ContaminantDB: Zolpidem

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:52 UTC

Update Date

2026-03-31 19:07:08 UTC

Accession Number

CHEM002192

Identification

Common Name

Zolpidem

Class

Small Molecule

Description

Zolpidem (sold under the brand names Ambien, Ambien CR, Stilnox, and Sublinox) is a prescription medication used for the treatment of insomnia, as well as some brain disorders. It is a short-acting nonbenzodiazepine hypnotic of the imidazopyridine class that potentiates gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, by binding to GABAA receptors at the same location as benzodiazepines. It works quickly (usually within 15 minutes) and has a short half-life (two to three hours). Zolpidem has not adequately demonstrated effectiveness in maintaining sleep (unless delivered in a controlled-release form); however, it is effective in initiating sleep. Some users take zolpidem recreationally for these side effects. However, it may be less common than benzodiazepine abuse. Zolpidem can become addictive if taken for extended periods of time, due to dependence on its ability to put one to sleep or to the euphoria it can sometimes produce.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Drug
Food Toxin
GABA Agonist
GABA-A Receptor Agonist
Hypnotic and Sedative
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine-3-acetamide	ChEBI
Zolpidemum	ChEBI
Sanval	Kegg
Ambien	HMDB
Hypnogen	HMDB
Myslee	HMDB
Stilnoct	HMDB
Stilnox	HMDB
Zolpidem ambien	HMDB
Zolpidem tartrate	HMDB
Bikalm	HMDB
Zolpidem 1a pharma	HMDB
N,N,6-Trimethyl-2-(4-methylphenyl)imidazo(1,2a)pyridine-3-acetamide hemitartrate	HMDB
Zolpidem abz	HMDB
Amsic	HMDB
Dalparan	HMDB
Zolpinox	HMDB
Zodormdura	HMDB
Zoldem	HMDB
Zolirin	HMDB
Zolpi-lich	HMDB
Zolpimist	HMDB
Zolpidem hemitartrate	HMDB
Zolpi lich	HMDB

Chemical Formula

C₁₉H₂₁N₃O

Average Molecular Mass

307.390 g/mol

Monoisotopic Mass

307.168 g/mol

CAS Registry Number

82626-48-0

IUPAC Name

N,N-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide

Traditional Name

zolpidem

SMILES

CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1

InChI Identifier

InChI=1S/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

InChI Key

ZAFYATHCZYHLPB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylimidazoles. These are polycyclic aromatic compounds containing a benzene ring linked to an imidazole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Phenylimidazoles

Alternative Parents

Substituents

5-phenylimidazole
4-phenylimidazole
Imidazopyridine
Imidazo[1,2-a]pyridine
Toluene
Methylpyridine
Monocyclic benzene moiety
N-substituted imidazole
Pyridine
Benzenoid
Tertiary carboxylic acid amide
Heteroaromatic compound
Carboxamide group
Carboxylic acid derivative
Azacycle
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazopyridine (CHEBI:10125 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Liver

Pathways

Not Available

Applications

Biological Roles

GABA agonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	196°C
Boiling Point	Not Available
Solubility	23 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	0.031 g/L	ALOGPS
logP	3.15	ALOGPS
logP	3.02	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	5.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.58 m³·mol⁻¹	ChemAxon
Polarizability	35.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-007c-4491000000-1f69c88ada0cbe422976	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4r-0196000000-6304f5b37ed9f071eb26	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-06ri-0093000000-df20eb1ec18c6314769f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0049000000-bc33df0258d99c887a5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bti-0095000000-53d24c4b41c278d039e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-1190000000-fcb2a47c2fab91af9648	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-ad3531d27ad6da8d9cc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-1097000000-084e5a788c15061e05a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08fs-2090000000-b2e3eaa1af64958efe10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-de69c65803e567e26cea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-074i-0093000000-612afe202f557c4a4c66	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0490000000-26b5c78b7009ce2e5c1c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0019000000-b660ca11ad7e4f91fd36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0092000000-37a7218a24afef1be815	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014r-0390000000-fe5078d60002f0380d8e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-1090000000-5429f5620534a2340098	Spectrum

Toxicity Profile

Route of Exposure

Oral. Zolpidem is rapidly absorbed from the GI tract.

Mechanism of Toxicity

Zolpidem modulates the alpha-subunit, known as the benzodiazepine receptor, within the GABA_A receptor chloride channel macromolecular complex. Unlike the benzodiazepines, which non-selectively interact with all three alpha-receptor subtypes, Zolpidem preferentially binds to the alpha-1 receptor.

Metabolism

Zolpidem is converted to inactive metabolites in the liver. Route of Elimination: Zolpidem tartrate tablets are converted to inactive metabolites that are eliminated primarily by renal excretion. Half Life: 2.6 hours

Toxicity Values

LD50: 695 mg/kg (Oral, Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the short-term treatment of insomnia.

Minimum Risk Level

Not Available

Health Effects

They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.

Symptoms

Symptoms of overdose include impairment of consciousness ranging from somnolence to light coma.

Treatment

General symptomatic and supportive measures should be used along with immediate gastric lavage where appropriate. Intravenous fluids should be administered as needed. sedative hypnotic effect was shown to be reduced by flumazenil and therefore may be useful; however, flumazenil administration may contribute to the appearance of neurological symptoms (convulsions). As in all cases of drug overdose, respiration, pulse, blood pressure, and other appropriate signs should be monitored and general supportive measures employed. Hypotension and CNS depression should be monitored and treated by appropriate medical intervention. Sedating drugs should be withheld following zolpidem overdosage, even if excitation occurs. The value of dialysis in the treatment of overdosage has not been determined, although hemodialysis studies in patients with renal failure receiving therapeutic doses have demonstrated that zolpidem is not dialyzable. (11)

Concentrations

Not Available

External Links

DrugBank ID

DB00425

HMDB ID

HMDB0005023

FooDB ID

FDB023594

Phenol Explorer ID

Not Available

KNApSAcK ID