Production Method 1

120-72-9

87-52-5

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Water ;  2 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt

Reference

The structural simplification of lysergic acid as a natural lead for synthesizing novel anti-Alzheimer agents

Alzweiri, Muhammed; et al, Bioorganic & Medicinal Chemistry Letters, 2021, 47,

Production Method 2

120-72-9

87-52-5

Reaction Conditions

1.1 Catalysts: Zinc chloride Solvents: Ethanol ;  90 min, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 7, rt

Reference

Efficient and practical synthesis of Mannich bases related to gramine mediated by zinc chloride

Dai, Hong-Guang; et al, Synthetic Communications, 2006, 36(13), 1829-1835

Production Method 3

120-72-9

51-80-9

87-52-5

Reaction Conditions

1.1 Reagents: Sulfur dioxide Solvents: Acetonitrile

Reference

The activation of aminals and aminol ethers by sulfur dioxide and their reactions with electron rich aromatic compounds

Heaney, Harry; et al, Tetrahedron, 1997, 53(39), 13361-13372

Production Method 4

143703-39-3

87-52-5

Reaction Conditions

1.1 Solvents: Water

Reference

A facile synthesis of 3-substituted indoles

Nagarathnam, Dhanapalan, Journal of Heterocyclic Chemistry, 1992, 29(4), 953-8

Production Method 5

487-89-8

87-52-5

Reaction Conditions

1.1 Solvents: Ethanol ,  Acetonitrile ;  2 h, rt
1.2 Reagents: Sodium borohydride Solvents: Ethanol ;  rt; 24 h, rt

Reference

Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity

Nimbarte, Vijaykumar D. ; et al, ChemMedChem, 2021, 16(10), 1667-1679

Production Method 6

23543-66-0

87-52-5

Reaction Conditions

Reference

Halogenation of 1-substituted skatoles. Preparation of 3-bromomethylindoles

Hino, Tohru; et al, Chemical & Pharmaceutical Bulletin, 1975, 23(11), 2990-7

Production Method 7

271-26-1

87-52-5

Reaction Conditions

1.1 Solvents: Acetic acid ,  1,4-Dioxane ,  Water ;  5 min, 0 °C
1.2 Solvents: Water ;  0 °C; 2 h, 0 °C; 0 °C → rt
1.3 Reagents: Sodium hydroxide Solvents: Water

Reference

Visible-light-induced cascade dearomatization cyclization between alkynes and indole-derived bromides: a facile strategy to synthesize spiroindolenines

Gao, Xiaoshuang; et al, Chemical Communications (Cambridge, 2020, 56(90), 14047-14050

Production Method 8

116482-39-4

87-52-5

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 9

120-72-9

5129-78-2

87-52-5

Reaction Conditions

1.1 Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ;  72 h, 40 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  rt; 2 h, 70 °C
2.2 Reagents: Water ;  cooled

Reference

Novel Preparation of Hemiaminal Derivatives with BPO and N,N-Dimethylamides and Their Synthetic Use for (Aminomethyl)indoles

Nakamura, Kohei; et al, European Journal of Organic Chemistry, 2020, 2020(30), 4713-4722

Production Method 10

120-72-9

87-52-5

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Water ;  20 min, 35 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 11 - 13

Reference

Improved synthesis of 3-(dialkylaminomethyl)-indole in acetic acid aqueous solution under ultrasound irradiation

Li, Ji-Tai; et al, Ultrasonics Sonochemistry, 2010, 18(1), 42-44

Production Method 11

120-72-9

51-80-9

87-52-5

Reaction Conditions

1.1 Reagents: Sulfur dioxide Solvents: Acetonitrile ;  4 d

Reference

Sulfur dioxide

Burke, Steven D., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-6

Production Method 12

120-72-9

51-80-9

87-52-5

Reaction Conditions

1.1 Reagents: Sulfur dioxide

Reference

Bis(dimethylamino)methane

Duplantier, Allen J., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 13

1373493-85-6

87-52-5

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  rt; 2 h, 70 °C
1.2 Reagents: Water ;  cooled

Reference

Novel Preparation of Hemiaminal Derivatives with BPO and N,N-Dimethylamides and Their Synthetic Use for (Aminomethyl)indoles

Nakamura, Kohei; et al, European Journal of Organic Chemistry, 2020, 2020(30), 4713-4722

Production Method 14

64258-88-4

87-52-5

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium ;  4 h, 3 bar, rt

Reference

The structural simplification of lysergic acid as a natural lead for synthesizing novel anti-Alzheimer agents

Alzweiri, Muhammed; et al, Bioorganic & Medicinal Chemistry Letters, 2021, 47,

Production Method 15

65283-32-1

87-52-5

Reaction Conditions

1.1 Reagents: Sodium borohydride

Reference

Reaction of nitro compounds with immonium salts. 1. Nitrovinylation of indoles

Babievskii, K. K.; et al, Izvestiya Akademii Nauk SSSR, 1977, (10), 2310-13

Production Method 16

27409-13-8

87-52-5

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Toluene ,  Hexane ;  10 min, 0 - 5 °C; 15 min, 0 - 5 °C
1.2 Reagents: Diisobutylaluminum hydride Solvents: Toluene ;  5 min, 0 - 5 °C; rt; 16 h, 50 °C
1.3 Reagents: Methanol ;  10 min, rt

