Naloxol

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

MedKoo CAT#: 535278

CAS#: 58691-01-3

Description: Naloxol is a bioactive chemical.


Chemical Structure

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Naloxol
CAS# 58691-01-3

Theoretical Analysis

MedKoo Cat#: 535278
Name: Naloxol
CAS#: 58691-01-3
Chemical Formula: C19H23NO4
Exact Mass: 329.16
Molecular Weight: 329.396
Elemental Analysis: C, 69.28; H, 7.04; N, 4.25; O, 19.43

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.

Request quote for custom synthesis

Synonym: Naloxol

IUPAC/Chemical Name: Morphinan-3,6,14-triol, 4,5-epoxy-17-(2-propen-1-yl)-, (5alpha)-

InChi Key: HMWHERQFMBEHNG-DMOGFEGYSA-N

InChi Code: InChI=1S/C19H23NO4/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/h2-4,13-14,17,21-23H,1,5-10H2/t13?,14-,17+,18+,19-/m1/s1

SMILES Code: OC1=CC=C2C[C@@H](N(CC=C)CC3)[C@]4(O)CCC(O)[C@@]5([H])[C@]43C2=C1O5

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

Shelf Life: >3 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 329.40 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.

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: Schulteis G, Chiang D, Archer C. Relative potency of the opioid antagonists naloxone and 6-alpha-naloxol to precipitate withdrawal from acute morphine dependence varies with time post-antagonist. Pharmacol Biochem Behav. 2009 Mar;92(1):157-63. doi: 10.1016/j.pbb.2008.11.007. Epub 2008 Nov 24. PMID: 19061911; PMCID: PMC2652854.


2: Haidari M, Mansani S, Ponds D, Romero L, Alsaab S. Consumption of Movantik™ (Naloxegol) results in detection of naloxone in the patient's urine evaluated by confirmatory urine drug testing. Clin Biochem. 2019 May;67:48-53. doi: 10.1016/j.clinbiochem.2019.03.006. Epub 2019 Mar 16. PMID: 30890414.


3: Roerig SC, Fujimoto JM, Wang RI. The stimulatory effect of morphine on metabolism of naloxone to 6alpha-naloxol in the guinea pig. Drug Metab Dispos. 1977 Sep-Oct;5(5):454-63. PMID: 20294.


4: Roerig SC, Christiansen KL, Jansen MA, Wang RI, Fujimoto JM, Nickerson M. Phylogenetic distribution of the hepatic enzyme system for reducing naloxone to 6 alpha- and 6 beta-naloxol in vertebrates. Comp Biochem Physiol C. 1980;65(2):93-7. doi: 10.1016/0306-4492(80)90027-1. PMID: 6102006.


5: Yamano S, Ichinose F, Todaka T, Toki S. Purification and characterization of two major forms of naloxone reductase from rabbit liver cytosol, new members of aldo-keto reductase superfamily. Biol Pharm Bull. 1999 Oct;22(10):1038-46. doi: 10.1248/bpb.22.1038. PMID: 10549852.


6: Shoblock JR, Maidment NT. Constitutively active micro opioid receptors mediate the enhanced conditioned aversive effect of naloxone in morphine- dependent mice. Neuropsychopharmacology. 2006 Jan;31(1):171-7. doi: 10.1038/sj.npp.1300782. PMID: 15956992.


7: Misra AL, Pontani RB, Vadlamani NL, Mulé SJ. Physiological disposition and biotransformation of [allyl-1', 3' - 14C naloxone in the rat and some comparative observations on nalorphine. J Pharmacol Exp Ther. 1976 Feb;196(2):257-68. PMID: 1255476.


8: Jiang H, Wang Y, Shet MS, Zhang Y, Zenke D, Fast DM. Development and validation of a sensitive LC/MS/MS method for the simultaneous determination of naloxone and its metabolites in mouse plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Sep 1;879(25):2663-8. doi: 10.1016/j.jchromb.2011.06.039. Epub 2011 Jul 3. PMID: 21798826.


