O-Desmethyltramadol

Death may occur when opiates are combined with depressants such as benzodiazepines, alcohol or other GABAergic substances. Taking large amounts of these substances together is strongly discouraged.

O-Desmethyltramadol
The skeletal formula of O-Desmethyltramadol
Chemical Nomenclature
Common names	O-Desmethyltramadol
Substitutive name	O-DSMT
Systematic name	3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenol
Class Membership
Psychoactive class	Depressant
Chemical class	Opioid
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 a summary of data gathered from users and resources. It is not a recommendation and should be verified with other sources for accuracy. Threshold < 10 mg Light 10 - 40 mg Common 40 - 60 mg Strong 60 - 80 mg Heavy > 80 mg Duration Total 6 - 8 hours Onset 15 - 60 minutes Peak 2 - 4 hours Offset 2 - 4 hours Afterglow 1 - 2 hours

Summary sheet: O-Desmethyltramadol

O-Desmethyltramadol (O-DSMT) is an opioid analgesic and the main active metabolite of tramadol. O-DSMT is the most important metabolite of tramadol produced in the liver after tramadol is consumed.

O-DSMT has recently been marketed as a currently legal substitute for illegal opioid drugs, either in powder form or mixed into various other preparations. One such blend is sold under the brand Krypton and contains powdered kratom leaf (Mitragyna speciosa) laced with O-DSMT and was reportedly linked to at least 9 accidental deaths from overdose during 2010–2011.

Chemistry

(+/-)O-Desmethyltramadol, or 3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenol, is an atypical synthetic opioid. O-Desmethyltramadol is loosely analogous to codeine, but is not a morphinan opiate. Instead, it contains two rings including a cyclohexane ring that is bonded to a phenyl ring at R₁. This phenyl ring is substituted at R₃ with a hydroxy group (OH-). An additional hydroxy group is found at the same location the cyclohexane ring is bonded to at the phenyl ring, R₁. O-DMST features a third substitution on its cyclohexane ring at R₂. Here the ring is bonded to a dimethylamine group connected through a methyl bridge.

O-Desmethyltramadol is atypical as it is found in a racemate (combination) of its stereoisomers. Stereoisomers are two molecules that share the same chemical structure, but are three-dimensional mirror images of each other. Tramadol is produced as a racemate of its two isomers because the combination is proven to be more effective. Flipping the direction of the R₂ and R₁ bonds results in the R- and S- enantiomers of O-Desmethyltramadol. O-DMST is nearly identical to tramadol, and is named for the lack of the methyl group of tramadol's R₃ methoxy substituion.

Pharmacology

O-DSMT is considerably more potent as a μ-opioid agonist compared to tramadol. Additionally, unlike tramadol, it is a high-affinity ligand of the δ- and κ-opioid receptors.

The two enantiomers of O-DSMT show quite distinct pharmacological profiles; both (+) and (−)-O-DSMT are inactive as serotonin reuptake inhibitors, but (−)-O-DSMT retains activity as a norepinephrine reuptake inhibitor, and so the mix of both the parent compound and metabolites contributes significantly to the complex pharmacological profile of tramadol. While the multiple receptor targets can be beneficial in the treatment of pain (especially complex pain syndromes such as neuropathic pain), it increases the potential for drug interactions compared to other opioids, and may also contribute to side effects.

The euphoric effects of this compound appear to stem from the way in which opioids mimic endogenous endorphins. Endorphins are responsible for analgesia (reducing pain), causing sleepiness, and feelings of pleasure. They can be released in response to pain, strenuous exercise, orgasm, or excitement. This mimicking of natural endorphins results in the drug's euphoric, analgesic (pain relief), and anxiolytic (anti-anxiety) effects.

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

The cognitive effects of O-Desmethyltramadol can be broken down into several components which progressively intensify proportional to dosage. The general head space of codeine is described by many as one of intense euphoria, relaxation, anxiety suppression and pain relief.

The most prominent of these cognitive effects generally include:

• Pain relief - This component is subjectively different from other anaesthetics as it does not necessarily remove the pain entirely whilst still remaining equal in terms of its effectiveness. Instead of directly suppressing pain, these substances simply dull the perceived sensation and cover it up with feelings of physical and emotional pleasure.
• Physical euphoria - This particular substance can be considered as less intense in its physical euphoria when compared with that of morphine or diacetylmorphine (heroin). The sensation itself can be described as extreme feelings of hyper intense physical comfort, snugglyness, warmth, love and blissful euphoria.
• Itchiness It presents greater amounts of itchiness due to higher amounts of histamine release.
• Respiratory depression - At low to moderate doses, this effect results in the sensation that the breath is slowed down mildly to moderately, but does not cause noticeable impairment. At high doses and overdoses, opioid-induced respiratory depression can result in a shortness of breath, abnormal breathing patterns, semi-consciousness, or unconsciousness. Severe overdoses can result in a coma or death without immediate medical attention.
• Constipation
• Cough suppression
• Difficulty urinating
• Nausea
• Sedation
• Pupil constriction

Cognitive effects

The physical effects of O-Desmethyltramadol can be broken down into several components which progressively intensify proportional to dosage.

These are described below and generally include:

• Cognitive euphoria - This particular substance can be considered as less intense in its cognitive euphoria when compared with that of morphine or diacetylmorphine (heroin). The sensation itself can be described as powerful and overwhelming feeling of emotional bliss, contentment, and happiness.
• Anxiety suppression
• Compulsive redosing

Toxicity and harm potential

O-Desmethyltramadol has not been shown to be toxic and is physically benign at reasonable dosages. As with all opioids, long-term effects can vary but can include diminished libido, apathy and memory loss.

Tolerance and addiction potential

Tolerance to many of the effects of tramadol develops with prolonged use, including therapeutic effects. The rate at which this occurs develops at different rates for different effects, with tolerance to the constipation-inducing effects developing particularly slowly for instance.

As with other opioid-based painkillers, chronic use of O-Desmethyltramadol can be considered as highly addictive and is capable of causing both physical and psychological dependence. When physical dependence has developed, withdrawal symptoms may occur if a person suddenly stops their usage.

Legal issues

This legality section is a stub. As such, it likely contains incomplete or wrong information. You can help by expanding it.

There is little information online regarding the international legalities of O-Desmethyltramadol possession but it is confirmed as a controlled substance within the United Kingdom.

See also

• Responsible use
• Tramadol
• O-Desmethyltramadol (Wikipedia)