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> G Protein-Coupled Receptor Ligands>Sigma Receptors>beta-funaltrexamine Hydrochloride

Sigma Receptors

SS-funaltrexamine Hydrochloride View larger

beta-funaltrexamine Hydrochloride

AOB5999

CAS 72786-10-8

Chemical Name: ß-FNA hydrochloride, (E)-4-[[(5a,6ß)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]amino]-4-oxo-2-butenoic acid methyl ester hydrochloride

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Quantity Discount Table - Order More To Get More Price Discount

QuantitymgUnit Price ($/mg or $/Unit)Final Price
15 $17.85 Total: $89.25
110 $15.12 Total: $151.20
125 $12.81 Total: $320.25
150 $10.92 Total: $546.00
1100 $9.45 Total: $945.00

Data sheet

Molecular FormulaC25H31ClN2O6
Molecular Weight490.98
CAS Numbers 72786-10-8
Storage Condition0°C (short term), -20°C (long term), desiccated
SolubilityDMSO
Purity98% by HPLC
Synonymß-FNA hydrochloride
IUPAC/Chemical Name(E)-4-[[(5a,6ß)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]amino]-4-oxo-2-butenoic acid methyl ester hydrochloride
InChl KeyBIPHUOBUKMPSQR-NQGXHZAGSA-N
InChl Code1S/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
SMILES CodeCl.COC(=O)C=CC(=O)N[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5OC1[C@]2(CCN3CC6CC6)c45
References1) Jiang et al (1990) μ Antagonist and κ agonist properties of β-funaltrexamine (β-FNA) in vivo: long lasting spinal analgesia in mice. J.Pharmacol.Exp.Ther. 252 1006 PMID: 2156986

2) Takemorei et al (1981) The irreversible narcotic antagonist and reversible agonist properties of the fumarate methyl ester derivative of naltr. Eur.J.Pharmacol. 70 445 PMID: 6263637

More info

Selective irreversible µ opioid receptor antagonist, also being a kappa opioid receptor agonist

β-FNA hydrochloride (β-funaltrexamine hydrochloride) is a potent, irreversible μ-opioid receptor antagonist used in research. Here’s its main functionality:

  • Mechanism of action:

    • It binds selectively and irreversibly to μ-opioid receptors (MORs) through alkylation of a nucleophilic amino acid residue in the receptor binding pocket.

    • By doing so, it blocks receptor activation by agonists like morphine, fentanyl, or endogenous endorphins.

  • Selectivity:

    • Highly selective for MOR over δ- and κ-opioid receptors.

    • Often used in experiments to distinguish μ-mediated effects from other opioid receptor activities.

  • Applications in research:

    • Mapping μ-opioid receptor distribution and function.

    • Studying the role of μ-receptors in analgesia, reward pathways, and dependence.

    • Evaluating the effects of long-term receptor blockade (since it’s irreversible, recovery requires new receptor synthesis).

Here’s a clear side-by-side table comparing β-FNA hydrochloride, Naloxone, and Naltrexone:

Featureβ-FNA hydrochlorideNaloxoneNaltrexone
TypeIrreversible μ-opioid receptor antagonistReversible competitive opioid antagonistReversible competitive opioid antagonist
SelectivityHighly selective for μ (MOR)μ > δ, κμ > δ, κ
BindingAlkylates MOR → permanent inactivationBinds competitively (reversible)Binds competitively (reversible)
Duration of actionVery long (days, until new receptors are made)Short (30–90 minutes)Long (24–72 hours)
Clinical use❌ Research only✅ Emergency opioid overdose reversal✅ Maintenance therapy for opioid/alcohol dependence
AdministrationLab use (in vitro/in vivo animal studies)IV, IM, intranasalOral tablets, IM depot injection
PurposeExperimental tool for studying MOR functionLife-saving antidote for overdoseLong-term relapse prevention

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