NBOMe-mescaline

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Summary

Identifiers
IUPAC name
CAS Number1354632-01-1 
PubChem CID57501069
ChemSpider25949200 
UNIINS6YSG7F4H
Chemical and physical data
FormulaC19H25NO4
Molar mass331.412 g·mol−1

NBOMe-mescaline or mescaline-NBOMe is a synthetic substituted phenethylamine that acts as a partial agonist of serotonin receptors. It has a 5-HT2A pKi of 7.3 (i.e., Ki of approximately 50nM) as initially reported.

However, more modern techniques have assayed it as 140nM at 5-HT2A and 640nM at 5-HT2C, making it one of the least potent compounds among the N-benzyl phenethylamines.

  • . The following are additional findings related to NBOMe-mescaline:NBOMe-mescaline and NBOMe-mescaline were first reported in 1999 as partial agonists at rat vascular 5-HT2A receptors
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  • NBOMe-mescaline was first reported in September 2008 to have been self-administered by humans as a psychedelic drug at some unspecified point prior
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  • NBOMe-mescaline first became available as a commodity in the research chemical market in May 2010, several months after a few 25x-NBOMes became available
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  • NBOMe-mescaline is a Class A drug in the United Kingdom as a result of the N-benzyl phenethylamine catch-all clause in the Misuse of Drugs Act 1971
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  • The substituted phenethylamines, including NBOMe-mescaline, have a biochemical pharmacology consistent with hallucinogenic activity, with little psychostimulant activity
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  • NBOMe-mescaline has a low to moderate selectivity for 5-HT2A receptors among the N-benzyl-substituted phenethylamines
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In summary, NBOMe-mescaline is a synthetic substituted phenethylamine that partially acts as a serotonin receptor agonist. It has a low potency among the N-benzyl phenethylamines and is classified as a Class A drug in the United Kingdom.

History

In 1999, the initial discovery of NBOMe-mescaline and NBOMe-mescaline originated from research conducted at the Free University of Berlin, focusing on their function as partial agonists at rat vascular 5-HT2A receptors. Subsequently, in September 2008, the self-administration of NBOMe-mescaline by individuals as a psychedelic substance was documented, although the exact timeframe remains unspecified. Notably, NBOMe-mescaline entered the research chemical market as a commercial product in May 2010, shortly after the emergence of a few 25x-NBOMes.

Properties and chemistry

The hydrochloride salt of NBOMe-mescaline exhibits various solubility characteristics: approximately 5 mg/ml in Phosphate Buffered Saline (PBS) at a pH of 7.2, around 10 mg/ml in ethanol and DMF (Dimethylformamide), and approximately 20 mg/ml in DMSO (Dimethyl Sulfoxide).
For the synthesis of NBOMe-mescaline, one approach involves utilizing mescaline and 2-methoxybenzaldehyde in a reductive alkylation process. This can be accomplished stepwise, with the initial formation of the imine, followed by reduction of the imine using sodium borohydride. Alternatively, it can be achieved through a direct reaction with sodium triacetoxyborohydride. An alternative method involves a one-pot response using 3,4,5-tri methoxyphenyl acetonitrile, where Lithium Aluminium Hydride acts as a reducing agent. This method offers an advantage by eliminating the need to procure mescaline as a separate precursor, thereby avoiding potential legal complications.

Psychedelic dosage in humans

Human use of NBOMe-mescaline has been infrequently documented. The onset of psychedelic effects, including visual, auditory, and cognitive alterations, typically occurs at approximately 50 mg when administered intranasally.

Legal status

According to the United Nations Single Convention on Narcotic Drugs from 1961 and their Convention on Psychotropic Substances from 1971, NBOMe-mescaline is not explicitly included in the scheduled substances list. Consequently, countries signatories to these international drug control agreements are not obligated to regulate NBOMe-mescaline under these specific treaties.
In the United States, NBOMe-mescaline is not currently listed among the scheduled controlled substances. However, it should be noted that although it is not federally organised, it could potentially be considered an analogue of mescaline, leading to the possibility of legal prosecution under the Federal Analogue Act.
On the other hand, in the United Kingdom, NBOMe-mescaline is classified as a Class A drug due to the N-benzyl phenethylamine catch-all clause in the Misuse of Drugs Act 1971.

