CAS 66164-07-6

N-Desmethyl Loperamide

Description:

N-Desmethyl Loperamide, with the CAS number 66164-07-6, is a chemical compound that serves as a metabolite of loperamide, an opioid used primarily to treat diarrhea. This substance is characterized by its structural modification, where a methyl group is removed from the nitrogen atom of loperamide. N-Desmethyl Loperamide exhibits similar pharmacological properties to its parent compound, although it is generally considered to have a lower potency as an opioid. It interacts with the opioid receptors in the gastrointestinal tract, contributing to its effects on motility and secretion. The compound is typically a white to off-white solid and is soluble in organic solvents. Its safety profile and potential side effects are important considerations, especially in the context of opioid use. As a metabolite, it may also be relevant in pharmacokinetic studies and toxicology assessments related to loperamide use. Understanding its characteristics is crucial for both clinical applications and research into opioid metabolism.

Formula: C₂₈H₃₁ClN₂O₂

InChI: InChI=1S/C28H31ClN2O2/c1-30-26(32)28(23-8-4-2-5-9-23,24-10-6-3-7-11-24)18-21-31-19-16-27(33,17-20-31)22-12-14-25(29)15-13-22/h2-15,33H,16-21H2,1H3,(H,30,32)

InChI key: InChIKey=ZMOPTLXEYOVARP-UHFFFAOYSA-N

SMILES: C(CCN1CCC(O)(CC1)C2=CC=C(Cl)C=C2)(C(NC)=O)(C3=CC=CC=C3)C4=CC=CC=C4

Synonyms:

• Desmethylloperamide
• 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N-methyl-α,α-diphenyl-
• 4-(4-Chlorophenyl)-4-hydroxy-N-methyl-α,α-diphenyl-1-piperidinebutanamide
• R 20905
• N-Desmethyl Loperamide

Desmethyl Loperamide

CAS: 66164-07-6

Formula: C₂₈H₃₁ClN₂O₂

Color and Shape: White To Off-White Solid

Molecular weight: 463.02

Ref: 4Z-L-092

N-Desmethyl Loperamide

CAS: 66164-07-6

N-Desmethyl Loperamide, Primary metabolite of Loperamide, P-gp substrate; Loperamide is a μ-opioid agonist with antidiarrheal effects.

Formula: C₂₈H₃₁ClN₂O₂

Purity: 99.73%

Color and Shape: Solid

Molecular weight: 463.01

Ref: TM-T33615

Loperamide-N-desmethyl 100 µg/mL in Acetonitrile

CAS: 66164-07-6

Formula: C₂₈H₃₁ClN₂O₂

Color and Shape: Single Solution

Molecular weight: 463.01

Ref: 04-A14647100AL-100

N-Desmethyl Loperamide

Controlled Product

CAS: 66164-07-6

Applications A metabolite of Loperamide; a new and improved PET radiotracer for imaging P-gp function.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Rahman, A., et al.: Cancer Res., 54, 5543 (1994), Sai, Y., et al.: Xenobiotica, 30, 327 (2000), Eneroth, A., et al.: Eur. J. Pharm. Sci., 12, 205 (2001), Kim, K., et al.: Drug Metab. Dispos., 31, 1090 (2003), Kannan et al. Drug Metab. Dispos., 38, 917 (2010)

Formula: C₂₈H₃₁ClN₂O₂

Color and Shape: White To Light Beige

Molecular weight: 463.01

Ref: TR-D291840

N-Desmethyl loperamide

CAS: 66164-07-6

N-Desmethyl loperamide is a prodrug of loperamide, which is a peripherally acting μ-opioid receptor agonist. It has been shown to be effective in reducing the uptake of radiation in wild-type mice. This drug also inhibits p-glycoprotein (p-gp), and has been shown to reduce the uptake of pyridinium ions and amide substrates. N-Desmethyl loperamide has been shown to have anticancer properties, including resistance to radiation, inhibition of tumor growth and metastasis, and induction of apoptosis, which may be due to its ability to inhibit cellular proliferation and induce cell death. The mechanism by which this drug functions is not yet clear but it may involve inhibition of the expression or function of p-gp or other efflux pumps in cells that are sensitive to these drugs.

Formula: C₂₈H₃₁ClN₂O₂

Purity: Min. 95%

Molecular weight: 463.01 g/mol

Ref: 3D-FD21287