6 α-naloxol - CAS 20410-95-1
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
6 α-naloxol
Catalog Number:
20410-95-1
Synonyms:
(4R,4aS,7S,7aR,12bS)-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol 6 alpha-hydroxynaloxone 6 alpha-naloxol 6 alpha-naloxol hydrochloride, 5alpha isomer 6 alpha-naloxol, 5alpha isomer
CAS Number:
20410-95-1
Description:
6 α-naloxol, a human metabolite of naloxone, is an opioid antagonist.
Molecular Weight:
329.394
Molecular Formula:
C19H23NO4
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C=CCN1CCC23C4C(CCC2(C1CC5=C3C(=C(C=C5)O)O4)O)O
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+/m0/s1
InChIKey:
HMWHERQFMBEHNG-AQQQZIQISA-N
Targets:
Opioid Receptor
Chemical Structure
CAS 20410-95-1 6 α-naloxol

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Reference Reading


1.Relative potency of the opioid antagonists naloxone and 6-alpha-naloxol to precipitate withdrawal from acute morphine dependence varies with time post-antagonist.
Schulteis G1, Chiang D, Archer C. Pharmacol Biochem Behav. 2009 Mar;92(1):157-63. doi: 10.1016/j.pbb.2008.11.007. Epub 2008 Nov 24.
The current study compared the potency of naloxone versus 6-alpha-naloxol to precipitate opioid withdrawal under varying conditions of morphine pretreatment history using suppression of operant responding for food reward as the index of withdrawal. Male Wistar rats trained to respond on a lever for food reward received pretreatment with either Vehicle (Morphine-Naïve), a single subcutaneous (SC) injection of 5.6 mg/kg morphine (Single Morphine), or two morphine injections at 24 h intervals (Repeat Morphine), with varying doses of naloxone or 6-alpha-naloxol injected SC 4 h post-morphine and 5 min prior to the 30 min test session. When responding over the entire 30 min operant session was examined, naloxone was only 5-fold more potent than 6-alpha-naloxol in suppressing operant responding under Morphine Naïve conditions, but this increased to a 65-fold potency difference after Single or Repeat Morphine pretreatment. Examination of the relative potency of these antagonists in the Early Phase of operant testing (5-15 min post-antagonist) revealed an even greater 100-fold potency difference between naloxone and 6-alpha-naloxol, but in the Late Phase of testing (25-35 min post-antagonist), this had declined to a 9-fold potency difference, comparable to the relative potency of naloxone to 6-alpha-naloxol under Morphine-Naïve conditions.