Basic information
- CAS
125-73-5- Standard SMILES
CN1CC[C@@]23CCCC[C@@H]2[C@@H]1Cc1ccc(O)cc13- InChIKey
JAQUASYNZVUNQP-PVAVHDDUSA-N- Molecular formula
- C17H23NO
- Average molar mass
- 257.37 g/mol
- Monoisotopic mass
- 257.17796436
Overview
Dextrorphan is a morphinane alkaloid.
Names & identifiers
- Preferred name
- Dextrorphan
- IUPAC
- (1S,9S,10S)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
- English name
- DEXTRORPHAN
- Molecular formula
- C17H23NO
- Molecular weight
- 257.38
Names & synonyms
DEXTRORPHAN125-73-5DextrorphaneDextrorphanumd-3-Hydroxy-N-methylmorphinanDextro-DromoranRo 1-6794D-levorphanol(+)-dextrorphan04B7QNO9WSEnt-17-methylmorphinan-3-ol(+)-N-Methylmorphinan-3-ol
Show more names
Dextromethorphan EP Impurity BD-morphanLevorphanol d-formd-Form of levorphanolDEXTRORPHAN D-TARTRATE
CHEBI:29133RO-1-6794DTXSID30101417817-methyl-9alpha,13alpha,14alpha-morphinan-3-olMorphinan-3-ol, 17-methyl-, (9alpha,13alpha,14alpha)-Levorphanol D-RefChem:132419DTXCID601436721
Database identifiers
- CAS
125-73-5- PubChem CID
- 5360697
- DTXSID
DTXSID301014178- ChEMBL
CHEMBL1254766- ChEBI
CHEBI:29133- UNII
- 04B7QNO9WS
- EC Number
- 204-754-3
- Nikkaji
- J5.377E
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 23.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 357
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Narcotics
Pharmaceuticals -> Metabolite of Dextromethorphan
LogP3.11
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section158.89 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 195 °C · ≥195 °C
- alpha
- 20 · D20 +56.3° (c = 3 in abs alcohol)
- Boiling point
- 400.62 °C · 400.62°C (rough estimate)
- Density
- 0.9711 · 0.9711 (rough estimate)
- refractive index
- 1.52 · 1.5200 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- saline: soluble(lit.)
- pka
- 10.07 · 10.07±0.20(Predicted)
- color
- white to off-white
- optical activity
- 54 ° · [α]/D ≥+54°
- FDA UNII
- 4 B7QNO9WS · 04B7QNO9WS
- EPA Substance Registry System
- -3 · Morphinan-3-ol, 17-methyl-, (9.alpha.,13.alpha.,14.alpha.)- (125-73-5)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- WGK Germany
- 3 · 3
- RTECS
- 1832000 · QD1832000
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- rtecs
- QD1832000
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
Metabolism/MetabolitesDextrorphan is a known human metabolite of dextromethorphan.
MeSH Pharmacological Classification
Drugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists.
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesVasospastic therapy adjunct.
Additional notes
DefinitionChEBI: Dextrorphan is a morphinane alkaloid.
Related reactions
4 records
Compound notes
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