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O003

Sigma-Aldrich

β-Funaltrexamine hydrochloride

solid

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Synonym(s):
β-FNA hydrochloride, (E)-4-[[(5α,6β)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]amino]-4-oxo-2-butenoic acid methyl ester hydrochloride
Empirical Formula (Hill Notation):
C25H30N2O6 · HCl
CAS Number:
72786-10-8
Molecular Weight:
490.98
MDL number:
MFCD10565941
UNSPSC Code:
12352116
PubChem Substance ID:
24897921
NACRES:
NA.77

form

solid

Quality Level

100

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

desiccated

color

white

solubility

H2O: 7.5 mg/mL (aqueous solutions should be promptly used)
methanol: 7.6 mg/mL (do not store in ethanolic solution; methanolic solutions may be stored for several weeks at 4 °C)

storage temp.

−20°C

SMILES string

Cl.COC(=O)\C=C\C(=O)N[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5OC1[C@]2(CCN3CC6CC6)c45

InChI

1S/C25H30N2O6.ClH/c1-32-20(30)7-6-19(29)26-16-8-9-25(31)18-12-15-4-5-17(28)22-21(15)24(25,23(16)33-22)10-11-27(18)13-14-2-3-14;/h4-7,14,16,18,23,28,31H,2-3,8-13H2,1H3,(H,26,29);1H/b7-6+;/t16-,18-,23+,24+,25-;/m1./s1

InChI key

BIPHUOBUKMPSQR-NQGXHZAGSA-N

Related Categories

Biochem/physiol Actions

Selective irreversible μ opioid receptor antagonist that is also a κ opioid receptor agonist.

Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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R B Rothman et al.
Synapse (New York, N.Y.), 8(2), 86-99 (1991-06-01)
beta-Funaltrexamine (beta-FNA) is an alkylating derivative of naltrexone. In addition to acting as an irreversible inhibitor of mu-receptor-mediated physiological effects, intracerebroventricular (i.c.v.) administration of beta-FNA to rat attenuates the ability of selective delta receptor antagonists and naloxone to reverse delta
Thomas J Martin et al.
Anesthesiology, 114(3), 633-642 (2011-02-05)
Neuropathic pain alters opioid self-administration in rats. The brain regions altered in the presence of neuropathic pain mediating these differences have not been identified, but likely involve ascending pain pathways interacting with the limbic system. The amygdala is a brain
Sarah A Nickolls et al.
Journal of biomolecular screening, 16(7), 706-716 (2011-05-10)
The correct interpretation of data is fundamental to the study of G-protein-coupled receptor pharmacology. Often, new assay technologies are assimilated into the drug discovery environment without full consideration of the data generated. In this study, the authors look at µ-opioid
Carlos Andres Lopez et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 301(4), R1105-R1111 (2011-07-22)
Melanin-concentrating hormone (MCH) exerts an orexigenic effect that resembles that of opioids, suggesting that the MCH and opioid systems could interact in controlling the food intake behavior. Three series of experiments were conducted in male Wistar rats: 1) to test
M Morales-Mulia et al.
Behavioural brain research, 235(2), 189-194 (2012-09-12)
Anxiolytic effects of alcohol participate in the reinforcing properties of the drug, in which nucleus accumbens (NAcc) is implicated. The opioidergic system in NAcc is considered a main pathway involved in the emotional responses of animals: rats microinjected with morphine
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