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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 08:27:43 UTC

Update Date

2022-03-07 02:49:11 UTC

HMDB ID

HMDB0001920

Secondary Accession Numbers

HMDB0014655
HMDB01920
HMDB14655

Metabolite Identification

Common Name

Dextromethorphan

Description

Dextromethorphan is an antitussive drug that is found in many over-the-counter cold and cough preparations, usually in the form of dextromethorphan hydrobromide. Dextromethorphan is a salt of the methyl ether dextrorotatory isomer of levorphanol, a narcotic analgesic. Dextromethorphan occurs as white crystals, is sparingly soluble in water, and freely soluble in alcohol. The drug is dextrorotatory in water (at 20 degrees Celsius, Sodium D-line) with a specific rotation of +27.6 degrees. Following oral administration, dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan. The therapeutic activity of dextromethorphan is believed to be caused by both the drug and this metabolite. Dextromethorphan is predominantly metabolized by the liver, by various hepatic enzymes. Through various pathways, the drug undergoes (O-demethylation (which produces dextrorphan), N-demethylation, and partial conjugation with glucuronic acid and sulfate ions. The inactive metabolite (+)-3-hydroxy-N-methylmorphinan is formed as a product of DXM metabolism by these pathways. One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6. A significant portion of the population has a functional deficiency in this enzyme (and are known as poor CYP2D6 metabolizers). As CYP2D6 is the primary metabolic pathway in the inactivation of dextromethorphan, the duration of action and effects of dextromethorphan are significantly increased in such poor metabolizers. Deaths and hospitalizations have been reported in recreational use by poor CYP2D6 metabolizers. -- Wikipedia . This compound is an NMDA receptor antagonist (receptors, N-methyl-D-aspartate) and acts as a non-competitive channel blocker. It is also used to study the involvement of glutamate receptors in neurotoxicity. [PubChem]

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0001920
     RDKit          3D
Dextromethorphan
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.5186   -0.7319   -0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1859   -1.0634   -0.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0944   -0.3670   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2174    0.7164    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0818    1.3824    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8219    0.9665    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983   -0.1081   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373   -0.7797   -0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101   -0.6362   -0.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5105   -2.1311   -0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7417   -2.7918    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7502   -2.3235    1.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9451   -0.8503    1.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675   -0.1400    0.3351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6113    1.3437    0.5135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3659    1.6974    1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222    1.9783   -0.7654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3193    3.1634   -0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7579    1.0886   -1.8789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -0.0765   -1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7463    0.3323   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1733   -1.3126   -0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7259   -1.0768    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219    1.0315    1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    2.2324    1.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -1.6385   -1.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3206   -2.4907   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -2.5036    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -3.8754    0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -2.4436   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180   -2.9212    2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362   -2.5705    1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -0.6744    1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3260   -0.4374    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878   -0.3036   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734    1.7293    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702    1.5669    2.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1654    2.7889    1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5686    3.3353   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092    4.0265   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371    3.1398   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323    1.6904   -2.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8234    0.7965   -1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030   -0.8932   -2.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1514    0.1346   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 14  9  1  0
 16  6  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  6
 15 36  1  1
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
M  END


  Mrv1652305271900082D          

 21 24  0  0  0  0            999 V2000
    6.6802   -1.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9679   -1.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2556   -1.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2556   -2.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2556   -4.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2556   -5.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9679   -5.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6802   -5.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3925   -3.8657    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3926   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6802   -2.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9679   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9679   -3.8657    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6802   -4.2820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5692   -3.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0955   -3.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1049   -4.2820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4018   -4.7259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5355   -1.3940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -1.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8296   -4.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
  2  1  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  2  0  0  0  0
  3  2  1  0  0  0  0
  4 12  1  0  0  0  0
 13 12  1  0  0  0  0
  4  3  2  0  0  0  0
  9 10  1  0  0  0  0
 14  9  1  0  0  0  0
  9 17  1  1  0  0  0
  5 13  1  0  0  0  0
 14 13  1  0  0  0  0
 13 15  1  1  0  0  0
  8 14  1  0  0  0  0
 14 18  1  1  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 19  1  0  0  0  0
  3 19  1  0  0  0  0
 17 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001920

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(OC)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m0/s1

> <INCHI_KEY>
MKXZASYAUGDDCJ-CGTJXYLNSA-N

> <FORMULA>
C18H25NO

> <MOLECULAR_WEIGHT>
271.3972

> <EXACT_MASS>
271.193614427

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.77171760859394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.493774350666667

