Structure via PubChem · Public domain (PubChem)
chlornaltrexamine
Sign in to saveβ-Chlornaltrexamine (β-CNA) is a non-selective irreversible antagonist of the μ-opioid receptor (MOR), the δ-opioid receptor (DOR), and the κ-opioid receptor (KOR), which forms a covalent bond to the binding sites of these receptors and has ultra-long-lasting opioid antagonist effects. Although it is predominantly antagonistic, β-CNA also shows some irreversible mixed agonist–antagonist activity at the MOR and KOR and some associated analgesic effects. Its alkylating group is a bis(chloroalkyl)amino-residue similar to that of the nitrogen mustards.
Chemical data
- Formula
- C24H32Cl2N2O3
- Molecular weight
- 467.4 g/mol
- IUPAC name
- (4R,4aS,7R,7aR,12bS)-7-[bis(2-chloroethyl)amino]-3-(cyclopropylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol
- SMILES
- C1C[C@]2([C@H]3CC4=C5[C@@]2(CCN3CC6CC6)[C@H]([C@@H]1N(CCCl)CCCl)OC5=C(C=C4)O)O
- InChIKey
- OSLQQDMGHVQLCH-HRMPSQMFSA-N
- XLogP
- 1.5
- Polar surface area
- 56.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
106 papers- Effects of beta-chlornaltrexamine on food intake, body weight and opioid-induced feeding.Life sciences · 1987
- Methocinnamox is a potent, long-lasting, and selective antagonist of morphine-mediated antinociception in the mouse: comparison with clocinnamox, beta-funaltrexamine, and beta-chlornaltrexamine.The Journal of pharmacology and experimental therapeutics · 2000
- Pharmacological profiles of beta-funaltrexamine (beta-FNA) and beta-chlornaltrexamine (beta-CNA) on the mouse vas deferens preparation.European journal of pharmacology · 1982
- Pharmacological studies with an alkylating narcotic agonist, chloroxymorphamine, and antagonist, chlornaltrexamine.The Journal of pharmacology and experimental therapeutics · 1980
- Body temperature, motor activity, and feeding behavior of mice treated with beta-chlornaltrexamine.Physiology & behavior · 1995
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Main subject
- opioid
- Mass
- 466.178998
Show 5 more facts
- chemical formula
- C₂₄H₃₂Cl₂N₂O₃
- isomeric SMILES
- C1C[C@]2([C@H]3CC4=C5[C@@]2(CCN3CC6CC6)[C@H]([C@@H]1N(CCCl)CCCl)OC5=C(C=C4)O)O
- canonical SMILES
- C1CC1CN2CCC34C5C(CCC3(C2CC6=C4C(=C(C=C6)O)O5)O)N(CCCl)CCCl
- subject has role
- opioid antagonist
- Commons category
- Chlornaltrexamine
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
β-Chlornaltrexamine (β-CNA) is a non-selective irreversible antagonist of the μ-opioid receptor (MOR), the δ-opioid receptor (DOR), and the κ-opioid receptor (KOR), which forms a covalent bond to the binding sites of these receptors and has ultra-long-lasting opioid antagonist effects. Although it is predominantly antagonistic, β-CNA also shows some irreversible mixed agonist–antagonist activity at the MOR and KOR and some associated analgesic effects. Its alkylating group is a bis(chloroalkyl)amino-residue similar to that of the nitrogen mustards.
The drug was first described by 1978. It should not be confused with its epimer and related drug α-chlornaltrexamine (α-CNA), which is likewise predominantly an irreversible antagonist of the opioid receptors but also shows some irreversible mixed agonist–antagonist activity.
Excerpted from Wikipedia’s “chlornaltrexamine” article, available under the CC BY-SA 4.0 licence.