6-Alpha Naloxol

Modify Date: 2025-09-07 18:31:43

6-Alpha Naloxol Structure
6-Alpha Naloxol structure
Common Name 6-Alpha Naloxol
CAS Number 20410-95-1 Molecular Weight 329.39000
Density 1.43g/cm3 Boiling Point 532.5ºC at 760mmHg
Molecular Formula C19H23NO4 Melting Point N/A
MSDS N/A Flash Point 275.8ºC

 Use of 6-Alpha Naloxol


6-Alpha Naloxol(Alpha-Naloxol) is an opioid antagonist closely related to naloxone; a human metabolite of naloxone.IC50 value:Target: opioid antagonistWhen 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 Na ve 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-Na ve conditions.

 Names

Name 6 α-naloxol
Synonym More Synonyms

 6-Alpha Naloxol Biological Activity

Description 6-Alpha Naloxol(Alpha-Naloxol) is an opioid antagonist closely related to naloxone; a human metabolite of naloxone.IC50 value:Target: opioid antagonistWhen 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 Na ve 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-Na ve conditions.
Related Catalog
References

[1]. Weinstein SH, et al. Metabolites of naloxone in human urine. J Pharm Sci. 1971 Oct;60(10):1567-8.

[2]. Csaba Simon, et al. Stereoselective synthesis of β-naltrexol, β-naloxol β-naloxamine, β-naltrexamine and related compounds by the application of the mitsunobu reac. Tetrahedron Volume 50, Issue 32, 1994, Pages 9757–9768.

[3]. Schulteis G, et al. 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.

 Chemical & Physical Properties

Density 1.43g/cm3
Boiling Point 532.5ºC at 760mmHg
Molecular Formula C19H23NO4
Molecular Weight 329.39000
Flash Point 275.8ºC
Exact Mass 329.16300
PSA 73.16000
LogP 1.03110
Vapour Pressure 3.62E-12mmHg at 25°C
Index of Refraction 1.701
InChIKey HMWHERQFMBEHNG-AQQQZIQISA-N
SMILES C=CCN1CCC23c4c5ccc(O)c4OC2C(O)CCC3(O)C1C5

 Synthetic Route

~93%

6-Alpha Naloxol Structure

6-Alpha Naloxol

CAS#:20410-95-1

Literature: MALLINCKRODT INC. Patent: WO2008/137672 A1, 2008 ; Location in patent: Page/Page column 25 ;

~%

6-Alpha Naloxol Structure

6-Alpha Naloxol

CAS#:20410-95-1

Literature: Rezaie, Robert; Bailey, Timothy S. Patent: US2010/36128 A1, 2010 ; Location in patent: Page/Page column 7 ;

~63%

6-Alpha Naloxol Structure

6-Alpha Naloxol

CAS#:20410-95-1

Literature: Hosztafi, Sandor; Berenyi, Sandor; Toth, Geza; Makleit, Sandor Monatshefte fuer Chemie, 1992 , vol. 123, # 5 p. 435 - 442

~%

6-Alpha Naloxol Structure

6-Alpha Naloxol

CAS#:20410-95-1

Literature: Hahn; Fishman Journal of Organic Chemistry, 1975 , vol. 40, # 1 p. 31 - 34

~%

6-Alpha Naloxol Structure

6-Alpha Naloxol

CAS#:20410-95-1

Literature: Hosztafi, Sandor; Berenyi, Sandor; Toth, Geza; Makleit, Sandor Monatshefte fuer Chemie, 1992 , vol. 123, # 5 p. 435 - 442

~%

6-Alpha Naloxol Structure

6-Alpha Naloxol

CAS#:20410-95-1

Literature: Hosztafi, Sandor; Berenyi, Sandor; Toth, Geza; Makleit, Sandor Monatshefte fuer Chemie, 1992 , vol. 123, # 5 p. 435 - 442

 Synonyms

6a-Naloxol
6-Alpha Naloxol
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