Naloxone HCl
featured

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

MedKoo CAT#: 329670

CAS#: 357-08-4 (HCl)

Description: Naloxone is a μ-opioid receptor (MOR) inverse agonist. Naloxone has an extremely high affinity for μ-opioid receptors in the central nervous system (CNS). Its rapid blockade of those receptors often produces rapid onset of withdrawal symptoms. Naloxone also has an antagonist action, though with a lower affinity, at κ- (KOR) and δ-opioid receptors (DOR). The mechanism of action is not completely understood, but studies suggest it functions to produce withdrawal symptoms by competing for opiate receptor sites within the CNS (a competitive antagonist, not a direct agonist), thereby preventing the action of both endogenous and xenobiotic opiates on these receptors without directly producing any effects itself. Naloxone was approved for opioid overdose by the Food and Drug Administration in 1971

Chemical Structure

img
Naloxone HCl
CAS# 357-08-4 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329670
Name: Naloxone HCl
CAS#: 357-08-4 (HCl)
Chemical Formula: C19H22ClNO4
Exact Mass: 0.00
Molecular Weight: 363.840
Elemental Analysis: C, 62.72; H, 6.10; Cl, 9.74; N, 3.85; O, 17.59

Price and Availability

Size Price Availability Quantity
200mg USD 110 Ready to ship
500mg USD 190 Ready to ship
1g USD 350 Ready to ship
2g USD 650 Ready to ship
5g USD 1350 Ready to ship
10g USD 2450 Ready to ship
20g USD 3850 2 weeks
Bulk inquiry

Related CAS #: 465-65-6 (free base)   51481-60-8 (HCl hydrate)   357-08-4 (HCl)    

Synonym: Naloxone HCl; EN-15304; EN15304; EN 15304; NIH7890; Naloxone hydrochloride; Narcan; Narcanti; Nalonee;

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

InChi Key: RGPDIGOSVORSAK-STHHAXOLSA-N

InChi Code: InChI=1S/C19H21NO4.ClH/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11;/h2-4,14,17,21,23H,1,5-10H2;1H/t14-,17+,18+,19-;/m1./s1

SMILES Code: O=C1[C@@](OC2=C(O)C=CC3=C24)([H])[C@@]54CCN(CC=C)[C@@](C3)([H])[C@]5(O)CC1.[H]Cl

Appearance: Solid powder

Purity: >99% (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: Naloxone was patented in 1961 and approved for opioid overdose by the Food and Drug Administration in 1971. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Naloxone is available as a generic medication. Its wholesale price in the developing world is between US$0.50 and 5.30 per dose. The vials of medication are not very expensive (less than 25 USD) in the United States. The price for a package of two auto-injectors in the US, however, has increased from $690 in 2014 to $4,500 in 2016. The Ki affinity values of (−)-naloxone for the MOR, KOR, and DOR have been reported as 0.559 nM, 4.91 nM, and 36.5 nM, respectively, whereas for (+)-naloxone, 3,550 nM, 8,950 nM, and 122,000 nM, respectively, have been reported. As such, (−)-naloxone appears to be the active isomer. Moreover, these data suggest that naloxone binds to the MOR with approximately 9-fold greater affinity relative to the KOR and around 60-fold greater affinity relative to the DOR.

