82626-48-0

Basic information

• Product Name: Zolpidem
• Synonyms: 2-a)pyridine-3-acetamide,2-(4-methylphenyl)-n,n,6-trimethyl-imidazo(;N,N,6-Trimethyl-2-p-tolylimidazo[1,2-a]pyridine-3-acetamide;N,N-Dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide;SL-80.0750;N,N,6-TRIMETHYL-2-(4-METHYLPHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-ACETAMIDE;N,N,6-TRIMETHYL-2-(4-METHYLPHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-ACETAMIDE HEMITARTRATE;N,N,6-TRIMETHYL-2-(4-METHYLPHENYL)IMIDAZO[1,2-A]PYRIMIDINE-3-ACETAMIDE;ZOLPIDEM
• CAS NO: 82626-48-0
• Molecular Formula: C₁₉H₂₁N₃O
• Molecular Weight: 307.39
• Product Categories: Pyridines derivates;(intermediate of zolpidem);Zolpidem;Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Isotopically Labeled Pharmaceutical Reference Standard
• Mol File: 82626-48-0.mol
• Article Data: 43

Chemical Properties

• Melting Point: 189-191°C
• Flash Point: 9℃
• Appearance: white/solid
• Density: 1.12 g/cm³
• Refractive Index: 1.601
• Storage Temp.: Store at RT
• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.3 mg/mL
• PKA: 6.2(at 25℃)
• Water Solubility: <10mg/L(room temperature)
• CAS DataBase Reference: Zolpidem(CAS DataBase Reference)
• NIST Chemistry Reference: Zolpidem(82626-48-0)
• EPA Substance Registry System: Zolpidem(82626-48-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• RTECS: NJ5109750
• Hazardous Substances Data: 82626-48-0(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 82626-48-0 differently. You can refer to the following data:
1. Zolpidem hemitamwe is a non-benzodiazepine hypnotic with specific agonist activity at type 1 benzodiazepine receptors, and is indicated for use in insomnia and other sleep disorders. Structurally zolpidem belongs to a chemically distinct class, thus lacking the side-effects and abuse potential of classical benzodiazepines. It is currently being studied as a pre-operative sedative.
2. Zolpidem (Item No. 15792) is an analytical reference material that is functionally categorized as a sedative. It is a non-benzodiazepine drug that is used in the treatment of insomnia, and it has been recreationally abused. This product is intended for research and forensic applications.
3. Zolpidem (Item No. 20648) is a certified reference material that is functionally categorized as a sedative. It is a non-benzodiazepine drug that is used in the treatment of insomnia, and it has been recreationally abused. This product is intended for research and forensic applications.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 82626-48-0 differently. You can refer to the following data:
1. A selective benzodiazepine receptor agonist not related chemically to benzodiazepines
2. A selective non-benzodiazepine GABAA receptor agonist. Sedative, hypnotic. Controlled substance (depresssant).

Definition

ChEBI: An imidazo[1,2-a]pyridine compound having a 4-tolyl group at the 2-position, an N,N-dimethylcarbamoylmethyl group at the 3-position and a methyl substituent at the 6-position.

Brand name

Ambien (Sanofi Aventis);Stilnox.

General Description

Zolpidem (Ambien, an imidazopyridine) andeszopiclone (Lunesta, a cyclopyrrolone) are nonbenzodiazepinesand have been introduced as short- and moderate-acting hypnotics, respectively. Zolpidem exhibits ahigh selectivity for the α1 subunit of benzodiazepinebindingsite on GABAA receptor complex, whereas eszopicloneis a “superagonist” at BzRs with the subunitcomposition α1β2γ2 and α1β2γ3. Zolpidem has a rapidonset of action of 1.6 hours and good bioavailability(72%), mainly because it is lipophilic and has no ionizablegroups at physiological pH. Food can prolong the time topeak concentration without affecting the half-life probablyfor the same reason. It has short elimination half-life, becauseits aryl methyl groups is extensively α-hydroxylatedto inactive metabolites by CYP3A4 followed by furtheroxidation by aldehyde dehydrogenase to the ionic carboxylicacid. The metabolites are inactive, short-lived, andeliminated in the urine. Its half-life in the elderly or the patientswith liver disease is increased. Therefore, dosingshould be modified in patients with hepatic insufficiencyand the elderly. Because it has longer elimination half-lifethan zaleplon, it may be preferred for sleep maintenance.It was the most commonly prescribed drug for insomniain 2001.

