3-Methoxymorphinan

Last updated
3-Methoxymorphinan
3-Methoxymorphinan.svg
Legal status
Legal status
  • US:uncontrolled
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard 100.014.764 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H23NO
Molar mass 257.377 g·mol−1
  • InChI=1S/C17H23NO/c1-19-13-6-5-12-10-16-14-4-2-3-7-17(14,8-9-18-16)15(12)11-13/h5-6,11,14,16,18H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1 Yes check.svgY
  • Key:ILNSWVUXAPSPEH-USXIJHARSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

3-Methoxymorphinan is an inactive metabolite of both dextromethorphan and levomethorphan, and has been shown to produce local anesthetic effects. [1] It is the CYP3A4 metabolite of the aforementioned drugs, [2] and is itself metabolized by the liver enzyme CYP2D6. [3]

See also

Related Research Articles

<span class="mw-page-title-main">Recreational use of dextromethorphan</span> Cough suppressant drug susceptible to misuse.

Dextromethorphan, or DXM, a common active ingredient found in many over-the-counter cough suppressant cold medicines, is used as a recreational drug and entheogen for its dissociative effects. It has almost no psychoactive effects at medically recommended doses. However, dextromethorphan has powerful dissociative properties when administered in doses well above those considered therapeutic for cough suppression. Recreational use of DXM is sometimes referred to in slang form as "robo-tripping", whose prefix derives from the Robitussin brand name, or "Triple Cs", which derives from the Coricidin brand whose tablets are printed with "CC+C" for "Coricidin Cough and Cold". However, this brand presents additional danger when used at recreational doses due to the presence of chlorpheniramine.

<span class="mw-page-title-main">Bupropion</span> Medication mainly used for depression and smoking cessation

Bupropion, formerly called amfebutamone, and sold under the brand name Wellbutrin among others, is an atypical antidepressant primarily used to treat major depressive disorder and to support smoking cessation. It is also popular as an add-on medication in the cases of "incomplete response" to the first-line selective serotonin reuptake inhibitor (SSRI) antidepressant. Bupropion has several features that distinguish it from other antidepressants: it does not usually cause sexual dysfunction, it is not associated with weight gain and sleepiness, and it is more effective than SSRIs at improving symptoms of hypersomnia and fatigue. Bupropion, particularly the immediate release formulation, carries a higher risk of seizure than many other antidepressants, hence caution is recommended in patients with a history of seizure disorder.

<span class="mw-page-title-main">Promethazine</span> Sedating Antihistamine

Promethazine, sold under the brand name Phenergan among others, is a first-generation antihistamine, antipsychotic, sedative, and antiemetic used to treat allergies, insomnia, and nausea. It may also help with some symptoms associated with the common cold and may also be used for sedating people who are agitated or anxious, an effect that has led to some recreational use. Promethazine is taken by mouth (oral), as a rectal suppository, or by injection into a muscle (IM).

<span class="mw-page-title-main">Dextrorphan</span> Psychoactive cough suppressant medication

Dextrorphan (DXO) is a psychoactive drug of the morphinan class which acts as an antitussive or cough suppressant and in high doses a dissociative hallucinogen. It is the dextrorotatory enantiomer of racemorphan; the levorotatory enantiomer is levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6. Dextrorphan is an NMDA antagonist and contributes to the psychoactive effects of dextromethorphan.

<span class="mw-page-title-main">Noscapine</span> Chemical compound

Noscapine is a benzylisoquinoline alkaloid, of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks significant hypnotic, euphoric, or analgesic effects affording it with very low addictive potential. This agent is primarily used for its antitussive (cough-suppressing) effects.

<span class="mw-page-title-main">Dextromethorphan</span> Cough suppressant, anti-depressent, and dissociative drug

Dextromethorphan (DXM), sold under the trade name Robitussin among others, is a cough suppressant used in many cough and cold medicines. It affects serotonin, norepinephrine, NMDA, and sigma-1 receptors in the brain, all of which have been implicated in the pathophysiology of depression. In 2022, the FDA approved the combination dextromethorphan/bupropion to serve as a rapid acting antidepressant in patients with major depressive disorder.

Sigma receptors (σ-receptors) are protein cell surface receptors that bind ligands such as 4-PPBP, SA 4503 (cutamesine), ditolylguanidine, dimethyltryptamine, and siramesine. There are two subtypes, sigma-1 receptors (σ1) and sigma-2 receptors (σ2), which are classified as sigma receptors for their pharmacological similarities, even though they are evolutionarily unrelated.

<span class="mw-page-title-main">Levorphanol</span> Opioid analgesic drug

Levorphanol is an opioid medication used to treat moderate to severe pain. It is the levorotatory enantiomer of the compound racemorphan. Its dextrorotatory counterpart is dextrorphan.

<span class="mw-page-title-main">Morphinan</span> Chemical compound

Morphinan is the prototype chemical structure of a large chemical class of psychoactive drugs, consisting of opiate analgesics, cough suppressants, and dissociative hallucinogens, among others. Typical examples include compounds such as morphine, codeine, and dextromethorphan (DXM). Despite related molecular structures, the pharmacological profiles and mechanisms of action between the various types of morphinan substances can vary substantially. They tend to function either as μ-opioid receptor agonists (analgesics), or NMDA receptor antagonists (dissociatives).

