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About This Item
Empirical Formula (Hill Notation):
C19H21NO3 · HCl
CAS Number:
Molecular Weight:
347.84
UNSPSC Code:
12352200
PubChem Substance ID:
EC Number:
200-321-8
MDL number:
InChI key
NAHATSPWSULUAA-HWXFZQNOSA-N
InChI
1S/C19H21NO3.ClH/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20;/h2-6,12-13,15,18,21-22H,1,7-10H2;1H/t12?,13-,15+,18+,19+;/m1./s1
SMILES string
Cl[H].O[C@H]1C=CC2[C@H]3Cc4ccc(O)c5O[C@@H]1[C@]2(CCN3CC=C)c45
form
solid
drug control
USDEA Schedule III; regulated under CDSA - not available from Sigma-Aldrich Canada
color
white
solubility
H2O: slightly soluble, dilute aqueous acid: soluble, ethanol: soluble
Biochem/physiol Actions
Mixed action opiate that is a partial agonist at μ and κ opioid receptors, and a low-affinity agonist at sigma receptors.
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G Bot et al.
Journal of neurochemistry, 70(1), 358-365 (1998-01-09)
To investigate the role of Asp114 in the cloned rat mu-opioid receptor for ligand binding, the charged amino acid was mutated to an asparagine to generate the mutant mu receptor D114N. The wild-type mu receptor and the D114N mutant were
P J Emmerson et al.
The Journal of pharmacology and experimental therapeutics, 278(3), 1121-1127 (1996-09-01)
In C6 glioma cells stably expressing a homogeneous population of the cloned rat mu opioid receptor, the binding affinities of opioid agonists and subsequent activation of G protein were examined. Opioid receptor number in membranes of these cells was high
A E Remmers et al.
The Journal of pharmacology and experimental therapeutics, 288(2), 827-833 (1999-01-26)
A C6 glioma cell line stably transfected with the human kappa opioid receptor (kappaOR) was used to characterize receptor binding and G protein activation via the kappaOR by a comprehensive series of opioid ligands. The ligand-binding affinity for [3H]5alpha,7alpha, 8beta(-)-N-methyl-N-(7-Cl-pyrrolidinyl)-1-oxaspiro(4
J M Musacchio
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 3(3), 191-200 (1990-06-01)
A critical review of the literature shows that the dysphoric and psychotomimetic side effects of sigma opiates reside in the levorotatory and not in the dextrorotatory or (+)-isomer, as currently believed. Nalorphine, levallorphan, (-)-pentazocine, (-)-3-hydroxy-N-propargylmorphinan, and MR 2034, all levorotatory
C D King et al.
Archives of biochemistry and biophysics, 332(1), 92-100 (1996-08-01)
Rat and human UDP-glucuronosyltransferase (UGT) 1.1 share > 70% identity in their deduced primary amino acid sequences. We have previously shown that rat UGT1.1, stably expressed in human embryonic kidney 293 cells, catalyzes the glucuronidation of bilirubin and the mixed
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