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MedKoo Cat#: 125239 | Name: 6beta-naltrexol HCl

Description:

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

6β-naltrexol is a peripherally selective opioid antagonist that inhibits morphine-induced slowing of gastrointestinal transit.

Chemical Structure

6beta-naltrexol HCl
6beta-naltrexol HCl
CAS#55488-86-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 125239

Name: 6beta-naltrexol HCl

CAS#: 55488-86-3 (HCl)

Chemical Formula: C20H26ClNO4

Exact Mass: 379.1600

Molecular Weight: 379.88

Elemental Analysis: C, 63.24; H, 6.90; Cl, 9.33; N, 3.69; O, 16.85

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
55488-86-3 (HCl) 49625-89-0 (free base)
Synonym
6beta-Naltrexol hydrochloride; 55488-86-3; 765G11MG24; CHEMBL558140; UNII-765G11MG24; 6.BETA.-NALTREXOL HYDROCHLORIDE
IUPAC/Chemical Name
(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-1,2,3,4,5,6,7,7a-octahydro-4aH-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol hydrochloride
InChi Key
FSQFFCPJTDFOAN-CDHBEYIESA-N
InChi Code
InChI=1S/C20H25NO4.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;/h3-4,11,14-15,18,22-24H,1-2,5-10H2;1H/t14-,15-,18+,19+,20-;/m1./s1
SMILES Code
OC1=C(O2)C3=C(C[C@]4([H])[C@]5(O)CC[C@](O)([H])[C@@]2([H])[C@]35CCN4CC6CC6)C=C1.Cl
Appearance
To be determined
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 379.88 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
1: Yancey-Wrona JE, Raymond TJ, Mercer HK, Sadée W, Bilsky EJ. 6beta-naltrexol preferentially antagonizes opioid effects on gastrointestinal transit compared to antinociception in mice. Life Sci. 2009 Sep 9;85(11-12):413-20. doi: 10.1016/j.lfs.2009.06.016. Epub 2009 Jul 5. PMID: 19583969. 2: Yancey-Wrona J, Dallaire B, Bilsky E, Bath B, Burkart J, Webster L, Magiera D, Yang X, Phelps M, Sadee W. 6β-naltrexol, a peripherally selective opioid antagonist that inhibits morphine-induced slowing of gastrointestinal transit: an exploratory study. Pain Med. 2011 Dec;12(12):1727-37. doi: 10.1111/j.1526-4637.2011.01279.x. Epub 2011 Nov 28. PMID: 22123184. 3: Li JX, McMahon LR, France CP. Comparison of naltrexone, 6alpha-naltrexol, and 6beta-naltrexol in morphine-dependent and in nondependent rhesus monkeys. Psychopharmacology (Berl). 2008 Jan;195(4):479-86. doi: 10.1007/s00213-007-0914-9. Epub 2007 Sep 16. PMID: 17874317. 4: Ko MC, Divin MF, Lee H, Woods JH, Traynor JR. Differential in vivo potencies of naltrexone and 6beta-naltrexol in the monkey. J Pharmacol Exp Ther. 2006 Feb;316(2):772-9. doi: 10.1124/jpet.105.094409. Epub 2005 Oct 28. PMID: 16258020. 5: Brünen S, Bekier NK, Hiemke C, Korf F, Wiedemann K, Jahn H, Kiefer F. Therapeutic Drug Monitoring of Naltrexone and 6β-Naltrexol During Anti-craving Treatment in Alcohol Dependence: Reference Ranges. Alcohol Alcohol. 2019 Jan 1;54(1):51-55. doi: 10.1093/alcalc/agy067. PMID: 30260366. 6: Porter SJ, Somogyi AA, White JM. Kinetics and inhibition of the formation of 6beta-naltrexol from naltrexone in human liver cytosol. Br J Clin Pharmacol. 2000 Nov;50(5):465-71. doi: 10.1046/j.1365-2125.2000.00281.x. PMID: 11069441; PMCID: PMC2014407. 7: Pelotte AL, Smith RM, Ayestas M, Dersch CM, Bilsky EJ, Rothman RB, Deveau AM. Design, synthesis, and characterization of 6beta-naltrexol analogs, and their selectivity for in vitro opioid receptor subtypes. Bioorg Med Chem Lett. 2009 May 15;19(10):2811-4. doi: 10.1016/j.bmcl.2009.03.095. Epub 2009 Mar 26. PMID: 19364645. 8: Porter SJ, Somogyi AA, White JM. In vivo and in vitro potency studies of 6beta-naltrexol, the major human metabolite of naltrexone. Addict Biol. 2002 Apr;7(2):219-25. doi: 10.1080/135562102200120442. PMID: 12006217. 9: Yan LD, Liu J, Dong HJ, Cui MX, Yao XJ, Liu YS, Gong ZH, Gong ZH. [Pharmacokinetics of 6beta-naltrexol after single and multiple intramuscular injections in Beagle dogs]. Yao Xue Xue Bao. 2009 Jul;44(7):722-5. Chinese. PMID: 19806909. 10: Raehal KM, Lowery JJ, Bhamidipati CM, Paolino RM, Blair JR, Wang D, Sadée W, Bilsky EJ. In vivo characterization of 6beta-naltrexol, an opioid ligand with less inverse agonist activity compared with naltrexone and naloxone in opioid- dependent mice. J Pharmacol Exp Ther. 2005 Jun;313(3):1150-62. doi: 10.1124/jpet.104.082966. Epub 2005 Feb 16. PMID: 15716384.