Biological target: Naloxone HCl is an opioid inverse agonist drug used to counter the effects of opiate overdose.
In vitro activity: The results showed that morphine directly enhanced microglia chemotaxis and membrane ruffling and that these actions were accompanied by an increase in Iba1 protein expression in the microglia, especially in the ruffling membrane. Pretreatment with 1nM (+)-naloxone significantly inhibited microglia migration, activation, and reduced Iba1 expression in microglia. On the basis of these results, Iba1 is involved in microglia migration and that ultralow dose (+)-naloxone may regulate actin cytoskeleton dynamics. Reference: J Formos Med Assoc. 2015 May;114(5):446-55. https://pubmed.ncbi.nlm.nih.gov/25649471/
In vivo activity: The addition of naloxone at 1.0 or 2.0 µM significantly inhibited the LPS-induced production of TNFα and IL-1β (P < 0.01 for all comparisons). The lowest concentration of naloxone (0.5 µM) significantly inhibited IL-1β (P < 0.05), but not TNF-α production. Western blotting showed that p38 MAPK, JNK and ERK were constitutively present in microglia (Fig. 2A). LPS treatment induced a visible increase in the amount of P-p38 MAPK, but p38 MAPK, JNK, P-JNK, ERK and P-ERK appeared unchanged. Pretreatment with naloxone dose-dependently reversed the LPS-induced increase in P-p38 MAPK (P < 0.05, Fig. 2B). Naloxone had no significant effect on the levels of P-JNK or P-ERK (Fig. 2B). Immunofluoresence microscopy showed weak P-p38 MAPK immunostaining in OX42-positive rat microglial cells in untreated cultures (Fig. 3A). LPS-activation was accompanied by an increase in P-p38 MAPK immunostaining (Fig. 3B). Pretreatment with naloxone (Fig. 3C) resulted in P-p38 MAPK staining similar to that seen in untreated control cultures. Reference: J Int Med Res. 2012;40(4):1438-48. https://pubmed.ncbi.nlm.nih.gov/22971495/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 3.0 8.20

Preparing Stock Solutions

The following data is based on the product molecular weight 363.84 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. Bimonte S, Barbieri A, Cascella M, Rea D, Palma G, Del Vecchio V, Forte CA, Del Prato F, Arra C, Cuomo A. The effects of naloxone on human breast cancer progression: in vitro and in vivo studies on MDA.MB231 cells. Onco Targets Ther. 2018 Jan 3;11:185-191. doi: 10.2147/OTT.S145780. PMID: 29379300; PMCID: PMC5757202. 2. Tsai RY, Cheng YC, Wong CS. (+)-Naloxone inhibits morphine-induced chemotaxis via prevention of heat shock protein 90 cleavage in microglia. J Formos Med Assoc. 2015 May;114(5):446-55. doi: 10.1016/j.jfma.2014.12.004. Epub 2015 Jan 31. PMID: 25649471. 3. Bimonte S, Barbieri A, Cascella M, Rea D, Palma G, Luciano A, Forte CA, Cuomo A, Arra C. Naloxone Counteracts the Promoting Tumor Growth Effects Induced by Morphine in an Animal Model of Triple-negative Breast Cancer. In Vivo. 2019 May-Jun;33(3):821-825. doi: 10.21873/invivo.11545. PMID: 31028203; PMCID: PMC6559888. 4. Xu YF, Fu LL, Jiang CH, Qin YW, Ni YQ, Fan JW. Naloxone inhibition of lipopolysaccharide-induced activation of retinal microglia is partly mediated via the p38 mitogen activated protein kinase signalling pathway. J Int Med Res. 2012;40(4):1438-48. doi: 10.1177/147323001204000422. PMID: 22971495.
In vitro protocol: 1. Bimonte S, Barbieri A, Cascella M, Rea D, Palma G, Del Vecchio V, Forte CA, Del Prato F, Arra C, Cuomo A. The effects of naloxone on human breast cancer progression: in vitro and in vivo studies on MDA.MB231 cells. Onco Targets Ther. 2018 Jan 3;11:185-191. doi: 10.2147/OTT.S145780. PMID: 29379300; PMCID: PMC5757202. 2. Tsai RY, Cheng YC, Wong CS. (+)-Naloxone inhibits morphine-induced chemotaxis via prevention of heat shock protein 90 cleavage in microglia. J Formos Med Assoc. 2015 May;114(5):446-55. doi: 10.1016/j.jfma.2014.12.004. Epub 2015 Jan 31. PMID: 25649471.
In vivo protocol: 1. Bimonte S, Barbieri A, Cascella M, Rea D, Palma G, Luciano A, Forte CA, Cuomo A, Arra C. Naloxone Counteracts the Promoting Tumor Growth Effects Induced by Morphine in an Animal Model of Triple-negative Breast Cancer. In Vivo. 2019 May-Jun;33(3):821-825. doi: 10.21873/invivo.11545. PMID: 31028203; PMCID: PMC6559888. 2. Xu YF, Fu LL, Jiang CH, Qin YW, Ni YQ, Fan JW. Naloxone inhibition of lipopolysaccharide-induced activation of retinal microglia is partly mediated via the p38 mitogen activated protein kinase signalling pathway. J Int Med Res. 2012;40(4):1438-48. doi: 10.1177/147323001204000422. PMID: 22971495.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Abd-Elsayed A, Albert CA, Fischer M, Anderson B. Naloxone Academic Detailing: Role of Community Outreach Teaching. Curr Pain Headache Rep. 2018 Aug 27;22(11):72. doi: 10.1007/s11916-018-0730-4. Review. PubMed PMID: 30151695.

