Remifentanil (CED0002088)

Record Information

Version

1.0

Creation Date

2016-05-25 18:23:33 UTC

Update Date

2026-08-20 06:30:27 UTC

Accession Number

CHEM022199

Identification

Common Name

Remifentanil

Class

Small Molecule

Description

Remifentanil is an organic compound with the formula C20H28N2O5 and an average molecular weight of 376.45 g/mol. Remifentanil belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. The substance is found in or released from seven recorded sources, which include anesthetics within healthcare, pharmaceuticals, and veterinary products. Other recorded sources include antennas, electric switches, electrically stimulated smoking devices, and video games under electrical and electronic equipment, as well as cigar cigarettes and non-electric simulated smoking devices under household cleaning and consumer products. The recorded route of exposure for this compound is intravenous. At the molecular level, remifentanil interacts with three recorded protein targets. It acts as an agonist of the mu-type opioid receptor (OPRM1), the delta-type opioid receptor (OPRD1), and the kappa-type opioid receptor (OPRK1).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ultiva	Kegg
Remifentanyl	HMDB
Remifentanil monohydrochloride	HMDB
Remifentanil hydrochloride	HMDB
3-(4-Methoxycarbonyl-4-((1-oxopropyl)phenylamino)-1-piperidine)propanoic acid methyl ester	HMDB

Chemical Formula

C₂₀H₂₈N₂O₅

Average Molecular Mass

376.447 g/mol

Monoisotopic Mass

376.200 g/mol

CAS Registry Number

132875-61-7

IUPAC Name

methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate

Traditional Name

remifentanil

SMILES

CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC

InChI Identifier

InChI=1S/C20H28N2O5/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2/h5-9H,4,10-15H2,1-3H3

InChI Key

ZTVQQQVZCWLTDF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Piperidinecarboxylic acid
Anilide
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Methyl ester
Carboxamide group
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Amine
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:8802 )
alpha-amino acid ester (CHEBI:8802 )
anilide (CHEBI:8802 )
piperidinecarboxylate ester (CHEBI:8802 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.59 g/L	ALOGPS
logP	1.75	ALOGPS
logP	1.52	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	7.51	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	76.15 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	100.56 m³·mol⁻¹	ChemAxon
Polarizability	40.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0cdj-3596000000-8aae94fe8a68982e79c1	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0009000000-b9035e2706d5ac9b57a7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-02di-0397000000-c610a2d0adc44d55166b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0930000000-436dbd271b442dcde5bf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03e9-4900000000-79234a6e65fb22f3b487	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01q9-9700000000-5ce11ade40e1a80e4958	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01q9-9700000000-5ce11ade40e1a80e4958	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-02di-0397000000-c610a2d0adc44d55166b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0009000000-b9035e2706d5ac9b57a7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0930000000-436dbd271b442dcde5bf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03e9-4900000000-79234a6e65fb22f3b487	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-02di-0397000000-edb4efa591a39769e8a7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002b-1019000000-895cd186455eca8fbeea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000j-6079000000-438fdbe9c2223c77db8a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-4090000000-85ac4b7ca639bae41a2e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004l-0009000000-d7edabb8bccdbfb37512	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-07g3-1139000000-25aef3cddeba2d8279a8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a7u-5391000000-1ecfe4cd5e7e949c2c35	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0119000000-bfa221650ef881388c5c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udl-3910000000-0ef79bd76c5c4b3d4532	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02t9-1981000000-bb61c5be324241844d65	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004l-0009000000-c51211999f5bc5653604	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a74-9687000000-2da80400bff88fa8c8ee	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0btl-2190000000-6f4a85e52197f65ecdfd	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
816.0	Log mg/kg	[460:1500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
369	Anesthetics	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
651	Purses Money Bags Wallets	Textiles, leather & furnishings	Not Available

Pathways

5 pathways

Remifentanil Action Pathway

Remifentanil Opioid Anasthetic Action Pathway

Remifentanil Opioid Analgesic Action Pathway

Remifentanil Drug Metabolism Action Pathway

Remifentanil Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q60492	Cavia porcellus	Predicted (SEA)	44.2962
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	153.363
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	187.461
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	200.695
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Predicted (SEA)	44.1405
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	210.971
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	267.023
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	332.805
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	340.98
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	821.387
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	173.682
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	337.165
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	347.752
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	232.691
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	189.329
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q9R0C9	Rattus norvegicus	Predicted (SEA)	153.752
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	142.931
Click to view 3D structure	Histamine H2 receptor	P25021	Humans	Predicted (SEA)	164.184
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	268.502
Click to view 3D structure	D(1A) dopamine receptor	P18901	Rattus norvegicus	Predicted (SEA)	180.532
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	415.637
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	318.325
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	658.527
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	825.202
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	783.319