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{{DepressantOD|opiates}}
{{SummarySheet}}
{{SubstanceBox/O-Desmethyltramadol}}
'''O-Desmethyltramadol''' (also known as '''O-DSMT''' and '''desmetramadol''') is an [[psychoactive class::opioid]] substance of the [[chemical class::phenylpropylamine]] class. It is an active metabolite of [[tramadol]].<ref name="Sevcik1993">{{cite journal | vauthors=((Sevcik, J.)), ((Nieber, K.)), ((Driessen, B.)), ((Illes, P.)) | journal=British Journal of Pharmacology | title=Effects of the central analgesic tramadol and its main metabolite, O-desmethyltramadol, on rat locus coeruleus neurones | volume=110 | issue=1 | pages=169–176 | date= September 1993 | issn=0007-1188 | doi=10.1111/j.1476-5381.1993.tb13788.x}}</ref>

O-DSMT has no documented history of human use before it appeared for sale on the [[research chemical]] market in the 2010s.

[[Subjective effects]] include [[sedation]], [[pain relief]], [[anxiety suppression]], [[muscle relaxation]], and [[euphoria]]. In comparison to [[tramadol]], O-DSMT is reported to be less [[stimulation|stimulating]] and feels considerably closer to a traditional [[opiate]]. Being the metabolite that is mainly responsible for the analgesic effect of tramadol, O-DSMT is significantly more potent by weight than its parent compound.

O-DSMT has a very short history of human use and not much is known about its toxicity and abuse potential. However a human clinical trial in 2019 ascertained that O-DSMT shares tramadol's safety profile when used in (low) therapeutic dosages<ref>Zebala JA, Searle SL, Webster LR, Johnson MS, Schuler AD, Maeda DY, Kahn SJ. Desmetramadol Has the Safety and Analgesic Profile of Tramadol Without Its Metabolic Liabilities: Consecutive Randomized, Double-Blind, Placebo- and Active Comparator-Controlled Trials. J Pain. 2019 Oct;20(10):1218-1235. doi: 10.1016/j.jpain.2019.04.005. Epub 2019 Apr 18. PMID: 31005596; PMCID: PMC6790288.</ref>. It is highly advised to use [[harm reduction practices]] if using this substance.

==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 methylene 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.<ref>{{cite journal | vauthors=((Dayer, P.)), ((Desmeules, J.)), ((Collart, L.)) | journal=Drugs | title=[Pharmacology of tramadol] | volume=53 Suppl 2 | pages=18–24 | date= 1997 | issn=0012-6667 | doi=10.2165/00003495-199700532-00006}}</ref> Additionally, unlike tramadol, it is a high-affinity ligand of the [[δ]]- and [[κ-opioid]] receptors.<ref>{{cite journal | vauthors=((Potschka, H.)), ((Friderichs, E.)), ((Löscher, W.)) | journal=British Journal of Pharmacology | title=Anticonvulsant and proconvulsant effects of tramadol, its enantiomers and its M1 metabolite in the rat kindling model of epilepsy | volume=131 | issue=2 | pages=203–212 | date= September 2000 | issn=0007-1188 | doi=10.1038/sj.bjp.0703562}}</ref>

The two enantiomers of O-DSMT show quite distinct pharmacological profiles;<ref>{{cite journal | vauthors=((Bamigbade, T. A.)), ((Davidson, C.)), ((Langford, R. M.)), ((Stamford, J. A.)) | journal=British Journal of Anaesthesia | title=Actions of tramadol, its enantiomers and principal metabolite, O-desmethyltramadol, on serotonin (5-HT) efflux and uptake in the rat dorsal raphe nucleus | volume=79 | issue=3 | pages=352–356 | date= September 1997 | issn=0007-0912 | doi=10.1093/bja/79.3.352}}</ref> both (+) and (−)-O-DSMT are inactive as [[serotonin]] [[reuptake inhibitor]]s,<ref name="Driessen1993">{{cite journal | vauthors=((Driessen, B.)), ((Reimann, W.)), ((Giertz, H.)) | journal=British Journal of Pharmacology | title=Effects of the central analgesic tramadol on the uptake and release of noradrenaline and dopamine in vitro | volume=108 | issue=3 | pages=806–811 | date= March 1993 | issn=0007-1188 | doi=10.1111/j.1476-5381.1993.tb12882.x}}</ref> but (−)-O-DSMT retains activity as a [[norepinephrine]] [[reuptake inhibitor]],<ref name="Driessen1993" /> 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.

[[Opioid]]s exert their effects by binding to and activating the [[Opioid#Mu_.28.CE.BC.29|μ-opioid]] [[receptor]]. This occurs because opioids structurally mimic endogenous endorphins which are naturally found within the body and also work upon the μ-opioid receptor set. The way in which opioids structurally mimic these natural endorphins results in their [[physical euphoria|euphoria]], [[pain relief]] and [[anxiolytic]] effects. This is because endorphins are responsible for reducing pain, causing sleepiness, and feelings of pleasure. They can be released in response to pain, strenuous exercise, orgasm, or general excitement.

