Naltrexone | CAS#16590-41-3 | CAS#16676-29-2 | Antidote

Naltrexone
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318302

CAS#: 16590-41-3 (free)

Description: Naltrexone is a drug that reverses the effects of opioids and is used primarily in the management of alcohol dependence and opioid dependence. It should not be confused with naloxone or nalorphine, which are used in emergency cases of opioid overdose.

Chemical Structure

Naltrexone

CAS# 16590-41-3 (free)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318302
Name: Naltrexone
CAS#: 16590-41-3 (free)
Chemical Formula: C20H23NO4
Exact Mass: 341.16
Molecular Weight: 341.401
Elemental Analysis: C, 70.36; H, 6.79; N, 4.10; O, 18.75

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 550
200mg	USD 950
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 16590-41-3 (free) 16676-29-2 (HCl)

Synonym: Naltrexone, Revia, Depade, Vivitrol, Celupan, EN-1639A, EN 1639A, EN1639A

IUPAC/Chemical Name: (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

InChi Key: DQCKKXVULJGBQN-XFWGSAIBSA-N

InChi Code: InChI=1S/C20H23NO4/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/t15-,18+,19+,20-/m1/s1

SMILES Code: C1CC1CN2CC[C@]34[C@@H]5C(=O)CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O

Appearance: Off-white to yellow 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, not in water

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

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Product Data:

Product Data

Instruction:

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Biological target:	Naltrexone is a drug that reverses the effects of opioids and is used primarily in the management of alcohol dependence and opioid dependence.
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/

Preparing Stock Solutions

The following data is based on the product molecular weight 341.40 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.

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.

3: Taylor R, Raffa RB, Pergolizzi JV. Opioid formulations with sequestered naltrexone: a perspective review. Ther Adv Drug Saf. 2014 Jun;5(3):129-37. doi: 10.1177/2042098614526769. Review. PubMed PMID: 25083268; PubMed Central PMCID: PMC4110852.

4: Goonoo N, Bhaw-Luximon A, Ujoodha R, Jhugroo A, Hulse GK, Jhurry D. Naltrexone: a review of existing sustained drug delivery systems and emerging nano-based systems. J Control Release. 2014 Jun 10;183:154-66. doi: 10.1016/j.jconrel.2014.03.046. Epub 2014 Apr 2. Review. PubMed PMID: 24704710.

5: Verpeut JL, Bello NT. Drug safety evaluation of naltrexone/bupropion for the treatment of obesity. Expert Opin Drug Saf. 2014 Jun;13(6):831-41. doi: 10.1517/14740338.2014.909405. Epub 2014 Apr 28. Review. PubMed PMID: 24766397.

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.

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