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Description

5-MeO-DMT Also known as:

  • 5-Methoxydimethyltryptamine
  • 1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl-[ACD/Index Name]
  • 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamin[German][ACD/IUPAC Name]
  • 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine[ACD/IUPAC Name]
  • 2-(5-Méthoxy-1H-indol-3-yl)-N,N-diméthyléthanamine[French][ACD/IUPAC Name]
  • 3-(2-dimethylaminoethyl)-5-methoxyindole
  • 3-[2-(Dimethylamino)ethyl]-5-methoxyindole
  • 5-Methoxy-DMT
  • 5-methoxyindole 3-(2-(N,N-Dimethylamino)ethyl)
  • 5-methoxy-N,N-dimethyl-1H-indole-3-ethanamine
  • 5-methoxy-N,N-dimethyl-1H-indole-3-ethylamine
  • 5-Methoxy-N,N-Dimethyltryptamine
  • Indole, 3-(2-(N,N-dimethylamino)ethyl)-5-methoxy-
  • Indole, 3-[2- (dimethylamino)ethyl]-5-methoxy-
  • MFCD00005658[MDL number]
  • N,N-Dimethyl-5-methoxy tryptamine
  • N,N-Dimethyl-5-methoxytryptamine
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N,N-dimethylamine
  • Bufotenine, 5-Methoxydimethyltryptamine
  • [1019-45-0]
  • [2-(5-methoxy-1H-indol-3-yl)ethyl]dimethylamine
  • [2-(5-Methoxy-1H-indol-3-yl)-ethyl]-dimethyl-amine
  • [2-(5-methoxyindol-3-yl)ethyl]dimethylamine
  • 2-(5-methoxy-1H-indol-3-yl)ethyl-dimethyl-amine
  • 2-(5-methoxy-1H-indol-3-yl)ethyl-dimethylammonium
  • 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine
  • 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethyl-ethanamine
  • 2-(5-methoxy-1H-indole-3-yl)-N,N-dimethylethanamine[ACD/IUPAC Name]
  • 3-(2-(N,N-Dimethyl)aminoethyl)-5-methoxyindole
  • 3-(2-(N,N-Dimethylamino)ethyl)-5-methoxyindole
  • 3-[2-(N,N-Dimethylamino)ethyl]-5-methoxyindole
  • 3-[2-(N,N-Dimethylamino)ethyl]-5-methoxy-indole
  • 5-methoxy DMT
  • 5-methoxy-3-N,N-dissopropylamino-ethylindole
  • Bufotenine, O-methyl-
  • cid_1832
  • Indole, 3-(2-(dimethylamino)ethyl)-5-methoxy-
  • Indole, 3-(2-(N,N-dimethylamino)ethyl)-5-methoxy
  • Indole, 3-[2-(dimethylamino)ethyl]-5-methoxy-
  • Indole, 3-[2-(N,N-dimethylamino)ethyl]-5-methoxy-
  • MeODMT
  • methoxybufotenin
  • Methoxydimethyltryptamine
  • Methoxydimethyltryptamines
  • Methylbufotenine
  • N,N-Dimethyl-5-methoxytryptamine, free base
  • O-methylbufotenine
  • WLN: T56 BMJ D2N1&1 GO1

A powerful psychedelic tryptamine found in many species of plants and some toad venom, with a history of use by native South Americans spanning thousands of years. Has similar qualities to DMT and related tryptamines. Very potent. Orally active in combination with an MAOI.

Summary

As with its structural relatives DMT and 5-HO-DMT (Bufotenin), 5-MeO-DMT has been used as an entheogen by South American shamans for thousands of years and has recently been demonstrated to induce mystical experiences. It is distributed in a wide variety of plant species, as well as in the venom of a single psychoactive toad species (Bufo Alvaris). It has also been shown to be produced endogenously in the human body in trace amounts, although its biological function is unclear.

In modern times, 5-MeO-DMT is primarily acquired and consumed in its synthetic powder form through the use of online research chemical vendors. When taken in its synthetic powder form, 5-MeO-DMT is typically vaporized, but can also be insufflated (although this is discouraged), and is active at a dose of as little as 2 mg. It has been suggested that it possesses roughly 4-5x the potency of DMT.

As with DMT, 5-MeO-DMT has been demonstrated to be active orally when taken with an MAOI, but according to numerous reports this combination tends to be extremely unpleasant, producing a strong body load in addition to the risk of hypertensive symptoms and serotonin syndrome, and is therefore strongly advised against. On both physical and psychological levels, it is considered to be substantially less safe than DMT. Anecdotal reports indicate that this substance is likely to be overly intense for those who are not already extensively experienced with hallucinogens, specifically powerful psychedelic tryptamines like DMT, ayahuasca and DPT.

