Dextromethorphan

Dextromethorphan
The skeletal formula of Dextromethorphan.
Chemical Nomenclature
Common names	Dextromethorphan, DXM
Substitutive name	DM, Robitussin, Delsym, DM, DexAlone, Duract
Systematic name	(4bS,8aR,9S)-3-Methoxy-11-methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene
Class Membership
Psychoactive class	Dissociative
Chemical class	Morphinan
Routes of Administration
Oral Dosage WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy. Threshold 80 - 90 mg Light 100 - 200 mg (plateau 1) Common 200 - 400 mg (plateau 2) Strong 300 - 600 mg (plateau 3) Heavy 600 - 1500 mg+ (plateau 4) Duration Total 6 - 8 hours Onset 20 - 60 minutes Peak 3 - 6 hours Offset 3 - 5 hours Afterglow 2 - 5 hours

Summary sheet: Dextromethorphan

Dextromethorphan (DXM or DM) is an antitussive (cough suppressant) drug of the morphinan class. It is one of the active ingredients in many over-the-counter common cold and cough medicines, including generic drug labels and store brands. Dextromethorphan has also found other uses in medicine, ranging from pain relief to psychological applications. In its pure form, dextromethorphan occurs as a white powder. but it is most commonly sold in syrup, tablet, spray, and throat lozenge forms.

DXM is also used recreationally. When exceeding label-specified maximum dosages, dextromethorphan acts as a dissociative hallucinogen. In high doses, this produces effects similar to, yet distinct from, the dissociative states created by other hallucinogens such as ketamine and phencyclidine.

Chemistry

General formula of morphinan molecule.

Dextromorphan is a dextratrorotatory molecule of the morphinan class. It contains a phenanthrene core structure with one aromatic ring (benzene) bound to two saturated rings (cyclohexane). Additionally it contains a nitrogen containing 6-membered saturated ring attached to R9 and R13 of the core structure. DXM is substituted at R_N with a methyl group and at R₃ with a methoxy group.

Pharmacology

Main article: NMDA receptor antagonist

DXM acts as an NMDA receptor antagonist. NMDA receptors allow for electrical signals to pass between neurons in the brain and spinal column; for the signals to pass, the receptor must be open. Dissociatives close the NMDA receptors by blocking them. This disconnection of neurons leads to loss of feeling, difficulty moving, and eventually the famous “hole”.

The mechanism of action behind DXM is via multiple effects, including actions as a nonselective serotonin reuptake inhibitor, alpha-3 beta-4 nicotinic receptor antagonist and a sigma-1 receptor agonist.

At high doses, DXM can cause an increase in systolic and diastolic blood pressure of 20.8 mm Hg and 14.6mm Hg respectively along with an increase of a 26bpm increase in heart rate. DXM also increases blood plasma levels of adrenocorticotropic hormone (ACTH) and corticosterone.

Metabolism

DXM is O-demethylated into Dextrorphan (DXO / D-3-hydroxy-N-methylmorphinan) by the CYP2D6 enzyme. DXM is also N-demethylated into 3-methoxymorphinan (MEM / Morphinan) by the CYP3A4 enzyme and to a lesser extent CYP3A5.

Dextrorphan and 3-methoxymorphinan are both metabolised into 3-hydroxymorphinan. Dextrorphan is N-demethylated by CYP3A4 and 3-Methoxymorphinan is O-demethylated by CYP2D6. CYP2D6 O-demethylation is more effective than CYP3A4 N-demethylation.

Dextrorphan

Dextrorphan is produced by O-demethylation of dextromethorphan through the CYP2D6 enzyme and contributes to the psychoactive effects of dextromethorphan. It is pharmacologically similar to that of dextromethorphan (DXM). However, dextrorphan is much more potent as an NMDA receptor antagonist as well as essentially inactive as a serotonin reuptake inhibitor. It is also about 3-fold less potent of a α3β4 nicotinic receptor antagonist than DXM and has a lower affinity for sigma-1 receptors.

3-Methoxymorphinan

3-Methoxymorphinan is produced by the N-demethylation of dextromethorphan by the CYP3A4 enzyme and inhibits the CYP2D6 enzyme.

Subjective effects

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.

