Beatrice (drug)
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| Other names | BEATRICE; 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 class | Serotonin receptor modulator; Psychoactive drug; Stimulant |
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| Duration of action | 6–10 hours[1] |
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| Chemical and physical data | |
| Formula | C13H21NO2 |
| Molar mass | 223.316 g·mol−1 |
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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 his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Beatrice's dose as above 30 mg orally and its duration as 6 to 10 hours.[1][2] At tested doses of 20 to 30 mg orally, the effects of Beatrice have been reported to include openness, eroticism, responsivity, stimulant-like effects, physical effects, muscle tremors, restlessness, sleeping difficulties, diarrhea, and no appetite loss.[1] No clear hallucinogenic effects were described.[1] It is on the order of 10-fold less potent as a psychoactive drug than DOM and is further less potent in terms of hallucinogenic effects.[1] Shulgin hypothesized that Beatrice might produce psychedelic effects at a dose of 75 mg orally, but did not feel comfortable exploring this level.[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 approximately 9-fold lower potency in comparison.[6][7][8]
Chemistry
Synthesis
The chemical synthesis of Beatrice has been described.[1]
Analogues
Analogues of Beatrice include N-methyl-DOET, N-methyl-DOI, N-methyl-DOB, IDNNA (N,N-dimethyl-DOI), N-methyl-TMA-2, and methyl-TMA (N-methyl-TMA), among others.[1][2][9][10] 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.[10]
History
Beatrice was first described in the scientific literature by Beng T. Ho and colleagues in 1970.[11] 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
Legal status
Canada
Beatrice is a controlled substance in Canada under phenethylamine blanket-ban language.[12]
United States
In the United States, Beatrice is a Schedule I isomer of DOET.[13][14]
See also
References
- ^ a b c d e f g h i j k l m Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. Beatrice Entry
- ^ 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.
- ^ Ger A, Ger D. "Triple Goddess of the Night". British Neuroscience Association Bulletin. 63: 28–30.
- ^ 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
- ^ 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.
- ^ Halberstadt AL (2017). "Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens". Curr Top Behav Neurosci. 32: 283–311. doi:10.1007/7854_2016_64. PMID 28097528.
For phenylalkylamine hallucinogens, N-alkyl substitution results in a marked reduction of 5-HT2A affinity and behavioral potency (Fig. 1). For example, 2,5-dimethoxy4-methylamphetamine (DOM; Ki = 100 nM) has higher affinity than N-methyl-DOM (Ki = 414 nM) for 5-HT2A sites labeled by [3 H]ketanserin in rat frontal cortex homogenates [17]. When tested in rats trained to discriminate DOM (1.0 mg/kg, IP) from saline [18], N-methyl-DOM (ED50 = 3.99 mg/kg, IP) was found to be ninefold less potent than DOM (ED50 = 0.44 mg/kg, IP). It has also been reported that addition of an N-methyl group to DOM produces a tenfold reduction of hallucinogenic potency in humans [19]. The presence of a longer alkyl group is apparently even more detrimental; compared to 2,5-dimethoxy-4-bromoamphetamine (DOB; Ki = 63 nM; [17]), N-propyl-DOB has much lower affinity for 5-HT2A sites (Ki = 1,930 nM [16]).
- ^ Glennon RA, Young R, Jacyno JM (April 1983). "Indolealkylamine and phenalkylamine hallucinogens. Effect of alpha-methyl and N-methyl substituents on behavioral activity". Biochem Pharmacol. 32 (7): 1267–1273. doi:10.1016/0006-2952(83)90281-2. PMID 6573879.
- ^ Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships" (PDF). NIDA Research Monograph. 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.
- ^ 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.
- ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
- ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
- ^ Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register.