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Human drug metabolites
Naloxol
Другие языки:

Naloxol

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Naloxol
α-naloxol
α-naloxol
β-naloxol
β-naloxol
Names
IUPAC names
α-naloxol: (4R,4aS,7S,7aR,12bS)-3-allyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
β-naloxol: (4R,4aS,7R,7aR,12bS)-3-allyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.236.696
PubChem CID
UNII
  • 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 ☒N
    Key: HMWHERQFMBEHNG-AQQQZIQISA-N ☒N
  • (α): InChI=1/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
    Key: HMWHERQFMBEHNG-AQQQZIQIBS
  • (β): InChI=1/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
    Key: HMWHERQFMBEHNG-CSJNCLCHBP
  • (β): 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
    Key: HMWHERQFMBEHNG-CSJNCLCHSA-N
  • (α): OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@H](O)[C@H](O2)[C@@]53CCN4CC=C
  • (β): OC1=C2C3=C(C=C1)C[C@@H]4[C@]5(O)CC[C@@H](O)[C@H](O2)[C@@]53CCN4CC=C
Properties
C19H23NO4
Molar mass 329.396 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Naloxol is an opioid antagonist closely related to naloxone. It exists in two isomeric forms, α-naloxol and β-naloxol.

α-naloxol is a human metabolite of naloxone. Synthetically, α-naloxol can be prepared from naloxone by reduction of the ketone group, and β-naloxol can be prepared from α-naloxol by a Mitsunobu reaction.

Naloxol can be said to be the oxymorphol analogue of naloxone.

See also



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