5-MeO-DMT

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Summary

5-MeO-DMT, scientifically known as 5-methoxy-N,N-dimethyltryptamine, and informally referred to as O-methyl-bufotenin, belongs to the tryptamine class of psychedelics. It’s widely distributed in various plant species and is notably secreted by the glands of specific toad species, such as the Colorado River toad. This compound, along with its close counterparts DMT and bufotenin (5-HO-DMT), has been employed as an entheogen in South America, where it holds spiritual and shamanic significance.

Informal terms used to describe 5-MeO-DMT include Five-methoxy, the power, bufo, and toad venom.

Identifiers
IUPAC name
CAS Number1019-45-0 
PubChem CID1832
IUPHAR/BPS145
ChemSpider1766 
UNIIX0MKX3GWU9
KEGGC08309 
ChEBICHEBI:2086 
ChEMBLChEMBL7257 
CompTox Dashboard (EPA)DTXSID70144324
ECHA InfoCard100.012.558
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1

Chemistry

The synthesis of 5-MeO-DMT dates back to 1936. In 1959, it was identified as one of the psychoactive compounds present in Anadenanthera peregrina seeds, which were traditionally used to create Yopo snuff. Initially, it was thought to be a primary contributor to the snuff’s psychoactive effects. However, recent research suggests otherwise, as the seeds contain only trace amounts or sometimes none of this compound. Instead, the psychoactive properties of the snuff are attributed to bufotenin, which is the O-demethylated metabolite of 5-MeO-DMT.
The metabolism of 5-MeO-DMT primarily involves the enzyme CYP2D6.

Effects

The duration of the 5-MeO-DMT experience can vary based on the method of administration. When smoked, the effects typically last around 10 minutes, while insufflation (snorting) can extend the experience for up to 2 hours. The effects are diverse and can include profound shifts in perspective, the perception of new insights, feelings of euphoria, immersive experiences, dissociation leading to non-responsiveness, sensual and erotic enhancement, as well as occasional experiences of dysphoria, fear, terror, and panic.

Uses

5-MeO-DMT exhibits anti-anxiety and anti-depressant effects.

Religious use: The Church of the Tree of Life, which was initially founded in California in 1971 by John Mann, though now defunct, declared the sacramental use of 5-MeO-DMT. During approximately 1971 to the late 1980s, 5-MeO-DMT was discreetly available to its members.Between 1970 and 1990, smoking 5-MeO-DMT on parsley was one of the most prevalent methods of ingestion in the United States.

Pharmacology

5-MeO-DMT, a methoxylated derivative of DMT, distinguishes itself from typical psychedelics. While many common psychedelics are believed to primarily induce psychological effects by activating serotonin 5-HT2A receptors, 5-MeO-DMT demonstrates an extraordinary 1000-fold greater affinity for 5-HT1A receptors than for 5-HT2A receptors, reflecting this preference for 5-HT1A receptors, 5-MeO-DMT profoundly suppresses the activity of dorsal raphe 5-HT neurons. Moreover, a study in rats found that its effects were diminished when a 5-HT1A selective antagonist (WAY-100635) was administered, while a 5-HT2A selective antagonist (volinanserin) didn’t bring about any significant change. Additional mechanisms of action, such as monoamine reuptake inhibition, might also play a role.
In a 2019 European study involving 42 volunteers, a single inhalation of 5-MeO-DMT resulted in a sustained improvement in life satisfaction, along with a reduction in anxiety, depression, and symptoms of post-traumatic stress disorder (PTSD). Another study conducted in 2018 showed that a single dose of 5-MeO-DMT promoted neurogenesis in mice.

Clinical Development

5-MeO-DMT is currently undergoing development and assessment for potential therapeutic applications in patients dealing with Treatment-Resistant Depression (TRD). The biopharmaceutical company GH Research has taken the initiative by sponsoring a phase 1 study conducted on healthy volunteers and a phase 1/2 study involving TRD patients. Remarkably, in the phase 2 portion of the study, 87.5% of TRD patients experienced remission on day 7. GH Research is now in the process of planning a phase 2b study for TRD patients, and they have received approval for further investigations involving patients with bipolar II disorder experiencing a current depressive episode and patients with postpartum depression.
In collaboration with King’s College London, Beckley Psytech is conducting a phase 1 study to examine the safety and tolerability of intranasal 5-MeO-DMT in healthy subjects. Beckley Psytech’s CEO, Cosmo Feilding-Mellen, highlights the potential of 5-MeO-DMT’s short-acting nature in comparison to psilocybin. He notes that the extended presence of a therapist during an MDMA or psilocybin experience, often encompassing an entire working day, may be resource-intensive and costly. Given the current global shortage of psychotherapists, this could potentially hinder patient access to treatment in the future.

