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F3886

Sigma-Aldrich

Fentanyl citrate salt

Synonym(s):

N-Phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide citrate salt

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About This Item

Empirical Formula (Hill Notation):
C22H28N2O · C6H8O7
CAS Number:
990-73-8
Molecular Weight:
528.59
EC Number:
213-588-0
MDL number:
MFCD00058359
UNSPSC Code:
12352200
PubChem Substance ID:
329799707
NACRES:
NA.77

Quality Level

200

drug control

USDEA Schedule II; Home Office Schedule 2; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; estupefaciente (Spain); Decreto Lei 15/93: Tabela IA (Portugal)

SMILES string

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCC(=O)N(C1CCN(CC1)CCc2ccccc2)c3ccccc3

InChI

1S/C22H28N2O.C6H8O7/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-12,21H,2,13-18H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

InChI key

IVLVTNPOHDFFCJ-UHFFFAOYSA-N

Gene Information

human ... OPRM1(4988)

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Biochem/physiol Actions

Phenylpiperidine analgesic that is 80 times more potent than morphine as an analgesic and 6000 times more potent than morphine as a μ opioid receptor agonist.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H336

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Willem M Otte et al.
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Hemispherectomy is often followed by remarkable recovery of cognitive and motor functions. This reflects plastic capacities of the remaining hemisphere, involving large-scale structural and functional adaptations. Better understanding of these adaptations may (1) provide new insights in the neuronal configuration
Anouk Wezel et al.
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Activated mast cells have been identified in the intima and perivascular tissue of human atherosclerotic plaques. As mast cells have been described to release a number of chemokines that mediate leukocyte fluxes, we propose that activated mast cells may play
Jennifer D Zwicker et al.
Journal of applied physiology (Bethesda, Md. : 1985), 117(8), 857-868 (2014-08-12)
Opioids activate glia in the central nervous system in part by activating the toll-like receptor 4 (TLR4)/myeloid differentiation 2 (MD2) complex. TLR4/MD2-mediated activation of glia by opioids compromises their analgesic actions. Glial activation is also hypothesized as pivotal in opioid-mediated
Houssam G Kotrach et al.
Journal of applied physiology (Bethesda, Md. : 1985), 118(11), 1406-1414 (2015-06-03)
Few therapies exist for the relief of dyspnea in restrictive lung disorders. Accumulating evidence suggests that nebulized opioids selective for the mu-receptor subtype may relieve dyspnea by modulating intrapulmonary opioid receptor activity. Our respective primary and secondary objectives were to
Ariana M Nelson et al.
Anesthesiology, 111(6), 1327-1333 (2009-11-26)
Opioids disrupt sleep and adenosine promotes sleep, but no studies have characterized the effects of opioids on adenosine levels in brain regions known to regulate states of arousal. Delivering opioids to the pontine reticular formation (PRF) and substantia innominata (SI)
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