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]
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| Names | |
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| 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
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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Use and effects
editIn 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
editBeatrice 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
editAnalogues 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
editLegal status
editIn the United States, Beatrice is a Schedule I isomer of DOET.
See also
editReferences
edit- ^ a b c d e f g Beatrice Entry in PiHKAL
- ^ a b c d e 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.
- ^ a b c d 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
- ^ a b c d 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.
- ^ 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.
- ^ 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.
- ^ a b 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.