NBOMe-mescaline

NBOMe-mescaline

Systematic (IUPAC) name
N-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-amine
Clinical data
Routes of administration	Oral, intranasal, bucal, sublingual, intravenous
Legal status
Legal status	AU: ? CA: ? UK: ? US: not scheduled
Pharmacokinetic data
Biological half-life	?
Identifiers
CAS Number	N/A
ATC code	none
PubChem	CID 57501069
ChemSpider	25949200
Synonyms	mescaline-NBOMe; 345-NBOMe; N-(2-methoxybenzyl)-3,4,5-trimethoxyphenethylamine; 2-(3,4,5-trimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine; 3,4,5-Trimethoxy-N-(2-methoxybenzyl)phenethylamine
Chemical data
Formula	C19H25NO4
Molar mass	331.4061 g/mol
SMILES COC1=CC(CCNCC2=C(OC)C=CC=C2)=CC(OC)=C1OC.Cl
InChI InChI=1S/C19H25NO4/c1-21-16-8-6-5-7-15(16)13-20-10-9-14-11-17(22-2)19(24-4)18(12-14)23-3/h5-8,11-12,20H,9-10,13H2,1-4H3 Key:USPSMWCGHVXKMN-UHFFFAOYSA-N

NBOMe-mescaline or mescaline-NBOMe is a synthetic substituted phenethylamine. It is a partial agonist of serotonin receptors with preference for 5-HT2A over 5-HT2C (EC50 = 4 and 24 μM, respectively).^[1]

History

NBOMe-mescaline was first reported in the scientific literature in 1997 as a serotonin receptor agonist in the Journal of Medicinal Chemistry.^[1] NBOMe-mescaline and NBOMe-escaline were reported in 1999 resulting from research performed at Free 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 a psychedelic drug at some unspecified point prior.^[3] It first became available as a commodity in the research chemical market in May of 2010 several months after a few 25x-NBOMes became available.

Psychedelic dosage in humans

There have been very few reports of human use of NBOMe-mescaline. Psychedelic visual, auditory and mental effects start around 2 mg intranasally.^[4]

Synthesis

NBOMe-mescaline can be synthesized from mescaline and 2-methoxybenzaldehyde, via reductive alkylation. That can be done stepwise by first making the imine and then reducing the formed imine with sodium borohydride, or by direct reaction with sodium triacetoxyborohydride. An alternative production method which removes the need to obtain the illegal compound mescaline as an isolated precursor can be achieved via a one-pot reaction utilizing 3,4,5-trimethoxyphenylacetonitrile with Lithium Aluminium Hydride as a reducing agent.

Legal status

NBOMe-mescaline is not scheduled by the United Nations' Convention on Psychotropic Substances.^[5]

United States

NBOMe-mescaline is not scheduled at the federal level in the United States,^[6] but it could possibly be legally considered an analog of mescaline, in which case, sales or possession with ultimate intent for human consumption could be prosecuted under the Federal Analogue Act.^[7]

See also

• Mescaline
• 25I-NBOMe
• NBOMe

External Links

• NBOMe-mescaline @ IsomerDesign
• NBOMe-mescaline @ PubChem
• The Big & Dandy NBOMe-Mescaline Thread @ BlueLight.org
• Erowid Experience Vaults: Mescaline-NBOMe (also 345-NBOMe)

References

1. Monte, A. P.; Waldman, S. R.; Marona-Lewicka, D.; et al. (1997-09-12). "Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives". J Med Chem 40 (19): 2997–3008. doi:10.1021/jm970219x. ISSN 0022-2623. PMID 9301661.
2. Pertz, HH; Rheineck, A; Elz, S (1999-01-01). "N-Benzylated derivatives of the hallucinogenic drugs mescaline and escaline as partial agonists at rat vascular 5-HT2A receptors". Naunyn-Schmiedeberg's Archives of Pharmacology 359: R29.
3. 25B-NB (n-Benzyl-2C-B) @ BlueLight.org
4. The Big & Dandy NBOMe-Mescaline Thread @ BlueLight.org
5. Convention on Psychotropic Substances, 1971
6. §1308.11 Schedule I.
7. Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary