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5-MeO-DMT

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5-MeO-DMT
INN: Mebufotenin
Clinical data
Other names5-Methoxy-N,N-dimethyltryptamine; 5-Methoxy-N,N-DMT; O-Methylbufotenin; Mebufotenin; Methylbufotenin; BPL-002; BPL-003; LSR-1019
Routes of
administration		Inhalation, insufflation, sublingual, intramuscular, intravenous, oral (with an MAOITooltip monoamine oxidase inhibitor)[1][2]
Drug classSerotonergic psychedelic (hallucinogen)
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: inactive (without an MAOITooltip monoamine oxidase inhibitor) or weak[1][2]
MetabolismOxidative deamination (MAOTooltip monoamine oxidase), O-demethylation (CYP2D6)[2][1][4]
Metabolites
Onset of action
Elimination half-lifeMinutes[4] (12–19 min in mice, 6–16 min in rats)[2][5]
Duration of action
Identifiers
  • 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.558 Edit this at Wikidata
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
  • COc2ccc1[nH]cc(CCN(C)C)c1c2
  • InChI=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 checkY
  • Key:ZSTKHSQDNIGFLM-UHFFFAOYSA-N checkY
  (verify)

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine), also known as O-methylbufotenin or mebufotenin (INNTooltip International Nonproprietary Name), is a naturally occurring psychedelic of the tryptamine family.[5][1][4][2] It is found in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad.[5] It may occur naturally in humans as well.[5] Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America.[5][6] Slang terms include Five-methoxy, the power, bufo, and toad venom.[7]

The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT1A and 5-HT2A receptors among others.[1][4][8] However, 5-MeO-DMT differs from most other serotonergic psychedelics in having 100- to 1,000-fold higher affinity for the serotonin 5-HT1A receptor over the serotonin 5-HT2A receptor.[1][4][8] In relation to this, 5-MeO-DMT has been described as an "atypical" psychedelic and as producing subjective effects notably distinct from those of DMT and other psychedelics, for instance having a relative lack of visual effects.[5][1][4] Like DMT, 5-MeO-DMT has a very rapid onset of action and short duration.[1][4] However, 5-MeO-DMT is 4- to 10-fold more potent than DMT in humans.[2]

5-MeO-DMT was first synthesized in 1936 by Toshio Hoshino[9] (ja), professor of Tokyo Institute of Technology, and was first isolated from a natural source in 1959.[5] It is a controlled substance in some countries, for instance the United States, United Kingdom, Australia, and New Zealand.[5] The drug is used recreationally and several deaths have been reported in association with its use.[5][10] 5-MeO-DMT is being developed for potential use in medicine in the treatment of neuropsychiatric disorders such as depression.[5][1][4]

Chemistry

[edit]

5-MeO-DMT, also known as 5-methoxy-N,N-dimethyltryptamine, is a substituted tryptamine derivative. It is the 5-methoxylated derivative of N,N-dimethyltryptamine (DMT), the N,N-dimethylated derivative of 5-methoxytryptamine (5-MT; mexamine), and the O-methylated derivative of bufotenin (5-HO-DMT).

It has a relatively high experimental log P of 3.30.[2][11]

Analogues of 5-MeO-DMT include 4-MeO-DMT, 5-MeO-AMT, 5-MeO-DET, 5-MeO-DPT, 5-MeO-DIPT, 5-MeO-MiPT, 5-EtO-DMT, and 5-MeO-MET. Other analogues include dimemebfe and EMDT.

