DEXTRORPHAN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H23NO
Molecular Weight	257.3706
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC4=CC=C(O)C=C34

InChI

InChIKey=JAQUASYNZVUNQP-PVAVHDDUSA-N

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

HIDE SMILES / InChI

Molecular Formula	C17H23NO
Molecular Weight	257.3706
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27139517 | https://www.ncbi.nlm.nih.gov/pubmed/24393077 | https://www.ncbi.nlm.nih.gov/pubmed/2897648

Dextrorphan is an active metabolite of dextromethorphan, is an antitussive agent, which was found in cough medicines. Dextrorphan is a noncompetitive N-methyl-D-aspartate receptor (NMDAR) antagonist, sigma 1 receptor agonist, so as is an agonist of mu and kappa opioid receptors. In addition was found, that dextrorphan possessed anticonvulsive and neuroprotective effects.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14742749	Antagonist 2849
Sigma opioid receptor 64 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10064839	Agonist 2752	144.0 nM [Ki]
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24393077	Agonist 2752	520.0 nM [Ki]
Kappa opioid receptor 115 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24393077	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2897648	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Simultaneous determination of dextromethorphan, dextrorphan, and guaifenesin in human plasma using semi-automated liquid/liquid extraction and gradient liquid chromatography tandem mass spectrometry.	2007-01-17	16930908
CYP2D6 genotype and phenotype relationship in South Indians.	2006-11-15	17102541
Comparative effects of dextromethorphan and dextrorphan on nicotine discrimination in rats.	2006-11	17112574
The impact of experimental design on assessing mechanism-based inactivation of CYP2D6 by MDMA (Ecstasy).	2006-11	16478752
Standardization of method for the analysis of dextromethorphan in urine.	2006-09-12	16837153
Dextromethorphan, 3-methoxymorphinan, and dextrorphan have local anaesthetic effect on sciatic nerve blockade in rats.	2006-08-21	16844109
Potential interactions of methylphenidate and atomoxetine with dextromethorphan.	2006-08-18	16913391
Selective effects of nitric oxide on the disposition of chlorzoxazone and dextromethorphan in isolated perfused rat livers.	2006-07	16621933
Opioid peptides and receptors in joint tissues: study in the rat.	2006-06	16649179
CYP2D6 genotype and phenotype in Amerindians of Tepehuano origin and Mestizos of Durango, Mexico.	2006-05	16638736
Effects of N-methyl-D-aspartate receptor antagonism on neuroleptic-induced orofacial dyskinesias.	2006-04	16518645
Agents that act by different mechanisms modulate the activity of protein kinase CbetaII isozyme in the rat spinal cord during peripheral inflammation.	2006	16360284
Effect of low-dose ritonavir (100 mg twice daily) on the activity of cytochrome P450 2D6 in healthy volunteers.	2005-12	16338282
Dextromethorphan psychosis, dependence and physical withdrawal.	2005-12	16318953
Measurement of CYP2D6 and CYP3A4 activity in vivo with dextromethorphan: sources of variability and predictors of adverse effects in 419 healthy subjects.	2005-12	16315033
The effect of CYP2D6 polymorphisms on dextromethorphan metabolism in Mexican Americans.	2005-11	16239355
Effect of methamphetamine on the pharmacokinetics of dextromethorphan and midazolam in rats.	2005-10-28	16250257
Enhancing the uptake of dextromethorphan in the CNS of rats by concomitant administration of the P-gp inhibitor verapamil.	2005-10-21	15964599
[The action of dextrorphan and sigma ligands on the spontaneous secretion of interleukins by jurkat cell line].	2005-10	16308450
QT and QTc interval with standard and supratherapeutic doses of darifenacin, a muscarinic M3 selective receptor antagonist for the treatment of overactive bladder.	2005-09	16100298
Conserved structural and functional control of N-methyl-D-aspartate receptor gating by transmembrane domain M3.	2005-08-19	15970596
Differential binding properties of [3H]dextrorphan and [3H]MK-801 in heterologously expressed NMDA receptors.	2005-07	15992576
Dextromethorphan to dextrorphan urinary metabolic ratio does not reflect dextromethorphan oral clearance.	2005-07	15821042
Evaluation of dextromethorphan metabolism using hepatocytes from CYP2D6 poor and extensive metabolizers.	2005-06	15988119
[Pharmacogenetic study of the response to flecainide and propafenone in patients with atrial fibrillation].	2005-06	15970126
Validation of a liquid chromatography-mass spectrometry method to assess the metabolism of dextromethorphan in rat everted gut sacs.	2005-05-05	15797528
Sol-gel-based solid-phase microextraction and gas chromatography-mass spectrometry determination of dextromethorphan and dextrorphan in human plasma.	2005-04-25	15734154
The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan.	2005-04	15723099
Frequency distribution of dextromethorphan O-demethylation in a Greek population.	2005-03	15792399
Determination of dextromethorphan and its metabolite dextrorphan in human urine using high performance liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry: a study of selectivity of a tandem mass spectrometric assay.	2005-02-25	15664362
Intravenous dextromethorphan to human volunteers: relationship between pharmacokinetics and anti-hyperalgesic effect.	2005-02	15661445
Dextromethorphan metabolic phenotyping in an Iranian population.	2005-02	15657780
Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity.	2005-02	15356218
On-line solid phase extraction using the Prospekt-2 coupled with a liquid chromatography/tandem mass spectrometer for the determination of dextromethorphan, dextrorphan and guaifenesin in human plasma.	2005	16046804
High-throughput biological sample analysis using on-line turbulent flow extraction combined with monolithic column liquid chromatography/tandem mass spectrometry.	2005	15988727
LC-MS/MS analysis of dextromethorphan metabolism in human saliva and urine to determine CYP2D6 phenotype and individual variability in N-demethylation and glucuronidation.	2004-12-25	15556536
Multiple night-time doses of valerian (Valeriana officinalis) had minimal effects on CYP3A4 activity and no effect on CYP2D6 activity in healthy volunteers.	2004-12	15328251
Plasma profile and pharmacokinetics of dextromethorphan after intravenous and oral administration in healthy dogs.	2004-10	15500572
Pharmacokinetics of dextromethorphan after single or multiple dosing in combination with quinidine in extensive and poor metabolizers.	2004-10	15342614
Development of a chromatographic bioreactor based on immobilized beta-glucuronidase on monolithic support for the determination of dextromethorphan and dextrorphan in human urine.	2004-09-03	15336363
Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats.	2004-08-06	15240177
[Determination of dextrorphan in human plasma and pharmacokinetic study].	2004-06	15491104
Modulation of morphine analgesia by site-specific N-methyl-D-aspartate receptor antagonists: dependence on sex, site of antagonism, morphine dose, and time.	2004-06	15157688
Validated assays for human cytochrome P450 activities.	2004-06	15155557
Metabolic activity of dextromethorphan O-demethylation in healthy Japanese volunteers carrying duplicated CYP2D6 genes: duplicated allele of CYP2D6*10 does not increase CYP2D6 metabolic activity.	2004-06	15149890
Dimemorfan prevents seizures induced by the L-type calcium channel activator BAY k-8644 in mice.	2004-05-05	15084442
The effect of cimetidine on dextromethorphan O-demethylase activity of human liver microsomes and recombinant CYP2D6.	2004-04	16680870
Influence of concomitant quinidine administration on dextromethorphan disposition in rats.	2004-04	15096109
Glutamate receptor antagonists block cocaine-induced convulsions and death.	1991-11	1684527
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.	1991-03-01	1685312