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.84630398780882

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
82.5632

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001920
     RDKit          3D
Dextromethorphan
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.5186   -0.7319   -0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1859   -1.0634   -0.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0944   -0.3670   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2174    0.7164    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0818    1.3824    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8219    0.9665    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983   -0.1081   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373   -0.7797   -0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101   -0.6362   -0.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5105   -2.1311   -0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7417   -2.7918    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7502   -2.3235    1.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9451   -0.8503    1.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675   -0.1400    0.3351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6113    1.3437    0.5135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3659    1.6974    1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222    1.9783   -0.7654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3193    3.1634   -0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7579    1.0886   -1.8789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -0.0765   -1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7463    0.3323   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1733   -1.3126   -0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7259   -1.0768    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219    1.0315    1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    2.2324    1.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -1.6385   -1.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3206   -2.4907   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -2.5036    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -3.8754    0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -2.4436   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180   -2.9212    2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362   -2.5705    1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -0.6744    1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3260   -0.4374    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878   -0.3036   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734    1.7293    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702    1.5669    2.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1654    2.7889    1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5686    3.3353   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092    4.0265   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371    3.1398   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323    1.6904   -2.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8234    0.7965   -1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030   -0.8932   -2.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1514    0.1346   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 14  9  1  0
 16  6  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  6
 15 36  1  1
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      12.470  -3.382   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.140  -2.623   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.810  -3.382   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.810  -4.919   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.810  -7.993   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.810  -9.513   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.140 -10.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.470  -9.513   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.799  -7.216   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.800  -5.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.470  -4.919   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.140  -5.696   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.140  -7.216   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.470  -7.993   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.263  -6.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.112  -6.439   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      15.129  -7.993   0.000  0.00  0.00           N+0
HETATM   18  H   UNK     0      13.817  -8.822   0.000  0.00  0.00           H+0
HETATM   19  O   UNK     0       8.466  -2.602   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.119  -3.376   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.482  -8.729   0.000  0.00  0.00           C+0
CONECT    1   11    2                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4   12    3                                                       
CONECT    5   13    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8   14    7                                                       
CONECT    9   10   14   17                                                  
CONECT   10   11    9                                                       
CONECT   11    1   10   12                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12    5   14   15                                             
CONECT   14    9   13    8   18                                             
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17    9   16   21                                                  
CONECT   18   14                                                            
CONECT   19   20    3                                                       
CONECT   20   19                                                            
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0001920
HETATM    1  C1  UNL     1       5.519  -0.732  -0.260  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.186  -1.063  -0.573  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.094  -0.367  -0.098  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.217   0.716   0.725  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.082   1.382   1.175  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.822   0.967   0.802  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.698  -0.108  -0.015  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.837  -0.780  -0.469  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.610  -0.636  -0.476  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.510  -2.131  -0.531  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.742  -2.792   0.090  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.750  -2.323   1.551  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.945  -0.850   1.644  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.768  -0.140   0.335  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.611   1.344   0.513  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.366   1.697   1.298  1.00  0.00           C  
HETATM   17  N1  UNL     1      -1.522   1.978  -0.765  1.00  0.00           N  
HETATM   18  C16 UNL     1      -2.319   3.163  -0.885  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.758   1.089  -1.879  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.814  -0.076  -1.891  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.746   0.332  -0.382  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.173  -1.313  -0.964  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.726  -1.077   0.786  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.222   1.031   1.011  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.245   2.232   1.825  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.745  -1.639  -1.122  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.321  -2.491  -1.556  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.353  -2.504   0.093  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.586  -3.875   0.067  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.630  -2.444  -0.455  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.518  -2.921   2.054  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.736  -2.571   1.940  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.015  -0.674   1.957  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.326  -0.437   2.465  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.688  -0.304  -0.262  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.473   1.729   1.103  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.470   1.567   2.374  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.165   2.789   1.116  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.569   3.335  -1.947  1.00  0.00           H  
HETATM   40  H20 UNL     1      -1.709   4.027  -0.522  1.00  0.00           H  
HETATM   41  H21 UNL     1      -3.237   3.140  -0.261  1.00  0.00           H  
HETATM   42  H22 UNL     1      -1.532   1.690  -2.806  1.00  0.00           H  
HETATM   43  H23 UNL     1      -2.823   0.796  -1.984  1.00  0.00           H  
HETATM   44  H24 UNL     1      -1.303  -0.893  -2.461  1.00  0.00           H  
HETATM   45  H25 UNL     1       0.151   0.135  -2.358  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   16
CONECT    7    8    8    9
CONECT    8   26
CONECT    9   10   14   20
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   33   34
CONECT   14   15   35
CONECT   15   16   17   36
CONECT   16   37   38
CONECT   17   18   19
CONECT   18   39   40   41
CONECT   19   20   42   43
CONECT   20   44   45
END