9: Floettmann E, Bui K, Sostek M, Payza K, Eldon M. Pharmacologic Profile of Naloxegol, a Peripherally Acting µ-Opioid Receptor Antagonist, for the Treatment of Opioid-Induced Constipation. J Pharmacol Exp Ther. 2017 May;361(2):280-291. doi: 10.1124/jpet.116.239061. Epub 2017 Mar 23. PMID: 28336575; PMCID: PMC5399635.


10: Yamano S, Nakamoto N, Toki S. Purification and characterization of rat liver naloxone reductase that is identical to 3alpha-hydroxysteroid dehydrogenase. Xenobiotica. 1999 Sep;29(9):917-30. doi: 10.1080/004982599238164. PMID: 10548452.


11: Kumagai Y, Todaka T, Yamano S, Toki S. Stimulation mechanism of guinea pig liver-mediated reduction of naloxone by morphine. Drug Metab Dispos. 1990 Jul- Aug;18(4):462-6. PMID: 1976068.


12: Garrett ER, Shyu WC, Ulubelen A. Pharmacokinetics of morphine and its surrogates. VIII: Naloxone and naloxone conjugate pharmacokinetics in dogs as a function of dose and as affected by simultaneously administered morphine. J Pharm Sci. 1986 Dec;75(12):1127-36. doi: 10.1002/jps.2600751203. PMID: 3559921.


13: Wang D, Raehal KM, Bilsky EJ, Sadée W. Inverse agonists and neutral antagonists at mu opioid receptor (MOR): possible role of basal receptor signaling in narcotic dependence. J Neurochem. 2001 Jun;77(6):1590-600. doi: 10.1046/j.1471-4159.2001.00362.x. PMID: 11413242.


14: Shoblock JR, Maidment NT. Enkephalin release promotes homeostatic increases in constitutively active mu opioid receptors during morphine withdrawal. Neuroscience. 2007 Nov 9;149(3):642-9. doi: 10.1016/j.neuroscience.2007.05.011. Epub 2007 Oct 1. PMID: 17905519.


15: Roerig S, Fujimoto JM, Wang RI, Pollock SH, Lange D. Preliminary characterization of enzymes for reduction of naloxone and naltrexone in rabbit and chicken liver. Drug Metab Dispos. 1976 Jan-Feb;4(1):53-8. PMID: 56258.


16: Roerig SC, Fujimoto JM, Wang RI. The stimulatory effect of morphine on reduction of naltrexone to 6 alpha-naltrexol in the guinea pig. Drug Metab Dispos. 1980 Sep-Oct;8(5):295-9. PMID: 6107224.


17: Webster L, Dhar S, Eldon M, Masuoka L, Lappalainen J, Sostek M. A phase 2, double-blind, randomized, placebo-controlled, dose-escalation study to evaluate the efficacy, safety, and tolerability of naloxegol in patients with opioid- induced constipation. Pain. 2013 Sep;154(9):1542-50. doi: 10.1016/j.pain.2013.04.024. Epub 2013 Apr 16. PMID: 23726675.


18: Cone EJ. General procedure for the isolation and identification of 6-alpha- and 6-beta-hydroxy metabolites of narcotic agonists and antagonists with a hydromorphone structure. J Chromatogr. 1976 Dec 22;129:355-61. doi: 10.1016/s0021-9673(00)87795-x. PMID: 1002794.


19: Yamano S, Nishida F, Toki S. Guinea-pig liver morphine 6-dehydrogenase as a naloxone reductase. Biochem Pharmacol. 1986 Dec 1;35(23):4321-6. doi: 10.1016/0006-2952(86)90712-4. PMID: 3539118.


20: Malspeis L, Bathala MS, Ludden TM, Bhat HB, Frank SG, Sokoloski TD, Morrison BE, Reuning RH. Metabolic reduction of naltrexone. I. Synthesis, separation and characterization of naloxone and naltrexone reduction products and qualitative assay of urine and bile following administration of naltrexone, alpha-naltrexol, or beta-naltrexol. Res Commun Chem Pathol Pharmacol. 1975 Sep;12(1):43-65. PMID: 810832.