ContaminantDB: Alfentanil hydrochloride

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:50:36 UTC

Update Date

2016-11-09 01:16:08 UTC

Accession Number

CHEM020144

Identification

Common Name

Alfentanil hydrochloride

Class

Small Molecule

Description

Alfentanil (R-39209, trade name Alfenta, Rapifen in Australia) is a potent but short-acting synthetic opioid analgesic drug, used for anaesthesia in surgery. It is an analogue of fentanyl with around 1/4 to 1/10 the potency of fentanyl and around 1/3 of the duration of action, but with an onset of effects 4x faster than fentanyl. Alfentanil has a pKa of approximately 6.5, which leads to a very high proportion of the drug being uncharged at physiologic pH. This unique characteristic is responsible for its rapid onset. It is an agonist at mu opioid receptors. While alfentanil tends to cause fewer cardiovascular complications than other similar drugs such as fentanyl and remifentanil, it tends to give stronger respiratory depression and so requires careful monitoring of breathing and vital signs. Almost exclusively used by anesthesia providers during portions of a case where quick, fast acting (though not long lasting) pain control is needed (i.e. during a nerve block, head pinning etc..) Alfentanil is administered by the parenteral (injected) route for fast onset of effects and precise control of dosage. Alfentanil is a restricted drug which is classified as Schedule II in the US, according to the U.S. DEA website.Alfentanil was discovered at Janssen Pharmaceutica in 1976. Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Limifen	MeSH
Alfentanil	MeSH
Alfenta	MeSH
Rapifen	MeSH
Fanaxal	MeSH
Alfentanyl	MeSH
Alfentanil HCL	ChEMBL
Alfentanil hydrochloride	MeSH
Esteve brand OF alfentanil hydrochloride	MeSH
Janssen brand OF alfentanil hydrochloride	MeSH
ICI brand OF alfentanil hydrochloride	MeSH

Chemical Formula

C₂₁H₃₃ClN₆O₃

Average Molecular Mass

452.980 g/mol

Monoisotopic Mass

452.230 g/mol

CAS Registry Number

69049-06-5

IUPAC Name

N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide hydrochloride

Traditional Name

alfentanil hydrochloride

SMILES

Cl.CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C2=CC=CC=C2)C1=O

InChI Identifier

InChI=1S/C21H32N6O3.ClH/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26;/h6-10H,4-5,11-17H2,1-3H3;1H

InChI Key

AQORHZJDCHLLJN-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
Piperidine
Azole
Heteroaromatic compound
Tertiary carboxylic acid amide
Tetrazole
Amino acid or derivatives
Carboxamide group
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Hydrochloride
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	0.25 g/L	ALOGPS
logP	2.2	ALOGPS
logP	2.81	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	7.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	81.05 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.59 m³·mol⁻¹	ChemAxon
Polarizability	45.66 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-1a3c5e33903698b7b5ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000900000-1a3c5e33903698b7b5ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0000900000-1a3c5e33903698b7b5ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000900000-8d6cb6bbf46b973b6d67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0000900000-8d6cb6bbf46b973b6d67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0000900000-8d6cb6bbf46b973b6d67	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Alfentanil

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

64761

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Alfentanil hydrochloride (CHEM020144)

Structure for CHEM020144: Alfentanil hydrochloride