Reference

A practical synthesis of indole-based heterocycles using an amidoaluminum-mediated strategy

Todd, Robert; et al, Synthesis, 2009, (11), 1846-1850

Production Method 17

17206-03-0

87-52-5

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  2 h, 160 °C

Reference

Synthesis of N-1-Skatyl Uracil Derivatives

Chernikova, I. B.; et al, Chemistry of Natural Compounds, 2017, 53(2), 333-337

Production Method 18

496-15-1

14002-21-2

87-52-5

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: (OC-6-42)-[2-[Bis(1-methylethyl)phosphino-κP]-N-[2-[bis(1-methylethyl)phosphino-… Solvents: Toluene ;  36 h, 140 °C

Reference

Divergence in CH alkylation of indoles under Mn catalysis

Mondal, Akash; et al, Catalysis Science & Technology, 2023, 13(19), 5745-5756

Production Method 19

120-72-9

33797-51-2

87-52-5

Reaction Conditions

1.1 Solvents: Dichloromethane ;  overnight, rt
1.2 Reagents: Sodium hydroxide Solvents: Water

Reference

Discovery of Potent, Selective, Orally Active, Nonpeptide Inhibitors of Human Mast Cell Chymase

Greco, Michael N.; et al, Journal of Medicinal Chemistry, 2007, 50(8), 1727-1730

Production Method 20

120-72-9

87-52-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  0 °C; 1 h, rt
1.2 1 h, rt
2.1 Solvents: Ethanol ,  Acetonitrile ;  2 h, rt
2.2 Reagents: Sodium borohydride Solvents: Ethanol ;  rt; 24 h, rt

Reference

Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity

Nimbarte, Vijaykumar D. ; et al, ChemMedChem, 2021, 16(10), 1667-1679

Production Method 21

120-72-9

87-52-5

Reaction Conditions

1.1 Solvents: Dimethylformamide
2.1 Reagents: Sodium borohydride

Reference

Reaction of nitro compounds with immonium salts. 1. Nitrovinylation of indoles

Babievskii, K. K.; et al, Izvestiya Akademii Nauk SSSR, 1977, (10), 2310-13

Production Method 22

52488-36-5

87-52-5

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Acetonitrile ,  Water ;  2 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt
2.1 Reagents: Hydrogen Catalysts: Palladium ;  4 h, 3 bar, rt

Reference

The structural simplification of lysergic acid as a natural lead for synthesizing novel anti-Alzheimer agents

Alzweiri, Muhammed; et al, Bioorganic & Medicinal Chemistry Letters, 2021, 47,

Gramine Raw materials

• 2,3-dihydro-1H-indole
• Indole
• [formyl(methyl)amino]methyl Benzoate
• N,N-dimethyl-1H-indole-3-carboxamide
• 3H-Indole
• 1H-Indole-3-methanamine,N,N-dimethyl-, N-oxide
• Methanol,1-(dimethylamino)-
• Formamide, N-(1H-indol-3-ylmethyl)-N-methyl-
• 4-Bromogramine
• Ethanone,1-(3-methyl-1H-indol-1-yl)-
• (1H-Indol-3-yl)-N,N-dimethylmethaniminium chloride
• 1H-Indole, 1-benzoyl-3-(bromomethyl)-
• Indole-3-carboxaldehyde
• 4-Bromo-1H-indole
• N,N,N',N'-Tetramethyldiaminomethane
• N,N-Dimethylmethyleneiminium Iodide
• Benzene, 1-(2-ethoxyethenyl)-2-nitro-, (E)- (9CI)

Gramine Preparation Products

• Gramine (87-52-5)

• 1. Distinctive size effects of Pt nanoparticles immobilized on Fe3O4@PPy used as an efficient recyclable catalyst for benzylic alcohol aerobic oxidation and hydrogenation reduction of nitroaromatics
  Yu Long,Bing Yuan,Jianrui Niu,Xin Tong,Jiantai Ma New J. Chem., 2015,39, 1179-1185
• 2. Enantiomeric two-fold interpenetrated 3D zinc(ii) coordination networks as a catalytic platform: significant difference between water within the cage and trace water in transesterification?
  Eunkyung Choi,Minjoo Ryu,Haeri Lee,Ok-Sang Jung Dalton Trans., 2017,46, 4595-4601
• 3. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
• 4. ETFE-based anion-exchange membrane ionomer powders for alkaline membrane fuel cells: a first performance comparison of head-group chemistry?
  Lianqin Wang,Rachida Bance-Soualhi,Julia Ponce-González,Pilar Ocón,Edson A. Ticianelli,Daniel K. Whelligan,John R. Varcoe J. Mater. Chem. A, 2018,6, 24330-24341
• 5. Estimating and correcting interference fringes in infrared spectra in infrared hyperspectral imaging
  Ghazal Azarfar,Ebrahim Aboualizadeh,Nicholas M. Walter,Simona Ratti,Camilla Olivieri,Alessandra Norici,Michael Nasse,Achim Kohler,Mario Giordano Analyst, 2018,143, 4674-4683

