2-[2-(aminomethyl)cyclohexyl]acetic Acid

Base Information

• Chemical Name: 2-[2-(aminomethyl)cyclohexyl]acetic Acid
• CAS No.: 60142-96-3
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.239
• Hs Code.: 29224999
• NSC Number: 759254
• Wikidata: Q27166908
• Mol file: 60142-96-3.mol

Synonyms:2-[2-(aminomethyl)cyclohexyl]acetic Acid;BSPBio_002312;SPECTRUM1505805;2-(Aminomethyl)cyclohexanessig;SCHEMBL3278947;CHEBI:95126;HMS1922H12;HMS2093F06;Pharmakon1600-01505805;NSC759254;CCG-213554;NCGC00095184-01;NCGC00095184-02;NCGC00095184-03;AB01563336_01;SR-05000001804;SR-05000001804-1;Q27166908

Chemical Property of 2-[2-(aminomethyl)cyclohexyl]acetic Acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 6.32E-05mmHg at 25°C
• Melting Point: 162 °C
• Refractive Index: 1.484
• Boiling Point: 314.4 °C at 760 mmHg
• PKA: pKa1 (25°) 3.68; pKa2 10.70
• Flash Point: 144 °C
• PSA: 63.32000
• Density: 1.058 g/cm³
• LogP: 2.07060
• Storage Temp.: Desiccate at +4°C
• Solubility.: H2O: 10 mg/mL
• Water Solubility.: H2O: 10 mg/mL
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 171.125928785
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

Gabapentin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi,F
• Statements: 61-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 53-26-36/37/39-45-36-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)CC(=O)O)CN
• Recommended First-Line Agent for Neuropathic Pain: Gabapentin is recommended as a first-line agent for treating neuropathic pain and has proven efficacy in chronic pain conditions.
• Mechanism of Action: Gabapentin primarily affects pain modulation by the central nervous system (CNS), with some evidence for peripheral activity. It binds to voltage-sensitive calcium channels at the 伪2未-1 site, affecting their function and receptor trafficking. Neuroimaging studies have shown that gabapentinoids affect brain function in models of central sensitization and in patients with chronic pain.
• History and Approval: Gabapentin, originally developed in 1976, was approved by the FDA in 1998 for the treatment of postherpetic neuralgia (PHN) and diabetic peripheral neuropathy (DPN). It was not metabolized hepatically and was not bound to plasma proteins. Gabapentinoid use has significantly increased since FDA approval, with gabapentin use tripling in the USA between 2002 and 2015.
• Use in Chronic Pain Management: Gabapentin has been increasingly used off-label for chronic pelvic pain due to its efficacy in other chronic pain conditions. It has been shown to inhibit astrocyte-derived thrombospondins (TSPs), which play a major role in chronic pain after neuronal injury. Gabapentin inhibits TSPs via 伪2未-1 to block synaptogenesis, leading to analgesia.
• Pharmacological Characteristics: Gabapentin's unique pharmacologic characteristics include its binding to voltage-sensitive calcium channels at the 伪2未-1 site. Through these mechanisms, gabapentin influences GABA and glutamate tone/activity, which can be clinically measured.
• Additional Uses: Gabapentin is efficacious for the treatment of acute alcohol withdrawal symptoms and provides short-term relapse prevention after medicated alcohol detoxification, possibly by normalizing sleep.
• General Description: Gabapentin hydrochloride, also known by names such as Neurontin and Serada, is an anticonvulsant drug effective in treating neuropathic pain by binding to the α₂δ subunit of voltage-gated calcium channels. While the study primarily explores novel gabapentin-mimetic compounds with enhanced binding affinities, it reinforces gabapentin's established role as a reference ligand in this pharmacological context. The research highlights the potential for developing more potent non-amino acid derivatives, such as compound 10, which exhibits superior binding affinity compared to gabapentin itself.

Technology Process of 2-[2-(aminomethyl)cyclohexyl]acetic Acid

There total 55 articles about 2-[2-(aminomethyl)cyclohexyl]acetic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(RR,SS)-trans-1,2-cyclobutanedicarboxylic acid (3396-14-3) → H-Gpn-OH (60142-96-3)

Guidance literature:

In tetrahydrofuran; water;

Reference yield: 98.0%

(RR,SS)-trans-1,2-cyclobutanedicarboxylic acid (3396-14-3) → (1α,3α,5α)(3-aminomethyl-bicyclo[3.2.0]hept-3-yl)-acetic acid hydrochloride (335671-48-2) + H-Gpn-OH (60142-96-3)

Guidance literature:

In tetrahydrofuran; water;

Reference yield: 95.5%

gabapentin hydroxybenzoate (756486-04-1) → H-Gpn-OH (60142-96-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; at 20 ℃; for 4h;

upstream raw materials:

methyl 3-oxo-2-azaspiro<4.5>decane-4-carboxylate

ethyl 3-oxo-2-azaspiro<4.5>decane-4-carboxylate

benzyl (1-cyanocyclohexyl)acetate

1-(aminomethyl)cyclohexaneacetic acid potassium salt

Downstream raw materials:

1-{[(α-chloroethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid

C₁₅H₂₈ClNO₄Si

gabapentin enacarbil

1-[3-(bromomethyl)phenoxycarbonylaminomethyl]cyclohexaneacetic acid

Refernces

N-Acridin-9-yl-butane-1,4-diamine derivatives: High-affinity ligands of the α₂δ subunit of voltage gated calcium channels

10.1016/j.bmcl.2004.01.087

In the research, gabapentin is described as an anticonvulsant agent that has been shown to be effective against neuropathic pain in both animal models and humans. The research aimed to discover novel gabapentin-mimetic compounds to better understand the mechanism of gabapentin's pharmacological actions and develop more effective drugs. The study focused on N-acridin-9-yl-butane-1,4-diamine derivatives, investigating their binding affinity to the a2d subunit of voltage-gated calcium channels. Key chemicals included compound 1 (IC50=220 nM), identified through high-throughput screening, and its enantiomers, with the (S)-enantiomer 2 showing higher binding affinity (IC50=110 nM). The researchers optimized the side chain length and structure, finding that compound 10 (IC50=9 nM) was more potent than gabapentin (IC50=27 nM). They also explored partial saturation of the acridine ring, resulting in the octahydro analogue 22 (IC50=160 nM), which was more potent than the parent compound. The study concluded that compound 10 is the first high-affinity, non-amino acid gabapentin-mimetic ligand reported, and its radiolabeled form [3H]-10 validated as a specific radioligand for in vitro binding assays.