Naloxone

Chemistry

45 atoms · Conformer computed and published by PubChem.

Formula: C19H21NO4
Molar mass: 327.4 g/mol
IUPAC name: (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
InChIKey: UZHSEJADLWPNLE-GRGSLBFTSA-N

Chemistry from PubChem CID 5284596.

Also known as

465-65-6
l-Naloxone
(-)-Naloxone
n-Allylnoroxymorphone
Naloxona
EN 1530 base
Naloxonum
Nalossone

Stereoisomers

15 distinct stereoisomers are registered for this structure.

Naloxone this area CID 5284596
(4S,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 CID 10064
(4R,4aR,7aS,12bR)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one CID 186822
(4S,4aR,7aS,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 CID 667494
Tocris-0599 CID 5390107
d-Naloxone CID 5491858
Lopac-N-7758 CID 6321250
(4S,4aR,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 CID 6918998
(4S,4aS,7aR,12bR)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one CID 13303869
(4R,4aR,7aR,12bR)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one CID 13303871
(4R,4aS,7aR,12bR)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one CID 13303874
(4R,4aS,7aS,12bR)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one CID 23786505
(4S,4aS,7aS,12bR)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one CID 51691054
(+)-Naloxone CID 71774987
(4S,4aS,7aS,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 CID 98185014
4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7-one mixture CID 4425

One defined stereoisomer. The mirror image is inactive at opioid receptors, and everything sold as naloxone — including every intranasal overdose-reversal kit — is the active form.

Photographs

Take-home naloxone kit as distributed in British Columbia: black zip case marked with a red cross, amber vial of naloxone 0.4 mg/mL, three syringes, alcohol pads, nitrile gloves, CPR face shield and step-by-step rescue card.

Single-dose Luer-Jet prefilled syringe of naloxone hydrochloride injection, USP (2 mg per 2 mL) with its salmon-colored carton; the clear cartridge is labeled for IM, IV or subcutaneous use.

Prefilled naloxone syringe fitted with a white cone-shaped nasal mucosal atomizer, the improvised intranasal setup used before purpose-made nasal sprays; carton shown behind.

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