UCSF

ZINC03201907

Draw Identity 99% 90% 80% 70%

Substance Information

In ZINC since Heavy atoms Benign functionality
November 7th, 2004 20 Yes

Popular Name: dextromethorphan dextromethorphan

Find On: PubMed — Wikipedia — Google

CAS Numbers: 125-69-9 , 125-70-2 , 125-71-3 , 18609-21-7 , 510-53-2 , 524713-56-2 , 6700-34-1 , 6700-34-1, 125-69-9 [anhydrous], 125-71-3 [dextromethorphan] , [6700-34-1]

Other Names:

(9alpha,13alpha,14alpha)-3-Methoxy-17-methylmorphinan hydrobromide; 9-alpha,13-alpha,14-alpha-Morphinan, 3-methoxy-17-methyl-, hydrobromide; Antussan; BROMANATE DM; BROMFED-DM; C18H25NO.HBr; DEXTROMETHORPHAN HYDROBROMIDE; DIMETANE-DX; Demorphan; Dextromet

(E)-N-(2-fluorophenyl)-2-(hydroxyimino)acetamide

orphan

125-71-3; D03742; Dextromethorphan (USP)

3-Methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan hydrobromide monohydrate; Bayer Select Flu Relief; Bayer Select Head & Chest Cold; Bayer Select Night Time Cold; Benylin DM; C18H25NO.HCl; Cerose-DM; Chloraseptic DM; Contac Cough & Sore Throat Formula

6700-34-1; Benylin DM (TN); D00848; Dextromethorphan hydrobromide (USP); Dextromethorphan hydrobromide hydrate (JP16)

6700-34-1; Dextromethorphan hydrobromide monohydrate; Prestwick_686

77

BAN

BRD-K33211335-337-03-7

CPD000326694; d-3-Methoxy-N-methylmorphinan hydrobromide

CPD000326694; Dextromethorphan Hydrobromide, Monohydrate; SAM001247062; d-3-Methoxy-N-methylmorphinan hydrobromide

CPD000326694; SAM001247062; d-3-Methoxy-N-methylmorphinan hydrobromide

DCF

DCL000773

Dextromethorphan (BAN

Dextromethorphan (hydrobromide)

Dextromethorphan (USP

Dextromethorphan hydrobromide

Dextromethorphan hydrobromide monohydrate

Dextromethorphan+quinidine

Dextromethorphan-d3

DEXTROMETHORPHANHYDROBROMIDE

Dextromethorphanhydrochloride

DM

DXM

FDA

INN

INN); Dextromethorphan Polistirex (FDA

JAN

JAN)

MFCD00866833

MFCD02173901

MI)

Morphinan, 3-methoxy-17-methyl-, hydrochloride, (9α,13α,14α)-

Racemethorphan (BAN

Robitussin Pediatric Cough; Triaminic;Bayer Select Flu Relief;Bayer Select Head & Chest Cold;Bayer Select Night Time Cold;Benylin DM;Benylin DM (TN);Cerose-DM;Chloraseptic DM;Contac Day & Night Cold/Flu Day Caplets;Contac Jr. Non-drowsy Formula;Contac Nig

USAN); Dextromethorphan Hydrobromide (BAN

USAN); Dextromethorphan Hydrobromide (FDA

USP

USP)

USP); Dextromethorphan Hydrobromide (BAN

USP); Dextromethorphan Polistirex (FDA

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 3.94 8.86 -39.89 1 2 1 14 272.412 1 ↓

Vendor Notes

Note Type Comments Provided By
Molecular_Solubility 4.531 Bitter DB
Purity 97 Fluorochem
biological_use Anticonvulsant and neuroprotective props. IBScreen Bioactives
Therapy antitussive SMDC Pharmakon IBScreen Bioactives
PUBCHEM_PATENT_ID EP0264081A2; EP0264081B1; EP0344919A2; EP0344919B1; EP0351049A1; EP0351049B1; EP0379147B1; EP0432956B1; EP0463395A1; EP0463395B1; EP0555411A1; EP0575977A2; EP0575977A3; EP0661022A1; EP0661022B1; EP0773780A1; EP0914446A2; EP0946145A2; EP0963161A1; EP104502 IBM Patent Data
PUBCHEM_SUBSTANCE_COMMENT NCC_SAMPLE_SUPPLIER : Tocris Cookson Ltd.; NCC_SUPPLIER_STRUCTURE_ID : 101433; 1 water; 1 hydrogen bromide NIH Clinical Collection via PubChem
mechanism NMDA receptor antagonist IBScreen Bioactives
PUBCHEM_SUBSTANCE_COMMENT SAMPLE_SUPPLIER: Tocris Bioscience; SUPPLIER_STRUCTURE_ID: 101433; SALT: 1 water; 1 hydrogen bromide NIH Clinical Collection via PubChem

