Naloxone

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MedKoo CAT#: 318301

CAS#: 465-65-6 (free base)

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

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Naloxone
CAS# 465-65-6 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318301
Name: Naloxone
CAS#: 465-65-6 (free base)
Chemical Formula: C19H21NO4
Exact Mass: 327.15
Molecular Weight: 327.374
Elemental Analysis: C, 69.71; H, 6.47; N, 4.28; O, 19.55

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

Synonym: Naloxone, Narcan, Evzio, Naloxona, Naloxonum

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

InChi Key: UZHSEJADLWPNLE-GRGSLBFTSA-N

InChi Code: InChI=1S/C19H21NO4/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/t14-,17+,18+,19-/m1/s1

SMILES Code: C=CCN1CC[C@]23[C@@H]4C(CC[C@@]2(O)[C@H]1CC5=C3C(O4)=C(O)C=C5)=O

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, 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

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Naloxone is a μ-opioid receptor (MOR) inverse agonist.
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/

Preparing Stock Solutions

The following data is based on the product molecular weight 327.37 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.

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1: McDonald R, Strang J. Are take-home naloxone programmes effective? Systematic review utilizing application of the Bradford Hill criteria. Addiction. 2016 Mar 30. doi: 10.1111/add.13326. [Epub ahead of print] Review. PubMed PMID: 27028542.

2: Sivilotti ML. Flumazenil, naloxone and the 'coma cocktail'. Br J Clin Pharmacol. 2016 Mar;81(3):428-36. doi: 10.1111/bcp.12731. Epub 2015 Sep 21. Review. PubMed PMID: 26469689; PubMed Central PMCID: PMC4767210.

3: Strang J, McDonald R, Alqurshi A, Royall P, Taylor D, Forbes B. Naloxone without the needle - systematic review of candidate routes for non-injectable naloxone for opioid overdose reversal. Drug Alcohol Depend. 2016 Mar 9. pii: S0376-8716(16)00141-1. doi: 10.1016/j.drugalcdep.2016.02.042. [Epub ahead of print] Review. PubMed PMID: 26996745.

4: Howlett C, Gonzalez R, Yerram P, Faley B. Use of naloxone for reversal of life-threatening opioid toxicity in cancer-related pain. J Oncol Pharm Pract. 2016 Feb;22(1):114-20. doi: 10.1177/1078155214551589. Epub 2014 Sep 16. Review. PubMed PMID: 25227231.

5: de Biase S, Valente M, Gigli GL. Intractable restless legs syndrome: role of prolonged-release oxycodone-naloxone. Neuropsychiatr Dis Treat. 2016 Feb 23;12:417-25. doi: 10.2147/NDT.S81186. eCollection 2016. Review. PubMed PMID: 26966363; PubMed Central PMCID: PMC4770072.

6: Kim HK, Nelson LS. Reducing the harm of opioid overdose with the safe use of naloxone : a pharmacologic review. Expert Opin Drug Saf. 2015 Jul;14(7):1137-46. doi: 10.1517/14740338.2015.1037274. Epub 2015 Apr 12. Review. PubMed PMID: 25865597.

7: Wermeling DP. Review of naloxone safety for opioid overdose: practical considerations for new technology and expanded public access. Ther Adv Drug Saf. 2015 Feb;6(1):20-31. doi: 10.1177/2042098614564776. Review. PubMed PMID: 25642320; PubMed Central PMCID: PMC4308412.

8: Soyka M. Buprenorphine-naloxone buccal soluble film for the treatment of opioid dependence: current update. Expert Opin Drug Deliv. 2015 Feb;12(2):339-47. doi: 10.1517/17425247.2014.953479. Epub 2014 Aug 25. Review. PubMed PMID: 25156759.

9: Bunavail: another buprenorphine/naloxone formulation for opioid dependence. Med Lett Drugs Ther. 2015 Feb 2;57(1461):19-20. Review. PubMed PMID: 25629812.

10: Fanelli G, Fanelli A. Developments in managing severe chronic pain: role of oxycodone-naloxone extended release. Drug Des Devel Ther. 2015 Jul 22;9:3811-6. doi: 10.2147/DDDT.S73561. eCollection 2015. Review. PubMed PMID: 26229442; PubMed Central PMCID: PMC4516191.

11: Soyka M. New developments in the management of opioid dependence: focus on sublingual buprenorphine-naloxone. Subst Abuse Rehabil. 2015 Jan 6;6:1-14. doi: 10.2147/SAR.S45585. eCollection 2015. Review. PubMed PMID: 25610012; PubMed Central PMCID: PMC4293937.

12: Ahmad SA, Scolnik D, Snehal V, Glatstein M. Use of naloxone for clonidine intoxication in the pediatric age group: case report and review of the literature. Am J Ther. 2015 Jan-Feb;22(1):e14-6. doi: 10.1097/MJT.0b013e318293b0e8. Review. PubMed PMID: 23782760.

13: Morlion B, Clemens KE, Dunlop W. Quality of life and healthcare resource in patients receiving opioids for chronic pain: a review of the place of oxycodone/naloxone. Clin Drug Investig. 2015 Jan;35(1):1-11. doi: 10.1007/s40261-014-0254-6. Review. PubMed PMID: 25479959; PubMed Central PMCID: PMC4281369.

14: Robinson A, Wermeling DP. Intranasal naloxone administration for treatment of opioid overdose. Am J Health Syst Pharm. 2014 Dec 15;71(24):2129-35. doi: 10.2146/ajhp130798. Review. PubMed PMID: 25465584.

15: Hard B. Management of opioid painkiller dependence in primary care: ongoing recovery with buprenorphine/naloxone. BMJ Case Rep. 2014 Nov 28;2014. pii: bcr2014207308. doi: 10.1136/bcr-2014-207308. Review. PubMed PMID: 25432908.

16: Davis CS, Southwell JK, Niehaus VR, Walley AY, Dailey MW. Emergency medical services naloxone access: a national systematic legal review. Acad Emerg Med. 2014 Oct;21(10):1173-7. doi: 10.1111/acem.12485. Review. PubMed PMID: 25308142.

17: Administration of Naloxone in a Home or Community Setting: A Review of the Clinical Effectiveness, Cost-effectiveness, and Guidelines [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2014 Jun 20. Available from http://www.ncbi.nlm.nih.gov/books/NBK259232/ PubMed PMID: 25520990.

18: Clark AK, Wilder CM, Winstanley EL. A systematic review of community opioid overdose prevention and naloxone distribution programs. J Addict Med. 2014 May-Jun;8(3):153-63. doi: 10.1097/ADM.0000000000000034. Review. PubMed PMID: 24874759.

19: Chen KY, Chen L, Mao J. Buprenorphine-naloxone therapy in pain management. Anesthesiology. 2014 May;120(5):1262-74. doi: 10.1097/ALN.0000000000000170. Review. PubMed PMID: 24509068; PubMed Central PMCID: PMC3999180.

20: Rosa P, Federica M, Annamaria V, Fabiana S, Anna V. Combined administration of oxycodone/naloxone in chronic osteo-articular diseases pain therapy. Transl Med UniSa. 2014 Apr 24;9:38-42. eCollection 2014 Apr. Review. PubMed PMID: 24809034; PubMed Central PMCID: PMC4012374.