Beatrice (drug)

Last updated
Beatrice
Beatrice (psychedelic).png
Beatrice-3d-sticks.png
Names
Preferred IUPAC name
1-(2,5-Dimethoxy-4-methylphenyl)-N-methylpropan-2-amine
Other names
Béa; 4-Methyl-2,5-dimethoxy-N-methylamphetamine; N-Methyl-DOM; MDO-D; MDOM
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H21NO2/c1-9-6-13(16-5)11(7-10(2)14-3)8-12(9)15-4/h6,8,10,14H,7H2,1-5H3 Yes check.svgY
    Key: IWYGVDBZCSCJGT-UHFFFAOYSA-N Yes check.svgY
  • O(c1cc(c(OC)cc1CC(NC)C)C)C
Properties
C13H21NO2
Molar mass 223.316 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Beatrice, also known as 4-methyl-2,5-dimethoxy-N-methylamphetamine or as N-methyl-DOM, MDOM, or MDO-D, is a lesser-known psychoactive drug of the phenethylamine, amphetamine, and DOx families. [1] [2] It is a substituted methamphetamine and a homolog of 2,5-dimethoxy-4-methylamphetamine (DOM). [1] [2] Beatrice was first synthesized by Alexander Shulgin. [1] [2]

Contents

Use and effects

In Shulgin's book PiHKAL , the minimum dosage is listed as 30 mg, and the duration is listed as 6 to 10 hours. [1] [2] Beatrice produces a vague feeling of openness and receptiveness, and causes a stimulative effect. [1] It also causes diarrhea. [1]

Pharmacology

Beatrice shows affinity for serotonin receptors. [3] [4] Its affinities (Ki) were 415 nM for the 5-HT2 receptor and 3,870 nM for the 5-HT1 receptor. [3] [4] The affinity of Beatrice for the serotonin 5-HT2 receptor was about 4-fold lower than that of DOM. [3] [4] Functional activities were not reported. [3] [4]

Beatrice substituted for DOM in rodent drug discrimination tests, albeit with relatively low potency. [5]

Analogues

Analogues of Beatrice include N-methyl-DOET, N-methyl-DOI (N-Me-DOI), N-methyl-DOB, and IDNNA (N,N-dimethyl-DOI). [1] [2] [6] [7] N-Methyl-DOI is a potent agonist of the serotonin 5-HT2A receptor similarly to DOI, but with several-fold reduced potency and slightly reduced efficacy. [7]

Society and culture

In the United States, Beatrice is a Schedule I isomer of DOET.

See also

References

  1. 1 2 3 4 5 6 7 Beatrice Entry in PiHKAL
  2. 1 2 3 4 5 Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN   978-0-9630096-3-0.
  3. 1 2 3 4 Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID   3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
  4. 1 2 3 4 Shannon M, Battaglia G, Glennon RA, Titeler M (June 1984). "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)". Eur J Pharmacol. 102 (1): 23–29. doi:10.1016/0014-2999(84)90333-9. PMID   6479216.
  5. ↑ Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Res Monogr. 94: 43–67. PMID   2575229.
  6. ↑ Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 834–835, 878. ISBN   978-3-03788-700-4. OCLC   858805226. 8.5.26. N-Substitution von 2,4,5-trisubstituierten Phenylalkylaminen: Einerseits wurde der Einfluss von N-Alkyl-, andererseits derjenige von N-Heterogruppen-Substituenten geprüft. Allgemein ist bekannt, dass das Einführen von Alkylsubstituenten am Stickstoff von psychedelischen Phenylalkylaminen eine Abnahme der HT2-Rezeptoraffinitäten zur Folge hat [29, 150, 151]. Die Wirkungsabschwächung konnte mit den potenten Substanzen DOB (2) und DOM (8) im Menschen bestätigt werden [8]: N-Methyl-DOM (316; BEATRICE) und METHYL-DOB (317) erwiesen sich im Vergleich zu den beiden unmethylierten Verbindungen als massiv weniger aktiv; die aktive Dosis wurde dabei noch nicht eruiert. METHYL-DOET (318; DOETM) erwies sich bei einer Dosierung von 18mg bereits als deutlich aktiv [140]; die Wirkungen wurden im Vergleich zu DOET (14) als ruhiger und angenehmer beschrieben. [...] 318; METHYL-DOET, 18mg, 8-10h. [...] [140] P. Rausch. Persönliche Mitteilung, 2009.
  7. 1 2 McCorvy JD (16 January 2013). Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics (Ph.D. thesis). Purdue University. Archived from the original on 25 March 2025 – via Purdue e-Pubs.
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