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
NMD3A-3-E Glutamate [NMDA] Receptor Subunit 3A (cluster #3 Of 6), Eukaryotic Eukaryotes 490 0.44 Binding ≤ 10μM
NMD3A-3-E Glutamate [NMDA] Receptor Subunit 3A (cluster #3 Of 6), Eukaryotic Eukaryotes 1680 0.40 Binding ≤ 10μM
NMD3B-3-E Glutamate [NMDA] Receptor Subunit 3B (cluster #3 Of 6), Eukaryotic Eukaryotes 490 0.44 Binding ≤ 10μM
NMD3B-3-E Glutamate [NMDA] Receptor Subunit 3B (cluster #3 Of 6), Eukaryotic Eukaryotes 1680 0.40 Binding ≤ 10μM
NMDE1-2-E Glutamate [NMDA] Receptor Subunit Epsilon 1 (cluster #2 Of 5), Eukaryotic Eukaryotes 490 0.44 Binding ≤ 10μM
NMDE1-2-E Glutamate [NMDA] Receptor Subunit Epsilon 1 (cluster #2 Of 5), Eukaryotic Eukaryotes 1680 0.40 Binding ≤ 10μM
NMDE2-1-E Glutamate [NMDA] Receptor Subunit Epsilon 2 (cluster #1 Of 5), Eukaryotic Eukaryotes 490 0.44 Binding ≤ 10μM
NMDE2-1-E Glutamate [NMDA] Receptor Subunit Epsilon 2 (cluster #1 Of 5), Eukaryotic Eukaryotes 1680 0.40 Binding ≤ 10μM
NMDE3-1-E Glutamate [NMDA] Receptor Subunit Epsilon 3 (cluster #1 Of 4), Eukaryotic Eukaryotes 490 0.44 Binding ≤ 10μM
NMDE3-1-E Glutamate [NMDA] Receptor Subunit Epsilon 3 (cluster #1 Of 4), Eukaryotic Eukaryotes 1680 0.40 Binding ≤ 10μM
NMDE4-3-E Glutamate [NMDA] Receptor Subunit Epsilon 4 (cluster #3 Of 6), Eukaryotic Eukaryotes 490 0.44 Binding ≤ 10μM
NMDE4-3-E Glutamate [NMDA] Receptor Subunit Epsilon 4 (cluster #3 Of 6), Eukaryotic Eukaryotes 1680 0.40 Binding ≤ 10μM
NMDZ1-2-E Glutamate (NMDA) Receptor Subunit Zeta 1 (cluster #2 Of 6), Eukaryotic Eukaryotes 490 0.44 Binding ≤ 10μM
NMDZ1-2-E Glutamate (NMDA) Receptor Subunit Zeta 1 (cluster #2 Of 6), Eukaryotic Eukaryotes 1680 0.40 Binding ≤ 10μM
OPRD-1-E Delta Opioid Receptor (cluster #1 Of 3), Eukaryotic Eukaryotes 2000 0.40 Binding ≤ 10μM
OPRK-1-E Kappa Opioid Receptor (cluster #1 Of 6), Eukaryotic Eukaryotes 2000 0.40 Binding ≤ 10μM
OPRM-1-E Mu-type Opioid Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 2000 0.40 Binding ≤ 10μM
SCN1A-1-E Sodium Channel Protein Type I Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 1300 0.41 Binding ≤ 10μM
SCN1A-1-E Sodium Channel Protein Type I Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 1300 0.41 Binding ≤ 10μM
SCN2A-1-E Sodium Channel Protein Type II Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 1300 0.41 Binding ≤ 10μM
SCN2A-1-E Sodium Channel Protein Type II Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 1300 0.41 Binding ≤ 10μM
SCN3A-1-E Sodium Channel Protein Type III Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 1300 0.41 Binding ≤ 10μM
SCN3A-1-E Sodium Channel Protein Type III Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 1300 0.41 Binding ≤ 10μM
SCN8A-1-E Sodium Channel Protein Type VIII Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 1300 0.41 Binding ≤ 10μM
SCN8A-1-E Sodium Channel Protein Type VIII Alpha Subunit (cluster #1 Of 2), Eukaryotic Eukaryotes 1300 0.41 Binding ≤ 10μM
SGMR1-1-E Sigma Opioid Receptor (cluster #1 Of 6), Eukaryotic Eukaryotes 2000 0.40 Binding ≤ 10μM
SGMR1-1-E Sigma Opioid Receptor (cluster #1 Of 6), Eukaryotic Eukaryotes 5070 0.37 Binding ≤ 10μM
CP2D6-1-E Cytochrome P450 2D6 (cluster #1 Of 3), Eukaryotic Eukaryotes 3400 0.38 ADME/T ≤ 10μM
CP2DQ-1-E Cytochrome P450 2D2 (cluster #1 Of 1), Eukaryotic Eukaryotes 5600 0.37 ADME/T ≤ 10μM
Z104302-1-O Glutamate NMDA Receptor (cluster #1 Of 7), Other Other 590 0.44 Binding ≤ 10μM