Physical effects

• Tactile disconnection
• Spontaneous tactile sensations - The DXM "body high" is a sharp, pleasurable tingling sensation which is location specific to the hands, feet and head.
• Tactile suppression - This partially to entirely suppresses one's own sense of touch, creating feelings of numbness within the extremities. It is responsible for the anaesthetic properties of this substance.
• Physical autonomy
• Motor control loss - A loss of gross and fine motor control along side of balance and coordination is prevalent within DXM and becomes especially strong at higher dosages. This means that one should be sitting down before the onset unless they are experienced in case of falling over and injuring oneself.
• Euphoria - This results in feelings of physical euphoria which range between mild pleasure to powerful all-encompassing bliss.
• Perception of decreased weight - This creates the sensation that the body is floating and has become entirely weightless. This effect is strangely stimulating and encourages physical activities at low to moderate dosages by making the body feel light and effortless to move.
• Dizziness - Although uncommon, some people report dizziness under the influence of DXM.
• Nausea - It's worth noting that high dose DXM trips can sometimes result in nausea and vomiting at the peak of trip. This is more intense than the nausea found within ketamine and MXE. For most people, however, this is surprisingly not as unpleasant as they would initially expect due to the accompanying detachment from the physical senses.
• Cough suppression

Cognitive effects

The head space of DXM is often described as particularly impairing, disorientating and generally less clear-headed in comparison to that of MXE and ketamine. The cognitive effects of DXM can be broken down into several separate subcomponents which are listed and described below:

• Depersonalization
• Derealization
• Consciousness disconnection
• Memory suppression
• Immersion enhancement
• Time distortion
• Thought deceleration
• Information processing suppression
• Déjà vu
• Personal bias suppression
• Conceptual thinking
• Unity and interconnectedness
• Cognitive euphoria - The main reason this comes about is due the serotonin reuptake inhibition.
• Creativity enhancement

Visual effects

Suppression

• Visual disconnection - This eventually results in the DXM's equivalent of the famous "K-hole" or more specifically, holes, spaces and voids alongside of structures.
• Visual acuity suppression
• Visual sliding
• Double vision - This component is prevalent at moderate to heavy dosages and makes reading impossible unless one closes an eye.
• Pattern recognition suppression - This effect generally occurs at higher dosages and makes one unable to recognize and interpret perceivable visual data.
• Frame rate suppression

Distortions

• Perspective distortions
• Environmental cubism
• Environmental orbism
• Scenery slicing

Geometry

The visual geometry found within DXM can be described as very bright, colourful, psychedelic and intricate when compared to that of ketamine or MXE. It does not extend beyond level 4 and can be comprehensively described through its variations as intricate in complexity, algorithmic in style, synthetic in feel, unstructured in organization, brightly lit in lighting, multicoloured in scheme, glossy in shading, soft in edges, small in size, slow in speed, smooth in motion, equal in rounded and angular corners, immersive in depth and consistent in intensity.

Hallucinatory states

At high dosages, DXM can produce a full range of high level hallucinatory states in a fashion that is less consistent and reproducible than that of many other commonly used psychedelics. These effects include:

• External hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots) - In comparison to other dissociatives, this effect can occur at heavy dosages, but is extremely infrequent in comparison to the same effect found within deliriants. It can be comprehensively described through its variations as delirious in believability, autonomous in controllability and solid in style. The most common theme for this effect to follow is one of experiencing and talking to friends around oneself when they are not actually present.
• Internal hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots) - In comparison to other dissociatives, this effect can occur at heavy dosages, but is considerably less common than the same effect found within psychedelics and deliriants. It can be comprehensively described through its variations as delirious in believability, fixed in style, equal in new experiences and memory replays in content, autonomous in controllability and solid in style.
• Effect::Closed eye hallucinations

Auditory effects

• Enhancements
• Suppression
• Distortions
• Hallucinations

Afterglow

The afterglow is a feeling that often occurs within the 24 hours after the trip itself. It is long-lasting and as equally enjoyable as the trip itself to many people. It can be be described in terms of its physical sensation as one of euphoria, rejuvenation, relaxation and a light bounciness. In terms of its mental thought processes, however, it can be described as a complete loss of anxiety, feelings of content, and an extremely high appreciation for music.

Potentiation

Grape fruit juice

It's worth noting that grapefruit juice is extremely efficient for potentiating and enhancing the DXM trip if approximately 1 glass of white grapefruit juice or more is drunk every hour throughout the day before the trip. The effects will be considerably stronger and more intense. For people who are drinking store brought syrup, this is extremely useful as it means drinking less foul syrup.

The grapefruit juice acts on DXM by inhibiting the activity of cytochrome P450 enzymes of the 3A and 1A groups. DXM is converted to DXO by this same enzyme, only with different groups. Therefore, with enough grapefruit juice, the overall trip should be significantly more intense, as the DXM is converted into DXO at a faster rate.

Cannabis

Through the same mechanism, CBD contained in the cannabis plant potentiates the DXM metabolization, thus increases the quantity of DXO in the body.

Available Forms

DXM is available in several different forms and these can all be found over the counter or online.

