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SML0277

Sigma-Aldrich

Methylnaltrexone bromide

≥97% (HPLC)

Synonym(s):

17-(Cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxy-17-methyl-6-oxomorphinanium bromide, MNTX, Methylnaltrexonium, Mrz-2663, N-Methylnaltrexone, Naltrexone MB, Quaternary ammonium naltrexone

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About This Item

Empirical Formula (Hill Notation):
C21H26NO4 · Br
CAS Number:
73232-52-7
Molecular Weight:
436.34
MDL number:
MFCD06407831
UNSPSC Code:
12352200
PubChem Substance ID:
329825285
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: ≥5 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

[Br-].C[N@+]1(CC[C@]23[C@H]4Oc5c(O)ccc(C[C@@H]1[C@]2(O)CCC4=O)c35)CC6CC6

InChI

1S/C21H25NO4.BrH/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13;/h4-5,12,16,19,25H,2-3,6-11H2,1H3;1H/t16-,19+,20+,21-,22?;/m1./s1

InChI key

IFGIYSGOEZJNBE-KNLJMPJLSA-N

Gene Information

human ... OPRM1(4988)

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General description

Methylnaltrexone does not cross blood brain barrier and does not affect the opioid effects in the brain, such as analgesia. It is used to treat opioid-induced constipation (OIC).

Application

Methylnaltrexone bromide has been used as a drug to measure plasma protein binding (PPB), permeability (Pm) and the membrane coefficient (KIAM) for the prediction of blood brain barrier (BBB) penetration. It is also used as a mu-opioid receptor (MOR) antagonist to abrogate morphine tolerance and opioid-induced hyperalgesia (OIH).

Biochem/physiol Actions

Methylnaltrexone bromide is a narcotic antagonist. It is a peripheral mu-opiod receptor antagonist that cannot cross the blood-brain barrier. It reverses many opioid side-effects without interfering with pain relief.

Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H371

Hazard Classifications

STOT SE 2 Oral

Target Organs

Gastrointestinal tract

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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A Brokjaer et al.
Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society, 27(5), 693-704 (2015-03-27)
Opioid antagonists are increasingly used to abolish the gastrointestinal side effects of opioids. However, they can potentially interfere with local analgesia exerted via opioid receptors in the gut. Thus, in the current study we aimed to explore the effect of
Loss of mu-opioid receptor signaling in nociceptors, but not microglia, abrogates morphine tolerance without disrupting analgesia
Corder G, et al.
Nature Medicine, 23(2), 164-164 (2017)
Expanding LogP: Present possibilities
Vraka C, et al.
Nuclear Medicine and Biology, 58, 20-32 (2018)
Peter Holzer
Current pharmaceutical design, 18(37), 6010-6020 (2012-07-04)
The therapeutic action of opioid analgesics is compromised by peripheral adverse effects among which opioid-induced constipation (OIC) is the most disabling, with a prevalence reported to vary between 15 and 90 %. Although OIC is usually treated with laxatives, there
Methylnaltrexone for reversal of constipation due to chronic methadone use: a randomized controlled trial
Yuan CS, et al.
JAMA : The Journal of the American Medical Association, 283(3), 367-372 (2000)
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