β-Naltrexamine

β-Naltexamine
Clinical data
Other names	β-Naltrexamine; 6β-Aminonaltrexol; 6β-Amino-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-3,14-diol
Identifiers
	IUPAC name (4R,4aS,7R,7aR,12bS)-7-amino-3-(cyclopropylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol;
CAS Number	67025-97-2;
PubChem CID	5486948;
ChemSpider	4589147;
ChEMBL	ChEMBL3303188;
CompTox Dashboard (EPA)	DTXSID20217239 ;
Chemical and physical data
Formula	C20H26N2O3
Molar mass	342.439 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1C[C@]2([C@H]3CC4=C5[C@@]2(CCN3CC6CC6)[C@H]([C@@H]1N)OC5=C(C=C4)O)O;
	InChI InChI=1S/C20H26N2O3/c21-13-5-6-20(24)15-9-12-3-4-14(23)17-16(12)19(20,18(13)25-17)7-8-22(15)10-11-1-2-11/h3-4,11,13,15,18,23-24H,1-2,5-10,21H2/t13-,15-,18+,19+,20-/m1/s1; Key:SPPAUICKSNQRNC-GNUVVZJLSA-N;

β-Naltrexamine, or 6β-naltrexamine, is an opioid receptor antagonist related to naltrexol and naltrexone.^[1]^[2]^[3] It has served as a parent pharmacophore for irreversible antagonists of the μ-opioid receptor (MOR) such as β-chlornaltrexamine (β-CNA) and β-funaltrexamine (β-FNA).^[1]^[2] Naltrexamine itself is a neutral antagonist of the MOR and the δ-opioid receptor (DOR) with similarly high affinity for both receptors.^[3]

References

^ ^a ^b Fulton BS (2014). Drug Discovery for the Treatment of Addiction: Medicinal Chemistry Strategies. Wiley. p. 220. ISBN 978-1-118-88957-2. Retrieved 14 September 2024.
^ ^a ^b Testa B (2013). Advances in Drug Research. ISSN. Elsevier Science. p. 184. ISBN 978-1-4832-8798-0. Retrieved 14 September 2024.
^ ^a ^b Wang D, Raehal KM, Bilsky EJ, Sadée W (June 2001). "Inverse agonists and neutral antagonists at mu opioid receptor (MOR): possible role of basal receptor signaling in narcotic dependence". J Neurochem. 77 (6): 1590–1600. doi:10.1046/j.1471-4159.2001.00362.x. PMID 11413242.

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