Effects

[edit]

When smoked, the duration of effects can be as little as ten minutes; when insufflated, up to two hours. Effects vary and can range from radical perspective shifting and perception of new insights, euphoria, immersive experiences, dissociation and non-responsiveness, sensual/erotic enhancement, to dysphoria, fear, terror, panic, and ego death.[12][better source needed]

The subjective effects of 5-MeO-DMT are described as distinct from those of DMT and other psychedelics.[4][5] Whereas DMT is described as producing more "information-rich" experiences, with "rich sensory phenomenology", visuals, and experiences of encountering entities and visiting other worlds, 5-MeO-DMT is described as having a relative lack of visual effects, producing a sense of "nothingness", and causing experiences that are said to be "content-free" and sometimes known as "whiteouts".[4][5] These experiences have been described as "beyond ordinary human comprehension", with a subjective impression of a void or amnesia of the experience.[4][5] In spite of this however, some have described the experiences as orgasmic, ecstatic, and blissful, whereas others have described them as terror or "information overwhelm".[4] As with DMT and other psychedelics, the experiences with 5-MeO-DMT are often described as overwhelming, profound, spiritual, religious, and/or mystical.[4][5]

The experiences of 5-MeO-DMT have been related to the experience of ecstatic seizures.[4]

Uses

[edit]

Preliminary clinical findings suggest that 5-MeO-DMT might have antidepressant and anxiolytic effects.[13][14]

Religious use

[edit]

The Church of the Tree of Life, founded in California in 1971 by John Mann but now defunct, declared the use of 5-MeO-DMT to be a sacrament. From approximately 1971 to the late 1980s, 5-MeO-DMT was discreetly available to its members.[15][16] Between 1970 and 1990, smoking of 5-MeO-DMT on parsley was probably one of the two most common forms of ingestion in the United States.[16][unreliable source?]

Pharmacology

[edit]

Pharmacodynamics

[edit]
Activities of 5-MeO-DMT
Target Affinity (Ki, nM)
5-HT1A 1.9–28 (Ki)
3.92–1,060 (EC50Tooltip half-maximal effective concentration)
68–98% (EmaxTooltip maximal efficacy)
5-HT1B 14–351 (Ki)
1.53 (EC50)
78% (Emax)
5-HT1D 2.3–20 (Ki)
37 (EC50)
98% (Emax)
5-HT1E 360–528 (Ki)
92–160 (EC50)
119% (Emax)
5-HT1F 37 (Ki)
14 (EC50)
93% (Emax)
5-HT2A 15–2,011 (Ki)
1.80–3.87 (EC50)
82–101% (Emax)
5-HT2B 36–3,884 (Ki)
5.87 (EC50)
73% (Emax)
5-HT2C 42–538 (Ki)
31 (EC50)
84% (Emax)
5-HT3 >10,000
5-HT4 >10,000 (EC50)
5-HT5A 277–505 (Ki)
110 (EC50)
107% (Emax)
5-HT6 6.5–78 (Ki)
0.24 (EC50)
125% (Emax)
5-HT7 3.9–30 (Ki)
65.7 (EC50)
107% (Emax)
MT1 210 (Ki)
257 (EC50)
MT2 16 (Ki)
112 (EC50)
α1A 4,373–>10,000
α1B 2,188–>10,000
α1D ND
α2A 938–1,890
α2B 430–2,640
α2C 206–508
β1 >10,000
β2 2,679–>10,000
β3 >10,000
D1 80–>10,000
D2 3,562–>10,000
D3 498–>10,000
D4 3,120–>10,000
D5 >10,000
H1 7,580
H2–H4 >10,000
M1–M5 >10,000
σ1 >10,000
σ2 >10,000
SERTTooltip Serotonin transporter 2,032–3,603 (Ki)
2,184 (IC50)
>10,000 (EC50)
NETTooltip Norepinephrine transporter 2,859–>10,000 (Ki)
>10,000 (IC50)
>10,000 (EC50)
DATTooltip Dopamine transporter >10,000 (Ki)
>10,000 (IC50)
>10,000 (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. Proteins are mostly but not exclusively human. Refs: [5][8][17][18][19][20][21][22][23][24]