HMDB0001920
     RDKit          3D
Dextromethorphan
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.5186   -0.7319   -0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1859   -1.0634   -0.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0944   -0.3670   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2174    0.7164    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0818    1.3824    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8219    0.9665    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983   -0.1081   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373   -0.7797   -0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101   -0.6362   -0.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5105   -2.1311   -0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7417   -2.7918    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7502   -2.3235    1.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9451   -0.8503    1.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675   -0.1400    0.3351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6113    1.3437    0.5135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3659    1.6974    1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222    1.9783   -0.7654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3193    3.1634   -0.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7579    1.0886   -1.8789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8140   -0.0765   -1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7463    0.3323   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1733   -1.3126   -0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7259   -1.0768    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219    1.0315    1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    2.2324    1.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -1.6385   -1.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3206   -2.4907   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -2.5036    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -3.8754    0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -2.4436   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180   -2.9212    2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362   -2.5705    1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -0.6744    1.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3260   -0.4374    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878   -0.3036   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734    1.7293    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702    1.5669    2.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1654    2.7889    1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5686    3.3353   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092    4.0265   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371    3.1398   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323    1.6904   -2.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8234    0.7965   -1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030   -0.8932   -2.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1514    0.1346   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 14  9  1  0
 16  6  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  6
 15 36  1  1
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-3-Methoxy-17-methylmorphinan	ChEBI
(-)-3-Methoxy-N-methylmorphinan	ChEBI
L-3-Methoxy-17-methylmorphinan	ChEBI
L-Methorphan	ChEBI
Levomethorphane	ChEBI
Levomethorphanum	ChEBI
Levometorfano	ChEBI
D-Methorphan	HMDB
delta-Methorphan	HMDB
DXM	HMDB
Δ-methorphan	HMDB
Robitussin pediatric cough	HMDB
Triaminic	HMDB
Bayer select flu relief	HMDB
Bayer select head & chest cold	HMDB
Bayer select night time cold	HMDB
Benylin DM	HMDB
Cerose-DM	HMDB
Chloraseptic DM	HMDB
Contac day & night cold/flu day caplets	HMDB
Contac jr. non-drowsy formula	HMDB
Contac nighttime cold medicine	HMDB
Contac severe cold formula maximum strength	HMDB
Contac severe cold formula non-drowsy	HMDB
Coricidin syrup	HMDB
Cough-X	HMDB
D-Methorphan hydrobromide	HMDB
Demorphan	HMDB
Demorphan hydrobromide	HMDB
Demorphine	HMDB
Destrometerfano	HMDB
Dextromethorphan bromhydrate	HMDB
Dextromethorphan bromide	HMDB
Dextromethorphan hydrobromide monohydrate	HMDB
Dextromethorphan hydrobromide oros tablets	HMDB
Dextromethorphan hydrobromide	HMDB
Dextrometorphan	HMDB
Dextromorphan	HMDB
Dexyromethorphan	HMDB
Dimacol	HMDB
Dimetapp DM	HMDB
Drixoral cough	HMDB
Drixoral cough & congestion	HMDB
Drixoral cough & sore throat	HMDB
Endotussin-NN	HMDB
Endotussin-NN pediatric	HMDB
Hold	HMDB
Levomethorphan	HMDB
Methorate	HMDB
Naldecon-DX	HMDB
Ornex severe cold formula	HMDB
Orthoxicol	HMDB
PediaCare 1	HMDB
PediaCare cough-cold formula	HMDB
Prestwick_686	HMDB
Robitussin CF	HMDB
Robitussin cold & cough	HMDB
Robitussin cough calmers	HMDB
Robitussin DM	HMDB
Robitussin maximum strength cough	HMDB
Robitussin pediatric cough & cold	HMDB
Robitussin pediatric night relief	HMDB
Romilar	HMDB
Rondec DM	HMDB
Ru-tuss expectorant	HMDB
St. joseph cough syrup	HMDB
Sudafed cough syrup	HMDB
Trind-DM	HMDB
Tussar DM	HMDB
Tussi-organidin	HMDB
Tussi-organidin DM NR	HMDB
Tussi-organidin DM-S NR	HMDB
Tylenol cold and flu multi-symptom	HMDB
Tylenol cold and flu no drowsiness	HMDB
Tylenol cold no drowsiness	HMDB
Tylenol cough + decongestant liquid	HMDB
Tylenol cough liquid	HMDB
Tylenol flu no drowsiness gelcaps	HMDB
Viro-med	HMDB
Dextromethorphan, (+-)-isomer	HMDB
Dextromethorphan hydrobromide, monohydrate	HMDB
Hydrochloride, dextromethorphan	HMDB
Racemethorphan	HMDB
Delsym	HMDB
Dextromethorphan hydrobromide, (+-)-isomer	HMDB
Dextromethorphan hydrochloride	HMDB
Hydrobromide, dextromethorphan	HMDB

