Naloxonazine Dihydrochloride
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MedKoo CAT#: 562325

CAS#: 880759-65-9

Description: Naloxonazine Dihydrochloride is a potent and selective antagonist for μ1 opioid receptors.


Chemical Structure

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Naloxonazine Dihydrochloride
CAS# 880759-65-9

Theoretical Analysis

MedKoo Cat#: 562325
Name: Naloxonazine Dihydrochloride
CAS#: 880759-65-9
Chemical Formula: C38H44Cl2N4O6
Exact Mass: 0.00
Molecular Weight: 723.692
Elemental Analysis: C, 63.07; H, 6.13; Cl, 9.80; N, 7.74; O, 13.26

Price and Availability

Size Price Availability Quantity
10mg USD 250
50mg USD 600
250mg USD 1450
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Synonym: Naloxonazine Dihydrochloride; Naloxonazine 2HCl;

IUPAC/Chemical Name: (4aS,7aS,Z)-3-allyl-7-(((4aS,7aS,12bS,Z)-3-allyl-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-ylidene)hydrazono)-1,2,3,4,5,6,7,7a-octahydro-4aH-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol dihydrochloride

InChi Key: VIAIHLLKDJKEKM-PATAXOJOSA-N

InChi Code: InChI=1S/C38H42N4O6.2ClH/c1-3-15-41-17-13-35-29-21-5-7-25(43)31(29)47-33(35)23(9-11-37(35,45)27(41)19-21)39-40-24-10-12-38(46)28-20-22-6-8-26(44)32-30(22)36(38,34(24)48-32)14-18-42(28)16-4-2;;/h3-8,27-28,33-34,43-46H,1-2,9-20H2;2*1H/b39-23-,40-24-;;/t27?,28?,33-,34-,35+,36?,37-,38-;;/m1../s1

SMILES Code: C=CCN1CCC2([C@H](O3)/C(CC4)=N\N=C5CC[C@](C(C6)N(CC=C)CC7)(O)[C@]87[C@@H]\5OC9=C(O)C=CC6=C98)[C@]4(O)C1CC%10=C2C3=C(O)C=C%10.Cl.Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Naloxonazine dihydrochloride is a specific μ-opioid receptor antagonist with an IC50 of 5.4 nM.
In vitro activity: Naloxonazine, on the other hand, produces a potent, dose-dependent inhibition of binding at opiate binding sites which is resistant to washing. Despite the washes, naloxonazine at 50 nm abolishes high affinity binding with some inhibition seen at concentrations down to 10 nM. Reference: Life Sci. 1982 Sep 20-27;31(12-13):1385-8. https://pubmed.ncbi.nlm.nih.gov/6292633/
In vivo activity: This study investigates the effects of naloxonazine, a specific mu-opioid receptor antagonist, on the locomotor behavioral response and phosphorylation pattern of dopamine and cAMP-regulated phosphoprotein of Mr32 (DARPP-32) in striatal dopaminergic transmissions induced by acute administration of METH to mice. Mice were injected with a single dose of naloxonazine (20 mg/kg, i.p.) 60 min before injecting (i.p.) either saline or 1 mg/kg of METH. Results show that pretreatment with naloxonazine significantly attenuated the acute METH-induced increase in locomotor activity and phosphor-Thr75 DARPP-32 levels. Reference: Toxicol Lett. 2012 Jul 7;212(1):61-5. https://pubmed.ncbi.nlm.nih.gov/22564758/

Preparing Stock Solutions

The following data is based on the product molecular weight 723.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. De Muylder G, Vanhollebeke B, Caljon G, Wolfe AR, McKerrow J, Dujardin JC. Naloxonazine, an Amastigote-Specific Compound, Affects Leishmania Parasites through Modulation of Host-Encoded Functions. PLoS Negl Trop Dis. 2016 Dec 30;10(12):e0005234. doi: 10.1371/journal.pntd.0005234. PMID: 28036391; PMCID: PMC5201425. 2. Hahn EF, Pasternak GW. Naloxonazine, a potent, long-lasting inhibitor of opiate binding sites. Life Sci. 1982 Sep 20-27;31(12-13):1385-8. doi: 10.1016/0024-3205(82)90387-3. PMID: 6292633. 3. Chien CC, Lee YJ, Fan LW, Ho IK, Tien LT. Naloxonazine, a specific mu-opioid receptor antagonist, attenuates the increment of locomotor activity induced by acute methamphetamine in mice. Toxicol Lett. 2012 Jul 7;212(1):61-5. doi: 10.1016/j.toxlet.2012.04.022. Epub 2012 May 4. PMID: 22564758. 4. Mhatre M, Holloway F. Micro1-opioid antagonist naloxonazine alters ethanol discrimination and consumption. Alcohol. 2003 Feb;29(2):109-16. doi: 10.1016/s0741-8329(03)00021-1. PMID: 12782252.
In vitro protocol: 1. De Muylder G, Vanhollebeke B, Caljon G, Wolfe AR, McKerrow J, Dujardin JC. Naloxonazine, an Amastigote-Specific Compound, Affects Leishmania Parasites through Modulation of Host-Encoded Functions. PLoS Negl Trop Dis. 2016 Dec 30;10(12):e0005234. doi: 10.1371/journal.pntd.0005234. PMID: 28036391; PMCID: PMC5201425. 2. Hahn EF, Pasternak GW. Naloxonazine, a potent, long-lasting inhibitor of opiate binding sites. Life Sci. 1982 Sep 20-27;31(12-13):1385-8. doi: 10.1016/0024-3205(82)90387-3. PMID: 6292633.
In vivo protocol: 1. Chien CC, Lee YJ, Fan LW, Ho IK, Tien LT. Naloxonazine, a specific mu-opioid receptor antagonist, attenuates the increment of locomotor activity induced by acute methamphetamine in mice. Toxicol Lett. 2012 Jul 7;212(1):61-5. doi: 10.1016/j.toxlet.2012.04.022. Epub 2012 May 4. PMID: 22564758. 2. Mhatre M, Holloway F. Micro1-opioid antagonist naloxonazine alters ethanol discrimination and consumption. Alcohol. 2003 Feb;29(2):109-16. doi: 10.1016/s0741-8329(03)00021-1. PMID: 12782252.

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1: Xia M, Guo V, Huang R, Shahane SA, Austin CP, Nirenberg M, Sharma SK. Inhibition of morphine-induced cAMP overshoot: a cell-based assay model in a high-throughput format. Cell Mol Neurobiol. 2011 Aug;31(6):901-7. doi: 10.1007/s10571-011-9689-y. Epub 2011 May 20. PubMed PMID: 21598037; PubMed Central PMCID: PMC3146558.

2: Joly N, Vaillant C, Cohen AM, Martin P, El Essassi M, Massoui M, Banoub J. Structural determination of the novel fragmentation routes of zwitteronic morphine opiate antagonists naloxonazine and naloxone hydrochlorides using electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(6):1062-74. PubMed PMID: 17310471.