Naltrexone HCl
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MedKoo CAT#: 413539

CAS#: 16676-29-2 (HCl)

Description: Naltrexone HCl is a derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.


Chemical Structure

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Naltrexone HCl
CAS# 16676-29-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 413539
Name: Naltrexone HCl
CAS#: 16676-29-2 (HCl)
Chemical Formula: C20H24ClNO4
Exact Mass: 377.1394
Molecular Weight: 377.865
Elemental Analysis: C, 63.57; H, 6.40; Cl, 9.38; N, 3.71; O, 16.94

Price and Availability

Size Price Availability Quantity
100.0g USD 282.0 2 Weeks
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Related CAS #: 16590-41-3 (free)   16676-29-2 (HCl)  

Synonym: Naltrexone HCl; Naltrexone hydrochloride; En1639A; En-1639A; En 1639A

IUPAC/Chemical Name: (5alpha)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride

InChi Key: RHBRMCOKKKZVRY-ITLPAZOVSA-N

InChi Code: InChI=1S/C20H23NO4.ClH/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11;/h3-4,11,15,18,22,24H,1-2,5-10H2;1H/t15-,18+,19+,20-;/m1./s1

SMILES Code: O=C1[C@@]2([H])[C@]34C5=C(O2)C(O)=CC=C5C[C@@H](N(CC6CC6)CC4)[C@]3(O)CC1.[H]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: 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

Product Data:

Biological target: Naltrexone HCl(PTI-901) is an opioid receptor antagonist.
In vitro activity: The aim of the present study was to assess the immunometabolic effects of naltrexone on microglia cells in in vitro conditions. LDN (low dose naltrexone) induced a shift from highly activated pro-inflammatory phenotype (iNOShighCD206low) to quiescent anti-inflammatory M2 phenotype (iNOSlowCD206high) in BV-2 microglia cells. Changes in the inflammatory profile were accompanied by cellular metabolic switching based on the transition from high glycolysis to mitochondrial oxidative phosphorylation (OXPHOS). LDN-treated cells were able to maintain a metabolically suppressive phenotype by supporting OXPHOS with high oxygen consumption, and also maintain a lower energetic state due to lower lactate production. Reference: Int J Mol Sci. 2021 Aug 5;22(16):8429. https://pubmed.ncbi.nlm.nih.gov/34445130/
In vivo activity: TBI (traumatic brain injury) significantly reduced locomotor activity and increased the expression of IBA1, iNOS, and CD4 in the lesioned cortex. Naltrexone significantly and equally antagonized the motor deficits and expression of IBA1 and iNOS in WT and KO mice. TBI-mediated CD4 protein production was attenuated by naltrexone in WT mice, but not in KO mice. Reference: CNS Neurosci Ther. 2021 Jul;27(7):831-841. https://pubmed.ncbi.nlm.nih.gov/34018697/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 40.0 105.86
Ethanol 10.0 26.46
Ethanol:PBS (pH 7.2) (1:1) 0.5 1.32
Water 56.4 149.25

