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N129

Sigma-Aldrich

Naloxone methiodide

≥98% (HPLC), solid

Synonym(s):

(5α,17R)-4,5-Epoxy-3,14-dihydroxy-17-methyl-6-oxo-17-(2-propenyl)-morphinanium iodide, N-Methylnaloxonium iodide

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About This Item

Empirical Formula (Hill Notation):
C20H24INO4
CAS Number:
93302-47-7
Molecular Weight:
469.31
MDL number:
MFCD00078592
UNSPSC Code:
12352200
PubChem Substance ID:
24897480
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

white to tan

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

SMILES string

[I-].[H][C@]12Oc3c(O)ccc4C[C@@H]5[C@](O)(CCC1=O)[C@@]2(CC[N@+]5(C)CC=C)c34

InChI

1S/C20H23NO4.HI/c1-3-9-21(2)10-8-19-16-12-4-5-13(22)17(16)25-18(19)14(23)6-7-20(19,24)15(21)11-12;/h3-5,15,18,24H,1,6-11H2,2H3;1H/t15-,18+,19+,20-,21?;/m1./s1

InChI key

ICONPJDAXITIPI-UXYWFNEESA-N

Application

Naloxone methiodide has been used as inhibitor of opioid receptor in fish and mice. Naloxone methiodide has been used to block opioid neurotransmission.

Biochem/physiol Actions

Naloxone methiodide has low affinity for opioid receptors than naloxone. Administration of naloxone inhibits opioid receptor and opioid-induced respiratory depression.
Quaternary salt of naloxone that, like the parent compound, is a nonselective antagonist at opioid receptors. It does not cross the blood-brain barrier.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Delta opioid receptors are essential to the antiallodynic action of Β2-mimetics in a model of neuropathic pain.
Mélanie Kremer et al.
Molecular pain, 16, 1744806920912931-1744806920912931 (2020-03-27)
Helvira Melo et al.
Scientific reports, 8(1), 15551-15551 (2018-10-21)
Opioids remain the gold standard for the treatment of moderate to severe pain. However, their analgesic properties come with important side effects, including pruritus, which occurs frequently after systemic or neuraxial administration. Although part of the opioid-induced itch is mediated
Naloxone methiodide reverses opioid-induced respiratory depression and analgesia without withdrawal
Lewanowitsch Tanya and Irvine RJ
European Journal of Pharmacology, 445(1-2), 61 -667 (2002)
Naloxone and its quaternary derivative, naloxone methiodide, have differing affinities for mu, delta, and kappa opioid receptors in mouse brain homogenates
Lewanowitsch Tanya and Irvine RJ
Brain Research, 964(2), 302 -3305 (2003)
G L Chien et al.
Basic research in cardiology, 94(2), 136-143 (1999-05-18)
The hypothesis that naloxone blockade of ischemic preconditioning (IP)-induced infarct limitation does not require central nervous system participation was evaluated using quaternary naloxone in anesthetized rabbits (Study I) and naloxone hydrochloride in isolated rabbit hearts (Study II). In Study I
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