Therefore it is highly advised to approach this very unpredictable, and powerful hallucinogenic substance with the proper amount of precaution, preparation, and harm reduction practices if one chooses to use it.

Chemistry

5-MeO-DMT

5-MeO-DMT

Tryptamines share a core structure comprised of a bicylic indole heterocycle attached at R3 to a terminal amine group via an ethyl side chain.

5-MeO-DMT is substituted at R5 of its indole heterocycle with a methoxy (MeO) functional group CH3O−; it also contains two methyl groups CH3- bound to the terminal amine RN of its tryptamine backbone (DMT).

5-MeO-DMT is the N-substituted methyl homologue of 5-MeO-MiPT and 5-MeO-DiPT, although it radically differs in its effects.

Common Name5-Methoxydimethyltryptamine
Systematic name5-Methoxydimethyltryptamine
FormulaC_{13}H_{18}N_{2}O
SMILESCN(C)CCc1c[nH]c2c1cc(cc2)OC
Std. InChiInChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
Std. InChiKeyZSTKHSQDNIGFLM-UHFFFAOYSA-N
Avg. Mass218.2948 Da
Molecular Weight218.2948
Monoisotopic Mass218.141907 Da
Nominal Mass218
ChemSpider ID1766

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Dose Chart

Smoked
Light2-5mg
Strong10-20mg
Insufflated
Light3-5mg
Common5-10mg
Strong8-15mg

Duration Chart

Smoked
Onset0-1 minutes
Duration5-15 minutes
After-effects1-2 hours

Interactions

Caution

  1. Mescaline
    • The 5-MeO class of tryptamines can be unpredictable in their interactions
  2. DOx
    • The 5-MeO class of tryptamines can be unpredictable in their interactions, particularly increasing the risk of unpleasant physical side effects.
  3. NBOMes
    • The 5-MeO class of tryptamines can be unpredictable in their interactions and the NBOMes are known to be unpredictable even alone. This combination is best avoided
  4. 2C-x
    • The 5-MeO psychedelics can interact unpredictably to potentiate other psychedelics
  5. 2C-T-x
    • Both classes of compounds can be unpredictable alone
  6. Cannabis
    • Cannabis has an unexpectedly strong and somewhat unpredictable synergy with psychedelics.
  7. MDMA
    • Some of the 5-MeO tryptamines are a bit unpredictable and should be mixed with MDMA with care

Dangerous

  1. DXM
    • Little information exists about this combination.
  2. Amphetamines
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally unnecessary because of the stimulating effects of psychedelics.
  3. Cocaine
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally unnecessary because of the stimulating effects of psychedelics.
  4. Tramadol

No Synergy

  1. Caffeine
    • High doses of caffeine may cause anxiety which is less manageable when tripping, and since both are stimulating the combination may cause some physical discomfort.
  2. Opioids

High Synergy

  1. Mushrooms
  2. LSD
  3. DMT
  4. MXE
    • Little information exists about this combination.
  5. Ketamine
  6. N2O

Auditory Effects

Psychological Effects

Pharmacological Effects

5-Meo-DMT’s psychedelic effects are primarily believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. Specifically, this molecule shows high binding affinity for the 5-HT2A and 5-HT1A subtypes. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive. Additional mechanisms of action such as reuptake inhibition of neurotransmitters such as serotonin, noradrenaline and dopamine are also thought to be involved to an extent. This can result in 5-MeO-DMT becoming dangerously toxic when combined with MAOIs, RIMAs, SSRIs, stimulants or any substance which acts as a releasing agent or reuptake inhibitor of monoamine neurotransmitters. 5-MeO-DMT is O-demethylated by polymorphic cytochrome P450 2D6 (CYP2D6) to an active metabolite, bufotenin.

Physical Effects

The physical effects of 5-MeO-DMT can be broken down into several components which progressively intensify proportional to dosage. In comparison to its often relatively mild accompanying cognitive and visual effects, 5-MeO-DMT seems to have by far the most proportionally intense and overwhelming physical sensations found within the known psychedelic experience. These individual components are complex, overwhelming and seem to be equally capable of being interpreted as either extremely pleasurable and euphoric or uncomfortable and dysphoric.

Sensory Effects

  • Synaesthesia - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.