==Subjective effects==
{{Preamble/SubjectiveEffects}}
{{effects/base

|{{effects/physical|
The general sensation of O-DSMT can be described as one of intense euphoria, relaxation, anxiety suppression and pain relief.
*'''[[Effect::Pain relief]]'''
*'''[[Effect::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 intense physical comfort, warmth, love and bliss.
*'''[[Effect::Itchiness]]'''
*'''[[Effect::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.
*'''[[Effect::Constipation]]'''
*'''[[Effect::Cough suppression]]'''
*'''[[Effect::Difficulty urinating]]'''
*'''[[Effect::Nausea]]'''
*'''[[Effect::Sedation]]'''
*'''[[Effect::Pupil constriction]]'''
*'''[[Effect::Decreased libido]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Orgasm suppression]]'''

}}
|{{effects/cognitive|
*'''[[Effect::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.
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Dream potentiation]]'''

}}
}}
===Experience reports===
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:

*[https://www.erowid.org/experiences/subs/exp_ODesmethyltramadol.shtml Erowid Experience Vaults: O-Desmethyltramadol]

==Toxicity and harm potential==
{{Further|Research chemicals#Toxicity and harm potential}}
O-DSMT has a [[Toxicity::moderate potential toxicity relative to its dose due to its potency]]. As with all opioids, long-term effects can vary but can include diminished libido, apathy and memory loss. It is also [[Toxicity::potentially [[respiratory depression|lethal]] when mixed with [[depressants]] like [[alcohol]] or [[benzodiazepines]]]].

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 was 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.<ref>{{cite journal | vauthors=((Arndt, T.)), ((Claussen, U.)), ((Güssregen, B.)), ((Schröfel, S.)), ((Stürzer, B.)), ((Werle, A.)), ((Wolf, G.)) | journal=Forensic Science International | title=Kratom alkaloids and O-desmethyltramadol in urine of a “Krypton” herbal mixture consumer | volume=208 | issue=1–3 | pages=47–52 | date=20 May 2011 | issn=1872-6283 | doi=10.1016/j.forsciint.2010.10.025}}</ref><ref>{{cite journal | vauthors=((Bäckstrom, B. G.)), ((Classon, G.)), ((Löwenhielm, P.)), ((Thelander, G.)) | journal=Lakartidningen | title=[Krypton--new, deadly Internet drug. Since October 2009 have nine young persons died in Sweden] | volume=107 | issue=50 | pages=3196–3197 | date=15 December 2010 | issn=0023-7205}}</ref><ref>{{cite journal | vauthors=((Kronstrand, R.)), ((Roman, M.)), ((Thelander, G.)), ((Eriksson, A.)) | journal=Journal of Analytical Toxicology | title=Unintentional Fatal Intoxications with Mitragynine and O-Desmethyltramadol from the Herbal Blend Krypton | volume=35 | issue=4 | pages=242–247 | date=1 May 2011 | url=https://academic.oup.com/jat/article-lookup/doi/10.1093/anatox/35.4.242 | issn=0146-4760 | doi=10.1093/anatox/35.4.242}}</ref>

It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.

===Tolerance and addiction potential===
As with other [[opioids]], the chronic use of O-DSMT can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[Opioids#Discontinuation|withdrawal symptoms]] may occur if a person suddenly stops their usage.

Tolerance to many of the effects of O-DSMT [[Time to full tolerance::develops with prolonged and repeated use]]. 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. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). O-DSMT presents cross-tolerance with [[Cross-tolerance::all other [[opioids]]]], meaning that after the consumption of O-DSMT all [[opioid]]s will have a reduced effect.

===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Opioids}}

====[[Serotonin syndrome]] risk====
{{DangerousInteractions/SerotoninSyndrome}}

==Legal status==
{{legalStub}}
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.<ref>http://www.legislation.gov.uk/ukdsi/2013/9780111532980/pdfs/ukdsi_9780111532980_en.pdf</ref>

*'''Germany:''' O-DSMT is not a controlled substance under the BtMG.<ref>{{Citation | title=Anlage I BtMG - Einzelnorm | url=http://www.gesetze-im-internet.de/btmg_1981/anlage_i.html}}</ref> It is legal, as long as it is not sold for human consumption, according to §2 AMG.<ref>{{Citation | title=§ 2 AMG - Einzelnorm | url=https://www.gesetze-im-internet.de/amg_1976/__2.html}}</ref>
*'''Sweden''': O-DSMT is a controlled substance and considered a narcotic by law.
*'''Switzerland:''' O-DSMT is not controlled under Buchstabe A, B, C and D. It could be considered legal.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''United Kingdom:''' It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>{{Citation | title=Psychoactive Substances Act 2016 | url=https://www.legislation.gov.uk/ukpga/2016/2/contents/enacted}}</ref>

==See also==

*[[Responsible use]]
*[[Tramadol]]
*[[Opioid]]

==External links==

*[http://en.wikipedia.org/wiki/O-Desmethyltramadol O-Desmethyltramadol (Wikipedia)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=10529 O-Desmethyltramadol (Isomer Design)]

==References==
<references />
{{#set:Featured=true}}

[[Category:Phenylpropylamine]]
[[Category:Cycloalkylamine]]
[[Category:Opioid]]

O-Desmethyltramadol - Revision history

Sysop: 1 revision imported

en>Tracer: Added Category:Cycloalkylamine