Preparing Stock Solutions

The following data is based on the product molecular weight 377.865 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. Kučić N, Rački V, Šverko R, Vidović T, Grahovac I, Mršić-Pelčić J. Immunometabolic Modulatory Role of Naltrexone in BV-2 Microglia Cells. Int J Mol Sci. 2021 Aug 5;22(16):8429. doi: 10.3390/ijms22168429. PMID: 34445130; PMCID: PMC8395119. 2. Liu N, Yan L, Shan F, Wang X, Qu N, Handley MK, Ma M. Low-dose naltrexone plays antineoplastic role in cervical cancer progression through suppressing PI3K/AKT/mTOR pathway. Transl Oncol. 2021 Apr;14(4):101028. doi: 10.1016/j.tranon.2021.101028. Epub 2021 Feb 1. PMID: 33540155; PMCID: PMC7859308. 3. Dehe L, Shaqura M, Nordine M, Habazettl H, von Kwiatkowski P, Schluchter H, Shakibaei M, Mousa SA, Schäfer M, Treskatsch S. Chronic Naltrexone Therapy Is Associated with Improved Cardiac Function in Volume Overloaded Rats. Cardiovasc Drugs Ther. 2021 Aug;35(4):733-743. doi: 10.1007/s10557-020-07132-4. Epub 2021 Jan 23. PMID: 33484395; PMCID: PMC8266787. 4. Wang YS, Hung TW, Bae EK, Wu KJ, Hsieh W, Yu SJ. Naltrexone is neuroprotective against traumatic brain injury in mu opioid receptor knockout mice. CNS Neurosci Ther. 2021 Jul;27(7):831-841. doi: 10.1111/cns.13655. Epub 2021 May 21. PMID: 34018697; PMCID: PMC8193702.
In vitro protocol: 1. Kučić N, Rački V, Šverko R, Vidović T, Grahovac I, Mršić-Pelčić J. Immunometabolic Modulatory Role of Naltrexone in BV-2 Microglia Cells. Int J Mol Sci. 2021 Aug 5;22(16):8429. doi: 10.3390/ijms22168429. PMID: 34445130; PMCID: PMC8395119. 2. Liu N, Yan L, Shan F, Wang X, Qu N, Handley MK, Ma M. Low-dose naltrexone plays antineoplastic role in cervical cancer progression through suppressing PI3K/AKT/mTOR pathway. Transl Oncol. 2021 Apr;14(4):101028. doi: 10.1016/j.tranon.2021.101028. Epub 2021 Feb 1. PMID: 33540155; PMCID: PMC7859308.
In vivo protocol: 1. Dehe L, Shaqura M, Nordine M, Habazettl H, von Kwiatkowski P, Schluchter H, Shakibaei M, Mousa SA, Schäfer M, Treskatsch S. Chronic Naltrexone Therapy Is Associated with Improved Cardiac Function in Volume Overloaded Rats. Cardiovasc Drugs Ther. 2021 Aug;35(4):733-743. doi: 10.1007/s10557-020-07132-4. Epub 2021 Jan 23. PMID: 33484395; PMCID: PMC8266787. 2. Wang YS, Hung TW, Bae EK, Wu KJ, Hsieh W, Yu SJ. Naltrexone is neuroprotective against traumatic brain injury in mu opioid receptor knockout mice. CNS Neurosci Ther. 2021 Jul;27(7):831-841. doi: 10.1111/cns.13655. Epub 2021 May 21. PMID: 34018697; PMCID: PMC8193702.

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1: Christou GA, Kiortsis DN. The efficacy and safety of the naltrexone/bupropion combination for the treatment of obesity: an update. Hormones (Athens). 2015 Jul-Sep;14(3):370-5. doi: 10.14310/horm.2002.1600. Review. PubMed PMID: 26188223.

2: Garbutt JC, Greenblatt AM, West SL, Morgan LC, Kampov-Polevoy A, Jordan HS, Bobashev GV. Clinical and biological moderators of response to naltrexone in alcohol dependence: a systematic review of the evidence. Addiction. 2014 Aug;109(8):1274-84. doi: 10.1111/add.12557. Epub 2014 May 23. Review. PubMed PMID: 24661324.

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6: Billes SK, Sinnayah P, Cowley MA. Naltrexone/bupropion for obesity: an investigational combination pharmacotherapy for weight loss. Pharmacol Res. 2014 Jun;84:1-11. doi: 10.1016/j.phrs.2014.04.004. Epub 2014 Apr 19. Review. PubMed PMID: 24754973.

7: Younger J, Parkitny L, McLain D. The use of low-dose naltrexone (LDN) as a novel anti-inflammatory treatment for chronic pain. Clin Rheumatol. 2014 Apr;33(4):451-9. doi: 10.1007/s10067-014-2517-2. Epub 2014 Feb 15. Review. PubMed PMID: 24526250; PubMed Central PMCID: PMC3962576.

8: Larney S, Gowing L, Mattick RP, Farrell M, Hall W, Degenhardt L. A systematic review and meta-analysis of naltrexone implants for the treatment of opioid dependence. Drug Alcohol Rev. 2014 Mar;33(2):115-28. doi: 10.1111/dar.12095. Epub 2013 Dec 3. Review. PubMed PMID: 24299657.

