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| CAS No.: | 3176-03-2 |
|---|---|
| Name: | Drotebanol |
| Molecular Structure: | |
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| Formula: | C19H27 N O4 |
| Molecular Weight: | 333.428 |
| Synonyms: | Morphinan,6b,14-dihydroxy-3,4-dimethoxy-N-methyl-(7CI); Morphinan-6b,14-diol, 3,4-dimethoxy-17-methyl- (8CI); 6b,14-Dihydroxy-3,4-dimethoxy-N-methylmorphinan;Dihydro-14-hydroxy-4-O-methyl-6b-thebainol; Dihydro-14-hydroxy-6b-thebainol 4-methyl ether; Drotebanol; Metebanyl;Oxymetebanol; Oxymethebanol |
| Density: | 1.27g/cm3 |
| Melting Point: | 165.5-166.5° |
| Boiling Point: | 506.7°Cat760mmHg |
| Flash Point: | 260.2°C |
| Safety: | Poison by subcutaneous and intravenous routes. Moderately toxic by ingestion. An antitussive agent. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS. |
| PSA: | 62.16000 |
| LogP: | 1.41560 |
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Chemistry
Product Name: Drotebanol (CAS NO.3176-03-2)
Molecular Formula: C19H27NO4
Molecular Weight: 333.47g/mol
Mol File: 3176-03-2.mol
Boiling point: 506.7 °C at 760 mmHg
Flash Point: 260.2 °C
Density: 1.27 g/cm3
Surface Tension: 58.1 dyne/cm
Enthalpy of Vaporization: 81.77 kJ/mol
Vapour Pressure: 4.35E-11 mmHg at 25°C
XLogP3-AA: 1.6
H-Bond Donor: 2
H-Bond Acceptor: 5
Structure Descriptors of Drotebanol (CAS NO.3176-03-2):
Canonical SMILES: CN1CCC23CC(CCC2(C1CC4=C3C(=C(C=C4)OC)OC)O)O
Isomeric SMILES: CN1CC[C@]23C[C@@H](CC[C@]2([C@H]1CC4=C3C(=C(C=C4)OC)OC)O)O
InChI: InChI=1S/C19H27NO4/c1-20-9-8-18-11-13(21)6-7-19(18,22)15(20)10-12-4-5-14(23-2)17(24-3)16(12)18/h4-5,13,15,21-22H,6-11H2,1-3H3/t13-,15-,18-,19-/m1/s1
InChIKey: LCAHPIFLPICNRW-SVYNMNNPSA-N
Uses
Drotebanol (CAS NO.3176-03-2) has powerful antitussive (cough suppressant) effects. It also has analgesic effects several times stronger than codeine, but weaker than morphine. It was previously marketed for human use under the brand name Metebanyl, although it is now no longer used in medicine. In animal studies it was found to be moderately addictive and produced limited physical dependence, but not as severe as that seen with morphine or pethidine.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| guinea pig | LD50 | subcutaneous | 919mg/kg (919mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 43, 1970. |
| mouse | LD50 | intravenous | 87mg/kg (87mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 535, 1979. | |
| mouse | LD50 | oral | 697mg/kg (697mg/kg) | Drugs in Japan Vol. -, Pg. 282, 1995. | |
| mouse | LD50 | subcutaneous | 1150mg/kg (1150mg/kg) | BEHAVIORAL: ANALGESIA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Chemical and Pharmaceutical Bulletin. Vol. 19, Pg. 1, 1971. |
| rat | LD50 | intravenous | 122mg/kg (122mg/kg) | Drugs in Japan Vol. 6, Pg. 156, 1982. | |
| rat | LD50 | oral | 339mg/kg (339mg/kg) | Drugs in Japan Vol. -, Pg. 282, 1995. | |
| rat | LD50 | subcutaneous | 120mg/kg (120mg/kg) | Drugs in Japan Vol. 6, Pg. 156, 1982. |
Safety Profile
Poison by subcutaneous and intravenous routes. Moderately toxic by ingestion. An antitussive agent. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS.
Specification
Drotebanol , its CAS NO. is 3176-03-2, the synonyms are 14-Hydroxy-6-beta-thebainol 4-methyl ether ; 14-Hydroxydihydro-6-beta-thebainol 4-methyl ether ; 3,4-Dimethoxy-17-methylmorphinan-6-beta,14-diol ; 6-beta,14-Dihydroxy-3,4-dimethoxy-N-methylmorphinan ; Dihydro-14-hydroxy-4-O-methyl-6-beta-thebainol ; Dihydro-14-hydroxy-6-beta-thebainol 4 methyl ester ; Drotebanolum ; Metebanyl ; Morphinan, 6-beta,14-dihydroxy-3,4-dimethoxy-N-methyl- ; Oxymetebanol ; Oxymethebanol ; RAM-326 ; UNII-7RS2Q8MCK8 .