<span class="mw-page-title-main">Levomethorphan</span> Opioid analgesic

Levomethorphan (LVM) (INN, BAN) is an opioid analgesic of the morphinan family that has never been marketed. It is the L-stereoisomer of racemethorphan (methorphan). The effects of the two isomers of racemethorphan are quite different, with dextromethorphan (DXM) being an antitussive at low doses and a dissociative hallucinogen at much higher doses. Levomethorphan is about five times stronger than morphine.

<span class="mw-page-title-main">NMDA receptor antagonist</span> Class of anesthetics

NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the N-Methyl-D-aspartate receptor (NMDAR). They are commonly used as anesthetics for humans and animals; the state of anesthesia they induce is referred to as dissociative anesthesia.

<span class="mw-page-title-main">Tipepidine</span> Chemical compound

Tipepidine (INN), also known as tipepidine hibenzate (JAN), is a synthetic, non-opioid antitussive and expectorant of the thiambutene class. It acts as an inhibitor of G protein-coupled inwardly-rectifying potassium channels (GIRKs). The drug was discovered in the 1950s, and was developed in Japan in 1959. It is used as the hibenzate and citrate salts.

<span class="mw-page-title-main">Dimemorfan</span> Cough suppressant

Dimemorfan (INN), or dimemorfan phosphate (JAN), also known as 3,17-dimethylmorphinan, is an antitussive of the morphinan family that is widely used in Japan and is also marketed in Spain and Italy. It was developed by Yamanouchi Pharmaceutical and introduced in Japan in 1975. It was later introduced in Spain in 1981 and Japan in 1985.

<span class="mw-page-title-main">Alazocine</span> Synthetic opioid analgesic

Alazocine, also known more commonly as N-allylnormetazocine (NANM), is a synthetic opioid analgesic of the benzomorphan family related to metazocine, which was never marketed. In addition to its opioid activity, the drug is a sigma receptor agonist, and has been used widely in scientific research in studies of this receptor. Alazocine is described as a potent analgesic, psychotomimetic or hallucinogen, and opioid antagonist. Moreover, one of its enantiomers was the first compound that was found to selectively label the σ1 receptor, and led to the discovery and characterization of the receptor.

The alpha-3 beta-4 nicotinic receptor, also known as the α3β4 receptor and the ganglion-type nicotinic receptor, is a type of nicotinic acetylcholine receptor, consisting of α3 and β4 subunits. It is located in the autonomic ganglia and adrenal medulla, where activation yields post- and/or presynaptic excitation, mainly by increased Na+ and K+ permeability.

<span class="mw-page-title-main">Dextrallorphan</span> Chemical compound

Dextrallorphan (DXA) is a chemical of the morphinan class that is used in scientific research. It acts as a σ1 receptor agonist and NMDA receptor antagonist. It has no significant affinity for the σ2, μ-opioid, or δ-opioid receptor, or for the serotonin or norepinephrine transporter. As an NMDA receptor antagonist, in vivo, it is approximately twice as potent as dextromethorphan, and five-fold less potent than dextrorphan.

<span class="mw-page-title-main">FG-8205</span> Chemical compound

FG-8205 (L-663,581) is an imidazobenzodiazepine derivative related to bretazenil, which acts as a partial agonist at GABAA receptors, with slight selectivity for the α1-containing subtype. In animal tests it has anxiolytic and anticonvulsant effects but with little sedation or ataxia produced.

<span class="mw-page-title-main">3-Hydroxymorphinan</span> Chemical compound

3-Hydroxymorphinan (3-HM), or morphinan-3-ol, is a psychoactive drug of the morphinan family. It is the racemic counterpart to norlevorphanol.

Dextromethorphan/quinidine, sold under the brand name Nuedexta, is a fixed-dose combination medication for the treatment of pseudobulbar affect (PBA). It contains dextromethorphan (DXM) and the class I antiarrhythmic agent quinidine.

<span class="mw-page-title-main">Dextromethorphan/bupropion</span> Combination medication

Dextromethorphan/bupropion (DXM/BUP), sold under the brand name Auvelity, is a combination medication for the treatment of major depressive disorder (MDD). Its active components are dextromethorphan (DXM) and bupropion. Patients who stayed on the medication had an average of 11% greater reduction in depressive symptoms than placebo in an FDA approval trial. It is taken as a tablet by mouth.

References

  1. Hou CH, Tzeng JI, Chen YW, Lin CN, Lin MT, Tu CH, Wang JJ (August 2006). "Dextromethorphan, 3-methoxymorphinan, and dextrorphan have local anaesthetic effect on sciatic nerve blockade in rats". European Journal of Pharmacology. 544 (1–3): 10–16. doi:10.1016/j.ejphar.2006.06.013. PMID   16844109.
  2. Min DI, Ku YM, Vichiendilokkul A, Fleckenstein LL (June 1999). "A urine metabolic ratio of dextromethorphan and 3-methoxymorphinan as a probe for CYP3A activity and prediction of cyclosporine clearance in healthy volunteers". Pharmacotherapy. 19 (6): 753–759. doi:10.1592/phco.19.9.753.31536. PMID   10391422. S2CID   32243163.
  3. Strauch K, Lutz U, Bittner N, Lutz WK (August 2009). "Dose-response relationship for the pharmacokinetic interaction of grapefruit juice with dextromethorphan investigated by human urinary metabolite profiles". Food and Chemical Toxicology. 47 (8): 1928–1935. doi:10.1016/j.fct.2009.05.004. PMID   19445995.