9: Segal D, Macdonald JK, Chande N. Low dose naltrexone for induction of remission in Crohn's disease. Cochrane Database Syst Rev. 2014 Feb 21;2:CD010410. doi: 10.1002/14651858.CD010410.pub2. Review. PubMed PMID: 24558033.

10: Kunøe N, Lobmaier P, Ngo H, Hulse G. Injectable and implantable sustained release naltrexone in the treatment of opioid addiction. Br J Clin Pharmacol. 2014 Feb;77(2):264-71. doi: 10.1111/bcp.12011. Review. PubMed PMID: 23088328; PubMed Central PMCID: PMC4014017.

11: Raffa RB, Taylor R Jr, Pergolizzi JV Jr. Sequestered naltrexone in sustained release morphine or oxycodone - a way to inhibit illicit use? Expert Opin Drug Saf. 2014 Feb;13(2):181-90. doi: 10.1517/14740338.2013.841136. Epub 2013 Nov 11. Review. PubMed PMID: 24206269.

12: Caixàs A, Albert L, Capel I, Rigla M. Naltrexone sustained-release/bupropion sustained-release for the management of obesity: review of the data to date. Drug Des Devel Ther. 2014 Sep 18;8:1419-27. doi: 10.2147/DDDT.S55587. eCollection 2014. Review. PubMed PMID: 25258511; PubMed Central PMCID: PMC4174046.

13: Hulse GK. Improving clinical outcomes for naltrexone as a management of problem alcohol use. Br J Clin Pharmacol. 2013 Nov;76(5):632-41. doi: 10.1111/j.1365-2125.2012.04452.x. Review. PubMed PMID: 22946873; PubMed Central PMCID: PMC3853523.

14: Syed YY, Keating GM. Extended-release intramuscular naltrexone (VIVITROL®): a review of its use in the prevention of relapse to opioid dependence in detoxified patients. CNS Drugs. 2013 Oct;27(10):851-61. doi: 10.1007/s40263-013-0110-x. Review. PubMed PMID: 24018540.

15: Thorsell A. The μ-opioid receptor and treatment response to naltrexone. Alcohol Alcohol. 2013 Jul-Aug;48(4):402-8. doi: 10.1093/alcalc/agt030. Epub 2013 Mar 29. Review. PubMed PMID: 23543091.

16: Jarosz J, Miernik K, Wąchal M, Walczak J, Krumpl G. Naltrexone (50 mg) plus psychotherapy in alcohol-dependent patients: a meta-analysis of randomized controlled trials. Am J Drug Alcohol Abuse. 2013 May;39(3):144-60. doi: 10.3109/00952990.2013.796961. Review. PubMed PMID: 23721530.

17: Gahr M, Kölle MA, Schönfeldt-Lecuona C. [Relapse prevention in alcohol dependence: acamprosate and naltrexone as a combined pharmacological strategy]. Nervenarzt. 2013 May;84(5):584-9. doi: 10.1007/s00115-012-3633-3. Review. German. PubMed PMID: 22892944.

18: Maisel NC, Blodgett JC, Wilbourne PL, Humphreys K, Finney JW. Meta-analysis of naltrexone and acamprosate for treating alcohol use disorders: when are these medications most helpful? Addiction. 2013 Feb;108(2):275-93. doi: 10.1111/j.1360-0443.2012.04054.x. Epub 2012 Oct 17. Review. PubMed PMID: 23075288; PubMed Central PMCID: PMC3970823.

19: Jones HE, Chisolm MS, Jansson LM, Terplan M. Naltrexone in the treatment of opioid-dependent pregnant women: the case for a considered and measured approach to research. Addiction. 2013 Feb;108(2):233-47. doi: 10.1111/j.1360-0443.2012.03811.x. Epub 2012 Apr 4. Review. PubMed PMID: 22471668.

20: Bieńkowski P. [Pharmacological features of naltrexone and its use in the treatment of alcohol dependence]. Psychiatr Pol. 2013 Jan-Feb;47(1):117-26. Review. Polish. PubMed PMID: 23888749.