Z104302-1-O Glutamate NMDA Receptor (cluster #1 Of 7), Other Other 2246 0.40 Binding ≤ 10μM
Z50425-3-O Plasmodium Falciparum (cluster #3 Of 22), Other Other 794 0.43 Functional ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
NMDZ1_HUMAN Q05586 Glutamate (NMDA) Receptor Subunit Zeta 1, Human 240 0.46 Binding ≤ 1μM
Z104302 Z104302 Glutamate NMDA Receptor 590 0.44 Binding ≤ 1μM
NMD3A_HUMAN Q8TCU5 Glutamate [NMDA] Receptor Subunit 3A, Human 490 0.44 Binding ≤ 1μM
NMD3B_HUMAN O60391 Glutamate [NMDA] Receptor Subunit 3B, Human 240 0.46 Binding ≤ 1μM
NMDE1_HUMAN Q12879 Glutamate [NMDA] Receptor Subunit Epsilon 1, Human 240 0.46 Binding ≤ 1μM
NMDE2_HUMAN Q13224 Glutamate [NMDA] Receptor Subunit Epsilon 2, Human 240 0.46 Binding ≤ 1μM
NMDE3_HUMAN Q14957 Glutamate [NMDA] Receptor Subunit Epsilon 3, Human 240 0.46 Binding ≤ 1μM
NMDE4_HUMAN O15399 Glutamate [NMDA] Receptor Subunit Epsilon 4, Human 240 0.46 Binding ≤ 1μM
SGMR1_HUMAN Q99720 Sigma Opioid Receptor, Human 348 0.45 Binding ≤ 1μM
SGMR1_CAVPO Q60492 Sigma-1 Receptor, Guinea Pig 15.2 0.55 Binding ≤ 1μM
OPRD_MOUSE P32300 Delta Opioid Receptor, Mouse 2000 0.40 Binding ≤ 10μM
NMDZ1_HUMAN Q05586 Glutamate (NMDA) Receptor Subunit Zeta 1, Human 240 0.46 Binding ≤ 10μM
Z104302 Z104302 Glutamate NMDA Receptor 2000 0.40 Binding ≤ 10μM
NMD3A_HUMAN Q8TCU5 Glutamate [NMDA] Receptor Subunit 3A, Human 490 0.44 Binding ≤ 10μM
NMD3B_HUMAN O60391 Glutamate [NMDA] Receptor Subunit 3B, Human 240 0.46 Binding ≤ 10μM
NMDE1_HUMAN Q12879 Glutamate [NMDA] Receptor Subunit Epsilon 1, Human 240 0.46 Binding ≤ 10μM
NMDE2_HUMAN Q13224 Glutamate [NMDA] Receptor Subunit Epsilon 2, Human 240 0.46 Binding ≤ 10μM
NMDE3_HUMAN Q14957 Glutamate [NMDA] Receptor Subunit Epsilon 3, Human 240 0.46 Binding ≤ 10μM
NMDE4_HUMAN O15399 Glutamate [NMDA] Receptor Subunit Epsilon 4, Human 240 0.46 Binding ≤ 10μM
OPRK_MOUSE P33534 Kappa Opioid Receptor, Mouse 2000 0.40 Binding ≤ 10μM
OPRM_MOUSE P42866 Mu Opioid Receptor, Mouse 2000 0.40 Binding ≤ 10μM
SGMR1_MOUSE O55242 Sigma Opioid Receptor, Mouse 2000 0.40 Binding ≤ 10μM
SGMR1_RAT Q9R0C9 Sigma Opioid Receptor, Rat 5070 0.37 Binding ≤ 10μM
SGMR1_HUMAN Q99720 Sigma Opioid Receptor, Human 348 0.45 Binding ≤ 10μM
SGMR1_CAVPO Q60492 Sigma-1 Receptor, Guinea Pig 15.2 0.55 Binding ≤ 10μM
SCN1A_RAT P04774 Sodium Channel Protein Type I Alpha Subunit, Rat 1300 0.41 Binding ≤ 10μM
SCN2A_RAT P04775 Sodium Channel Protein Type II Alpha Subunit, Rat 1300 0.41 Binding ≤ 10μM
SCN3A_RAT P08104 Sodium Channel Protein Type III Alpha Subunit, Rat 1300 0.41 Binding ≤ 10μM
SCN8A_RAT O88420 Sodium Channel Protein Type VIII Alpha Subunit, Rat 1300 0.41 Binding ≤ 10μM
Z50425 Z50425 Plasmodium Falciparum 6309.57344 0.36 Functional ≤ 10μM
CP2DQ_RAT P10634 Cytochrome P450 2D2, Rat 5600 0.37 ADME/T ≤ 10μM
CP2D6_HUMAN P10635 Cytochrome P450 2D6, Human 1800 0.40 ADME/T ≤ 10μM

Reactome Annotations from Targets (via Uniprot)

Description Species
CREB phosphorylation through the activation of CaMKII
CYP2E1 reactions
EPHB-mediated forward signaling
Fatty acids
G alpha (i) signalling events
G-protein activation
Miscellaneous substrates
Opioid Signalling
Peptide ligand-binding receptors
Ras activation uopn Ca2+ infux through NMDA receptor
Unblocking of NMDA receptor, glutamate binding and activation
Xenobiotics

Analogs ( Draw Identity 99% 90% 80% 70% )