Naloxone
(4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
Molecular Identity
Naloxone
(4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
PubChem CID: 5284596
Naloxone is a synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose. It has a role as a central nervous system depressant, a mu-opioid receptor antagonist and an antidote to opioid poisoning. It is a morphinane alkaloid, a tertiary alcohol and an organic heteropentacyclic compound. It is a conjugate base of a naloxone(1+). It derives from a hydride of a morphinan.
2D Structure
Properties
C19H21NO4
Molecular Formula
327.40
Molecular Weight
g/mol
327.1471
Exact Mass
Da
2.1
XLogP
Drug-like (Lipinski: < 5)
70
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
5
H-Bond Acceptors
594
Complexity
SMILES
Canonical SMILES
SMILES: C=CCN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)OIsomeric SMILES
SMILES: C=CCN1CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)OSynonyms(20)
naloxone465-65-6l-Naloxone(-)-Naloxonen-AllylnoroxymorphoneNaloxonaEN 1530 baseNaloxonumNalossoneN-Allyl-noroxymorphoneDBL Naloxone1-N-Allyl-14-hydroxynordihydromorphinoneNaloxone Nasal Spray17-Allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-oneDTXSID8023349
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Naloxone
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