Methylnaltrexone (CED0008501)

Record Information

Version

1.0

Creation Date

2016-06-03 11:54:32 UTC

Update Date

2026-05-14 18:25:16 UTC

Accession Number

CHEM044239

Identification

Common Name

Methylnaltrexone

Class

Small Molecule

Description

Methylnaltrexone is an organic compound with the formula C21H26NO4 and an average molecular weight of 356.44 g/mol. Methylnaltrexone belongs to the phenanthrenes and derivatives, a class of benzenoids within the organic compounds. It is found in or released from two recorded sources: household cleaning and consumer products, specifically non electric simulated smoking devices, and healthcare, pharmaceuticals and veterinary products, specifically drugs for constipation. Recorded exposure routes for this compound include oral, subcutaneous, and topical administration. In terms of biological activity, methylnaltrexone interacts with three recorded protein targets. It acts as an agonist or antagonist of the mu-type opioid receptor (OPRM1), the kappa-type opioid receptor (OPRK1), and the melanocortin receptor 4 (MC4R).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Naltrexone methobromide	MeSH
Naltrexone methylbromide	MeSH
17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinanium-6-one	MeSH
MRZ 2663BR	MeSH
Methyl-naltrexone hydrobromide	MeSH
Naltrexonium methiodide	MeSH
Relistor	MeSH
Naltrexone MB	MeSH
Quaternary ammonium naltrexone	MeSH
Methylnaltrexone bromide	MeSH
N-Methylnaltrexone bromide	MeSH
(5alpha)-17-(Cyclopropylmethyl)-3,14-dihydroxy-17-methyl-4,5-epoxymorphinan-17-ium-6-one	MeSH

Chemical Formula

C₂₁H₂₆NO₄

Average Molecular Mass

356.435 g/mol

Monoisotopic Mass

356.186 g/mol

CAS Registry Number

73232-52-7

IUPAC Name

(1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-4-methyl-14-oxo-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-4-ium

Traditional Name

methylnaltrexone

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CC[N+](C)(CC3CC3)[C@]([H])(C4)[C@]1(O)CCC2=O

InChI Identifier

InChI=1S/C21H25NO4/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/p+1/t16-,19+,20+,21-,22?/m1/s1

InChI Key

JVLBPIPGETUEET-GAAHOAFPSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Isoquinolone
Tetralin
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aralkylamine
Piperidine
Cyclic alcohol
Tetraalkylammonium salt
Quaternary ammonium salt
Tertiary alcohol
1,2-aminoalcohol
Ketone
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Organic salt
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0073 g/L	ALOGPS
logP	0.59	ALOGPS
logP	-2.5	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.4	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.42 m³·mol⁻¹	ChemAxon
Polarizability	38.12 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-3009000000-9ba21a53169f9d6d1c7d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9006000000-0b2a741cb7267cd6516b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9000000000-88d4b6ab3013eb19d753	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
283.0	Log mg/kg	[160:500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
253	Drugs for constipation	Healthcare, pharmaceuticals & veterinary products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available

Pathways

3 pathways

Methylnaltrexone Opioid Antagonist Action Pathway

Methylnaltrexone Drug Metabolism

Methylnaltrexone Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Kappa-type opioid receptor	P33534	Mus musculus	Predicted (SEA)	13.7793
Click to view 3D structure	Mu-type opioid receptor	P79350	Bos taurus	Predicted (SEA)	7.70707
Click to view 3D structure	Nociceptin receptor	P41146	Humans	Predicted (SEA)	66.9503
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	435.099
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	259.549
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	365.58
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	O55242	Mus musculus	Predicted (SEA)	5.99439
Click to view 3D structure	Orexin/Hypocretin receptor type 1	O43613	Humans	Predicted (SEA)	45.3082
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q9R0C9	Rattus norvegicus	Predicted (SEA)	256.747
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	213.463
Click to view 3D structure	C-C chemokine receptor type 5	P51681	Humans	Predicted (SEA)	309.295
Click to view 3D structure	Mas-related G-protein coupled receptor member X2	Q96LB1	Humans	Predicted (SEA)	243.357
Click to view 3D structure	C-C chemokine receptor type 5	P51682	Mus musculus	Predicted (SEA)	20.3186
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	4895.7
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	3645.06
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	23.4326
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	22.8098
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	20.3965
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	62.2015
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	49.9792
Click to view 3D structure	Kappa-type opioid receptor	P34975	Rattus norvegicus	Predicted (SEA)	17.1268
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	36.7448
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	57.7641
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	42.6614
Click to view 3D structure	Mu-type opioid receptor	P42866	Mus musculus	Predicted (SEA)	15.492