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Beatrice (drug)

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(Redirected fromBeatrice (psychedelic))
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
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H21NO2
Molar mass223.316 g·mol−1
3D model (JSmol)
  • 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 as4-methyl-2,5-dimethoxy-N-methylamphetamine or asN-methyl-DOM,MDOM, orMDO-D, is apsychoactive drug of thephenethylamine,amphetamine, andDOx families.[1][2] It is a substitutedmethamphetamine and ahomologue of2,5-dimethoxy-4-methylamphetamine (DOM).[1][2]

Use and effects

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InAlexander Shulgin's bookPiHKAL (Phenethylamines I Have Known and Loved), the minimum dose is listed as 30 mg, and theduration is listed as 6 to 10 hours.[1][2] Beatrice produces a vague feeling of openness and receptiveness, and causes astimulative effect.[1] It also causesdiarrhea.[1] The drug is one of Shulgin's "ten classic ladies", a series ofmethylated DOMderivatives.[1][3]

Interactions

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See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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Beatrice showsaffinity forserotonin receptors.[4][5] Its affinities (Ki) were 415 nM for the5-HT2 receptor and 3,870 nM for the5-HT1 receptor.[4][5] The affinity of Beatrice for the serotonin 5-HT2 receptor was about 4-fold lower than that ofDOM.[4][5]Functional activities were not reported.[4][5]

Beatrice substituted forDOM in rodentdrug discrimination tests, albeit with relatively lowpotency.[6]

Chemistry

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Synthesis

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Thechemical synthesis of Beatrice has been described.[1]

Analogues

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Analogues of Beatrice includeN-methyl-DOET,N-methyl-DOI (N-Me-DOI),N-methyl-DOB, andIDNNA (N,N-dimethyl-DOI).[1][2][7][8]N-Methyl-DOI is apotentagonist of theserotonin5-HT2A receptor similarly toDOI, but with several-fold reduced potency and slightly reducedefficacy.[8]

History

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

Society and culture

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Legal status

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United States

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In theUnited States, Beatrice is a Schedule I isomer ofDOET.[citation needed]

See also

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References

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  1. ^abcdefghijkBeatrice Entry inPiHKAL
  2. ^abcdShulgin 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. ^abcdGlennon 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. ^abcdShannon 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. ^abMcCorvy 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 fromthe 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.

External links

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