Subjective Effects

Visual Effects

The visual effects of 5-MeO-DMT can be broken down into several components which progressively intensify proportional to dosage. In comparison to its consistently overwhelming and intense accompanying cognitive and physical effects, 5-MeO-DMT seems to have some of the most proportionally underwhelming visual effects found within the known varieties of the psychedelic experience.

Geometry

The visual geometry that is present throughout this trip does not usually occur and in notable contrast to DMT, does not extend beyond level 7 at its highest state (though some experiences involving nonvisual 8b have been reported). It is vaguely similar to DMT although significantly smaller in size and more likely to manifest in darkness or without distractions. In terms of appearance, it can be comprehensively described through its variations as intricate in complexity, abstract in form, equally organic and digital in feel, structured in organization, brightly lit, multicoloured in scheme, glossy in shading, equal in sharp and soft edges, small in size, fast in speed, smooth in motion, equal in rounded and angular corners, immersive in-depth and consistent in its intensity. 5-MeO-DMT is unique in that in breakthrough doses, it uniquely tends to result in 8B Geometry over level 8A.

Legal Status

  • Austria: 5-Meo-DMT is, as an ether of N,N-DMT, illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).
  • Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.
  • China: As of October 2015, 5-MeO-DMT is a controlled substance in China.
  • Denmark: As of December 2004, 5-MeO-DMT is legally restricted to "medical or scientific purposes".
  • Germany: 5-MeO-DMT is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of October 10, 2000. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • Greece: 5-MeO-DMT became a controlled substance in Greece on February 18, 2003 [EU Legal Database].
  • Latvia: 5-MeO-DMT is a Schedule I drug.
  • New Zealand: 5-MeO-DMT is Schedule I (Class A) in New Zealand.
  • Romania: 5-MeO-DMT is illegal in Romania since February 2010.
  • Sweden: 5-MeO-DMT was classified as a health hazard under the act "Lagen om förbud mot vissa hälsofarliga varor" (translated as the "Act on the Prohibition of Certain Goods Dangerous to Health") in their regulation SFS 2004:696, making it illegal to sell or possess as of Oct 1, 2004.
  • Switzerland: 5-MeO-DMT is Schedule I in Switzerland.
  • United Kingdom: 5-MeO-DMT is a Class A drug in the UK as it is an ether of the drug 5-HO-DMT, which is a Class A drug as a result of the tryptamine catch-all clause.
  • United States: 5-MeO-DMT was added to Schedule I, effective January 19, 2011. This means it is illegal to manufacture, buy, possess, or distribute (sell, trade or give) without a DEA license.
  • Sources

    References

    1. https://www.frontiersin.org/articles/10.3389/fpsyg.2018.02459/full
    2. Shen, H.-W., Jiang, X.-L., Winter, J. C., & Yu, A.-M. (2010). Psychedelic 5-Methoxy-N,N-dimethyltryptamine: Metabolism, Pharmacokinetics, Drug Interactions, and Pharmacological Actions. Current Drug Metabolism, 11(8), 659–666. https://doi.org/10.2174/138920010794233495
    3. Ott, J. (2011). Pharntepena-Psychonautics: Human Intranasal, Sublingual and Oral Pharmacology of, (October 2013), 37–41. https://doi.org/10.1080/02791072.2001.10399925
    4. https://erowid.org/chemicals/5meo_dmt/5meo_dmt_health.shtml
    5. http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=38
    6. The roles of 5-HT1A and 5-HT2 receptors in the effects of 5-MeO-DMT on locomotor activity and prepulse inhibition in rats (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/17013638
    7. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/17223101
    8. Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/20942780
    9. https://www.ncbi.nlm.nih.gov/pubmed/17223101
    10. http://www.ncbi.nlm.nih.gov/pubmed/15214625
    11. http://www.ncbi.nlm.nih.gov/pubmed/16356341
    12. http://portal.anvisa.gov.br/documents/10181/3115436/(1)RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
    13. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
    14. "Vierzehnte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in German). Bundesanzeiger Verlag. Retrieved December 10, 2019.
    15. "Anlage I BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
    16. "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
    17. Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (Triptamīni) | http://likumi.lv/doc.php?id=121086
    18. http://www.notisum.se/rnp/sls/sfs/20040696.pdf
    19. Misuse of Drugs Act 1971 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I/paragraph/3
    20. Misuse of Drugs Act 1971 (Legislation.gov.uk) |http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I#reference-M_F_c7632653-ddad-4420-f307-e3da1e36d30e
    21. "DEA_FRDOC_0001-0076".

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    3. PubChem National Center for Bio Informatics
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