Chemical Formula

C₁₈H₂₅NO

Average Molecular Weight

271.3972

Monoisotopic Molecular Weight

271.193614427

IUPAC Name

(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene

Traditional Name

(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene

CAS Registry Number

125-71-3

SMILES

[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(OC)C=C2

InChI Identifier

InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m0/s1

InChI Key

MKXZASYAUGDDCJ-CGTJXYLNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Phenanthrene
Benzazocine
Tetralin
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Ether
Organoheterocyclic compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:4470 )
organic heterotetracyclic compound (CHEBI:4470 )
morphinane-like compound (CHEBI:4470 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014655)

Source

Exogenous

Exogenous (HMDB: HMDB0014655)

Process

Not Available

Role

Biological role

NMDA receptor antagonist (HMDB: HMDB0014655)

Indirect biological role

Metabotoxin

Neurotoxin (HMDB: HMDB0014655)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8.51 mg/L	Not Available
LogP	3.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	166.3	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	3.75	ALOGPS
logP	3.49	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	9.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.56 m³·mol⁻¹	ChemAxon
Polarizability	31.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.273	31661259
DarkChem	[M-H]-	164.522	31661259
AllCCS	[M+H]+	167.884	32859911
AllCCS	[M-H]-	174.489	32859911
DeepCCS	[M-2H]-	198.983	30932474
DeepCCS	[M+Na]+	174.211	30932474
AllCCS	[M+H]+	167.9	32859911
AllCCS	[M+H-H2O]+	164.5	32859911
AllCCS	[M+NH4]+	171.1	32859911
AllCCS	[M+Na]+	172.0	32859911
AllCCS	[M-H]-	174.5	32859911
AllCCS	[M+Na-2H]-	174.4	32859911
AllCCS	[M+HCOO]-	174.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dextromethorphan	[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(OC)C=C2	3238.6	Standard polar	33892256
Dextromethorphan	[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(OC)C=C2	2164.8	Standard non polar	33892256
Dextromethorphan	[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(OC)C=C2	2141.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dextromethorphan EI-B (Non-derivatized)	splash10-0ab9-9640000000-22a67aaa9771bdc70ea1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dextromethorphan EI-B (Non-derivatized)	splash10-0ab9-9640000000-22a67aaa9771bdc70ea1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextromethorphan GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-0190000000-5d924eb9e80a3ad52d7b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextromethorphan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextromethorphan Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0006-2931000000-7ed39f5c12687bd18073	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextromethorphan Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-001i-9450000000-484ef060149382ae3835	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextromethorphan Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-004i-0296000000-9cc5da1af6297bf41d6a	2018-05-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 10V, Positive-QTOF	splash10-00di-0090000000-25cdbb74a0783952c40e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 20V, Positive-QTOF	splash10-00di-0090000000-8062e3b60f2d8d6c78b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 40V, Positive-QTOF	splash10-0btc-3290000000-e2bedc154835e1c44dbc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 10V, Negative-QTOF	splash10-00di-0090000000-cdc95ffda5c8ab176bc0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 20V, Negative-QTOF	splash10-00di-0090000000-82ba173765c1d557ad82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 40V, Negative-QTOF	splash10-0udl-0190000000-f4f99127c0b1de038b01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 10V, Positive-QTOF	splash10-00di-0090000000-01488ff14969daea9a7c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 20V, Positive-QTOF	splash10-00di-0090000000-a31adf377a9c1f79d0fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 40V, Positive-QTOF	splash10-0h2b-2790000000-0c7169ca6b6ad7325e80	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 10V, Negative-QTOF	splash10-00di-0090000000-429ffca83bb47ee26787	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 20V, Negative-QTOF	splash10-00di-0090000000-429ffca83bb47ee26787	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextromethorphan 40V, Negative-QTOF	splash10-0jba-0190000000-8b48abf42b5c1c70d082	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2018-05-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.16 +/- 0.085 uM	Adult (>18 years old)	Both	Peripheral Neuropathy	17157116	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.435 uM	Children (1-13 years old)	Not Specified	myoclonic seizures	8158182	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Peripheral neuropathy
Thisted RA, Klaff L, Schwartz SL, Wymer JP, Culligan NW, Gerard G, Pope LE, Berg JE: Dextromethorphan and quinidine in adult patients with uncontrolled painful diabetic peripheral neuropathy: a 29-day, multicenter, open-label, dose-escalation study. Clin Ther. 2006 Oct;28(10):1607-18. [PubMed:17157116 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022738