• Cough syrup is the most common form online and over the counter. Well-known brands include Benylin, Comtrex, Coricidin, CVS, Robitussin, Sudafed and Tylenol. Many of these products contain other medicines, including aspirin, paracetamol, caffeine, guaifenesin and pseudoephedrine. Care should be taken when using these products to ensure that there is no overdose on other medicines in the DXM-containing product. Within the UK, benylin non-drowsy dry cough syrup is available behind the counter within every ASDA, Tescos, Sainsburys, Morrisons and boots with a 450mg dosage per 150ml bottle at a price of £4.69. Generic brands are also available within these shops for a consistently cheaper price.
• Gel capsules are available online and over the counter. Well-known brands include Benylin, Comtrex, Coricidin, CVS, Robitussin, Sudafed and Tylenol. Many of these products contain other medicines, including aspirin, paracetamol, caffeine, guaifenesin and pseudoephedrine. Care should be taken when using these products to ensure that there is no overdose on other medicines in the DXM-containing product.
• Pure powder is available online. This is the safest way to use DXM, as there is no danger of overdose from secondary chemicals.

Toxicity and harm potential

The toxicity and long-term health effects of recreational DXM use in humans do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because DXM has very little history of human usage. Anecdotal evidence from people who have tried DXM within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

Despite early speculation that DXM (due to similarities with PCP) may cause neurotoxicty and Olneys lesions, it has not been shown to cause this effect in animals. In rats, oral administration of dextromethorphan did not cause neurotoxic effects in laboratory tests. Oral administration of dextromethorphan repeatedly during adolescence, however, has been shown to impair learning in those rats during adulthood.

It is strongly recommended that one use harm reduction practices when using this drug.

Tolerance and addiction potential

As with other NMDA receptor antagonists, the chronic use of DXM can be considered moderately addictive with a high potential for abuse and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and withdrawal effects may occur if a person suddenly stops their usage.

Tolerance to many of the effects of DXM develops with prolonged and repeated use. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3 - 7 days for the tolerance to be reduced to half and 1 - 2 weeks to be back at baseline (in the absence of further consumption). DXM presents cross-tolerance with all dissociatives, meaning that after the consumption of DXM all dissociatives will have a reduced effect.

A formal survey of dextromethorphan users showed that more than half of users reported experience of the following withdrawal symptoms individually for the first week after long-term/addictive dextromethorphan use: fatigue, apathy, flashbacks, and constipation. Over a quarter reported insomnia, nightmares, inability to feel pleasure, impaired memory, attention deficit and decreased libido. Rarer side effects included panic attacks, impaired learning, tremor, yellowing of the skin, hives and muscle pain. Frequent and long-term usage at very high doses could possibly lead to toxic psychosis and other permanent psychological problems.

Dangerous interactions

Although many drugs are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

• Depressants - This combination potentiates the muscle relaxation, sedation and amnesia caused by one another and can lead to unexpected loss of consciousness at high doses. There is also an increased risk of vomiting during unconsciousness and death from the resulting suffocation. If this occurs, users should attempt to fall asleep in the recovery position or have a friend move them into it. Examples include 1,4-butanediol, 2-methyl-2-butanol, benzodiazepines, GHB, GBL, and opioids. Also, this combination will produce a combined depressant effect which can cause dangerous levels of respiratory depression.
• Stimulants - A dangerous rise in blood pressure and heart rate can occur when DXM is combined with a stimulant such as amphetamine and/or cocaine.

Serotonin syndrome risk

Combinations in the list below may increase the amount of neurotransmitters such as serotonin and dopamine to dangerous or even fatal levels.

• MAOIs such as syrian rue, banisteriopsis caapi, 2C-T-2, 2C-T-7, αMT, and some antidepressants
• Serotonin releasers such as MDMA, 4-FA, MDAI and αMT
• Selective serotonin re-uptake inhibitors (SSRIs)
• 5-HTP

Other interactions

• DXM has been shown to attenuate trimethyltin-induced neurotoxicity in rats.
• Modafinil induces the CYP3A4 enzyme that DXM and its metabolite DXO are metabolized by.
• DXM has been shown to prevent and reverse morphine tolerance while also increasing analgesic effects as well as potentiating the analgesic activity of NSAIDs, ibuprofen, naproxen, piroxicam, etodolac, diclofenac, and ketorolac.

Legal issues

DXM is available either over the counter or by prescription in most countries. Some countries require the purchaser to be over 16, 18 or 21. However, it is easily accessible to legally purchase in a variety of forms online.

Preparation methods

Preparation methods for this compound within our preparation index include:

• Acid-base DXM extraction

Experience reports

Anecdotal reports which describe this compound within our experience index include:

• Experience:1000mg / 1200mg / 1400mg / 1600mg - heroic doses
• Experience:1064mgs - Fascinating DXM experience - Unusual effects
• Experience:700mg - To the dextroverse.
• Experience:DXM Itch and Trip Report

Additional experience reports can be found here:

• Erowid Experience Vaults: DXM

See also

• Responsible use
• DXM Trip Reports
• Dissociatives
• Arylcyclohexylamines

External links

• DXM (Wikipedia)
• DXM (Erowid)
• DXM (TripSit)
• DXM (Disregard Everything I Say)
• DXM (Bluelight)
• The DXM FAQ (Erowid)
• DXM experiences (Erowid)