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| Other names | Mescaline-NBOMe; 345-NBOMe; M-NBOMe; NBOMe-M;N-(2-Methoxybenzyl)-3,4,5-trimethoxyphenethylamine; 3,4,5-Trimethoxy-N-(2-methoxybenzyl)phenethylamine |
| Routes of administration | Oral, others[1] |
| Drug class | Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen |
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| Pharmacokinetic data | |
| Duration of action | ~2–3 hours[1] |
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| Chemical and physical data | |
| Formula | C19H25NO4 |
| Molar mass | 331.412 g·mol−1 |
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NBOMe-mescaline, also known asmescaline-NBOMe,M-NBOMe, orN-(2-methoxybenzyl)-3,4,5-trimethoxyphenethylamine, is aserotonin receptor agonist and putativepsychedelic drug of thephenethylamine,scaline, andN-benzylphenethylamine (NBOMe) families.[1][2][3] It is theN-(2-methoxybenzyl)derivative ofmescaline.[1][2][3]
The active dose range of NBOMe-mescaline in humans has not been clearly reported and hence is unknown.[4] This is in notable contrast to many other NBOMe drugs.[4]
However,Daniel Trachsel has reported that NBOMe-mescaline at anoral dose of 50 mg three times separated by 1.5 hours each (150 mg total over about 4.5 hours) producedhallucinogenic effects and was somewhat morepotent than mescaline, but only lasted 5 or 6 hours with the employed dosing scheme.[1] It was estimated that theduration if a single dose were to be taken would probably be about 2 to 3 hours.[1] NBOMe drugs are known to have very poor oralbioavailability, so NBOMe-mescaline could be much more potent byparenteralroutes such assublingual orintranasal administration.[1]
In terms of its effects, NBOMe-mescaline was described as somehow shifting the axis of the field of vision.[1] Its effects, or rather after-effects, were described as unpleasant.[1]
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 21,000 |
| 5-HT1B | ND |
| 5-HT1D | ND |
| 5-HT1E | ND |
| 5-HT1F | ND |
| 5-HT2A | 140 (Ki) 3,000 (EC50Tooltip half-maximal effective concentration) 33% (EmaxTooltip maximal efficacy) |
| 5-HT2B | ND (Ki) >20,000 (EC50) IA (Emax) |
| 5-HT2C | 640 (Ki) ND (EC50) ND (Emax) |
| 5-HT3 | ND |
| 5-HT4 | ND |
| 5-HT5A | ND |
| 5-HT6 | ND |
| 5-HT7 | ND |
| α1A | 3,000 |
| α1B,α1D | ND |
| α2A | 810 |
| α2B,α2C | ND |
| β1–β3 | ND |
| D1 | >14,000 |
| D2 | 9,600 |
| D3 | >17,000 |
| D4,D5 | ND |
| H1 | 14,000 |
| H2–H4 | ND |
| M1–M5 | ND |
| I1 | ND |
| σ1,σ2 | ND |
| ORs | ND |
| TAAR1Tooltip Trace amine-associated receptor 1 | >20,000 (Ki) (mouse) 13,000 (Ki) (rat) >30,000 (EC50) (mouse) >30,000 (EC50) (rat) >10,000 (EC50) (human) IA (Emax) (mouse) IA (Emax) (rat) |
| SERTTooltip Serotonin transporter | 24,000 (Ki) 85,000 (IC50Tooltip half-maximal inhibitory concentration) ND (EC50) |
| NETTooltip Norepinephrine transporter | 46,000 (Ki) 89,000 (IC50) ND (EC50) |
| DATTooltip Dopamine transporter | >30,000 (Ki) 449,000 (IC50) ND (EC50) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Refs:[5][3][6] | |
NBOMe-mescaline is apartial agonist ofserotonin receptors, with a5-HT2A pKi originally reported as 7.3 (i.e. Ki of approximately 50 nM),[2] though more modern techniques assayed it as 140 nM at 5-HT2A and 640 nM at 5-HT2C, making it one of the leastpotent compounds among theN-benzylphenethylamines.[3] Nonetheless, it is 68-fold more potent than mescaline as a serotonin 5-HT2A receptor agonistin vitro.[2] However, in another study, it was only about 3.3-fold more potent as a serotonin 5-HT2A receptor agonist compared to mescalinein vitro.[3] The interactions of NBOMe-mescaline with variousreceptors andtransporters have been characterized and described.[3]
Solubility of thehydrochloride salt: ~5 mg/ml in Phosphate Buffered Saline (PBS) @pH 7.2; ~10 mg/ml inethanol &DMF; ~20 mg/ml inDMSO.[7]
NBOMe-mescaline can be synthesized frommescaline and 2-methoxybenzaldehyde, via reductivealkylation. That can be done stepwise by first making theimine and then reducing the formed imine withsodium borohydride, or by direct reaction withsodium triacetoxyborohydride. An alternative production method which removes the need to obtain the illegal compound mescaline as an isolated precursor can be achieved via aone-pot reaction utilizing 3,4,5-trimethoxyphenylacetonitrile withLithium Aluminium Hydride as a reducing agent.