5-MeO-DMT is a methoxylated derivative of dimethyltryptamine (DMT). While most common psychedelics are believed to primarily elicit psychological effects through agonism of serotonin 5-HT2A receptors, 5-MeO-DMT shows 1,000-fold greater affinity for 5-HT1A over 5-HT2A;[25] In line with its affinity for 5-HT1A receptors, 5-MeO-DMT is extremely potent at suppressing the firing of dorsal raphe 5-HT neurons.[26] Further, its activity in rats was attenuated with the 5-HT1A selective antagonist WAY-100635 while 5-HT2A selective antagonist volinanserin failed to demonstrate any change.[27] Additional mechanisms of action such as inhibition of monoamine reuptake may be involved.[28] A 2019 European study with 42 volunteers showed that a single inhalation produced sustained enhancement of satisfaction with life, and easing of anxiety, depression, and post-traumatic stress disorder (PTSD).[29] A 2018 study demonstrated that a single dose of 5-MeO-DMT induced neurogenesis in mice.[30]

Similarly to other serotonergic psychedelics, 5-MeO-DMT is a non-selective serotonin receptor agonist, including of the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors, among others.[1][4][22][21] It is 4- to 10-fold more potent as a hallucinogen than DMT in humans.[2] In contrast to most serotonergic psychedelics however, it is has been said that it is unclear that the hallucinogenic effects of 5-MeO-DMT are principally mediated by activation of the serotonin 5-HT2A receptor.[4] In any case, 5-MeO-DMT does still activate the serotonin 5-HT2A receptor and does still produce psychedelic effects.[4] It has been proposed that 5-MeO-DMT be considered an "atypical" psychedelic.[4] This relates to the fact that 5-MeO-DMT has 100- to 1,000-fold selectivity for the serotonin 5-HT1A receptor over the serotonin 5-HT2A receptor and that the actions of 5-MeO-DMT appear to be primarily mediated by serotonin 5-HT1A receptor activation.[1][4][2][8] For example, the potencies of drugs substituting for 5-MeO-DMT in drug discrimination assays is well-correlated with their serotonin 5-HT1A receptor affinities, and the discriminative stimulus effects of 5-MeO-DMT are attenuated by serotonin 5-HT1A receptor antagonists.[2] However, there is partial generalization of 5-MeO-DMT to the selective serotonin 5-HT2 receptor agonist (–)-DOM in animals.[2] In accordance with the preceding findings, 5-MeO-DMT is reported to produce notably distinct subjective effects compared DMT and other psychedelics in humans.[4]

Although 5-MeO-DMT shows dramatically higher affinity for the serotonin 5-HT1A receptor than for the serotonin 5-HT2A receptor, the situation appears to be very different in terms of its actual activational potencies at these receptors.[31][21][18] Its EC50Tooltip half-maximal effective concentration values have been found to be 1.80 to 3.87 nM at the serotonin 5-HT2A receptor and 3.92 to 1,060 nM at the serotonin 5-HT1A receptor.[31][21][18][24] For comparison, the EC50 values of DMT were found to be 38.3 nM at the serotonin 5-HT2A receptor and >10,000 nM at the serotonin 5-HT1A receptor in one of the same studies.[31][21] Hence, 5-MeO-DMT appears to be similarly potent or as much as 200-fold more potent as an agonist of the serotonin 5-HT2A receptor than of the serotonin 5-HT1A receptor.[31][21][18] In addition, 5-MeO-DMT is 10-fold more potent than DMT as an agonist of the serotonin 5-HT2A receptor.[31][21]

Besides the serotonin receptors, 5-MeO-DMT is an agonist of the melatonin MT1 and MT2 receptors.[20][24][23] Unlike DMT, 5-MeO-DMT is not a ligand or agonist of the sigma receptors.[5][24][23] In contrast to certain other tryptamines, 5-MeO-DMT is inactive as a monoamine releasing agent, including of serotonin, norepinephrine, and dopamine.[21] However, it is a weak serotonin reuptake inhibitor, with an IC50Tooltip half-maximal inhibitory concentration value of 2,184 nM.[21] Conversely, it is inactive as a dopamine and norepinephrine reuptake inhibitor (IC50 = >10,000 nM).[21]

