Naltrindole

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MedKoo CAT#: 414393

CAS#: 111555-53-4

Description: Naltrindole is a delta opioid receptor antagonist.

Chemical Structure

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Naltrindole
CAS# 111555-53-4
Instruction

Theoretical Analysis

MedKoo Cat#: 414393
Name: Naltrindole
CAS#: 111555-53-4
Chemical Formula: C26H26N2O3
Exact Mass: 414.19
Molecular Weight: 414.510
Elemental Analysis: C, 75.34; H, 6.32; N, 6.76; O, 11.58

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Naltrindole; NIH10589; NIH-10589; NIH 10589

IUPAC/Chemical Name: 4,8-Methanobenzofuro(2,3-a)pyrido(4,3-b)carbazole-1,8a(9H)-diol, 7-(cyclopropylmethyl)-5,6,7,8,14,14b-hexahydro-, (4bS,8R,8aS,14bR)-

InChi Key: WIYUZYBFCWCCQJ-IFKAHUTRSA-N

InChi Code: InChI=1S/C26H26N2O3/c29-19-8-7-15-11-20-26(30)12-17-16-3-1-2-4-18(16)27-22(17)24-25(26,21(15)23(19)31-24)9-10-28(20)13-14-5-6-14/h1-4,7-8,14,20,24,27,29-30H,5-6,9-13H2/t20-,24+,25+,26-/m1/s1

SMILES Code: OC1=C(O2)C([C@@]34[C@]2([H])C(NC5=C6C=CC=C5)=C6C[C@@]3(O)[C@]7([H])N(CC8CC8)CC4)=C(C7)C=C1

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 414.51 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:
In vitro protocol:
In vivo protocol:

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1: Yang PP, Yeh TK, Loh HH, Law PY, Wang Y, Tao PL. Delta-opioid receptor antagonist naltrindole reduces oxycodone addiction and constipation in mice. Eur J Pharmacol. 2019 Jun 5;852:265-273. doi: 10.1016/j.ejphar.2019.04.009. Epub 2019 Apr 6. PMID: 30959048.

2: Moravčíková L, Královičová J, Lacinová Ľ. SNC80 and naltrindole modulate voltage-dependent sodium, potassium and calcium channels via a putatively delta opioid receptor-independent mechanism. Gen Physiol Biophys. 2018 May;37(3):299-307. doi: 10.4149/gpb_2018009. Epub 2018 Mar 28. PMID: 29589835.

3: Mundra JJ, Terskiy A, Howells RD. Naltrindole inhibits human multiple myeloma cell proliferation in vitro and in a murine xenograft model in vivo. J Pharmacol Exp Ther. 2012 Aug;342(2):273-87. doi: 10.1124/jpet.112.194159. Epub 2012 Apr 26. PMID: 22537770; PMCID: PMC3400794.

4: Iwamatsu C, Hayakawa D, Kono T, Honjo A, Ishizaki S, Hirayama S, Gouda H, Fujii H. Effects of N-Substituents on the Functional Activities of Naltrindole Derivatives for the δ Opioid Receptor: Synthesis and Evaluation of Sulfonamide Derivatives. Molecules. 2020 Aug 20;25(17):3792. doi: 10.3390/molecules25173792. PMID: 32825410; PMCID: PMC7503831.

5: Nikbakhsh R, Nikbakhsh R, Radmard M, Tafazolimoghadam A, Haj-Mirzaian A, Pirri F, Noormohammady P, Sabouri M, Shababi N, Ziai SA, Dehpour AR. The possible role of nitric oxide in anti-convulsant effects of Naltrindole in seizure-induced by social isolation stress in male mice. Biomed Pharmacother. 2020 Sep;129:110453. doi: 10.1016/j.biopha.2020.110453. Epub 2020 Jun 27. PMID: 32603891.

6: Patterson AB, Gordon FJ, Holtzman SG. Naltrindole, a selective delta-opioid receptor antagonist, potentiates the lethal effects of cocaine by a central mechanism of action. Eur J Pharmacol. 1997 Aug 20;333(1):47-54. doi: 10.1016/s0014-2999(97)01090-x. PMID: 9311660.

7: Nemoto T, Iihara Y, Hirayama S, Iwai T, Higashi E, Fujii H, Nagase H. Naltrindole derivatives with fluorinated ethyl substituents on the 17-nitrogen as δ opioid receptor inverse agonists. Bioorg Med Chem Lett. 2015 Aug 1;25(15):2927-30. doi: 10.1016/j.bmcl.2015.05.038. Epub 2015 May 22. PMID: 26048798.

8: Kamei J, Iwamoto Y, Suzuki T, Misawa M, Nagase H, Kasuya Y. Antitussive effects of naltrindole, a selective delta-opioid receptor antagonist, in mice and rats. Eur J Pharmacol. 1993 Nov 9;249(2):161-5. doi: 10.1016/0014-2999(93)90428-k. PMID: 8287897.

9: Granier S, Manglik A, Kruse AC, Kobilka TS, Thian FS, Weis WI, Kobilka BK. Structure of the δ-opioid receptor bound to naltrindole. Nature. 2012 May 16;485(7398):400-4. doi: 10.1038/nature11111. PMID: 22596164; PMCID: PMC3523198.

10: Chen YL, Law PY, Loh HH. Inhibition of akt/protein kinase B signaling by naltrindole in small cell lung cancer cells. Cancer Res. 2004 Dec 1;64(23):8723-30. doi: 10.1158/0008-5472.CAN-03-3091. PMID: 15574783.