Legal status

China

5-MeO-DMT was classified as a controlled substance in China as of October 2015.

Australia

Due to its structural similarity to N,N-dimethyltryptamine (DMT), 5-MeO-DMT is listed as a Schedule 9 prohibited substance under the Poisons Standard in Australia.

Sweden

In October 2004, the health ministry, Sveriges Grodminister, categorized 5-MeO-DMT, denoted as 5-metoxi-N,N-dimetyltryptamin (5-MeO-DMT) in their regulation SFS 2004:696, as a “health hazard” under the Act on the Prohibition of Certain Goods Dangerous to Health (Lagen om förbud mot vissa hälsofarliga varor), making it illegal to sell or possess in Sweden.

Germany

Since 2001, 5-MeO-DMT has been listed as a controlled substance, Attachment I BtMG (Betäubungsmittelgesetz), in Germany.

Turkey

Control measures for 5-MeO-DMT were established in Turkey in December 2013.

United States

In January 2011, 5-MeO-DMT was designated as a Schedule I controlled substance in the United States.

FAQ

  • What is 5-MeO-DMT?
  • 5-MeO-DMT, or 5-Methoxy-N, N-dimethyltryptamine, is a powerful psychedelic compound belonging to the tryptamine class. It’s closely related to DMT (Dimethyltryptamine) and is known for its profound and intense psychoactive effects.
  • How is 5-MeO-DMT typically consumed?
  • 5-MeO-DMT is often inhaled or smoked. It can also be consumed through vaporization or insufflation (snorting).
  • What are the effects of 5-MeO-DMT?
  • The effects of 5-MeO-DMT can vary from intense euphoria, mystical experiences, and radical shifts in perception to feelings of fear, anxiety, and even panic. Users often report experiencing a sense of unity with the universe during the peak of the experience.
  • Is 5-MeO-DMT safe to use?
  • While 5-MeO-DMT has been used for centuries in traditional rituals, its use can be risky, especially at higher doses. Excessive use may lead to nausea, vomiting, anxiety, and even extreme fear or panic. It is important to use this substance with caution and in a safe environment.
  • Is 5-MeO-DMT legal?
  • The legal status of 5-MeO-DMT varies by country and region. It is illegal in many countries, including the United States. Before considering its use, it’s crucial to research and understand the legal status in your area.
  • Can 5-MeO-DMT be used for therapeutic purposes?
  • Some ongoing research suggests potential therapeutic applications for 5-MeO-DMT, particularly in the treatment of conditions like depression, anxiety, and PTSD. Clinical trials are underway to explore these possibilities.
  • Is there a difference between 5-MeO-DMT and DMT?
  • While both are tryptamine compounds, 5-MeO-DMT and DMT have distinct effects. 5-MeO-DMT is often reported to induce a more intense and shorter-lasting experience compared to DMT.
  • What precautions should I take if I plan to use 5-MeO-DMT?
  • If you’re considering using 5-MeO-DMT, it’s important to be well-informed and take safety precautions. Ensure you’re in a safe and comfortable environment, preferably with a trusted and sober sitter. Always start with a low dose to assess your tolerance and response to the substance.
  • Are there any risks associated with using 5-MeO-DMT?
  • Yes, using 5-MeO-DMT carries potential risks, including psychological distress, physical discomfort, and the risk of accidents. People with a history of mental health issues or heart conditions should be especially cautious.
  • Is 5-MeO-DMT addictive?
  • There is limited evidence to suggest that 5-MeO-DMT is addictive in the traditional sense. However, like many psychedelics, it can be habit-forming if used irresponsibly or excessively. It’s essential to use it with care and moderation.

References

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