Similarly to DMT, but in contrast to most other psychedelics, like LSD and psilocybin,[32][33] there appears to be very little development of tolerance with 5-MeO-DMT.[5][21][1][4] In fact, there may even be sensitization to the effects of 5-MeO-DMT.[4] The lack of tolerance development with 5-MeO-DMT may be due to biased agonism of the serotonin 5-HT2A receptor.[5] More specifically, 5-MeO-DMT activates the Gq signaling pathway of the serotonin 5-HT2A receptor with much less potency in recruiting β-arrestin2.[5][21] Activation of β-arrestin2 is linked to receptor downregulation and tachyphylaxis.[33][34][35]

Pharmacokinetics

[edit]

5-MeO-DMT is lipophilic and is thought to easily cross the blood–brain barrier.[2] Accordingly, 5-MeO-DMT readily accumulates in the brain in animals with levels higher than in blood.[2] This is in notable contrast to bufotenin (5-HO-DMT or N,N-dimethylserotonin) and serotonin (5-HT), which are hydrophilic and peripherally selective.[2][36][11]

Bufotenin is an active metabolite of 5-MeO-DMT, formed by O-demethylation by cytochrome P450 CYP2D6.[2] Bufotenin notably has much higher affinity for the serotonin 5-HT2A receptor than 5-MeO-DMT itself.[2] However, bufotenin does not seem to be extensively produced from 5-MeO-DMT in the brain.[2] In addition, peripherally formed bufotenin may not be able to exert significant central effects due to its limited ability to cross into the brain.[2] Hence, the involvement of bufotenin in the psychoactive effects of 5-MeO-DMT is uncertain.[2]

The metabolism of 5-MeO-DMT can be dramatically reduced and its levels markedly augmented and prolonged by monoamine oxidase inhibitors (MAOIs).[2] In addition, MAOIs allow 5-MeO-DMT to become orally active in humans.[2] Combination of 5-MeO-DMT with MAOIs has sometimes resulted in serotonin syndrome and death in humans.[2]

Sources

[edit]

In addition to naturally-occurring sources, 5-MeO-DMT can be produced synthetically.[37][38]

Plant sources
Family Plants
Rutaceae Dictyoloma incanescens,[39] Limonia acidissima,[40] Melicope leptococca[41]
Fabaceae Anadenanthera peregrina,[42] Acacia auriculiformis,[42] Acacia victoriae,[42] Desmodium gangeticum,[42] Lespedeza bicolor,[41][40] Mimosa pudica,[42] Mucuna pruriens,[40][41] Phyllodium pulchellum[40][41]
Poaceae Phalaris tuberosa[42]
Malpighiaceae Diplopterys cabrerana[43]
Cactaceae Echinocereus salm-dyckianus,[40] Echinocereus triglochidiatus[40]
Myristicaceae Horsfieldia superba,[40] Iryanthera macrophylla,[40] Osteophloeum platyspermum,[43] Virola theiodora,[40] V. calophylla,[43] V. multinervia,[43] V. peruviana,[43] V. rufula,[43] V. venosa[43]
Colorado River toad
Animal Sources
Family Animals
Bufonidae Colorado River toad (Incilius alvarius)[44][29][41]

The Colorado River toad is a noted animal source of 5-MeO-DMT. First described in 1983 by Ken Nelson (writing under the pseudonym of Albert Most), smoking the parotoid secretions of the animal produces a powerful and short-lived psychedelic experience.[45] The smoking of I. alvarius secretions should not be confused with the urban legend of toad licking.[46] Since 1983, the animal has since became a popular source of 5-MeO-DMT for recreational or spiritual purposes.[47] Unfortunately, this increased demand and use of the toads as a source of 5-MeO-DMT has put strain on their populations.[48] Concerned with the ecological impacts of the growing use of I. alvarius secretions as a source of 5-MeO-DMT, Ken Nelson would later advocate for the use of synthetic 5-MeO-DMT and conservation of the Colorado River Toad.[49]

Fungal Sources
Family Fungi
Amanitaceae Amanita citrina,[43] Amanita porphyria[43]
[edit]

Australia

[edit]

As a structural analog of N,N-dimethyltryptamine (DMT), 5-MeO-DMT is a Schedule 9 prohibited substance under the Poisons Standard.[50]

Canada

[edit]

5-MeO-DMT is legal for personal use and possession in Canada,[51] though sale, distribution, and other activities involving the substance are illegal under Canadian federal law.