KNApSAcK ID

Not Available

Chemspider ID

4642423

KEGG Compound ID

C06947

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levomethorphan

METLIN ID

Not Available

PubChem Compound

5362449

PDB ID

Not Available

ChEBI ID

146176

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2. [PubMed:2660263 ]
Hargreaves RJ, Hill RG, Iversen LL: Neuroprotective NMDA antagonists: the controversy over their potential for adverse effects on cortical neuronal morphology. Acta Neurochir Suppl (Wien). 1994;60:15-9. [PubMed:7976530 ]
Hernandez SC, Bertolino M, Xiao Y, Pringle KE, Caruso FS, Kellar KJ: Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors. J Pharmacol Exp Ther. 2000 Jun;293(3):962-7. [PubMed:10869398 ]
Brooks BR, Thisted RA, Appel SH, Bradley WG, Olney RK, Berg JE, Pope LE, Smith RA: Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial. Neurology. 2004 Oct 26;63(8):1364-70. [PubMed:15505150 ]
Carliss RD, Radovsky A, Chengelis CP, O'Neill TP, Shuey DL: Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain. Neurotoxicology. 2007 Jul;28(4):813-8. Epub 2007 Apr 6. [PubMed:17573115 ]
Tang YW, Rys PN, Rutledge BJ, Mitchell PS, Smith TF, Persing DH: Comparative evaluation of colorimetric microtiter plate systems for detection of herpes simplex virus in cerebrospinal fluid. J Clin Microbiol. 1998 Sep;36(9):2714-7. [PubMed:9705419 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Enzyme Details

2. Glutamate [NMDA] receptor subunit 3A

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism
Gene Name:: GRIN3A
Uniprot ID:: Q8TCU5
Molecular weight:: 125464.1

Enzyme Details

3. Sigma non-opioid intracellular receptor 1

General function:: Involved in C-8 sterol isomerase activity
Specific function:: Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma membrane. Involved in the regulation of different receptors it plays a role in BDNF signaling and EGF signaling. Also regulates ion channels like the potassium channel and could modulate neurotransmitter release. Plays a role in calcium signaling through modulation together with ANK2 of the ITP3R-dependent calcium efflux at the endoplasmic reticulum. Plays a role in several other cell functions including proliferation, survival and death. Originally identified for its ability to bind various psychoactive drugs it is involved in learning processes, memory and mood alteration
Gene Name:: SIGMAR1
Uniprot ID:: Q99720
Molecular weight:: 25127.5

Enzyme Details

4. Neuronal acetylcholine receptor subunit alpha-2

General function:: Involved in extracellular ligand-gated ion channel activity
Specific function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Gene Name:: CHRNA2
Uniprot ID:: Q15822
Molecular weight:: 59764.8

Transporters

Enzyme Details

1. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

Showing metabocard for Dextromethorphan (HMDB0001920)

MOL for HMDB0001920 (Dextromethorphan)

3D MOL for HMDB0001920 (Dextromethorphan)

3D SDF for HMDB0001920 (Dextromethorphan)

3D-SDF for HMDB0001920 (Dextromethorphan)

PDB for HMDB0001920 (Dextromethorphan)

3D PDB for HMDB0001920 (Dextromethorphan)

SMILES for HMDB0001920 (Dextromethorphan)

INCHI for HMDB0001920 (Dextromethorphan)

Structure for HMDB0001920 (Dextromethorphan)

3D Structure for HMDB0001920 (Dextromethorphan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Transporters