Racemethorphan is a racemic mixture of the stereoisomers of methorphan , namely dextromethorphan , which is the active ingredient in "DM" cough syrups , and the lesser known levomethorphan which is described as a controlled substance in The Merck Index - likely because it has more potential for abuse than its dextro enantiomer . In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecules. ... The Merck Index is an encyclopedia of chemicals, drugs and biologicals with over 10,000 monographs on single substances or groups of related compounds. ...
levomethorphan is the methyl ether analog of levorphanol and these two substances are related in the same way that codeine (which is the methyl ether of morphine) is related to morphine . Levomethorphan is an optical isomer of dextromethorphan. ... Levorphanol is an opioid medication used to treat severe pain. ... Codeine (INN) or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. ... Morphine (INN) (IPA: ) is a potent opiate analgesic drug and is the principal active agent in opium. ... Morphine (INN) (IPA: ) is a potent opiate analgesic drug and is the principal active agent in opium. ...
"The Merck Index " http://en.wikipedia.org/wiki/Merck_Index The Merck Index is an encyclopedia of chemicals, drugs and biologicals with over 10,000 monographs on single substances or groups of related compounds. ...
It has been synthesized from a benzylisoquinoline (with a planar structure) by a process known as Grewe's cyclization (from the 1950's !) to give the corresponding morphinan (with a three dimensional structure).
The isoquinoline is 1,2,3,4,5,6,7,8-octahydro-1-(4-methoxybenzyl)isoquinoline (there is just one residual double bond at the fusion position of the two rings of the isoquinoline) is converted into the N-formyl derivative, cyclized to the N- formyl normorphinan, and the formyl group reduced to an N-methyl group, to give 3-methoxy-17-methylmorphinan, or Racemethorphan.
The racemic mixture (Racemethorphan) and the (-)-isomer (Levomethorphan) are both Schedule II drugs under the Controlled Substances Act, but the (+)-isomer (Dextromethorphan) has been exempted from scheduling (see 21 U.S.C. 812 (g)(2)).
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