MORPHINAN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H21N.ClH
Molecular Weight	263.806
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@@]12CC3=CC=CC=C3[C@]4(CCCC[C@@]14[H])CCN2

InChI

InChIKey=UTTZKIWMKFVYCK-CLUYDPBTSA-N

InChI=1S/C16H21N.ClH/c1-2-6-13-12(5-1)11-15-14-7-3-4-8-16(13,14)9-10-17-15;/h1-2,5-6,14-15,17H,3-4,7-11H2;1H/t14-,15+,16-;/m0./s1

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Transformation of opium poppy (Papaver somniferum L.) with antisense berberine bridge enzyme gene (anti-bbe) via somatic embryogenesis results in an altered ratio of alkaloids in latex but not in roots.	2004 Dec	15672841
Na+ modulation, inverse agonism, and anorectic potency of 4-phenylpiperidine opioid antagonists.	2004 Jun 28	15212965
Characterization of the complex morphinan derivative BU72 as a high efficacy, long-lasting mu-opioid receptor agonist.	2004 Sep 19	15363957
Formic acid catalysed rearrangement of 5beta-methyldihydrothevinols (= 3,6-dimethoxy-5,17-dimethyl-4,5-epoxy-6,14-ethanomorphinan-7-methanols): synthesis of new doubly bridged morphinan derivatives.	2005 Feb	17191974
Protective effect of dextromethorphan against endotoxic shock in mice.	2005 Jan 15	15627475
A role for intra- and intercellular translocation in natural product biosynthesis.	2005 Jun	15860426
Methods for regeneration and transformation in Eschscholzia californica: A model plant to investigate alkaloid biosynthesis.	2006	16673930
Drug development papers in PLoS Medicine: how we try to spot a winner.	2006 Dec	17526082
A plant-derived morphinan as a novel lead compound active against malaria liver stages.	2006 Dec	17194195
Non-competitive inhibitory activities of morphinan and morphine derivatives at the alpha 3 beta 4 Neuronal nicotinic acetylcholine receptor determined using nonlinear chromatography and chemometric techniques.	2006 Sep	16952007
Persistence of evolutionary memory: primordial six-transmembrane helical domain mu opiate receptors selectively linked to endogenous morphine signaling.	2007 Dec	18049446
QSAR study on the antinociceptive activity of some morphinans.	2007 Jul	17630995
In-vitro investigation of oxazol and urea analogues of morphinan at opioid receptors.	2007 Jun 15	17433695
Levorphanol: the forgotten opioid.	2007 Mar	17039381
High-affinity carbamate analogues of morphinan at opioid receptors.	2007 Mar 15	17276685
Sinomenine, a natural dextrorotatory morphinan analog, is anti-inflammatory and neuroprotective through inhibition of microglial NADPH oxidase.	2007 Sep 19	17880684
Neuroprotective effects of cannabidiol in endotoxin-induced uveitis: critical role of p38 MAPK activation.	2008	19052649
Antidepressant-like effects of the novel kappa opioid antagonist MCL-144B in the forced-swim test.	2008	18176093
Syntheses of 4,6'-epoxymorphinan derivatives and their pharmacologies.	2008 Apr 15	18337104
Quantitative 1H nuclear magnetic resonance metabolite profiling as a functional genomics platform to investigate alkaloid biosynthesis in opium poppy.	2008 Aug	18550684
NADPH oxidase as a therapeutic target in Alzheimer's disease.	2008 Dec 3	19090996
Enhancement of alkaloid production in opium and California poppy by transactivation using heterologous regulatory factors.	2008 Feb	17961129
Morphinane alkaloid dimers from Sinomenium acutum.	2008 Jan	18081254
Metabolic engineering of morphinan alkaloids by over-expression and RNAi suppression of salutaridinol 7-O-acetyltransferase in opium poppy.	2008 Jan	17854406
Concise synthesis of dimemorfan (DF) starting from 3-hydroxymorphinan (3-HM).	2008 Jul	18591815
Isolation and antimalarial activity of new morphinan alkaloids on Plasmodium yoelii liver stage.	2008 Jun 1	18456502
MLR-ANN and RTO approach to mu-opioid receptor-binding affinity. Pooling data from different sources.	2008 Mar	18248352
Neuronal apoptosis and inflammatory responses in the central nervous system of a rabbit treated with Shiga toxin-2.	2008 Mar 21	18355415
The presence of endogenous morphine signaling in animals.	2008 Oct	18777209
Synthesis of a stable iminium salt and propellane derivatives.	2008 Oct 17	18811203
Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae.	2008 Sep	18690217
Recent developments in the chemistry of thebaine and its transformation products as pharmacological targets.	2009	19548872
Bisbenzylisoquinoline alkaloids from Cocculus pendulus.	2009	19479625
Endogenous morphine and nitric oxide coupled regulation of mitochondrial processes.	2009 Dec	19946245
Univalent and bivalent ligands of butorphan: characteristics of the linking chain determine the affinity and potency of such opioid ligands.	2009 Dec 10	19634902
7α-Methoxy-carbonyl-6,7,8,14-tetra-hydro-6,14-endo-ethenothebaine.	2009 Mar 25	21582578
Visualisation and quantitative analysis of the rodent malaria liver stage by real time imaging.	2009 Nov 18	19924309
Synthesis and SAR study of opioid receptor ligands: mono- and bis-indolomorphinans.	2009 Oct	19691470
Evolution of morphine biosynthesis in opium poppy.	2009 Oct-Nov	19665152
Biochemistry and occurrence of o-demethylation in plant metabolism.	2010	21423357
Molecular characterization of O-methyltransferases involved in isoquinoline alkaloid biosynthesis in Coptis japonica.	2010	20689233
Biological indications of a novel "short" µ opiate receptor in domestic chicken.	2010 Aug 30	22371789
Harnessing biodiversity: the Malagasy Institute of Applied Research (IMRA).	2010 Dec 13	21144080
Morphinans and isoquinolines: acetylcholinesterase inhibition, pharmacophore modeling, and interaction with opioid receptors.	2010 Jul 15	20580236
Straightforward assembly of the octahydroisoquinoline core of morphinan alkaloids.	2010 May 21	20405954
Hasubanan alkaloids with delta-opioid binding affinity from the aerial parts of Stephania japonica.	2010 May 28	20426456
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures.	2010 Nov 18	21083930
Interactive effects of endogenous morphine, nitric oxide, and ethanol on mitochondrial processes.	2010 Oct	22419921
Total synthesis of (-)-morphine.	2010 Oct 4	20715192
In vitro and in vivo pharmacological profile of the 5-benzyl analogue of 14-methoxymetopon, a novel mu opioid analgesic with reduced propensity to alter motor function.	2010 Sep 11	20600882