2: Serafini G, Adavastro G, Canepa G, De Berardis D, Valchera A, Pompili M, Nasrallah H, Amore M. The Efficacy of Buprenorphine in Major Depression, Treatment-Resistant Depression and Suicidal Behavior: A Systematic Review. Int J Mol Sci. 2018 Aug 15;19(8). pii: E2410. doi: 10.3390/ijms19082410. Review. PubMed PMID: 30111745; PubMed Central PMCID: PMC6121503.

3: Adler JA, Mallick-Searle T. An overview of abuse-deterrent opioids and recommendations for practical patient care. J Multidiscip Healthc. 2018 Jul 11;11:323-332. doi: 10.2147/JMDH.S166915. eCollection 2018. Review. PubMed PMID: 30026658; PubMed Central PMCID: PMC6045950.

4: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK501681/ PubMed PMID: 30000741.

5: Mozaffari S, Nikfar S, Abdollahi M. Methylnaltrexone bromide for the treatment of opioid-induced constipation. Expert Opin Pharmacother. 2018 Jul;19(10):1127-1135. doi: 10.1080/14656566.2018.1491549. Epub 2018 Jul 6. Review. PubMed PMID: 29979903.

6: Peglow SL, Binswanger IA. Preventing Opioid Overdose in the Clinic and Hospital: Analgesia and Opioid Antagonists. Med Clin North Am. 2018 Jul;102(4):621-634. doi: 10.1016/j.mcna.2018.02.005. Review. PubMed PMID: 29933819; PubMed Central PMCID: PMC6029888.

7: Behar E, Bagnulo R, Coffin PO. Acceptability and feasibility of naloxone prescribing in primary care settings: A systematic review. Prev Med. 2018 Sep;114:79-87. doi: 10.1016/j.ypmed.2018.06.005. Epub 2018 Jun 15. Review. PubMed PMID: 29908763; PubMed Central PMCID: PMC6082708.

8: Kuczyńska K, Grzonkowski P, Kacprzak Ł, Zawilska JB. Abuse of fentanyl: An emerging problem to face. Forensic Sci Int. 2018 Aug;289:207-214. doi: 10.1016/j.forsciint.2018.05.042. Epub 2018 Jun 2. Review. PubMed PMID: 29902699.

9: Andresen V, Layer P. Medical Therapy of Constipation: Current Standards and Beyond. Visc Med. 2018 Apr;34(2):123-127. doi: 10.1159/000488695. Epub 2018 Apr 12. Review. PubMed PMID: 29888241; PubMed Central PMCID: PMC5981595.

