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UC205

Sigma-Aldrich

Dextrorphan

Synonym(s):

(+)-3-Hydroxy-17-methylmorphinan, 1,3,4,9,10,10a-Hexahydro-6-hydroxy-2H-10,4a-(iminoethano)-11-methylphenanthrene

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About This Item

Empirical Formula (Hill Notation):
C17H23NO
CAS Number:
125-73-5
Molecular Weight:
257.37
EC Number:
204-754-3
MDL number:
MFCD00864199
UNSPSC Code:
12161501
PubChem Substance ID:
24724648
NACRES:
NA.77

form

solid

Quality Level

200

optical activity

[α]/D ≥+54°

color

white to off-white

mp

≥195 °C

solubility

saline: soluble(lit.)

storage temp.

2-8°C

SMILES string

CN1CC[C@@]23CCCC[C@@H]2[C@@H]1Cc4ccc(O)cc34

InChI

1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1

InChI key

JAQUASYNZVUNQP-PVAVHDDUSA-N

Gene Information

human ... GRIN2A(2903)
rat ... Grin2a(24409)

Application

Dextrorphan has been studies as an N-methyl-D-aspartate (NMDA) receptor antagonist in Xenopus oocytes and hippocampal neuron cultures.
CYP2D6 O-Demethyl metabolite of dextromethorphan

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

Dextrorphan is soluble in water.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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F Girardin et al.
Journal of viral hepatitis, 19(8), 568-573 (2012-07-06)
Liver kidney microsomal type 1 (LKM-1) antibodies have been shown to decrease the CYP2D6 activity in vitro and are present in a minority of patients with chronic hepatitis C infection. We investigated whether LKM-1 antibodies might reduce the CYP2D6 activity
Chris G Parsons et al.
Methods in molecular biology (Clifton, N.J.), 403, 15-36 (2008-10-02)
Electrophysiological techniques can be used to great effect to help determine the mechanism of action of a compound. However, many factors can compromise the resulting data and their analysis, such as the speed of solution exchange, expression of additional ion
Gaëlle Magliocco et al.
Clinical pharmacokinetics, 58(11), 1373-1391 (2019-05-28)
Drug response is subject to an important within- and between-individual variability owing, mainly, to pharmacokinetic and pharmacodynamic factors. Pharmacokinetics includes metabolism by cytochrome P450 (CYP450), major enzymes of phase I reactions that are responsible for the biotransformation of around 60%
Xiaorong Liang et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(8-9), 799-806 (2009-02-25)
Dried blood spots (DBSs) technology was evaluated in an assay for the quantitation of dextromethorphan (DM) and its metabolite, dextrorphan (DT), in human whole blood using high performance liquid chromatography with tandem mass spectrometry method (LC-MS/MS). Both the parent drug
Ihab R Kamel et al.
Journal of neurosurgical anesthesiology, 20(4), 241-248 (2008-09-25)
Ketamine, an intravenous anesthetic and a major drug of abuse, is a noncompetitive N-methyl-D-aspartate (NMDA) receptor antagonist. Ketamine's enantiomer, S(+)-ketamine, acts stereoselectively on neuronal NMDA receptors. The purpose of this in vitro study was to compare the direct effects of
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