NBOMe-mescaline andNBOMe-escaline were first reported in 1999 resulting from research performed atFree University of Berlin concerning their activity as partial agonists at rat vascular 5-HT2A receptors.[2] NBOMe-mescaline was first reported in September 2008 to have been self administered by humans as apsychedelic drug at some unspecified point prior.[8] It first became available as a commodity in the research chemical market in May 2010 several months after a few 25x-NBOMes became available.
NBOMe-mescaline is not listed in the schedules set out by theUnited Nations'Single Convention on Narcotic Drugs from 1961 nor theirConvention on Psychotropic Substances from 1971,[9] so the signatory countries to these international drug control treaties are not required by said treaties to control NBOMe-mescaline.
This substance is aClass A drug in the United Kingdom as a result of theN-benzylphenethylamine catch-all clause in theMisuse of Drugs Act 1971.[10]
NBOMe-mescaline is not listed in thelist of scheduled controlled substances in the USA.[11] It is therefore notscheduled at thefederal level in theUnited States, but it is possible that NBOMe-mescaline could legally be considered ananalog ofmescaline, and therefore sales orpossession could potentially be prosecuted under theFederal Analogue Act.[12]
Aufgrund dieser Resultate blieben weitere Untersuchungen zur N-Alkylierung an Mescalinderivaten aus, bis man schließlich und überraschenderweise herausfand, dass N-Benzylderivate von Phenethylaminen die Affinität zu den Serotonin-5-HT -Rezep- toren deutlich zu steigern vermögen: Pertz, Rheineck und Elz präsentierten für eine Reihe von N-benzylierten Scalin-Derivaten die Serotonin-5-HT -Rezeptor-Affinitäten [551. Für N-(2-Methoxybenzyl)mescalin (M-NBOMe; 24) erhielten sie eine 68fach erhöhte Affi- nitåt (isolierte Rattenschwanzarterie, [3H]Ketanserin Markierung, Abb. 8) im Vergleich zu Mescalin (1). Es stellt sich natürlich die Frage, 0b denn im Menschen die Potenz im Vergleich zu Mes- calin (1) ebenfalls gesteigert ist, 0b N-(2-Methoxybenzyl)mescalin (M-NBOMe; 24) über- haupt eine \X'irkung zeigt, und wenn ja, welche. Ein Einzelversuch (3•50mg; getrennt durch je 1.5h) zeigte, dass die Substanz zwar etwas potenter ist, jedoch nur 5—6 Stunden wirkte, und die Wirkung sich von derjenigen von Mescalin (1) deutlich unterscheidet. Eine Einzeldosis würde demnach vermutlich 2—3h wirken. Die Wirkung schien die Achse des Sichtfeldes ir- gendwie zu verschieben, und die Effekte respektive die Nachwirkungen waren unangenehm. Es sei vermerkt, dass N-benzylierte Phenethylamine sublingual Oder nasal verabreicht of- fenbar um ein Vielfaches potenter Sind, als oral verabreicht. [...] Abb. 8. Das Anbringen eines (2-Methoxybenzyl)-Substituenten an den Stickstoff von Mescalin (1) bewirkt eine drastische Steigerung der Affinität zum 5-HT2A-Rezeptor (PH)Ketanserin markiert) [55).
Supplementary Table S2. Dose estimates and data sources for psychedelics.