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives 3-alkylindoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indoles 3-alkylindoles
• Natural Products and Extracts Plant Extracts Plant based Stenostomum lucidum
• Pharmaceutical and Biochemical Products Pharmaceutical Active Ingredients Standard Substances

Gamma-Aminobutyric Acid (GABA): A Comprehensive Overview of CAS No. 87-52-5 and Its Applications in Biomedical Research

Gamma-Aminobutyric Acid (GABA), a non-proteinogenic amino acid with the CAS No. 87-52-5, is a pivotal inhibitory neurotransmitter in the central nervous system (CNS). Structurally characterized by an amino group attached to a four-carbon chain terminating with a carboxylic acid, GABA exerts its physiological effects through interaction with GABAA and GABAB receptors, modulating neuronal excitability and maintaining homeostasis in neural networks. Recent advancements in neurochemistry have revealed its role beyond neurotransmission, including neuroprotective and anti-inflammatory functions.

Emerging studies published in Nature Neuroscience (2023) highlight the Gramine-derived analogs of GABA as potential therapeutic agents for epilepsy and anxiety disorders. These analogs, engineered to enhance receptor specificity, demonstrate superior efficacy compared to traditional benzodiazepines while minimizing side effects such as sedation. The structural modification of CAS No. 87-52-5 compounds involves substituting terminal functional groups to optimize binding affinity for GABAA α2/α3 subunits, which are critical for anxiolytic activity without compromising cognitive performance.

In the context of neurodegenerative diseases, Gamma-Aminobutyric Acid has gained attention for its neurotrophic properties. A landmark study in Cell Reports (2024) demonstrated that exogenous administration of GABA promotes hippocampal neurogenesis in Alzheimer’s disease models through activation of the mTOR signaling pathway. This discovery underscores the potential of Gramine-based formulations as adjunct therapies to slow cognitive decline, particularly when combined with amyloid-targeting drugs.

Synthetic methodologies for producing high-purity CAS No. 87-52-5 compounds have evolved significantly since its initial isolation from plant extracts in the mid-19th century. Modern approaches utilize enzymatic catalysis via recombinant glutamate decarboxylase (GAD), achieving yields exceeding 99% purity under controlled pH conditions (pH 6–7). This enzymatic synthesis pathway minimizes environmental impact compared to traditional chemical synthesis routes involving cyanide derivatives.

Clinical trials investigating Gramine-derived GABA supplements reveal promising results for insomnia management without tolerance development observed with benzodiazepines. A Phase II trial published in Sleep Medicine Reviews (2024) showed that oral administration improved sleep latency by 40% and increased slow-wave sleep duration in patients with chronic insomnia, correlating with increased cerebrospinal fluid GABA levels measured via magnetic resonance spectroscopy.

Beyond CNS applications, recent research explores the role of Gamma-Aminobutyric Acid CAS No. 87-52-5 in metabolic regulation. A collaborative study between MIT and Harvard revealed that peripheral GABA signaling modulates glucose homeostasis via pancreatic β-cell receptors, suggesting potential for type II diabetes management strategies targeting this pathway without insulin injections.

Innovative delivery systems are being developed to enhance bioavailability of Gramine-based therapeutics. Liposomal encapsulation techniques using PEGylated nanoparticles have achieved up to threefold increases in brain penetration efficiency compared to unformulated GABA solutions, as reported in a 2024 issue of Biomaterials Science. These nanocarriers also reduce first-pass metabolism effects seen with oral formulations.

Mechanistically, recent cryo-electron microscopy studies at Stanford University mapped the three-dimensional structure of GABAA receptor-GABA complexes at near atomic resolution (Nature Structural Biology, 2024). This structural data enables rational drug design for subtype-selective ligands addressing specific neurological conditions – a breakthrough facilitated by advances in computational chemistry modeling platforms like Schr?dinger's Maestro suite.

The pharmacokinetic profile of CAS No. 87-52-5 compounds shows rapid absorption following oral intake but limited CNS penetration due to blood-brain barrier restrictions unless administered via intranasal routes or using prodrug strategies such as palmitoyl-GABA conjugates developed by researchers at UC Berkeley's Chemical Biology Institute.

Ethical considerations remain critical when developing Gamma-Aminobutyric Acid-based products. Regulatory agencies require stringent quality control protocols under ICH guidelines to ensure absence of impurities like pyroglutamic acid isomers which can exhibit agonist activity at unrelated receptors systems leading to off-target effects.

In conclusion, the scientific landscape surrounding Gamma-Aminobutyric Acid CAS No. 87-52-5 continues evolving rapidly across multiple biomedical disciplines – from novel drug delivery mechanisms to groundbreaking insights into its role in systemic health maintenance systems beyond classical neurotransmission roles first described over half a century ago.

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