10: Candy B, Jones L, Vickerstaff V, Larkin PJ, Stone P. Mu-opioid antagonists for opioid-induced bowel dysfunction in people with cancer and people receiving palliative care. Cochrane Database Syst Rev. 2018 Jun 5;6:CD006332. doi: 10.1002/14651858.CD006332.pub3. Review. PubMed PMID: 29869799.

11: Musy SN, Ausserhofer D, Schwendimann R, Rothen HU, Jeitziner MM, Rutjes AW, Simon M. Trigger Tool-Based Automated Adverse Event Detection in Electronic Health Records: Systematic Review. J Med Internet Res. 2018 May 30;20(5):e198. doi: 10.2196/jmir.9901. Review. PubMed PMID: 29848467; PubMed Central PMCID: PMC6000482.

12: Anim-Somuah M, Smyth RM, Cyna AM, Cuthbert A. Epidural versus non-epidural or no analgesia for pain management in labour. Cochrane Database Syst Rev. 2018 May 21;5:CD000331. doi: 10.1002/14651858.CD000331.pub4. Review. PubMed PMID: 29781504.

13: Norman K, Nappe TM. Toxicity, Alpha Receptor Agonists. 2018 May 10. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2018 Jan-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500023/ PubMed PMID: 29763199.

14: Sanello A, Gausche-Hill M, Mulkerin W, Sporer KA, Brown JF, Koenig KL, Rudnick EM, Salvucci AA, Gilbert GH. Altered Mental Status: Current Evidence-based Recommendations for Prehospital Care. West J Emerg Med. 2018 May;19(3):527-541. doi: 10.5811/westjem.2018.1.36559. Epub 2018 Mar 8. Review. PubMed PMID: 29760852; PubMed Central PMCID: PMC5942021.

15: Anguelova GV, Vlak MHM, Kurvers AGY, Rijsman RM. Pharmacologic and Nonpharmacologic Treatment of Restless Legs Syndrome. Sleep Med Clin. 2018 Jun;13(2):219-230. doi: 10.1016/j.jsmc.2018.02.005. Review. PubMed PMID: 29759272.

16: Winkelmann J, Allen RP, Högl B, Inoue Y, Oertel W, Salminen AV, Winkelman JW, Trenkwalder C, Sampaio C. Treatment of restless legs syndrome: Evidence-based review and implications for clinical practice (Revised 2017)(§). Mov Disord. 2018 Jul;33(7):1077-1091. doi: 10.1002/mds.27260. Epub 2018 May 14. Review. PubMed PMID: 29756335.

17: Ragguett RM, Rong C, Rosenblat JD, Ho RC, McIntyre RS. Pharmacodynamic and pharmacokinetic evaluation of buprenorphine + samidorphan for the treatment of major depressive disorder. Expert Opin Drug Metab Toxicol. 2018 Apr;14(4):475-482. doi: 10.1080/17425255.2018.1459564. Epub 2018 Apr 6. Review. PubMed PMID: 29621905.

18: Ostling PS, Davidson KS, Anyama BO, Helander EM, Wyche MQ, Kaye AD. America's Opioid Epidemic: a Comprehensive Review and Look into the Rising Crisis. Curr Pain Headache Rep. 2018 Apr 4;22(5):32. doi: 10.1007/s11916-018-0685-5. Review. PubMed PMID: 29619569.

19: Ali S, Tahir B, Jabeen S, Malik M. Methadone Treatment of Opiate Addiction: A Systematic Review of Comparative Studies. Innov Clin Neurosci. 2017 Aug 1;14(7-8):8-19. eCollection 2017 Jul-Aug. Review. PubMed PMID: 29616150; PubMed Central PMCID: PMC5880371.

20: Parker CE, Nguyen TM, Segal D, MacDonald JK, Chande N. Low dose naltrexone for induction of remission in Crohn's disease. Cochrane Database Syst Rev. 2018 Apr 1;4:CD010410. doi: 10.1002/14651858.CD010410.pub3. Review. PubMed PMID: 29607497.