| Identification | Back Directory | [Name]
racemethorphan | [CAS]
510-53-2 | [Synonyms]
Dea no. 9732
Racemetorfano
Racemethorphane
DEXMETHORPHANUM
Einecs 208-114-4
Deoxydihydrothebacodine
Racemethorphane [inn-french]
Racemethorphanum [inn-latin]
dl-3-Methoxy-N-methylmorphinan | [EINECS(EC#)]
208-114-4 | [Molecular Formula]
C18H25NO | [MOL File]
510-53-2.mol | [Molecular Weight]
271.4 |
| Chemical Properties | Back Directory | [Melting point ]
81-83 °C | [Boiling point ]
414.48°C (rough estimate) | [density ]
1.0115 (rough estimate) | [refractive index ]
1.5740 (estimate) | [pka]
9.13±0.20(Predicted) | [Water Solubility ]
36g/L(37 ºC) |
| Hazard Information | Back Directory | [Originator]
Symptom 1 ,Parke Davis,US,1977 | [Uses]
Racemethorphan is the racemic mixture of Dextromethorphan (D299445) and Levomethorphan (L375850). Dextromethorphan is an antitussive compound showing analgesic properties; used in cough medication formulations. Levomethorphan is an antitussive medicine, a narcotic and controlled substance. | [Definition]
ChEBI: 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene is an organic heterotetracyclic compound that is 1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene which is substituted by a methoxy group at position 6 and a methyl group at position 11. It is an aromatic ether, a morphinane alkaloid, a morphinane-like compound and an organic heterotetracyclic compound. | [Manufacturing Process]
The methylation of 51.4 parts by weight of D,L-3-hydroxy-N-methylmorphinan is carried out with a methylating solution obtained from 51.5 parts
by weight of phenyl-trimethylammonium-chloride. The D,L-3-methoxy-Nmethyl-morphinan is isolated in the form of its hydrobromide, which melts
with 1 mol of water at 92°-94°C,without water at 239°-240°C. The base
isolated from the aqueous solution by means of sodium carbonate melts at
81°-83°C.
27.1 parts by weight of D,L-3-methoxy-N-methyl-morphinan base are
dissolved with 15.0 parts by weight of D-tartaric acid in 150 parts by volume
of hot alcohol. The solution is cooled and seeded with (+)-3-methoxy-Nmethyl-morphinan-tartrate.The (+)-form which is difficultly soluble in alcohol
separates, is filtered by suction and washed with a little alcohol.
[The (-)-form may be crystallized from the residue obtained by concentrating
the mother liquor, separating therefrom as much as possible of the (+)-form
and adding acetone].
The (+)-3-methoxy-N-methyl-morphinan-tartrate melts with 1 mol of water at
195°-196°C [α]D20 =+30.6° (c = 1.5 in water). The (+) base melting at
108°-109°C may be obtained from the tartrate by means of sodium
carbonate. The corresponding hydrobromide melts at 122°-124°C [α]D20
=+27.6° (c = 1.5 in water). | [Therapeutic Function]
Antitussive |
|