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Β-Chlornaltrexamine

Chemical compound

Chemical compound

FieldValue
Verifiedfieldsverified
Watchedfieldsverified
verifiedrevid434800318
drug_nameβ-Chlornaltrexamine
imageChlornaltrexamine.svg
image_classskin-invert-image
width250px
CAS_number_Ref
CAS_number67025-94-9
PubChem5486190
ChemSpiderID_Ref
ChemSpiderID4588895
ChEMBL3228678
synonymsβ-Chlornaltrexamine; Beta-Chlornaltrexamine; β-CNA; Beta-CNA; Chlornaltrexamine; CNA; 6β-[Bis(2-chloroethyl)amino]-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-3,14-diol
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
C24H=32Cl=2N=2O=3
SMILESC1C[C@]2([C@H]3CC4=C5[C@@]2(CCN3CC6CC6)C@HOC5=C(C=C4)O)O
StdInChI1S/C24H32Cl2N2O3/c25-8-11-27(12-9-26)17-5-6-24(30)19-13-16-3-4-18(29)21-20(16)23(24,22(17)31-21)7-10-28(19)14-15-1-2-15/h3-4,15,17,19,22,29-30H,1-2,5-14H2/t17-,19-,22+,23+,24-/m1/s1
StdInChIKeyOSLQQDMGHVQLCH-HRMPSQMFSA-N

| Drugs.com =

| elimination_half-life =

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.

References

References

  1. (June 1982). "Pharmacological profiles of beta-funaltrexamine (beta-FNA) and beta-chlornaltrexamine (beta-CNA) on the mouse vas deferens preparation". Eur J Pharmacol.
  2. (September 1988). "Estimation of opioid receptor agonist dissociation constants with beta-chlornaltrexamine, an irreversible ligand which also displays agonism". Br J Pharmacol.
  3. (September 2000). "Methocinnamox is a potent, long-lasting, and selective antagonist of morphine-mediated antinociception in the mouse: comparison with clocinnamox, beta-funaltrexamine, and beta-chlornaltrexamine". J Pharmacol Exp Ther.
  4. (July 1978). "6β-[N,N-Bis(2-chloroethyl)amino]-17-(cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxymorphinan(chlornaltrexamine) a potent opioid receptor alkylating agent with ultralong narcotic antagonist activity". J. Med. Chem..
  5. (February 1979). "Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties". J. Med. Chem..
  6. (June 1980). "Pharmacological studies with an alkylating narcotic agonist, chloroxymorphamine, and antagonist, chlornaltrexamine". J. Pharmacol. Exp. Ther..
  7. (December 1980). "Isolation of selective 3H-chlornaltrexamine-bound complexes, possible opioid receptor components in brains of mice". Life Sci..
  8. (July 1978). "6beta-[N,N-Bis(2-chloroethyl)amino]-17-(cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan(chlornaltrexamine) a potent opioid receptor alkylating agent with ultralong narcotic antagonist actitivty". J Med Chem.
  9. (February 1979). "Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties". J Med Chem.
  10. (April 1983). "Alkylation of opioid receptor subtypes by alpha-chlornaltrexamine produces concurrent irreversible agonistic and irreversible antagonistic activities". J Med Chem.
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4,5-epoxymorphinans alkylating-agents chloroethyl-compounds cyclopropyl-compounds delta-opioid-receptor-antagonists irreversible-agonists kappa-opioid-receptor-antagonists mu-opioid-receptor-antagonists nitrogen-mustards hydroxyarenes
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