。

6-Hydroxyharmaline has known human metabolites that include Harmol sulfate and Harmol glucuronide.

来源:NORMAN Suspect List Exchange

安全信息

• 海关编码：
  2933990090
• 安全说明：
  S24/25
• 储存条件：
  按照规定使用和储存，不会发生分解，应避免与氧化物接触。

SDS

Name:	Harmol hydrochloride dihydrate Material Safety Data Sheet
Synonym:	Harmol hydrochloride dihydrate; 1-Methyl-9H-pyrido[3,4,b]indol-7-ol monohydrochloride dihydrate
CAS:	40580-83-4

Section 1 - Chemical Product MSDS Name:Harmol hydrochloride dihydrate Material Safety Data Sheet
Synonym:Harmol hydrochloride dihydrate; 1-Methyl-9H-pyrido[3,4,b]indol-7-ol monohydrochloride dihydrate

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
40580-83-4	Harmol hydrochloride dihydrate	98	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# 40580-83-4: CAS# 149022-16-2: 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: Crystalline powder
Color: light yellow-green
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature: Not available.
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H10N2O.HCl.H2O
Molecular Weight: 252.70

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, 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# 40580-83-4: UV1048000 CAS# 149022-16-2 unlisted.
LD50/LC50:
Not available.
Not available.
Carcinogenicity:
Harmol hydrochloride anhydrous - Not listed by ACGIH, IARC, or NTP.
Harmol hydrochloride dihydrate - 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# 40580-83-4: No information available.
CAS# 149022-16-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 40580-83-4 is not listed on Canada's Ingredient Disclosure List.
CAS# 149022-16-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 40580-83-4 is not listed on the TSCA inventory.
It is for research and development use only.
CAS# 149022-16-2 is not on the TSCA Inventory because it is a hydrate.
It is considered to be listed if the CAS number for the anhydrous form
is on the inventory (40CFR720.3(u)(2)).

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备

在100 mL单口瓶中加入0.5 g（2.36 mmol）Harmine、18 mL冰乙酸和18 mL 40% 氢溴酸水溶液，加热回流10小时。用饱和碳酸氢钠调节pH至约8，观察到有沉淀产生。抽滤得到黄色绿色固体0.46 g。

用途

哈尔酚是一种β-咔啉类生物碱，可通过脱甲基Harmine制备。它可用于制备治疗肝硬化的西药组合物。

文献信息

• SMALL-MOLECULE INHIBITORS OF THE ANDROGEN RECEPTOR
  申请人：Diamond Marc

  公开号：US20080293766A1

  公开（公告）日：2008-11-27

  The present invention provides a method of inhibiting an androgen receptor by administering a compound of Formula I: or a compound of Formula II: wherein R 1 , R 2 , R 3 and R 8 are each independently hydrogen or C 1-6 alkyl. R 4 is absent or is hydrogen, C 1-6 alkyl or C 1-6 alkyl-OH. R 5 is hydrogen, C 1-6 alkyl or —NR 6 R 7 . R 6 and R 7 are each independently hydrogen or C 1-6 alkyl, or are combined with the nitrogen to which they are attached to form a heterocycloalkyl having from 5 to 7 ring members. L is a linker of C 1-6 alkylene, C 2-6 alkenylene, C 2-6 alkynylene or C 3-6 cycloalkylene. The compounds of Formula I include the salts, hydrates and prodrugs thereof. Each R 9 is H, C 1-6 alkyl, —OH or —O—C 1-6 alkyl. The compounds of Formulas I and II include the salts, hydrates and prodrugs thereof. By administering the compound of Formula I or II, the method inhibits the androgen receptor.

  本发明提供了通过给予式I的化合物或式II的化合物来抑制雄激素受体的方法：其中R1、R2、R3和R8分别独立地为氢或C1-6烷基。R4不存在或为氢、C1-6烷基或C1-6烷基-OH。R5为氢、C1-6烷基或-NR6R7。R6和R7分别独立地为氢或C1-6烷基，或与它们连接的氮原子结合形成具有5至7个环成员的杂环烷基。L为C1-6烷基、C2-6烯基、C2-6炔基或C3-6环烷基的连接剂。式I的化合物包括其盐、水合物和前药。每个R9为H、C1-6烷基、-OH或-O-C1-6烷基。式I和II的化合物包括其盐、水合物和前药。通过给予式I或II的化合物，该方法抑制雄激素受体。
• COMBINATION PRODUCT FOR THE TREATMENT OF NEUROLOGICAL AND/OR PSYCHIATRIC DISORDERS
  申请人：Consejo Superior de Investigaciones Científicas (CSIC)

  公开号：EP3713568A1

  公开（公告）日：2020-09-30
• US7696227B2
  申请人：——

  公开号：US7696227B2

  公开（公告）日：2010-04-13
• US8119660B2
  申请人：——

  公开号：US8119660B2

  公开（公告）日：2012-02-21
• [EN] SMALL-MOLECULE INHIBITORS OF THE ANDROGEN RECEPTOR<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DU RÉCEPTEUR DES ANDROGÈNES
  申请人：UNIV CALIFORNIA

  公开号：WO2008128100A1

  公开（公告）日：2008-10-23

  [EN] The present invention provides a method of inhibiting an androgen receptor by administering a compound of Formula (I): or a compound of Formula (II):, wherein R¹, R², R³ and R⁸ are each independently hydrogen or C_1-6 alkyl. R⁴ is absent or is hydrogen, C_1-6 alkyl or C_1-6 alkyl-OH. R⁵ is hydrogen, C_1-6 alkyl or -NR⁶R⁷, R⁶ and R⁷ are each independently hydrogen or C_1-6 alkyl, or are combined with the nitrogen to which they are attached to form a heterocycloalkyl having from 5 to 7 ring members. L is a linker of Ci-6 alkylene, C_2-6 alkenylene, C_2-6 alkynylene or C_3-6cycloalkylene. The compounds of Formula I include the salts, hydrates and prodrugs thereof. Each R⁹ is H, C_1-6 alkyl, -OH or -0-C_1-6 alkyl. The compounds of Formulas I and II include the salts, hydrates and prodrugs thereof. By administering the compound of Formula I or II, the method inhibits the androgen receptor.
  [FR] La présente invention concerne un procédé d'inhibition d'un récepteur des androgènes par l'administration d'un composé de formule (I) : ou d'un composé de formule (II) : dans lesquelles R¹, R², R³ et R⁸ sont indépendamment un atome d'hydrogène ou un groupe alkyle en C_1-6. R⁴ est absent ou est un atome d'hydrogène, un groupe alkyle en C_1-6 ou alkyle-OH en C_1-6. R⁵ est un atome d'hydrogène, un groupe alkyle en C_1-6 ou -NR⁶R⁷, R⁶ et R⁷ sont chacun indépendamment, un atome d'hydrogène ou un groupe alkyle en C_1-6, ou sont combinés avec l'atome d'azote auquel ils sont liés pour former un groupe hétérocycloalkyle ayant de 5 à 7 chaînons cycliques. L est un segment de liaison d'alkylène en C_1-6, alcénylène en C_2-6, alcynylène en C_2-6 ou cycloalkylène en C_3-6. Les composés de formule I comprennent les sels, hydrates et pro-médicaments de ceux-ci. Chaque R⁹ est un atome de H, un groupe alkyle en C_1-6, -OH ou -0-alkyle en C_1-6. Les composés des formules I et II comprennent les sels, hydrates et promédicaments de ceux-ci. Par l'administration du composé de formule I ou II, le procédé inhibe le récepteur des androgènes.