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Dextrorphan (DX) was evaluated for antiepileptic properties in vitro. Interictal bursts and prolonged ictal epileptiform afterdischarges, induced by perfusion of guinea pig neocortical brain slices with Mg2+-free solution, were blocked by DX (1-250 microM). Intracellular records showed that DX blocked N-methyl-D-aspartate (NMDA)-induced depolarizations without altering intrinsic membrane properties. DX blocked NMDA but not quisqualate-evoked multi-unit excitatory responses.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:01:46 GMT 2025` Edited by `admin` on `Mon Mar 31 19:01:46 GMT 2025`
Record UNII	04B7QNO9WS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVORPHANOL D-FORM

Preferred Name

English

DEXTRORPHAN

Official Name

English

DEXTRO-DROMORAN

Common Name

English

MORPHINAN-3-OL, 17-METHYL-, (9.ALPHA.,13.ALPHA.,14.ALPHA.) -

Systematic Name

English

(+)-N-METHYLMORPHINAN-3-OL

Systematic Name

English

DEXTROMETHORPHAN HYDROBROMIDE IMPURITY B [EP IMPURITY]

Common Name

English

17-METHYL-9.ALPHA.,13.ALPHA.,14.ALPHA.-MORPHINAN-3-OL

Common Name

English

DEXTRORPHAN [MART.]

Common Name

English

ENT-17-METHYLMORPHINAN-3-OL

Common Name

English

Dextrorphan [WHO-DD]

Common Name

English

RO-1-6794

Code

English

MORPHINAN-3-OL, 17-METHYL-, (9.ALPHA.,13.ALPHA.,14.ALPHA.)-

Common Name

English

dextrorphan [INN]

Common Name

English

RO 1-6794

Code

English

LEVORPHANOL D-FORM [MI]

Common Name

English

(+)-DEXTRORPHAN

Common Name

English

D-LEVORPHANOL

Common Name

English

Code System Code Type Description

CAS

125-73-5