InChI:InChI=1/C19H21N3O/c1-13-5-8-15(9-6-13)19-16(11-18(23)21(3)4)22-12-14(2)7-10-17(22)20-19/h5-10,12H,11H2,1-4H3

Upstream product

• 189005-44-5 6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid 
• 124-40-3 dimethyl amine 
• 371165-45-6 C₁₇H₁₅ClN₂O 
• 2682-34-0 N,N-dimethylpropynamide 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 1290559-61-3 C₂₀H₂₃NO₅S 
• 402470-91-1 N,N-dimethyl-4-oxo-4-(4-methylphenyl)butanamide 
• 193979-47-4 ethyl 6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetate 
• 1381932-38-2 C₁₅H₁₇NO₆ 
• 7559-36-6 4-methyl-β-nitrostyrene 
• 104-87-0 4-methyl-benzaldehyde 
• 400777-11-9 6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridine-3-carbaldehyde 
• 62285-47-6 2-diazo-N,N-dimethyl-acetamide 
• 88965-00-8 6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine 

Downstream Products

• 30223-73-5 (R,S)-2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 
• 189005-44-5 6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid 
• 118026-14-5 N,N,6-trimethyl-2-(4-methylphenyl)-imidazo[1,2-α]pyridine-3-α-hydroxyacetamide 

Relevant articles and documents

Structural and thermal characterization of zolpidem hemitartrate hemihydrate (Form E) and its decomposition products by laboratory x-ray powder diffraction

The crystal structure of zolpidem hemitartrate hemihydrate (I, Form E) has been solved from high-resolution laboratory powder diffraction data. It crystallizes in the orthorhombic P212121 space group with a=22.4664(6)?, b=26.0420(7)?, and c=7.4391(1)?. Protonation of zolpidem molecules could not be unambiguously determined. Thermal stability of Form E has been investigated by TG-DTA and in situ by temperature resolved X-ray powder diffraction. Water loss occurs between 508C≤t≤1008C while structure decomposition commences at approximately 120°C yielding zolpidem tartrate (II) and pure zolpidem base (III) in approximately equimolar amounts. Crystal structures of II and III have been solved simultaneously from a single powder pattern of thermally decomposed I. Zolpidem tartrate crystallizes in the orthorhombic P212121 space group with a=19.9278(8)?, b=15.1345(8)?, and c=7.6246(2)? (at 140°C). Zolpidem base crystallizes in the orthorhombic Pcab space group with a=9.9296(4)?, b=18.4412(9)?, and c=18.6807(9)? (at 140°C). In the reported crystal structures zolpidem molecules form stacks through π-π interaction or dipole-dipole interactions while tartrate moieties, if present, form hydrogen bonded chains. Water molecule in I forms a hydrogen bond to the imidazole nitrogen atom of the zolpidem molecule. Free space in the crystal structure of I could allow for the additional water molecules and thus a variable water content.

Zolpidem preparation method

The invention belongs to the technical field of drug synthesis, and provides a zolpidem preparation method which comprises the following steps: by taking SM-1 as a starting material, Rh (trop2N) (PPh3) as a catalyst and MMA as a hydrogen acceptor, carrying out catalytic dehydrogenation coupling reaction on the starting material, the catalyst and dimethylamine, and carrying out acid dissolution and alkali precipitation refining to obtain a product with higher purity. Compared with the prior art, the zolpidem preparation process has the advantages that the process route can be obviously shortened, and the preparation process is suitable for industrial production.

One-Pot Synthesis of C3-Alkylated Imidazopyridines from α-Bromocarbonyls under Photoredox Conditions

A convenient strategy is presented for the synthesis of C3-alkylated imidazopyridines through one pot condensation and alkylation of α-bromocarbonyl compounds with 2-aminopyridines. A series of C3-alkylated imidazopyridines were obtained in moderate to hi

Rhodium catalyzed direct C3-ethoxycarbonylmethylation of imidazo[1,2-a]pyridines with ethyl diazoacetate

An efficient and environment-friendly C3-ethoxycarbonylmethylation of imidazo[1,2-a]pyridines with ethyl diazoacetate in the presence of a Rh(II) catalyst was developed. Such strategy not only enables the synthesis of zolpidem, but also provides a way to