Gramine
- Iupac Name：1-(1H-indol-3-yl)-N,N-dimethylmethanamine
- CAS No.: 87-52-5
- Molecular Weight：174.247
- Modify Date.: 2022-11-29 04:31
- Introduction:
Gramine (Donaxine) is a natural alkaloid isolated from giant reed[2], acts as an active adiponectin receptor (AdipoR) agonist, with IC50s of 3.2 and 4.2 μM for AdipoR2 and AdipoR1, respectively[1]. Gramine is also a human and mouse β2-Adrenergic receptor (β2-AR) agonist[2]. Gramine (Donaxine) has anti-tumor, anti-viral and anti-inflammatory properties[1].
Solid
Gramine is an aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3. It has a role as a plant metabolite, a serotonergic antagonist, an antiviral agent and an antibacterial agent. It is an aminoalkylindole, an indole alkaloid and a tertiary amino compound. It is a conjugate base of a gramine(1+).
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1. Names and Identifiers
- 1.1 Name
- Gramine
- 1.2 Synonyms
[(1H-Indol-3-yl)methyl]dimethylamine 1-(1H-Indol-3-yl)-N,N-dimethylmethanamine 1H-Indole-3-methanamine, N,N-dimethyl- 3-(Dimethylaminomethyl)indole 3-(dimethylaninomethy)in dole 3-(N,N-Dimethylaminomethyl)indole 3-[(Dimethylamino)methyl]-1H-indole 3-[(Dimethylamino)methyl]indole Donaxin Donaxine GCLH / for Cefixime Gramin indol-3-ylmethyldimethylamine Indole, 3-[(dimethylamino)methyl]- n,n-dimethyl-1h-indole-3-methanamin n,n-dimethyl-1h-indole-3-methanamine N,N-Dimethyl-1H-indole-3-methylamine NSC 16892 TIMTEC-BB SBB003799 β-(Dimethylaminomethyl)indole
- 1.3 CAS No.
- 87-52-5
- 1.4 CID
- 6890
- 1.5 EINECS(EC#)
- 201-749-8
- 1.6 Molecular Formula
- C11H14N2 (isomer)
- 1.7 Inchi
- InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
- 1.8 InChkey
- OCDGBSUVYYVKQZ-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CN(C)CC1=CNC2=CC=CC=C21
- 1.10 Isomers Smiles
- CN(C)CC1=CNC2=CC=CC=C21
2. Properties
- 2.1 Density
- 0.7692 (20 C)
- 2.1 Melting point
- 131-139℃
- 2.1 Refractive index
- 1.44 (20 C)
- 2.1 Flash Point
- 167℃
- 2.1 Precise Quality
- 174.11600
- 2.1 PSA
- 19.03000
- 2.1 logP
- 2.22950
- 2.1 Appearance
- Beige Powder
- 2.2 Chemical Properties
- beige powder
- 2.3 Color/Form
- Powder
- 2.4 Physical
- Solid
- 2.5 pKa
- 17.00±0.30(Predicted)
- 2.6 Water Solubility
- Practically insoluble in water
- 2.7 StorageTemp
- Refrigerator (+4°C)
3. Use and Manufacturing
- 3.1 GHS Classification
- Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 48 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
H314 (97.92%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (97.92%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
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.
Precautionary Statement Codes
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501
- 3.2 Methods of Manufacturing
- Derived from the condensation of indole with formaldehyde and dimethylamine. Cool dimethylamine to -5°C and add it to glacial acetic acid. Under the condition that the temperature does not exceed 5°C, add formaldehyde and indole, react at 30-40°C for 8 hours, cool to 5°C, adjust the pH to 1 with 40% sodium hydroxide, and cool the crystals of luzhuine. After filtering, washing with water, draining the crude product, heating and dissolving with acetone, cooling, precipitation of crystals, filtering and drying to obtain the finished product.
- 3.3 Purification Methods
- Crystallise gramine from diethyl ether, ethanol or acetone. It sublimes at 59o/0.001mm. The hydrochloride crystallises from EtOH/Et2O with m 190.5-191.0o(dec). [Culvenor et al. Aust J Chem 17 1301 1964, Beilstein 22 III/IV 4302, 22/10 V 25.] Gramine Preparation Products And Raw materials Preparation Products
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- R36
- 4.1 Safety Statements
- S26;S46
- 4.1 Hazard Declaration
- H314
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- NL7525000
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin corrosion, Category 1B
Serious eye damage, Category 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Danger |
| Hazard statement(s) | H314 Causes severe skin burns and eye damage |
| Precautionary statement(s) | |
| Prevention | P260 Do not breathe dust/fume/gas/mist/vapours/spray. P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
| Storage | P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
87-52-5Total: 12 Synthesis Route
9. Other Information
- 9.0 Storage Conditions
- Derived from the condensation of indole with formaldehyde and dimethylamine. Cool dimethylamine to -5°C and add it to glacial acetic acid. Under the condition that the temperature does not exceed 5°C, add formaldehyde and indole, react at 30-40°C for 8 hours, cool to 5°C, adjust the pH to 1 with 40% sodium hydroxide, and cool the crystals of luzhuine. After filtering, washing with water, draining the crude product, heating and dissolving with acetone, cooling, precipitation of crystals, filtering and drying to obtain the finished product.
- 9.1 Collision Cross Section
- 134.9 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
- 9.2 Mesh Entry Terms
- 3-(dimethylaminomethyl)indole
- 9.3 Manufacturing Info
- 1H-Indole-3-methanamine, N,N-dimethyl-: ACTIVE
10. Computational chemical data
- Molecular Weight: 174.247g/mol
- Molecular Formula: C11H14N2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 174.115698455
- Monoisotopic Mass: 174.115698455
- Complexity: 168
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 1
- Topological Polar Surface Area: 19
- Heavy Atom Count: 13
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBzAAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgB8AAAHAAQAAAADAjBHgQ+wPPJkACgAzRnRACCgCAxAiAI2aA4ZJgIIOLA0ZGEIAhgkADIyAcQgMAOgAAAAAACAAAAAAAAAAQAAAAAAAAAAA==
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Gramine
- Purity:99%Packing: 200kg/bag FOB
- Price: 3 USD/kilogram
- Time: 2023/06/02
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Gramine
- Purity:99%Packing: 200kg/bag FOB
- Price: 100 USD/gram
- Time: 2023/06/05
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Gramine
- Purity:99%Packing: 200kg/bag FOB
- Price:
- Time: 2023/06/05
Inquire
12. Realated Product Infomation
-120YR
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