China

[edit]

As of October 2015, 5-MeO-DMT is a controlled substance in China.[52]

Germany

[edit]

As of 2001 5-MeO-DMT is listed as a controlled substance. Attachement I BtMG. BGBl. I 2001, 1180 - 1186;

Sweden

[edit]

The Swedish government classified 5-MeO-DMT, listed as 5-metoxi-N,N-dimetyltryptamin (5-MeO-DMT) in their regulation SFS 2004:696, as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) in October 2004, making it illegal to sell or possess.[53]

Turkey

[edit]

5-MeO-DMT has been controlled in Turkey since December 2013.[54]

United States

[edit]

5-MeO-DMT was made a Schedule I controlled substance in January 2011.[55]

Research

[edit]

5-MeO-DMT is being developed and evaluated for potential therapeutic effects in patients with treatment-resistant depression (TRD).[56] Biopharmaceutical company GH Research has sponsored a completed phase 1 study in healthy volunteers[57] and phase 1/2 study in TRD patients where 87.5% of patients with TRD were brought into remission on day 7 in the phase 2 part of the study.[58] GH Research is currently planning a phase 2b study in TRD patients and have received approval for studies in patients with bipolar II disorder and a current depressive episode and patients with postpartum depression.[59]

Beckley Psytech in collaboration with King's College London is evaluating the safety and tolerability of intranasal 5-MeO-DMT in healthy subjects, in a phase 1 study.[60][61] Beckley Psytech CEO Cosmo Feilding-Mellen sees a potential in the short-acting nature of 5-MeO-DMT compared to psilocybin: "Requiring one or two therapists to sit in a room with a single patient for the entire duration of an MDMA or psilocybin experience, which is essentially a whole working day, is probably going to be very resource-intensive and expensive. There is already a global shortage of psychotherapists, and this poses a potential bottleneck to patient access in the future."[62]

See also

[edit]

References

[edit]
  1. ^ a b c d e f g h i j k l m n o p q r Reckweg JT, Uthaug MV, Szabo A, Davis AK, Lancelotta R, Mason NL, Ramaekers JG (July 2022). "The clinical pharmacology and potential therapeutic applications of 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT)". J Neurochem. 162 (1): 128–146. doi:10.1111/jnc.15587. PMC 9314805. PMID 35149998.
  2. ^ a b c d e f g h i j k l m n o p q r s t u v w x y Shen HW, Jiang XL, Winter JC, Yu AM (October 2010). "Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions". Curr Drug Metab. 11 (8): 659–666. doi:10.2174/138920010794233495. PMC 3028383. PMID 20942780.
  3. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  4. ^ a b c d e f g h i j k l m n o p q r s t u v w x Dourron HM, Nichols CD, Simonsson O, Bradley M, Carhart-Harris R, Hendricks PS (December 2023). "5-MeO-DMT: An atypical psychedelic with unique pharmacology, phenomenology & risk?". Psychopharmacology (Berl). doi:10.1007/s00213-023-06517-1. PMID 38072874.
  5. ^ a b c d e f g h i j k l m n o p q r s Ermakova AO, Dunbar F, Rucker J, Johnson MW (March 2022). "A narrative synthesis of research with 5-MeO-DMT". J Psychopharmacol. 36 (3): 273–294. doi:10.1177/02698811211050543. PMC 8902691. PMID 34666554.
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  23. ^ a b c "PDSP Database". UNC (in Zulu). Retrieved 27 November 2024.
  24. ^ a b c d Liu T. "BindingDB BDBM30707 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethyl-ethanamine::2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine::2-(5-methoxy-1H-indol-3-yl)ethyl-dimethyl-amine::3-(2-DIMETHYLAMINOETHYL)-5-METHOXYINDOLE::CHEMBL7257::MLS000069438::Methoxydimethyltryptamines::SMR000059066::US20240166618, Compound 5-MeO-DMT::WO2023019367, Compound 5-MeO-DMT::cid_1832". BindingDB. Retrieved 27 November 2024.
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