Beatrice (drug)
Psychoactive drug

Pharmaceutical compound
Beatrice
Clinical data
Other namesBEATRICE; Béa; 4-Methyl-2,5-dimethoxy-N-methylamphetamine; 2,5-Dimethoxy-4-methyl-N-methylamphetamine; 2,5-Dimethoxy-4,N-dimethylamphetamine; N-Methyl-DOM; MDO-D; MDOM
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Psychoactive drug; Stimulant
ATC code
  • None
Pharmacokinetic data
Duration of action6–10 hours[1]
Identifiers
  • 1-(2,5-dimethoxy-4-methylphenyl)-N-methylpropan-2-amine
CAS Number
  • 92206-37-6 checkY
PubChem CID
  • 212480
ChemSpider
  • 184247 checkY
UNII
  • 4TM7A9W7KW
ChEMBL
  • ChEMBL19044 checkY
CompTox Dashboard (EPA)
  • DTXSID20947125
Chemical and physical data
FormulaC13H21NO2
Molar mass223.316 g·mol−1
3D model (JSmol)
  • Interactive image
  • O(c1cc(c(OC)cc1CC(NC)C)C)C
  • 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 checkY
  • Key:IWYGVDBZCSCJGT-UHFFFAOYSA-N checkY
  (verify)

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

Use and effects

In Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved), the minimum dose 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] The drug is one of Shulgin's "ten classic ladies", a series of methylated DOM derivatives.[1][3]

Interactions

Pharmacology

Pharmacodynamics

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

Beatrice substituted for DOM in rodent drug discrimination tests, albeit with relatively low potency.[6]

Chemistry

Synthesis

The chemical synthesis of Beatrice has been described.[1]

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][7][8] 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.[8]

History

Beatrice was first described in the scientific literature by Beng T. Ho and colleagues in 1970.[9] Subsequently, it was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]

Society and culture

United States

In the United States, Beatrice is a Schedule I isomer of DOET.[citation needed]

See also

References

  1. ^ a b c d e f g h i j k Beatrice Entry in PiHKAL
  2. ^ a b c d Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  3. ^ Ger A, Ger D. "Triple Goddess of the Night". British Neuroscience Association Bulletin. 63: 28–30.
  4. ^ a b c d Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". Journal of Medicinal Chemistry. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
  5. ^ 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)". European Journal of Pharmacology. 102 (1): 23–29. doi:10.1016/0014-2999(84)90333-9. PMID 6479216.
  6. ^ Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Research Monograph. 94: 43–67. PMID 2575229.
  7. ^ 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.
  8. ^ 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.
  9. ^ Ho BT, Tansey LW, Balster RL, An R, McIsaac WM, Harris RT (January 1970). "Amphetamine analogs. II. Methylated phenethylamines". Journal of Medicinal Chemistry. 13 (1): 134–135. doi:10.1021/jm00295a034. PMID 5412084.
  • N-Methyl-DOM - Isomer Design
  • Beatrice - PiHKAL - Erowid
  • Beatrice - PiHKAL - Isomer Design
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