FAQ

1. What is NBOMe-mescaline?

  • NBOMe-mescaline is a synthetic compound structurally related to mescaline, a naturally occurring psychedelic substance in certain cacti. It is known for its hallucinogenic effects.

2. How is NBOMe-mescaline typically used?

  • NBOMe-mescaline is often used recreationally and is typically ingested orally, though it can also be taken through other routes like intranasal administration.

3. What are the effects of NBOMe-mescaline?

  • The effects of NBOMe-mescaline can include psychedelic experiences such as altered perception, visual hallucinations, and changes in mood and thought patterns. The intensity and duration of products can vary.

4. Is NBOMe-mescaline safe?

  • The safety of NBOMe-mescaline is a matter of concern. It is associated with a risk of severe adverse effects, including anxiety, paranoia, and even life-threatening situations. It is not well-researched, and the long-term effects are not fully understood.

5. Is NBOMe-mescaline legal?

  • The legal status of NBOMe-mescaline varies by country. In some places, it is not explicitly controlled or scheduled; in others, it may be regulated or considered illegal. It’s essential to check the local laws and regulations in your area.

6. Can I use NBOMe-mescaline safely?

  • The safety of using NBOMe-mescaline is uncertain, and its risks are not well-documented. Given the potential for adverse effects, it is generally advised to approach this substance cautiously or avoid its use altogether.

7. Are there any risks or side effects associated with NBOMe-mescaline?

  • Yes, there are risks and potential side effects associated with NBOMe-mescaline use. These may include nausea, anxiety, paranoia, cardiovascular issues, and, in extreme cases, seizures or death.

8. Can NBOMe-mescaline be tested for and detected in drug screenings?

  • It is possible to detect NBOMe-mescaline in drug tests, but standard drug screenings may not specifically target this substance. Customized tests may be required to identify its presence.

9. Is there any harm reduction advice for those considering using NBOMe-mescaline?

  • Harm reduction measures for NBOMe-mescaline include starting with a low dose, having a sober and trusted friend present, staying hydrated, and being in a safe and comfortable environment. However, it’s essential to remember that this substance cannot guarantee complete safety.

10. Where can I find more information about NBOMe-mescaline?

  • It’s advisable to consult reputable sources, seek guidance from healthcare professionals, or refer to harm reduction organizations for more information about NBOMe-mescaline and its potential risks. Additionally, you can stay informed about legal updates and regulations in your area.

References

  1. Pertz HH, Rheineck A, Elz S (1999). “Exploring N-Benzylated Variants of the Hallucinogenic Compounds Mescaline and Escaline as Partial Agonists at Rat Vascular 5-HT2A Receptors.” This research is published in Naunyn-Schmiedeberg’s Arch Pharmacol, Volume 359, Supplement 3, Page R29. The original publication can be accessed through an archived source dated September 25, 2015.
  2. Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). “Investigating Receptor Interaction Profiles of Novel N-2-Methoxybenzyl (NBOMe) Derivatives of 2,5-Dimethoxy-Substituted Phenethylamines (2C Drugs).” This study is published in Neuropharmacology, Volume 99, Pages 546-553, with a DOI of 10.1016/j.neuropharm.2015.08.034. The PMID is 26318099, and the S2CID is 10382311.
  3. Information about 25B-NB (n-Benzyl-2C-B) can be found on BlueLight.org.
  4. To access the Material Safety Data Sheet (MSDS) for Mescaline NBOMe HCl, you can refer to Cayman Chemical.
  5. For discussions and insights into NBOMe-Mescaline, you can explore “The Big & Dandy NBOMe-Mescaline Thread” on BlueLight.org.
  6. Information about the United Nations International Drug Control Conventions.
  7. The United States Controlled Substances Act, Section 1308.11, pertains to Schedule I substances.
  8. The Erowid Analog Law Vault provides a comprehensive summary of the Federal Controlled Substance Analogue Act.
  9. The “Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014” is accessible on the official legislation.gov.uk website.

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