Dextrorphan
Encyclopedia
Dextrorphan is a psychoactive drug
of the morphinan
chemical class which acts as an antitussive or cough suppressant and dissociative
hallucinogen. It is the dextro
-stereoisomer of racemorphan, the levo-half being levorphanol
. Dextrorphan is produced by O-demethylation of dextromethorphan
by CYP2D6
. Dextrorphan is an NMDA antagonist
and contributes to the abuse liability of dextromethorphan
.
The pharmacology of dextrorphan is similar to that of dextromethorphan
(DXM). However, dextrorphan is much more potent as an NMDA receptor antagonist and much weaker as a serotonin reuptake inhibitor, producing a noticeably more body-affecting, "stoned" feeling.
in the United States
, but was unscheduled on October 1, 1976.
Psychoactive drug
A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...
of the morphinan
Morphinan
Morphinan is the base chemical structure of a large chemical class of psychoactive drugs, consisting of opioid analgesics, cough suppressants, and dissociative hallucinogens, among others.- Chemical Derivatives :Immediate derivatives of morphinan include:...
chemical class which acts as an antitussive or cough suppressant and dissociative
Dissociative drug
Dissociatives are a class of psychoactive drugs which are said to reduce or block signals to the conscious mind from other parts of the brain...
hallucinogen. It is the dextro
Dextro
Dextro is the pseudonym given to the Scottish Falkirk born DIY musician, Ewan Mackenzie. Under the Dextro moniker he has released a number of works, most notably the albums Winded , Consequence Music and the 12" single Do You Need Help...
-stereoisomer of racemorphan, the levo-half being levorphanol
Levorphanol
Levorphanol is an opioid medication used to treat severe pain. It is the levorotatory stereoisomer of the synthetic morphinan and a pure opioid agonist, first described in Germany in 1948 as an orally active morphine-like analgesic...
. Dextrorphan is produced by O-demethylation of dextromethorphan
Dextromethorphan
Dextromethorphan is an antitussive drug. It is one of the active ingredients in many over-the-counter cold and cough medicines, such as Robitussin, NyQuil, Dimetapp, Vicks, Coricidin, Delsym, and others, including generic labels. Dextromethorphan has also found other uses in medicine, ranging...
by CYP2D6
CYP2D6
Cytochrome P450 2D6 , a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body. Also, many substances are bioactivated by CYP2D6 to form their active compounds...
. Dextrorphan is an NMDA antagonist
NMDA receptor antagonist
NMDA receptor antagonists are a class of anesthetics that work to antagonize, or inhibit the action of, the N-methyl d-aspartate receptor . They are used as anesthesia for animals and, less commonly, for humans; the state of anesthesia they induce is referred to as dissociative anesthesia...
and contributes to the abuse liability of dextromethorphan
Dextromethorphan
Dextromethorphan is an antitussive drug. It is one of the active ingredients in many over-the-counter cold and cough medicines, such as Robitussin, NyQuil, Dimetapp, Vicks, Coricidin, Delsym, and others, including generic labels. Dextromethorphan has also found other uses in medicine, ranging...
.
Pharmacology
- Noncompetitive N-methyl-D-aspartate receptorNMDA receptorThe NMDA receptor , a glutamate receptor, is the predominant molecular device for controlling synaptic plasticity and memory function....
(NMDAR) antagonist. - σ1Sigma-1 receptorThe sigma-1 receptor is a chaperone protein at the endoplasmatic reticulum that modulates calcium signaling through the IP3 receptor. In humans, the sigma-1 receptor is encoded by the SIGMAR1 gene....
and σ2Sigma receptorThe sigma receptors σ1 and σ2 bind to ligands such as 4-PPBP, SA 4503, ditolylguanidine, dimethyltryptamine and siramesine.- Classification :...
sigma receptorSigma receptorThe sigma receptors σ1 and σ2 bind to ligands such as 4-PPBP, SA 4503, ditolylguanidine, dimethyltryptamine and siramesine.- Classification :...
agonist. - α3β4, α4β2, and α7 nicotinic acetylcholine receptorNicotinic acetylcholine receptorNicotinic acetylcholine receptors, or nAChRs, are cholinergic receptors that form ligand-gated ion channels in the plasma membranes of certain neurons and on the postsynaptic side of the neuromuscular junction...
antagonist. - L-type voltage-gated calcium channelL-type calcium channelThe L-type calcium channel is a type of voltage-dependent calcium channel. "L" stands for long-lasting referring to the length of activation. Like the others of this class, the α1 subunit is the one that determines most of the channel's properties....
(LVGCC) blockerCalcium channel blockerA calcium channel blocker is a chemical that disrupts the movement of calcium through calcium channels.CCB drugs devised to target neurons are used as antiepileptics. However, the most widespread clinical usage of calcium channel blockers is to decrease blood pressure in patients with...
.
The pharmacology of dextrorphan is similar to that of dextromethorphan
Dextromethorphan
Dextromethorphan is an antitussive drug. It is one of the active ingredients in many over-the-counter cold and cough medicines, such as Robitussin, NyQuil, Dimetapp, Vicks, Coricidin, Delsym, and others, including generic labels. Dextromethorphan has also found other uses in medicine, ranging...
(DXM). However, dextrorphan is much more potent as an NMDA receptor antagonist and much weaker as a serotonin reuptake inhibitor, producing a noticeably more body-affecting, "stoned" feeling.
Legality
Dextrorphan was formerly a Schedule I controlled substanceControlled substance
A controlled substance is generally a drug or chemical whose manufacture, possession, or use are regulated by a government. This may include illegal drugs and prescription medications ....
in the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
, but was unscheduled on October 1, 1976.
See also
- DextromethorphanDextromethorphanDextromethorphan is an antitussive drug. It is one of the active ingredients in many over-the-counter cold and cough medicines, such as Robitussin, NyQuil, Dimetapp, Vicks, Coricidin, Delsym, and others, including generic labels. Dextromethorphan has also found other uses in medicine, ranging...
- Cough syrup
- Dissociative
- MorphanolMorphanolRacemorphan is the racemic mixture of the two stereoisomers of 17-methylmorphinan-3-ol, each with differing pharmacology and effects:* Dextrorphan - A dissociative hallucinogen and cough suppressant....
- MorphinanMorphinanMorphinan is the base chemical structure of a large chemical class of psychoactive drugs, consisting of opioid analgesics, cough suppressants, and dissociative hallucinogens, among others.- Chemical Derivatives :Immediate derivatives of morphinan include:...
- MetaboliteMetaboliteMetabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
- phenethylamines