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Name	Drotebanol	EINECS	N/A
CAS No.	3176-03-2	Density	1.27g/cm³
PSA	62.16000	LogP	1.41560
Solubility	N/A	Melting Point	165.5-166.5°
Formula	C19H27 N O4	Boiling Point	506.7°Cat760mmHg
Molecular Weight	333.428	Flash Point	260.2°C
Transport Information	N/A	Appearance	N/A
Safety	Poison by subcutaneous and intravenous routes. Moderately toxic by ingestion. An antitussive agent. When heated to decomposition it emits toxic fumes of NO_x. See also ESTERS.	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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

Drotebanol Chemical Properties

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

Drotebanol 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.

Drotebanol 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.

Drotebanol Safety Profile

Poison by subcutaneous and intravenous routes. Moderately toxic by ingestion. An antitussive agent. When heated to decomposition it emits toxic fumes of NO_x. See also ESTERS.

Drotebanol 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 .